Florida Keys Vacation Rentals, Florida Keys Home Rentals, Homes, & More

1-50 of 220 Florida Keys Rentals

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1 / 28

Key Largo Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$210

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$210 - $350
Per week:$1,300 - $1,990
Pets allowed:Yes
Internet:Yes

Enjoy your own private paradise and have fun in the Keys! This beautiful, clean, spacious and airy vacation rental home has three wonderfully decorated, clean and cozy bedrooms. Two and 1/2 comfortable and clean bathrooms. Full kitchen is stocked with all necessary cookware, ...

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Great little place right on the water!

“ Excellent ”
March 6, 2015
We had a wonderful time at this great house in Key Largo! The is a cute little house that is well maintained with an updated kitchen and bathroom - the pictures don't do it justice! The house is on a little marina that attaches to the canal. We were able to use the available paddleboard and kayak and get right in the water from the backyard. There is ample space to lay in the sun or under one of the new tiki umbrellas, or sit and enjoy the beautiful view of the canal. The house also comes with private beach access to a couple nearby beaches - we rode there on some bikes that were left for us to use as well which was a lot of fun. We had 4 adults sharing the house and the one bathroom - which we were able to do with very little issues. This would be a great place for a family or a few couples/friends to stay.Maggie was a wonderful host and really helped to make our trip great! She gave advice on the best place to go snorkeling and info on restaurants and other things to do in the area. We also had some car issues on our last day and Maggie graciously helped us out!We would recommend this place to anyone who is interested - it is a great little house and Maggie was a pleasure to meet and work with on this rental :-)
Alison Brosius, Ashburn, Virginia

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Key West Florida Vacation Rentals - Yacht
1 / 13

Key West Yacht
2 Bedrooms / 2 Bathrooms / 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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Key West Florida Vacation Rentals - Home
1 / 15

Key West Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$386

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$386 - $857
Per week:$2,699 - $5,999
Pets allowed:Yes
Internet:Yes

Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid- century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district of Key West. Walking distance to all Old Town has ...

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Amazing Experience Each and Every Time!!!

“ Excellent ”
October 10, 2010
I have stayed at the Brass Palm Villa several times and I would never stay anywhere else on the island. It is decorated beautifully and exceptionally well maintained. There are many places to relax inside and outside the home. I especially enjoy the outside dining area. If you are looking to rent I would highly recomend the Brass Palm Villa!
Lynne Martino, New Jersey

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Front View
1 / 29

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”5 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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Villa Marlin

“ Excellent ”
March 27, 2015
We were looking for a quiet place to relax and snorkel. The villa is just as lovely as the pictures. Anything you would need is provided. The grounds are shady and comfortable and the location is quiet. We canoed in the canal and saw Manatee. We bicycled to the beach in the evening. We snorkeled all around Islamorada and out of Key largo, amazing corral and fish. The Villa owners were always available and helpful. We rent on trip advisor frequently and we can highly recommend Villa Marlin.
Stephanie Romm, Loveland, CO

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1 / 9

Key Largo Home
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”10 Reviews

from

$125

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Home
Per night:$125
Per week:$770
Pets allowed:No
Internet:Yes

MINI VACATIONS 3 DAYS 2 NIGHTS $199. 00 April 1 - May 15, 2015 This Key Largo property is a paradise in a gated private community. This comfortable park model trailer includes cable TV, full kitchen, bathroom, Queen size bed in master bedroom and much more. Outside terrace...

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Enjoyed our stay!

“ Excellent ”
May 25, 2014
Husband and I stayed here and we loved this place! The campground is patrolled by guards and the rules are strictly enforced. We felt very safe and secure. Very nice pool, marina, laundry facility, basketball and tennis court, playground. We stayed at Lot #488 and it was very spacious and comfortable. My husband's family lives nearby in Homestead/Miami so we had a lot of people coming by to hang out with us and to check out the place for renting themselves. We picked this campground because it is on the Bay side and we brought our flats boat and kayaks for fishing and recreation. The general atmosphere of the place is a fun and friendly community. Spanish is the primary language spoken but it is SE FL and it is mentioned on the campground website to expect Latin music and dominoes games. :). The campground itself was neat and clean. I loved seeing all the stray cats wandering around. One of the reasons I love the keys is all the "Gatos" everywhere. The weekends do get crazy...lots of kids roaming around on golf carts cruising the same spot over and over and over and the pool does get packed. We hope to get back soon!
FelixandChristina Gonzalez, North Central Florida

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1 / 9

Key Colony Beach Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$183

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$183
Per week:$1,275
Pets allowed:No
Internet:Yes

Spectacular 2 story ocean front condo with heated pool and spacious grounds. Relaxing beach with tiki hut. Beach front deck with gas grills. First floor features a spacious living room with balcony that overlooks the heated pool, a fully equipped kitchen with breakfast bar and ...

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Marathon Florida Vacation Rentals - Home
1 / 40

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$571

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$571 - $828
Per week:$3,995 - $5,795
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 / 23

Key Largo Home
5 Bedrooms / 3.5 Bathrooms / Sleeps 12

“ Excellent ”2 Reviews

from

$275

/ night

Email Owner
Bedrooms:5
Bathrooms:3.5
Sleeps:12
Type:Home
Per night:$275 - $475
Per week:$1,700 - $2,250
Pets allowed:Yes
Internet:Yes

Escape to your own private paradise nestled in one of the most picturesque bay coves in all of Key Largo within Black Water Sound. Enjoy fishing, snorkeling, scuba diving, water skiing, or kayaking from your own pier and dock. Bring your boat and launch away into the mysteries...

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Beautiful view!

“ Excellent ”
January 20, 2015
Beautiful view! The dock was the best part of the house. The house was very clean and inviting. The only thing was the kitchen was disorganized and had to get creative with things to cook with. Also, when we booked, there was no mention of people living on the property. A little awkward sharing yourmorning coffee out on the dock with other people. They were other wise very nice and respectful people.
Lauren Champion, Salt Lake City, UT USA

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Key West Florida Vacation Rentals - Villa
1 / 28

Key West Villa
6 Bedrooms / 7 Bathrooms / 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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Marathon Florida Vacation Rentals - Cottage
1 / 6

Marathon Cottage
2 Bedrooms / 2 Bathrooms / 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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View from the balcony
1 / 16

Key Largo Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”3 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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Great Time and Awesome location

“ Excellent ”
March 11, 2015
We stayed here the first week in March/15 in the three bedroom unit. the place was amazing, had everything we needed and the view is unreal. Norman was a great host. we cant wait to come back!
Dan MacPherson, Thamesford, ON Canada

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Key West Florida Vacation Rentals - Apartment
1 / 16

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$215

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$215 - $400
Per week:$1,500 - $2,800
Pets allowed:No
Internet:Yes

7 day minimum please This fully furnished newly updated getaway is so close to all the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... A car is really not necessary in Key west (though parking space for one auto is ...

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Marathon Florida Vacation Rentals - Home
1 / 31

Marathon Home
4 Bedrooms / 4 Bathrooms / Sleeps 10

“ Excellent ”1 Review

from

$414

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$414 - $671
Per week:$2,895 - $4,695
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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Tavernier Florida Vacation Rentals - Home
1 / 40

Tavernier Home
6 Bedrooms / 6 Bathrooms / Sleeps 22

“ Excellent ”1 Review

from

$567

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:22
Type:Home
Per night:$567
Per week:$3,967
Pets allowed:No
Internet:Yes

This three story house, with a breathtaking view , sits on the edge of the Atlantic Ocean with no end in sight. To accompany the great Atlantic is a grand 3, 800 sq ft. 8 bedroom and 6 bathroom home with a pool and a large and complete Kitchen and can accommodate up to 27 people...

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Great reunion spot!

“ Excellent ”
January 2, 2014
This beautiful home was perfect for our recent Christmas get together with family from far and wide. Eighteen of us, including a baby, enjoyed spacious rooms and lovely amenities. The channel offered a great launch spot for the paddle boat ( included) and the kayaks we rented. The indoor dining room and the patio eating area made for terrific family meals. The nearby community center provided fun swimming and tennis at no cost. We really enjoyed our vacation in this beautiful location!
Tim Riazzi, Dayton, Ohio USA

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Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Condo
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88. 5 on the bay side and boasting a great 60 slip marina, it provides quick access...

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Marathon Florida Vacation Rentals - Home
1 / 3

Marathon Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$343

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$343
Per week:$2,400
Pets allowed:Yes
Internet:Yes

Thank You For Your Interest In The Peninsularhouse/ Mangrove Treehouse. Under New Ownership And Management. A 3 Bedroom, 2 Bathroom Single Family Vacation Rental Home, In Marathon, Bayside At Mile Marker 58. 6 On Grassy Key. Located Across The Water From The Dolphin...

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Duck Key Florida Vacation Rentals - Villa
1 / 24

Duck Key Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$900

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$900
Per month:$27,000
Pets allowed:No
Internet:No

Duplex in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait and tackle shop, bank, jewelry store, and much more. Two marinas that you can use, rental of jet skis, kayak boat, sailing boats, snorkeling and fishing...

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Tavernier Florida Vacation Rentals - Home
1 / 6

Tavernier Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$84

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$84
Per week:$584
Pets allowed:Yes
Internet:Yes

Immaculate stilt home in one of the most desirable neighborhoods. Located at mile marker 92. 5 (between Key Largo and Islamorada) on the oceanside. House sits on deep water canal with direct ocean access (a few houses from open ocean). Bring your boat or just rent one so you can...

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Marathon Florida Vacation Rentals - Home
1 / 45

Marathon Home
8 Bedrooms / 6 Bathrooms / Sleeps 20

from

$757

/ night

Email Owner
Bedrooms:8
Bathrooms:6
Sleeps:20
Type:Home
Per night:$757 - $1,085
Per week:$5,295 - $7,595
Pets allowed:Yes
Internet:Yes

WHAT IS UNIQUE ABOUT THIS VACATION HOME? This home offers a great option for multi- family vacationing by providing two 4- bedroom homes side- by- side. This gives you 2 kitchens, 2 pools, 2 100' long deep water docks, sandy shoreline, teak lounge chairs, 2 gas grills, 6 kayaks,...

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Key West Florida Vacation Rentals - Home
1 / 21

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$513

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$513
Per week:$3,590
Pets allowed:No
Internet:Yes

CASA ROSA is a classic four bedroom, four bath "eyebrow" style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large living room and dining room with a kitchen that overlooks your own...

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Marathon Florida Vacation Rentals - Home
1 / 20

Marathon Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”18 Reviews

from

$193

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$193 - $343
Per week:$1,349 - $2,399
Pets allowed:No
Internet:Yes

New home with wide open view of the Gulf of Mexico. 3 Bedroom 3 bath, pool home - perfect for three couples or a family. As close as you can get to the 7- mile bridge for great sunsets and quick boating access for bridge fishing or the oceanside. Fabulous views of the open water...

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Wonderful Vacation

“ Excellent ”
February 9, 2015
We had a wonderful vacation. The owner of the home was in contact with us on our first day to ensure everything went smoothly as well as the on-site maint. person. She was a dream to work with!! Loved the home and look forward to booking it again next year!!
Courtney Dunn, Louisville, KY USA

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Cudjoe Key Florida Vacation Rentals - Home
1 / 8

Cudjoe Key Home
2 Bedrooms / 1 Bathroom / Sleeps 5

“ Excellent ”5 Reviews

from

$110

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:5
Type:Home
Per night:$110
Per week:$650
Pets allowed:Yes
Internet:Yes

Colorful tropical vacation home. The living room nicely decorated with tropical flare, has a flat screen TV with DVD, Directv W/DVR, two sofas, one is a queen size sleeper and comfortable bamboo chair. Dining area conveniently located to kitchen has a wood dining table and...

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Treat for a soldier and his wife

“ Excellent ”
November 26, 2014
I had a slight problem booking the place but owner genell was extremely helpful. My son. Just got back from his fifth tour in the desert and wanted to come for a visit. I thought it would be nice to show his new wife the keys. She is from Germany. The place was clean and homey nothing fancy but a great location in a well managed mobile community nice pool close to key west locked community on the water. We had our pets and there were no restrictions and a small fee. We decided to,stay an extra day and genell contacted the real estate agent and everything was taken care of seamlessly. It happened to be the week of the aweful snow storm in buffalo and the kids are from Niagara falls so they were thrilled to be in the warm weather. There were plenty of instructions for us when we got there so we were able to find everything we needed. Thank you again Genell and family for sharing your home with us
Dale Davis, Holiday florida and Niagara Falls New York

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Bedrooms:1
Bathrooms:2
Sleeps:3
Type:Apartment
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Lovely Furnished Apartment On A 25th Floor Of One Of The Highest Buildings In San Juan, With Marblle Floors, Facias, Indirectr Lighting Central Air Conditioned, New Kitchen With Stainless Steel Appliances Where You Can Have A Couple And A Child Sleeping Comfortably. The Two Bathrooms...

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Key Largo Florida Vacation Rentals - Cottage
1 / 16

Key Largo Cottage
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”40 Reviews

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$175 - $225
Per month:$5,250 - $6,750
Pets allowed:Yes
Internet:Yes

Cozy cottage with sandy beach located in Key Largo on an acre of tropical waterfront. The children will enjoy playing on the beach with toys provided. Or fish from the 100ft dock with fishing equipment provided. Bring a boat and have FREE dockage. Lounge in the hammock under the palm...

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A little Slice of Paradise !

“ Excellent ”
February 10, 2015
Each evening we would sit on the dock watching the sun slowly set over the water. The cottage was perfect, the owners Al & Martha were very gracious hosts. A perfect vacation retreat.
Jeffrey Vickers, Rio Vista, California

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Key West Florida Vacation Rentals - Condo
1 / 12

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$250

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$250 - $600
Per week:$2,100 - $3,475
Pets allowed:No
Internet:Yes

TAKE 25% OFF: - - Stay April 4- 6 (2 nights) and pay a reduced rate of $765 for both nights instead of $1, 025. - - Stay April 11- 14 (3 nights) and pay a reduced rate of $1, 125 for all three nights instead of $1, 500. - - Note, taxes and fees will be added to all rates....

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Better than ice cream!

“ Excellent ”
May 16, 2014
I spend a week in Key west this time every year with my cousins, in celebration of one's birthday. We have a goal to always find a place to stay that allows us the most time all together. We have found some nice places on VRBO but this welcoming home captured our hearts the moment we entered. The attention to detail was impeccable. The view was gorgeous. The beds were cozy. Linens comparable to a four star hotel. Peaceful and serene. All the wants taken care of. We fell in love, so will everyone.
April Rubenstrunk, New York

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Marathon Florida Vacation Rentals - Home
1 / 34

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 8

from

$428

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:8
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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Marathon Florida Vacation Rentals - Home
1 / 17

Marathon Home
4 Bedrooms / 4 Bathrooms / Sleeps 10

“ Excellent ”5 Reviews

from

$400

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$400 - $458
Per week:$2,800 - $3,200
Pets allowed:No
Internet:Yes

Superb views of the Gulf from your screened patio, living room, dining room, master bedroom, junior master suite and pool deck! Deep water dockage, great for fishing and snorkeing also. Two Dolphin Pilings for secure dockage. Fsh cleaning table and bait freezer. Enjoy the ...

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A Great Week At The Keys!

“ Excellent ”
July 17, 2014
Very spacious house with the convenience of the canal and pool. Our friends rented the house next door so we were able to share their view with our awesome house and all of its room! Everything was well maintained,clean and perfect for our family.
Teresa Austin, Jacksonville , Fl

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Tavernier Florida Vacation Rentals - Condo
1 / 16

Tavernier Condo
3 Bedrooms / 2 Bathrooms / Sleeps 7

from

$161

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Condo
Per night:$161 - $218
Per week:$1,125 - $1,525
Pets allowed:No
Internet:Yes

Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit community with a 53 slip marina and accommodations available for that tranquil tropical getaway you've always imagined. Futura Yacht Club is a gated community ...

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1 / 18

Key Largo Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$300

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$300 - $350
Per week:$1,960 - $2,275
Pets allowed:No
Internet:Yes

Villa Los- Montes Beautiful Summer Gate- away, Paradise in the Keys. Rates quoted included base rental & taxes, standard Security Deposit $500. 00, $175. 00 Cleaning Fee and PDP Fee. There being no damages, the security deposit is FULLY REFUNDED after check out. Are you...

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summer get away

“ Excellent ”
August 18, 2014
Troy, Thanks for letting us rent your home for the month of July, we loved the location of your house. It was 2 seconds from the bay and not far from the ocean (which was a beautiful ride). We had manatees that came to the dock on many late afternoons (the kids loved this). We look forward to coming back next year. The Klopf's
Jeroline Klopf, Tampa, Fl

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Duck Key Florida Vacation Rentals - Villa
1 / 24

Duck Key Villa
3 Bedrooms / 2 Bathrooms / Sleeps 6

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$1,200
Per week:$8,400
Pets allowed:No
Internet:No

Duplex in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait and tackle shop, bank, jewelry store, and much more. Two marinas that you can use, rental of jet skis, kayak boat, sailing boats, snorkeling and fishing...

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Key West Florida Vacation Rentals - Townhouse
1 / 3

Key West Townhouse
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”9 Reviews

from

$205

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Townhouse
Per night:$205 - $300
Per month:$6,150 - $9,000
Pets allowed:No
Internet:Yes

"Island Wind" welcomes you to a sun drenched oasis in the heart of Old Town. Charming Bahamian style townhome with tin roof and white spindled porches reminiscent of Old Key West Just a block off Duval Street at the corner of Truman & Simonton in Windward Park a gated community consisting...

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Amazing place

“ Excellent ”
July 28, 2014
Amazing place just like we thought. Close to everything and beautiful. We will deffinatly be staying here again!!!!
James Edwards, Charlotte NC

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Marathon Florida Vacation Rentals - Home
1 / 9

Marathon Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 8

“ Excellent ”5 Reviews

from

$265

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$265
Per week:$1,850
Pets allowed:Yes
Internet:Yes

The property is located at the end of the block. It has an open garage that two full size trucks could park in. It has 4 bedrooms, 2 1/2 bathrooms, if you have a boat we've got you covered with approx 200 feet of canal. Dock facilities include fresh water, electricity, and a cutting...

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good place with great backyard

“ Excellent ”
January 4, 2014
The house was a bit small for 8 people, If they had gone for a smaller furniture in the living/dining room,the room would have seemed bigger. But the Backyard and the view compensated for any flaws inside the house. It was just so beautiful and relaxing.
lavanya srinath, HIghtstown, New Jersey

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Key West Florida Vacation Rentals - Cottage
1 / 8

Key West Cottage
4 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”9 Reviews

from

$580

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Cottage
Per night:$580 - $900
Per month:$17,400 - $27,000
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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If you don't like sleep great stay

“ Average ”
February 26, 2015
The beds are uncomfortable, no extra blanks, had extra pillows but no pillow cases, no free parking had to pay 30 a day to park, the futton had a spring broke in it, but the worst was the cigar store in front of cottage it played real loud music on a Sundaynight until 2:00 am and then on Monday night again played the same. Would not stay again until the cigar store is evicted. The court yard was a great place to hang out and get together with friends.
P Scott Purdin, Jensen Beach fl

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Tavernier Florida Vacation Rentals - Home
1 / 14

Tavernier Home
5 Bedrooms / 5 Bathrooms / Sleeps 15

“ Excellent ”5 Reviews

from

$429

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:15
Type:Home
Per night:$429 - $715
Per week:$3,000 - $5,000
Pets allowed:Yes
Internet:Yes

This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featuring 5 bedrooms and 5 bathrooms, this private residence offers plenty of balconies for water viewing, expansive cathedral ceilings, top of the line appliances and...

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Seaside sanctuary 12/27 thru 1/3/15

“ Excellent ”
January 6, 2015
The house was outstanding. It exceeded all expectations. The pictures don't do it justice. We had 8 adults and 8 Kids, ages 1 3/4 to 14. It worked great.
Denny Webb, Atlanta

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Key West Florida Vacation Rentals - Home
1 / 25

Key West Home
5 Bedrooms / 5.5 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$865

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:12
Type:Home
Per night:$865 - $1,225
Per month:$25,950 - $36,750
Pets allowed:No
Internet:Yes

THE VICTORIA HOUSE - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. It is located just three blocks from Duval Street, in the heart of Key West’s Old Town, within walking distance of restaurants,...

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Amazing location for fun filled girls getaway!

“ Excellent ”
September 12, 2013
I was very impressed with the house. It was perfectly located so that we didn't have to rent bikes or move the car often. We absolutely loved lounging at the pool and couldn't have asked for a better lay out for our 7 girls retreat weekend. We will absolutely stay here again. I am missing it already and we all can't stop talking about it. Thank you for the perfect long weekend away!
Katie Skiff, Washington, DC

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Marathon Florida Vacation Rentals - Condo
1 / 33

Marathon Condo
2 Bedrooms / 2 Bathrooms / Sleeps 5

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Condo
Per night:$107
Per week:$747
Pets allowed:No
Internet:Yes

1214 Square Feet On 1st Floor With Walk Out Patio To All Common Amenities.. Beautiful View Of Atlantic Ocean From All Rooms. Heated Swimming Pool, Tennis Court And Fitness Center, Fishing Dock, Outdoor Pavilions And Outdoor Barbecues....

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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 6

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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Key West Florida Vacation Rentals - Condo
1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

from

$250

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$250 - $500
Per month:$7,500 - $15,000
Pets allowed:No
Internet:Yes

"TEE BY THE SEA" vacation rental (we include 7 bikes free for our guests! ! ! ) If you love... GOLF, SPORT FISHING/BOATING, ART/THEATER AND FANTASTIC LIVE ENTERTAINMENT... than you'll love "Tee by the Sea". We're less then 1/2 mile outside of Key West, located in Stock Island....

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Key West

“ Excellent ”
May 6, 2013
The unit was very comfortable and well equipped. The pool area was terrific and location to Key West couldn't be better. The only thing we found negative at all was the close proximity to the road but that being said it did not ruin our visit. We would stay here again.
Veronica Laliberte, Oakville, Ontario Canada

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Marathon Florida Vacation Rentals - Home
1 / 32

Marathon Home
2 Bedrooms / 1 Bathroom / Sleeps 6

from

$428

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Home
Per night:$428 - $643
Per week:$2,995 - $4,500
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 / 17

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$150 - $450
Per week:$1,050 - $3,150
Pets allowed:No
Internet:Yes

2 bedroom 2 bathroom vacation villas on Atlantic Ocean. Heated pool overlooking a natural sand beach & Tiki huts & hammocks. All homes have full kitchen, 3 TV’s, and Washer & Dryer. Boat docks are available on site. Bar B Q grills. 2 Zone air- conditioning in every villa....

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Great location

“ Excellent ”
February 16, 2015
You couldn't ask for a better view of the beach and ocean .! Easy walk to beach, pool and hot tub. The inside of the home is a little dated but we didn't go to be impressed with fancy furnishings it had everything we needed and as I said you couldn't beat the view!,
Peggy Moore, North brunswick NJ

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Marathon Florida Vacation Rentals - Home
1 / 16

Marathon Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”12 Reviews

from

$379

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$379 - $450
Per week:$2,650 - $3,150
Pets allowed:No
Internet:No

High- end Estate overlooking tranquil "Bonefish Flats" in picturesque Marathon. Brand new, Designer decorated with contemporary colors, loads of fine architectural details, Crema Marfil marble, Granite, fine Hardwood floors, open air porches and balconies. This is a superb, ...

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Mar Azul is perfect!

“ Excellent ”
November 3, 2014
The house and lush landscaping are beautiful! We enjoyed the pool so much. The private dock is a great touch even though we don't have a boat. We would recommend this property highly! Quaint restaurants in Marathon have some great food, too! We were excited to have iguanas on the property having never seen one before.
Rhonda Wilburn, Olive Hill, KY USA

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Key West Florida Vacation Rentals - Home
1 / 23

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$134

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$134 - $234
Per week:$934 - $1,634
Pets allowed:No
Internet:Yes

Monthly rental. Key West private home right on the water - family owned for three generations (former home to WWII war hero Admiral Edward McCarthy, the former mayor of Key West (Mayor Alan Cleare), and the former District Attorney (Alan B. Cleare)). Just a few doors down from ...

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Incredible house!

“ Excellent ”
March 10, 2015
This house is immaculately kept and one of the few houses on a canal in KW. Beautiful interior and plenty of room in the bedrooms. The pool overlooks the canal and has an absolutely beautiful view! If you want a house that makes you feel like you're on a tropical island (and you are) then this is the house for you! Close to everything and we're going to be staying there again every year we go.
Travis Haddock, Memphis

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Key West Florida Vacation Rentals - Villa
1 / 55

Key West Villa
5 Bedrooms / 5.5 Bathrooms / Sleeps 12

from

$785

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:12
Type:Villa
Per night:$785 - $1,780
Per month:$23,550 - $53,400
Pets allowed:Yes
Internet:Yes

CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off- street - - a bonus in Old Town where parking is worth its weight in...

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Marathon Florida Vacation Rentals - Home
1 / 23

Marathon Home
4 Bedrooms / 4 Bathrooms / Sleeps 10

“ Excellent ”2 Reviews

from

$415

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$415 - $843
Per week:$2,900 - $5,900
Pets allowed:No
Internet:Yes

Private wide waterfront home. 4, 200 square foot with banquet hall, seats 14. Three central air conditioners, the house is so big. Party room with unique Bar embedded with sand dollars, a real $100 bill that only kids can find, sometimes drunken adults; watch out for the 6 piranhas....

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GREAT FAMILY VACATION HOME!!!

“ Excellent ”
March 22, 2015
8 of us with plenty of room for more! We had a blast, and everything was as described....only better! Patty was a great host, and was there if we needed her. No interference , just help with little details, and very much appreciated. Location was perfect.....the only neighbors we saw were the resident iguanas next door. Fishing??? We caught everything off the sea wall , and a word to the wise is to use fresh shrimp!! We're looking forward to another vacation at Canon Point, but right now we have to get another daughter married (got engaged here! Must be the water??!!??) next June. Thanks again, Patty , for a great time.
Ward Shaw, Chicago, where winter never seems to end

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Marathon Florida Vacation Rentals - Villa
1 / 22

Marathon Villa
5 Bedrooms / 5.5 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$658

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:12
Type:Villa
Per night:$658 - $1,158
Per week:$4,600 - $8,100
Pets allowed:Yes
Internet:Yes

Ocean Front - Villa Bali inspired Florida Keys beauty on Privately owned Walker's Island. This is a spacious 5 bedroom, 5. 5 bath home with luxury in every detail and design. Sleeps up to 12 guests. Features include cathedral ceilings, marble, stainless steel and mahogany finishes,...

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Great Vacation with Family

“ Excellent ”
December 1, 2014
We stayed at this house with our extended family. I was very apprehensive but it wound up being wonderful. Beautiful location, secluded from the world. Tons of space for us to all move about, access to cottage amenities, quick drive to Marathon and Islamorada. Lovely pool and hot tub just for us. Dock area is too shallow to really swim off of it, but there is a beach entry by the cottages. Will definitely return. Only complaint is the house is worn from the many people who visit this property. I saw this as confirmation that it is well used and popular, but the bathrooms could use a coat of paint. If that is your only worry, you are truly enjoying paradise. Thank you Conch Key for all your help and recommendations. Spot on for them all!!!
Nina Felt, Dallas, TX USA

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Marathon Florida Vacation Rentals - Cottage
1 / 15

Marathon Cottage
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 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

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. This is a completely furnished home with an open living room, dining room,...

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Great family vacation!

“ Excellent ”
June 19, 2014
We had a great time in the keys! The house is easy to get to and beautiful! There was plenty if space for all of us. The kids loved swimming in the pool and fishing off the dock. We saw a manatee and hooked a tarpon in the canal. We rented kayaks and explored the area. Check in and check out were easy. Can't wait to visit again!
Kathy Ford Goldstein, Colorado, USA

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1 / 9

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

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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Our Beautiful Sunsets
1 / 23

Key Largo Condo
3 Bedrooms / 1.5 Bathrooms / Sleeps 7

“ Excellent ”2 Reviews

from

$136

/ night

Email Owner
Bedrooms:3
Bathrooms:1.5
Sleeps:7
Type:Condo
Per night:$136 - $172
Per week:$950 - $1,200
Pets allowed:No
Internet:Yes

Bay front Vacation Condo in Key Largo, Florida. We book early so don't wait, beat the rest to one of the best and most reasonable, clean, and well appointed condos in beautiful Key Largo, Florida. Max 4 adults, up to 3 children. 2 large bedrooms with Kings size beds,...

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Key Largo vacation Condo

“ Excellent ”
January 9, 2015
Exelent!
Milos Krunic, Woodbridge, ON, Canada

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1 / 16

Key Largo Villa
3 Bedrooms / 3 Bathrooms / Sleeps 6

Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Villa
No rental rates available - please contact the owner
 
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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EXTERIOR OF HOUSE
1 / 9

Islamorada Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

“ Excellent ”4 Reviews

Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

This beautiful 4 bedroom/ 4 bathroom home has a 70' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs there are 2 bedrooms/ 2...

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Wonderful Month in Key Largo

“ Excellent ”
January 9, 2015
It had been several years since we've been in the Keys, and my family and I decided it would be nice to spend Christmas there this year. We rented this property for the month of December. It was absolutely fantastic. The outside space is wonderful; the pictures just don't fully convey how great this space is. Each morning I'd spend time on the deck in "tequilaville" having coffee and watching the manatees in the canal. It was so relaxing. The flowers are spectacular; and the lights at night in the garden and the fountain are breathtaking. The house itself is comfortable and perfect; it's decorated in a caribbean/keys style which is perfect.Deborah is a job to deal with. She kept me very informed as we went through the rental process. And, she personally met me at the property for check in and to give me the grand tour. It was fantastic.There are so many things in the area to take advantage of. There is a flea market/farmers market within short walking distance; Pennekamp state park is close by; and there are so many restaurants in the area.I can't recommend this property highly enough. If you're looking for the perfect Keys experience, this property is great!! I've been home for over a week now, and I already miss Key Largo.
steve weigler, Woodbridge, VA

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1  2  3  4  5 

Florida Keys Travel Tips

The Florida Keys are a wonderful vacation spot for families in search of a little relaxation or adventure. Made up of Key Largo, Islamorada, Marathon, Key West, and Big Pine Key and the lower keys, these islands have plenty of family-friendly activities. The best way to visit this beautiful area is by choosing to stay in vacation rentals by owner. Florida Keys tourists can choose from a variety of different sized properties designed to make your time in the Keys comfortable and memorable. For families visiting the Florida Keys, vacation rentals by owner offer the maximum amount of space and privacy for the price. Your entire family will love exploring the islands and coming home to a private, spacious home or condo.
Beaches and Parks
While staying in one of the area's beautiful vacation rentals, Florida Keys tourists can enjoy a leisurely day at one of the best parks in the nation. These are just a few of the Keys most popular destinations:
  • John Pennekamp Coral Reef State Park is the oldest underwater park in the world. Located in Key Largo, families can explore the 47 campsites located on 67,845 acres, split between land and underwater areas. Nature trails, beaches, kayak and canoe rentals, and glass-bottom boat tours are available.
  • Everglades National Park has many fun activities for families. Kids can become Junior Rangers or go on a wildlife hike.
  • Bahia Honda State Park is known for its beautiful beaches and crystal clear water. Visitors can book a snorkeling tour online and enjoy over an hour of snorkeling in the Looe Key National Marine Sanctuary, where swimmers will explore the gorgeous Elkhorn and Star coral.
Things to Do
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 Key West, 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.
Local History
While staying in one of the area's many vacation rentals, Florida Keys visitors may want to learn a little about the history of these breathtaking islands.
  • Ernest Hemingway Home and Museum is a must for literature enthusiasts. Located in Key West, this historical landmark was Hemingway's home from 1931 to 1939, and the place in which he penned some of his most-loved work.
  • The Florida Keys Eco-Discovery Center is sure to be a hit with the kids. Housing over 6,000 square-feet of interactive exhibits, this museum is a great way to introduce kids to underwater and wildlife ecosystems. And admission is free!
Sightseeing Tours are one of the best ways to learn about the islands. Glass-bottom boat rides, sunset tours, and dinner cruises are all available. Remember to reserve your spot online ahead of time to save on ticket prices.
Fun With Kids
While vacationing in the Florida Keys, rental homes leased by owner are a great choice for families with a few kids who need a little extra space. Florida Keys rental homes are a much better choice than hotels, because families will have a cozy home base to return to after a day of sightseeing. Some of the top activities for kids are:
  • The Key West Butterfly and Nature Conservatory was voted the #1 attraction in Key West by TripAdvisor and People's Choice Awards. Take a stroll through the conservatory, which houses between 50 and 60 species of plants, waterfalls, colorful birds, and of course--butterflies.
  • The Conch Tour Train is a fun way to see Key West with the kids. In operation since 1958, the 90-minute tour will take you through all of the island's most popular attractions.
  • Tropic Cinema has been named "Best Florida Cinema" by Florida Monthly magazine for four consecutive years. This landmark theater screens Hollywood blockbusters, documentaries, and foreign films.
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