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Islamorada Florida Vacation Rentals - Home
1 / 20

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$110

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$110 - $164
Per week:$770 - $1,144
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 MONTH: Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on ...

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SunSet Water side Tiki Hut Key Largo Cottages, A Great day of rest & relaxation
1 / 24

Key Largo Cottage
2 Bedrooms / 1 Bathroom / Sleeps 62 BR / 1 BA / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6
(1) Excellent 1 Review

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Cottage
Per night:$225 - $275
Per week:$1,575 - $1,925
Pets allowed:No
Internet:No

The Owner's Unit is also right in front of the bay with 2 bedrooms; it can sleep 2 adults and 1 to 3 kids plus plus. The main bedroom has a queen size bed, the second bedroom has a queen size loft bed and a twin bed on the ground floor. Theres also a queen size pullout sofa bed ...

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Just what we expected and more

“ Excellent ”
May 2, 2015
After reading other reviews, we knew we were not going into a Hilton, and that was why we chose the Key Lime Sailing Club! We are not sailors, but we do love the outdoors. Having the canoes, kayaks, stand up paddle boards, bikes, fishing and snorkel equipment at our disposal was the main reason. If it was available, you could use it, for as long as you wanted, no need to sign anything out and you were not timed at how long you had it. We stayed in the Captains Cottage, it was clean, bedding and towels (even beach) were provided. The kitchen was really small, however we didn't do a lot of cooking. Bagels in the morning, sandwiches in the afternoon, outside grill for a dinner or two. Now the cottage could use some sprucing up (yes, I'm being picky but unfortunately I watch too much HGTV) but we didn't spend a lot of time in the cottage because the fun was outside. We kayaked to Pelican Key, rode bikes up/down Overseas Highway, paddle boarded right outside, met wonderful people under the tiki hut, went on a sunset cruise and never missed a sunset! And a highlight was the manatee that came to visit the dock! SO ADORABLE! Everyone one of the crew were great, they pretty much let you do want you wanted, they were very friendly and down to earth. If you want a real laid back Keys experience, I think this is the place to stay, and we won't hesitate to go back. And next time, we will try learning to sail!
Amy Cathro Guimond, Portland, Maine

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Marathon Florida Vacation Rentals - Home
1 / 8

Marathon Home
1 Bedroom / 1 Bathroom / Sleeps 41 BR / 1 BA / Sleeps 4
Home / 1 Bedroom / Sleeps 4
(1) Excellent 1 Review

from

$122

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Home
Per night:$122 - $128
Per week:$850 - $895
Pets allowed:No
Internet:Yes

Welcome to the Florida Keys! Make yourselves comfortable as our guests at Conch Key Vacations, the best view of the Florida Gulf Coast, great fishing from your very own dock in the FL Keys, gorgeous setting to watch wildlife, and the most beautiful sunrise and sunset that Florida...

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Great Views

“ Excellent ”
January 7, 2015
I stayed a week with my girlfriend. We come down to the keys every winter to get away from the cold. It has been recently updated and comes with linens and kitchen stuffs. the bed is decent and has xfinity HDTV and WIFI. fresh paint and floors are nice. Bathroom is TINY but functional as well as clean. Kitchen is very small but it works well. the couch is comfortable. I spent alot of time enjoying wildlife in the canal and cooking out on the grill. (the grill that is there doesnt work well it just heats things up however there is a propane crab steamer thing and i brought a cast iron grill so that was what we used. The view is great you don't have people staying on the other side of the canal just a lot of mangroves and maybe a fisherman's wharf behind that. to the right you can see a small island with 3 trees and next to that you can see the bridge to conch key from layton. Lots of birdwatching and tropical fish come to right to the patio. we fed them bread and corn then you will see many more. Overall we had a nice time here as long as you don't mind the small size.
Aaron Marks, PA USA

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Islamorada Florida Vacation Rentals - Condo
1 / 25

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$97 - $134
Per week:$677 - $934
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH: A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room furnishings...

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Marathon Florida Vacation Rentals - Home
1 / 6

Marathon Home
5 Bedrooms / 4 Bathrooms / Sleeps 105 BR / 4 BA / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

from

$428

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Home
Per night:$428
Per week:$2,990
Pets allowed:No
Internet:Yes

PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN Walk to Sunset Park - Located on Your Block! Island Bay Tropical large five- bedroom, four bathroom home on a deep water canal with boat dockage in Key Colony Beach. Private upper level king master ...

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Marathon Florida Vacation Rentals - Home
1 / 8

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$155

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$155 - $178
Per week:$1,082 - $1,240
Pets allowed:No
Internet:Yes

This cozy, single family home in the middle of Marathon, is on a deep canal just a few houses in from the ocean. You can be on the Atlantic Ocean in minutes to go fishing, snorkeling, or diving. Sit out on the comfortable porch overlooking the canal, sip a cool drink and enjoy...

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Marathon Florida Vacation Rentals - Cottage
1 / 6

Marathon Cottage
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6

from

$349

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$349 - $499
Per month:$10,470 - $14,970
Pets allowed:No
Internet:Yes

Sleeping accommodations include a luxurious king bed in the master bedroom and queen bed in the 2nd bedroom queen size sleeper sofa in the living room. These units will accommodate 6 people including children. Delicious Continental Breakfast Daily Fresh Florida Juicing Oranges In...

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Marathon Florida Vacation Rentals - Home
1 / 8

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Home / 2 Bedrooms / Sleeps 6
(2) Excellent 2 Reviews

from

$229

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$229 - $272
Per week:$1,600 - $1,900
Pets allowed:Yes
Internet:Yes

Welcome to Marathon, located halfway down the Keys, and welcome to our home. We recently bought and fell in love with Coco Plum. This single- family home was provided to us with all the finest amenities which we would love to pass on to you. For the avid fisherman we are located...

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Top 3 Greatest Vacations Ever!

“ Excellent ”
July 6, 2015
This was an amaizing vacation and this home was perfect fom my family! The home is everything advertised amd more. The owners were helpful, responsive, and it's obvious they are very proud of their home. It shows in every detail! We had all the privacy we wanted. A private pool to swim as we wanted. The kids loved it. We were able to easily go anywhere we needed. Coco Plum Beach is walking distance. Shopping at Publix or Winn Dixie is only 10 minutes away. You have to eat breakfast at the Wooden Spoon and check out Herbie's for lunch or dinner. Fishing, Dolphin Research Center, Feed sharks, all within minutes. We are definitely looking to go back in the next year or two. This place is a treasure for a couple or a small family.
Nathan Corlew, Orlando, Fl. USA

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1 / 22

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$358

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps up to 6 people...

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1 / 16

Islamorada Townhouse
2 Bedrooms / 1.5 Bathrooms / Sleeps 62 BR / 1.5 BA / Sleeps 6
Townhouse / 2 Bedrooms / Sleeps 6
(6) Excellent 6 Reviews

from

$94

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Townhouse
Per night:$94
Per week:$654
Pets allowed:No
Internet:No

Vacation in beautiful peaceful Islamorada, in the Florida Keys. Islamorada, "Fishing Capital of the World". Bayside access Townhouse is a newly redone 2 bedroom, loft, 1 1/2 bath, comfortably sleeps 6 adults, patio with BBQ. Fully furnished and kitchen totally equipped. Washer/Dryer,...

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nice quiet complex

“ Excellent ”
May 3, 2015
We loved the pool and the condo was beautifully furnished--retreat-like
Jean Fuller Gest, Massachusetts

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Key Largo Florida Vacation Rentals - Home
1 / 18

Key Largo Home
3 Bedrooms / 2 Bathrooms / Sleeps 73 BR / 2 BA / Sleeps 7
Home / 3 Bedrooms / Sleeps 7
(4) Excellent 4 Reviews

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$250
Per week:$1,500
Pets allowed:Yes
Internet:Yes

lovely Key Largo retreat is located on the Bay side. our home sleeps 7 comfortably with 3 bedrooms and 2 bath. we offer Beautiful direct open bay view from almost every room in the home. 150 foot dock area and plenty of parking ! After a long day of fun in the sun head back...

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Rock Lobster Bungalow

“ Excellent ”
August 18, 2015
We had a wonderful time! The house was wonderfully decorated and had everything we needed. We caught lobsters right off the dock. We will be back next year.
Karen Angilello, Jacksonville, FL

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1 / 18

Key Largo Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$112

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$112 - $133
Per week:$784 - $931
Pets allowed:No
Internet:Yes

Exceptional 3 story townhouse located in a quiet oceanfront complex with heated pool and marina. Inspiring ocean views from two balconies and a ground level patio to BBQ. Protected marina and deeded boat slip easily accommodates a boat up to 30' (33' from bow to engine. ) Boat lift...

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Islamorada Florida Vacation Rentals - Home
1 / 14

Islamorada Home
1 Bedroom / 2 Bathrooms / Sleeps 41 BR / 2 BA / Sleeps 4
Home / 1 Bedroom / Sleeps 4

from

$379

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:4
Type:Home
Per night:$379
Per week:$2,650
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH: Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed...

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1 / 16

Key Largo Villa
3 Bedrooms / 3 Bathrooms / Sleeps 63 BR / 3 BA / Sleeps 6
Villa / 3 Bedrooms / Sleeps 6

from

$229

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Villa
Per night:$229
Per week:$1,600
Pets allowed:No
Internet:Yes

Welcome to our home in Key Largo! ! ! We want you to feel the warmth, tranquility and love we have put in this "Little Piece of Paradise" for you to enjoy. Every square inch has been designed by the inspiration that surrounds this little secret spot nestled within the beauty...

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Marathon Florida Vacation Rentals - Cottage
1 / 15

Marathon Cottage
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Cottage / 3 Bedrooms / Sleeps 6
(3) Excellent 3 Reviews

from

$413

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$413
Per week:$2,890
Pets allowed:No
Internet:Yes

PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN Sunset Bay is a 3 bedroom, 2 bathroom home located on the clear, aquamarine waters of the beautiful Gulf of Mexico. This beautiful waterfront cottage features a screened veranda and a natural native garden....

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Wonderful dock for sunsets and sea life!!

“ Excellent ”
April 7, 2015
This was our first visit to the Florida Keys. My husband, myself, our 18 year old son and 16 year old daughter had a wonderful stay here. We were all really happy with our choice of this property. The house looked exactly as shown online. We really enjoyed the pool and hot tub. But our favorite part was the dock! We would walk out onto the dock for every sunset and it was always breath taking. We would also walk out onto the dock several times a day to see what was swimming by in the Gulf. We saw a sea turtle, a shark, a horseshoe crab, a puffer fish, parrot fish, a manatee, lots of sting rays and lots of fish of all sizes. The kids snorkeled and enjoyed seeing all the sea life. As my husband and I stood on the dock making sure they were safe! My son even bought a fishing pole and enjoyed dropping a line several times a day. The location was really convenient to take in a day in Key West as well as the Island Fest in Islamorada. We found the No Name Pub and saw Key Deer. Marathon has a lot to offer too. We were able to buy supplies there and went to The Aquarium. We have so much more we want to do in The Keys but a few days we just wanted to stay at the house and enjoy all it had to offer us. Mary from Dolphin Vacations even called to see if we needed anything. We loved our stay and hope to return someday, very possibly to this house! My only suggestion would be to add a built in bench on the dock.
Karla Haire Sommers, Rogers, MN USA

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Islamorada Florida Vacation Rentals - Home
1 / 24

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 83 BR / 3 BA / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$175

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$175 - $240
Per week:$1,225 - $1,680
Pets allowed:Yes
Internet:No

MINIMUM RENTAL 1 MONTH: Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in...

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Islamorada Florida Vacation Rentals - Home
1 / 20

Islamorada Home
2 Bedrooms / 1.5 Bathrooms / Sleeps 42 BR / 1.5 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$135

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:4
Type:Home
Per night:$135 - $158
Per week:$940 - $1,100
Pets allowed:No
Internet:No

MINIMUM STAY 1 MONTH: This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens and fresh...

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Marathon Florida Vacation Rentals - Home
1 / 37

Marathon Home
4 Bedrooms / 4 Bathrooms / Sleeps 104 BR / 4 BA / Sleeps 10
Home / 4 Bedrooms / Sleeps 10
(1) Excellent 1 Review

from

$400

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$400 - $693
Per week:$2,795 - $4,850
Pets allowed:Yes
Internet:Yes

This is a rare 4 bedroom, 4 bath waterfront home near the Vaca Cut on the Gulf of Mexico. This home features a 9x20 foot splash pool, beach sand backyard and kayaks. Bring your own boat or rent one from us for $695/week (17 foot center console with 50HP engine). This property...

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FUN!!!

“ Excellent ”
December 3, 2014
We had a wonderful stay here.The location is perfect.Lots to do and see!!Thank you
Heather Gerhold, Florida

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Key Largo Florida Vacation Rentals - Villa
1 / 16

Key Largo Villa
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Villa / 2 Bedrooms / Sleeps 6
(6) Excellent 6 Reviews

from

$250

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$250 - $500
Per week:$995 - $2,495
Pets allowed:Yes
Internet:Yes

2 bedroom, 2 bathroom Ocean Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2013. It has dockage for boats up to 50 feet. This Villa is 20 feet from the Ocean and has a private beach 50 feet from the patio. We provide a golf cart, Kayaks, fishing equipment,...

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Wedding and stay was wonderful!

“ Excellent ”
July 24, 2015
Norman rented an ocean front unit to me and many units to my friends and family for my wedding. We had the wedding on the beach behind the unit and it was wonderful. Everyone that attended said that the location was absolutely beautiful. And everyone who stayed on the property, loved their stay. We have wonderful pictures thanks to this beautiful location. Norman made our stay comfortable and easy. He definitely helped make our wedding a memorable one! Norman is very kind and easy to work with. I would highly suggest staying in his properties as you will be very happy.
Celina Wilder, Atlanta, GA

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1 / 16

Key Largo Home
1 Bedroom / 1 Bathroom / Sleeps 41 BR / 1 BA / Sleeps 4
Home / 1 Bedroom / Sleeps 4
(6) Excellent 6 Reviews

from

$113

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Home
Per night:$113
Per week:$785
Pets allowed:No
Internet:No

IF YOUR DESIRED DATES ARE BOOKED FOR THIS PROPERTY, THERE IS ANOTHER MOBILE HOUSE JUST NEAR BY! SEND US AN EMAIL FOR AVAILABILITY REQUEST! IT IS EVERYTHING ABOUT LOCATION! ! ! Lay back and enjoy – our beautiful Manatee Bay oceanfront Key West Style mobile home is an ...

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WONDERFUL!

“ Excellent ”
June 6, 2015
A truly wonderful getaway with all the amenities. The view is AMAZING!! Great for one or two people. Gated community with very friendly people as neighbors. Key Largo is just minutes away with beaches, grocery stores (Publix & Winn-Dixie), restaurants, live music, parks. The Thai restaurant is great for sushi - the outdoor market has great vegetables and fruits (their salsa is terrific!) Laundry mat is in Key Largo - but I just washed my clothes in the sink and hung them on the chairs outdoors to dry - plenty of towels and linens - I would take those to the laundromat. Fishing rods in the house - Just 2 hours from Key West if you want to visit and ride scooters around town. Owners Jelena, Silvia and Jose were great to work with - the neighbors are GREAT people!! So helpful and welcoming. I would highly recommend this great little place - the sunrise is AMAZING.
Jodi HMerck, Davidson, NC

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The Lion's Paw is a Catalina Morgan 440 with two cabins, two heads.
1 / 13

Key West Yacht
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Yacht / 2 Bedrooms / Sleeps 4

from

$325

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Yacht
Per night:$325
Per week:$2,275
Pets allowed:No
Internet:No

Make your next Key West vacation on the Lion's Paw, a roomy monohull sailboat located in Key West premier marina resort - the Key West Harbour Marina. Three night to seven day vacation packages have options for half day, full day, and overnight sails. The yacht club has it's own...

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Islamorada Florida Vacation Rentals - Home
1 / 25

Islamorada Home
4 Bedrooms / 3 Bathrooms / Sleeps 124 BR / 3 BA / Sleeps 12
Home / 4 Bedrooms / Sleeps 12

from

$117

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:12
Type:Home
Per night:$117 - $167
Per week:$817 - $1,167
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 MONTH: Enjoy your stay in this gorgeous single family home. You’ll love the convenient location in the Ocean Shores area of Key Largo. There’s easy ocean access from this 90' concrete dock. Water, electricity, fish cleaning station and gas barbecue grill are all...

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The Conch Cottage
1 / 3

Key West Guesthouse
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Guesthouse / 2 Bedrooms / Sleeps 4
(1) Excellent 1 Review

from

$393

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Guesthouse
Per night:$393 - $472
Per week:$2,750 - $3,300
Pets allowed:No
Internet:Yes

Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully...

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Great Get-a-Way

“ Excellent ”
February 8, 2010
We rented this cottage on the beautiful property of Sea Vista Estate for our 4oth wedding anniversary. We wanted a place to feel relaxed and renewed from the everyday complications of life. This was the perfect place for us. The property is beautiful, the cottage clean and neat with wonderful sunrise vistas and cool ocean breezes. The property owners were gracious and provided delicious key lime pie, daily newspapers and were ready to help with any needs we might have. The beach is quiet and private only shared with the three other houses' renters. The pool area is also very special in a lush tropical setting. We would love to come again and would highly recommend this place which is a quiet oasis to come back to after a fun trip to Key West and all the fun things to do in the area. Don't miss the restaurants, Blue Heaven in Key West and Square Grouper at Mile Marker 22!
Connie Simpson, Oak Ridge, Tennessee

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1 / 20

Key Largo Home
6 Bedrooms / 5.5 Bathrooms / Sleeps 176 BR / 5.5 BA / Sleeps 17
Home / 6 Bedrooms / Sleeps 17
Bedrooms:6
Bathrooms:5.5
Sleeps:17
Type:Home
Per night:$1,358
Per week:$9,500
Pets allowed:No
Internet:Yes

Southern Diversion Estate Key Largo - Brand New private gated 1 acre estate on the ocean with private beach, tiki hut , tropical private pool and deepwater dockage. There are 300 feet of direct ocean access with stunning views. The estate has marble floors throughout , two living...

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Marathon Florida Vacation Rentals - Home
1 / 23

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$178

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$178 - $236
Per week:$1,240 - $1,648
Pets allowed:No
Internet:Yes

Seven night minimum. Canal front home on the Atlantic Ocean side of Marathon. This stilted home has two bedrooms, 2 baths, and comfortably furnished for your stay. Enjoy the breezes and gaze at the stars. There is 30 feet of dockage for your boat, Located in a quiet neighborhood....

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Islamorada Florida Vacation Rentals - Cottage
1 / 19

Islamorada Cottage
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6

from

$358

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a full bath. To the right is a large bedroom with a king bed and full bath. The laundry area with a full size washer and dryer is also located in this room....

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1 / 15

Key Largo Townhouse
2 Bedrooms / 1.5 Bathrooms / Sleeps 82 BR / 1.5 BA / Sleeps 8
Townhouse / 2 Bedrooms / Sleeps 8
(4) Excellent 4 Reviews

from

$143

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:8
Type:Townhouse
Per night:$143 - $215
Per week:$1,000 - $1,500
Pets allowed:No
Internet:No

This bayview townhouse has a great layout. Bottom level offers kitchen, dining , 1/2 bath , and big screen tv in living area . Sliding glass doors lead to screened in porch with beautiful bayviews. You can see your boat slip. NEWS YEARS AND 4TH OF JULY SEE FIREWORKS FROM YOUR...

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Moon Bay Slice of Paradise!

“ Excellent ”
August 5, 2014
Our unit was perfect. It needs a little TLC. But overall it was great. The grounds are well kept, pools were clean, marina was fantastic and we could see our boat from our townhouse and security was good. Parking is at a premium, tight but workable. Our reservation/property manager was very though and helpful.
Maureen Foster, Melbourne Beach FL

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Marathon Florida Vacation Rentals - Condo
1 / 16

Marathon Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 62 BR / 2.5 BA / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6
(3) Excellent 3 Reviews

from

$178

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$178 - $206
Per week:$1,240 - $1,442
Pets allowed:No
Internet:Yes

Beautiful condominium unit at Gulfpointe in Marathon, heart of the Florida Keys. Two bedroom, two and one half bath townhouse overlooking the pool area. Limited views of the Gulf, beautifully decorated, boat dockage, tennis court, and covered parking. First level has kitchen,...

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Gulfpointe I - Marathon, Florida Keys

“ Excellent ”
April 9, 2015
Had a fantastic time at the Gulfpointe condo in Marathon, FL. The location was great, the condo was spacious and had all the items needed to make our trip memorable for our family of three. The pool is great - spent a lot of time there. Beaches in the Keys are less than average compared to the rest of Florida and in other states...just too many rocks. The balconies on both floors provide great outdoor square footage to enjoy grill, meals, reading a book or just enjoying the warmth. We have never had such a great week of weather. Our March/April stay saw high temps in the lower 80s and lows in the lower 70s. We traveled down to Key West one day, and had a good time. Wouldn't recommend any more time than that for those with families. Marathon has just about every thing you need in terms of groceries, shopping, restaurants, etc. Great places to walk and just enjoy the warmth are everywhere. There is a fair amount of traffic on Hwy 1. Didn't bother us much, but you will have to deal with it on occasion. Only negatives about the condo: -king size mattress in master suite is a little uncomfortable -early morning garbage pickup was extremely loud (two days) I would definitely recommend this condo for a family / romantic / getaway vacation.
Paul Kinsella, Chanhassen, MN

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Front View
1 / 29

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6
(6) Excellent 6 Reviews

from

$415

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$415 - $458
Per week:$2,900 - $3,200
Pets allowed:No
Internet:Yes

Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA Accommodations: House, 3 Bedrooms, 2 Baths , Sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74. 5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of...

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Beautiful Tropical Paradise

“ Excellent ”
June 23, 2015
We came down with another couple to spend the week on vacation. The house is very nicely updated with granite counters and well stocked kitchen. We brought our boat down and enjoyed the convenience of the dock and the nearby boat ramp to launch upon arrival. Bonus, there is a commercial size ice maker in the laundry area for our fishing escapades. A canal away from the Gulf and ten minutes by boat to the Atlantic. Another bonus was the private sandy beach which is only five minutes my foot. Kayaks, bikes, waterfront property...who could want anymore! Life is good at Villa Marlin!!
Susan Helms, Merritt Island, FL

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Marathon Florida Vacation Rentals - Home
1 / 40

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Home / 2 Bedrooms / Sleeps 6
(1) Excellent 1 Review

from

$428

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$428 - $715
Per week:$2,995 - $5,000
Pets allowed:Yes
Internet:Yes

WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own tropical island in a quiet cove of protected mangroves in the Gulf of Mexico. You stay on a 2 bedroom houseboat that is docked on the island. You have your own 17 foot center console boat with 50HP...

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Like NO other!

“ Excellent ”
July 13, 2015
My family and extended family enjoyed room to relax, plenty of things to do (fishing, kayaking, snorkeling, and scuba diving), room enough to enjoy the serenity of peace and quiet, the luxury of easy access to shore, and exploring all the native wildlife and aquatic inhabitants in and around the island. Dan was great and immediately responded with solutions to our unique situations and was very accomodating and gracious! Loved it!
Cindy Ciener Knowlton, Orange City, FL

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1 / 25

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 43 BR / 2 BA / Sleeps 4
Home / 3 Bedrooms / Sleeps 4

from

$140

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:4
Type:Home
Per night:$140 - $175
Per week:$980 - $1,225
Pets allowed:No
Internet:Yes

MINIMUM STAY 29 DAYS. BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This home was completely remodeled in 2013. There is 936 square feet of living area on the main level with 2 bedrooms, a full bath and an open living area. ...

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1 / 25

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 73 BR / 2 BA / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$184

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$184 - $250
Per week:$1,284 - $1,750
Pets allowed:No
Internet:Yes

MINIMUM STAY: 29 DAYS You and your entire family will love this serene, quaint part of paradise, in this ultra- charming BEACH HOUSE just footsteps from the SEA. Come and stay in this adorable home located on the crystal clear Atlantic Ocean! The home has plenty of room for your...

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1 / 22

Islamorada Villa
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Villa / 2 Bedrooms / Sleeps 4

from

$100

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Villa
Per night:$100 - $134
Per week:$700 - $933
Pets allowed:Yes
Internet:Yes

MINIMUM RENTAL 1 MONTH: Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity...

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Penthouse
#1 of 2 pools with waterfall
1 / 28

Key West Villa
6 Bedrooms / 7 Bathrooms / Sleeps 166 BR / 7 BA / Sleeps 16
Villa / 6 Bedrooms / Sleeps 16
Bedrooms:6
Bathrooms:7
Sleeps:16
Type:Villa
Per night:$1,143 - $2,000
Per week:$7,995 - $13,995
Pets allowed:No
Internet:Yes

Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless...

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Pool/Hot Tub
1 / 24

Key Largo Home
4 Bedrooms / 4 Bathrooms / Sleeps 104 BR / 4 BA / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$284

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$284 - $332
Per week:$1,984 - $2,322
Pets allowed:Yes
Internet:No

MINIMUM STAY: 1 MONTH Exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. Open concept living area on the middle level of the home offers a formal dining with 8 chairs and 3 bar stools at the kitchen counter. There...

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Marathon Florida Vacation Rentals - Home
1 / 32

Marathon Home
2 Bedrooms / 1 Bathroom / Sleeps 62 BR / 1 BA / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$428

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Home
Per night:$428 - $714
Per week:$2,995 - $4,995
Pets allowed:Yes
Internet:Yes

Escape to your own private tropical island! This Vacation Rental home combines the best of both worlds, a modern, fully furnished, waterfront shore home with all the amenities for your nights and your own private tropical island for your days. This vacation home rents from...

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Marathon Florida Vacation Rentals - Home
1 / 13

Marathon Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$858

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$858 - $1,143
Per week:$6,000 - $8,000
Pets allowed:No
Internet:No

You own private island on the ocean side off the City of Marathon in the Florida Keys. The island is built on a coral reef. Beautiful snorkeling, diving, fishing, and all types of water sports. The island is a short 3 minute boat ride from the City of Marathon in the Heart of the...

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1 / 22

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

from

$167

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$167 - $200
Per week:$1,167 - $1,400
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 MONTH: New on the rental market. This is your opportunity to secure your winter getaway at a luxurious oceanfront condo in one of Islamorada's most prestigious condominium communities. Ocean front dockage is available for boats up to 28' in length (separate rental);...

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Islamorada Florida Vacation Rentals - Home
1 / 15

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 73 BR / 2 BA / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$133

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$133 - $158
Per week:$931 - $1,103
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH: Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the...

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Marathon Florida Vacation Rentals - Home
1 / 46

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 62 BR / 2 BA / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$571

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$571 - $836
Per week:$3,995 - $5,850
Pets allowed:Yes
Internet:Yes

WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own private tropical island in the Gulf of Mexico. You have your own 17 foot center console boat with 50 HP 4 cycle engine for the entire week! This island (unlike most) has full power and water piped...

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1 / 9

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4
(1) Excellent 1 Review

from

$136

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$136 - $186
Per week:$950 - $1,300
Pets allowed:No
Internet:Yes

Two oceanfront condominiums ranch style situated on floor 2 and 5 about 50 ft from the water . You can hear and see the fish break the water in the morning. There are a variety of large tropical birds to watch . We have a beautiful pool among lush tropical foliage on the ocean. We...

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Great location and well appointed

“ Excellent ”
June 24, 2015
We really enjoyed our stay. Location was close to our family that we were visiting as well as close to many restaurants and activities. Next time we will have kayaks and paddle boards delivered and paddle right out to the sandbar that you see from the pool. Loved the linens and very comfortable beds. Plenty of room inside for everyone to have space. My nephew caught snapper right off the beach here. Great time and will be back soon!
Terri Moran, Portland, OR

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Marathon Florida Vacation Rentals - Home
1 / 16

Marathon Home
5 Bedrooms / 3 Bathrooms / Sleeps 105 BR / 3 BA / Sleeps 10
Home / 5 Bedrooms / Sleeps 10
(4) Excellent 4 Reviews

from

$499

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:10
Type:Home
Per night:$499
Per week:$3,490
Pets allowed:No
Internet:Yes

PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN Margarita on the Gulf is a spacious 5 bedroom, 4 bath home located on the Gulf of Mexico. Enjoy endless gulf views as you relax at this private tropical setting with large pool, hot tub, and sun deck...

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Sensational feeling of relaxation

“ Excellent ”
March 30, 2015
Great position excellent view Of Dolphins sharks and birds Great local neighbours
John Davies, Cornwall uk

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1 / 20

Key Largo Home
3 Bedrooms / 3 Bathrooms / Sleeps 83 BR / 3 BA / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$250 - $289
Per week:$1,750 - $2,023
Pets allowed:Yes
Internet:Yes

MINIMUM RENTAL 1 MONTH: Villa Bella is a fabulous 3 BR/3 BA two- story townhouse. This end unit townhome "lives" on the 2nd floor. The kitchen, dining and living areas are all open to each other in a great room with a gorgeous vaulted ceiling. There are 2 bedrooms and 2 baths on ...

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Key Largo Florida Vacation Rentals - Home
1 / 34

Key Largo Home
4 Bedrooms / 4 Bathrooms / Sleeps 144 BR / 4 BA / Sleeps 14
Home / 4 Bedrooms / Sleeps 14
(1) Excellent 1 Review

from

$200

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:14
Type:Home
Per night:$200 - $267
Per week:$1,400 - $1,867
Pets allowed:No
Internet:Yes

Spectacular Waterfront Ocean side 4/4 3 story home with Pool & 50 Ft Dock Oceanfront home with 2 wrap around balconies and great views. Ocean access with no bridges. Next to John Pennekamp, Jacobs Aquatic Center Water park, Publix, Dolphin Cove, and restaurants like the famous...

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Annual Family Keys Vacation

“ Excellent ”
July 20, 2015
Thank you for letting us use your home for our family vacation. We enjoyed every part of it. Used the kayaks several times, used the pool 24/7 and really enjoyed the out doors. We brought our boat and we managed to get in and out of the narrow canal daily. It is rather shallow at low tide. We hope to be back next year. The B's nest is a great vacation home and the owner is very helpful and pleasant to deal with.
connnie jankuhn, Groveland, FL

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ENDLESS VIEWS FROM DECK
1 / 13

Ramrod Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Home / 3 Bedrooms / Sleeps 6
(3) Excellent 3 Reviews

from

$134

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$134 - $200
Per week:$934 - $1,400
Pets allowed:Yes
Internet:Yes

3bd/2ba home w/ sliding glass doors off entire back of house provides never ending views of the Atlantic Ocean Fully equipped home just 25 min from Key West, 10 minutes from beautiful Bahia Honda State Park. Deep water access w/ mean draft of 3ft. Ramrod Key features Looe key ...

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All around, great experience!

“ Excellent ”
July 6, 2015
The home is very well equipped - it had a surprising amount of kitchen equipment, including herbs and spices and utensils. Everything was very clean and organized and comfortable. The drive to the keys was closer to around 30-45 minutes because of traffic, but still not a bad drive. The two sliding glass doors leading out to the porch were very heavy and hard to open. One of them also didn't shut completely the entire time we were there. If you have any Mac products, connecting to the WiFi is a bit more challenging, since Mac products don't like the Push-To-Connect routers. The password for the WiFi is in the top left drawer of the entertainment unit and it is circled on the manual for the router - it is NOT on a sticky note on the fridge, no matter how many times the property manager insists that it is :p. My non-Mac laptop had no issues connecting to the WiFi. The floor area of the outside is covered in abrasive rocks, which you cannot walk around on barefoot. Bring water shoes! Also, seaweed was built up on the boat dock and we slipped and fell multiple times getting the kayaks in and out, but no one got injured. There are almost zero fish off of the boat lift dock, so don't try fishing there unless you have a good luck streak. The house has a stunning view, with no built up condos or resorts anywhere near it. It's very close to two restaurants that play live music, Looe Key and Boondocks, but it's far back enough that it is very quiet and serene. There are also board games to play, which was an unexpected treat. The nearest grocery store is a Winn-Dixie that you will easily miss from the road, unless you're really looking for it. It's about 15 minutes away. Bahia Honda, a beautiful beach, is only about 20 minutes away.
Jaclyn Janero, Fort Collins, Colorado

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Pool
1 / 8

Key West Cottage
4 Bedrooms / 3 Bathrooms / Sleeps 84 BR / 3 BA / Sleeps 8
Cottage / 4 Bedrooms / Sleeps 8
(10) Excellent 10 Reviews

from

$580

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Cottage
Per night:$580 - $967
Per month:$17,400 - $29,010
Pets allowed:No
Internet:Yes

Daily price varies by season, and length of stay. Range of prices shown above. Private compound right in the heart of old town. 1 minute or less from Schooner Wharf with all the water activities imaginable; Sloppy Joe's and Conch Republic (with some of the best music on the rock)...

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perfect location, relaxing space

“ Excellent ”
June 28, 2015
This place has it all. Lounging on the private deck in the mornings drinking coffee in front of the pool. So everyone had privacy and then our central spot was at the pool. Plenty of seating and space to dip your legs in and watch the water fall from the conchs and coral. The pool is much bigger than the photos show! Its a perfect little pool actually. There is a huge grill with a sideburner in addition to the kitchenette in Pilar. The space is very large and accomodating. Plenty of linens and towels. The rooms are super cold (actually my husband said if i could come up with anything to complain about it would be the rooms are cold lol...not really just turn the a/c up if you are cold) Literally you walk outside and are two minutes from Schooner Wharf, Alonsos, AB Lobster House, White Tarpon. ...all our favorites. And if you take a left out of the gate two blocks and you are at Sloppy Joes on Duval. There is a perfect little antique store next door and plenty of corner markets within walking distance. The price is competitive and reasonable. I spent weeks comparing and searching vacation rentals for our trip and i was quite pleased. We will stay again and again. Everyone in my family loved my choice and even people who walk by kept stopping and tried to peak in to see whats back there in our private little oasis. Dont worry they cant see anything bc of the landscaping and layout and anyway the cute little picket fence is locked :)
Cori Moss, miami beach, fl

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Marathon Florida Vacation Rentals - Home
1 / 24

Marathon Home
3 Bedrooms / 3 Bathrooms / Sleeps 83 BR / 3 BA / Sleeps 8
Home / 3 Bedrooms / Sleeps 8
(2) Excellent 2 Reviews

from

$900

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$900 - $1,143
Per week:$6,295 - $7,995
Pets allowed:No
Internet:Yes

Seabird Key is a private 10 acre tropical island hideaway located one- half mile offshore Marathon in the heart of the Florida Keys. As our guest, you have the entire Island to yourself, including an exquisite hardwood beach house (the only house on the Island) and a 19' Boston ...

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This place is like no other in the U.S.

“ Excellent ”
February 25, 2010
This was our second time to Seabird Key and the place is a true Paradise and just when you think it can't get better, the Davidson's added an outdoor kitchen...the pathways and the grounds are maintined so well and the private beach with all the hammocks is just wonderful....it doesn't get better than this!
Susan and Don Wolter, Roanoke, VA USA

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1 / 17

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$147

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$147 - $167
Per week:$1,027 - $1,167
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 MONTH: Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2 spacious...

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Key Largo Florida Vacation Rentals - Cottage
1 / 24

Key Largo Cottage
3 Bedrooms / 2 Bathrooms / Sleeps 63 BR / 2 BA / Sleeps 6
Cottage / 3 Bedrooms / Sleeps 6

from

$84

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$84
Per week:$584
Pets allowed:No
Internet:No

This is a totally remodeled in 2014 Mobile home available with 3 bedroom 2 bath for $2500. 00 a month / It could also be rented as a 2 bedroom 1 bath unit for $2200. 00 a Month. Plus Utilities, Water and Electric we pay Cable. It is in a very quite development on the bay side in ...

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Islamorada Florida Vacation Rentals - Condo
1 / 32

Islamorada Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 62 BR / 2.5 BA / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$179

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$179 - $257
Per week:$1,250 - $1,795
Pets allowed:No
Internet:Yes

MINIMUM STAY 7 NIGHTS, SATURDAY TO SATURDAY RENTAL ONLY BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina....

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About Florida Keys

While all the Florida Keys serve up a high dose of tropical leisure, each has its own personality and flavor. The Florida Keys are a wonderful vacation spot for families in search of a little relaxation or adventure. Enjoy Key Largo’s reputation as the dive capital of the world; Islamorada’s spectacular fishing; Marathon’s family friendly beaches; Big Pine Key and the Lower Keys' slowed pace and natural playground; and the unforgettable Key West, the Southernmost city in the continental U.S. and playground to Presidents, authors, and a number of bon vivants. And each has it's own unique offering of Florida Keys oceanfront vacation rentals to choose from. For families visiting the Florida Keys, vacation rentals by owner offer the maximum amount of space and privacy for the price.

Things to Do

Decide what sorts of fun in the sun you enjoy best and there’s a Key for that. If sports fishing and boating interests you, spend some time on Islamorada and take a dip in the Gulf Stream. If you wonder what inspired one of America’s top writers, don’t miss Key West and the historic Hemingway House. While you’re there, check out the descendants of his famous six-toed cats. No matter which Key you choose, the water is a draw around all of them. The crystalline blue surrounding these islands makes a drive up Highway 1 a spectacular way to spend some time, particularly if you’re in a convertible.

​The Keys have plenty of fun things to do for every activity level. Families who enjoy the outdoors can take advantage of the wide availability of Florida Keys condo rentals and stay right on the beach!
  • Fishing enthusiasts visiting the Florida Keys will be very excited to hear that Islamorada is known as the sport fishing capital of the world, offering a variety of game fish.
  • Water sports are also very popular in the Keys. Hang gliding, parasailing, kayaking, and paddle boarding are great choices for adventurous families.
  • Swimming with dolphins is a unique experience that every tourist of the Florida Keys should try! Through Dolphins Plus in Key Largo, visitors can go on a structured or natural swim with the dolphins or visit the sea lions through the Sea Lion Encounters program. In Islamorada, Theater of the Sea offers a wonderful opportunity to swim with dolphins, sea lions, and rays. Kids will have a blast learning about these delightful creatures.

Climate

The ...

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Top 10 Activities in Florida Keys

Top 10 Activities in Florida Keys
Whether you prefer swimming, fishing, or sunning, there’s no shortage of things to do in the Florida Keys. Read on for the top 10 activities on these tropical islands.
 

Seven Mile Bridge

To get to the Florida Keys, you’ll have to traverse the Seven Mile Bridge, which is an attraction in its own right. For nearly seven miles, this bridge travels over the ocean, connecting the Middle Keys to the Lower Keys and providing travelers with stunning views.
 

John Pennekamp Coral Reef State Park

John Pennekamp Coral Reef State Park, the first underwater park in the U.S., offers a fascinating look under the surface of the Keys. Snorkel or scuba dive to get up close and personal with the reefs, or book a glass bottom boat tour to gaze from above. The admission fee is $8 per car, and there’s an extra charge for tours.
 

Lignumvitae Key Botanical State Park

Though it’s only accessible by private boat, this secluded island is worth a visit, since it ...

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Three Day Itinerary: Florida Keys

Three Day Itinerary: Florida Keys
The Florida Keys are an island archipelago off of Florida's southeast coast. Though the Keys include more than 1,700 islands, most are unpopulated, and only 43 are connected by bridge. The Keys enjoy warm tropical weather year-round, but are very exposed to hurricanes and tropical cyclones. The best time to visit is between March and May, before hurricane season commences on June 1. Weather permitting, a diverse array of historic and natural highlights await you throughout the year.
 

Day 1: Culture and History in Key West

Begin your visit at one of Key West's most famous sites. Take a 30-minute tour of the Ernest Hemingway Home and Museum, and see where the celebrated author penned many of his great works. Around 40 to 50 six-toed cats also live on the property, exhibiting the same polydactyl trait that distinguished Hemingway's own cat.

Explore more of Key West's history at the Harry S. Truman Little White House. The building originally served as a ...

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