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

1-50 of 229 Florida Keys Rentals

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Dolphin Jump Key, your island for day time-play time!
1 / 27

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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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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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$79

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$79 - $84
Per week:$549 - $584
Pets allowed:No
Internet:No

Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation rental is neat and clean with a 40' wood boat dock and fish cleaning area to clean all that great, fresh fish you're gonna catch. Easy ride under some bridges to Pine...

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Key West Florida Vacation Rentals - Townhouse
1 / 28

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Townhouse
Per night:$225 - $360
Per month:$6,750 - $10,800
Pets allowed:No
Internet:Yes

DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local galleries and artists. The theme is "Key West" from scenes around...

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Key West Get Away

“ Excellent ”
October 20, 2014
We could not have picked a better place to stay. Within walking distance to the beach and all locations down on Duval. Very clan location great for two couples. Look forward to booking this location again for next years trip.
Mike Moore, Germantown Ohio

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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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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$120

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$120 - $130
Per week:$840 - $910
Pets allowed:Yes
Internet:No

Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool or jump in your boat to go explore some of the best fishing and diving the Florida Keys has to offer. This home offers...

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Evening View
1 / 5

Big Pine Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 10

“ Excellent ”7 Reviews

from

$313

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:10
Type:Home
Per night:$313
Per week:$2,188
Pets allowed:Yes
Internet:Yes

This house is located in Long Beach Estates, one of the most private neighborhoods in the Keys. It is a private peninsula that is cushioned by a large beautiful wildlife preserve with deep water access within minutes to Looe Key. This is a spacious, waterfront home on open water,...

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Excellent week at a wonderful house!

“ Excellent ”
June 9, 2014
My husband and I took my daughter her husband and our 3 grandchildren for a week. The house was perfect for our size group. Huge kitchen and great room, 3 big bedrooms and the best part 3 bathrooms! We used our boat everyday, getting out of the canal is really easy and there is a boat ramp right around the corner from the house.The tiki hut out back is awesome. And of course the Key deer are one of our favorite things about Big Pine and they just wander around the neighborhood. My grandchildren thought that was the coolest thing.We had a blast and would definitely rent this house again.
Carlene Rozalsky, Grant, FL

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beach and dock
1 / 29

Long Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 9

“ Excellent ”6 Reviews

from

$243

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:9
Type:Home
Per night:$243 - $300
Per week:$1,700 - $2,100
Pets allowed:Yes
Internet:Yes

Huge Master Bedroom With View Of Beach And Large Balcony, Refrigerator And Microwave And Bar In 2nd Floor... Master Suite. Beautifull Sunrise Off You Private Balcony. First Floor Large Bedroom With Bath, Large Living Room, Dining Room, Sitting Area With Single Bed, Perfect...

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Family reunion

“ Excellent ”
August 4, 2014
We were a party of 7 and there was plenty of room for everyone. The house sets up beautifully for those wishing to take advantage of the view and use the patio. We brought our two dogs and with the gate in front we never felt they were in danger. Stayed from Saturday to Saturday which was the perfect amount of time. Plenty of good restaurants between Islamorada and Marathon which takes about 15 minutes to get to. Great charter fishing in Marathon ("Main Attraction"), both captain and mate were fantastic. Highly recommend this property if you really want to sit back, relax and enjoy The Keys the way they are meant to be.
Tom Gieseking, Orlando, Florida

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Enjoy Endless Sunshine & Breezes
1 / 12

Marathon Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$715

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$715
Per week:$5,000
Pets allowed:No
Internet:Yes

This luxurious executive home is located in the Heart of the Florida Keys on Yacht Harbor Island in Marathon. Come and enjoy the new private pool surrounded by paver decking and two tiki huts for plenty of shade. The 120' of deep water dockage is perfect for your boat, jet skis, ...

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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$84

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$84 - $94
Per week:$584 - $654
Pets allowed:Yes
Internet:Yes

Manatee Bay located in the Port Pine Height area is just the right spot to bring your family and friends for an unbelievable Keys vacation. Great gulf side boating is at your fingertips and just a short run out to the Atlantic side to fish and dive all the great reef spots. The...

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Cudjoe Key Florida Vacation Rentals - Home
1 / 8

Cudjoe Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$97

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$97 - $114
Per week:$677 - $794
Pets allowed:No
Internet:Yes

From the private balcony located off the master bedroom living area, to airy and vaulted ceilings, this Cape Cod style home promises all the comforts of home, and so much more! The 40' dock and yard is landscaped with native foliage and offers wandering pathways throughout....

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Little Torch Key Florida Vacation Rentals - Home
1 / 8

Little Torch Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$408

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$408 - $429
Per week:$2,850 - $3,000
Pets allowed:No
Internet:Yes

This Florida Style home was built in 1965 and wonderful surprises await you on the inside. The ground level house is painted in bright tropical colors to give you that that old island feel. This spacious 2, 000 square foot house has plenty of room to spread out. On one side are...

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Super Holiday

“ Excellent ”
December 30, 2014
Can't say enough good things about the stay. The house was even better than advertised.
warren compton, Frenchtown, NJ

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1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$175 - $324
Per month:$5,250 - $9,720
Pets allowed:Yes
Internet:Yes

CORAL GARDEN: A 2- bedroom 2. 5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to start...

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view from the apt
1 / 1

Key Largo Apartment
1 Bedroom / 1 Bathroom / Sleeps 4

from

$143

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$143
Per week:$999
Pets allowed:No
Internet:Yes

I have one week available at "ANCHORAGE RESORT AND YACHT CLUB" starting SUNDAY, Feb 15th, to SUNDAY Feb 22nd. Condo is on the 5th floor of a nice building overlooking Black Water Sound, facing West... You can sit on the large balcony and watch the beautiful sunsets or the boats...

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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$77

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$77 - $84
Per week:$537 - $584
Pets allowed:No
Internet:Yes

Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys. Fully fenced for privacy and lots of yard space ...

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Key West Florida Vacation Rentals - Apartment
1 / 8

Key West Apartment
Studio / 1 Bathroom / Sleeps 2

“ Excellent ”5 Reviews

from

$269

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$269 - $419
Per month:$8,070 - $12,570
Pets allowed:No
Internet:No

See if this unit is for you! RATE – BOOK – POLICY all in description. This override any other site rates. Last min. Specials for Ocean view studio for Jan. Mar. Apr. runtime may end soon! Jan to 31 $CALL FOR BEST LAST MINUTE SPECIAL WEEK RATE or Be 1st Jan weekly not ...

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Rooms with a View

“ Excellent ”
April 15, 2012
When we first entered the 2nd floor apartment ( via a spiral staircase- heavy luggage is a little tricky.) we were blown away by the view out of every window! ( And so many windows!) It is everything that it claimed to be and more!! We never tired of looking at the ocean, the pier and the activity all around. Holly was so helpful, even offering to pick up a few things for us at the grocery store, as she was going herself. The location was great for us, on the quieter side of the island. But nothing is too far away. We did a lot of walking, as we chose not to rent a car. We took cabs when we didn't want to walk and that worked out just great. We visited Duval Street frequently. We ate out most of the time, but there is an oven, microwave and full size refrigerator. We ordered in pizza one night and our "around the back" location was no problem for our deliveryman. The only unusual thing is arrangement of the bathroom. The toilet area and shower are seperate and there is no bathroom sink, you need to use the kitchen sink. But we were fine with that, and Holly mentioned it ahead of time so it wasn't a surprise to us. Our last day (we spent a week.) we decided to just stay at "home" and enjoy the ocean and pool next door. It was wonderful and relaxing. Holly had a list of things to do and see and restaurants that she recommended. They were outstanding. "Louie's Backyard" restaurant (a stone's tthrow away) was pricey but awesome. We were very happy with our selection of a place to stay in Key West. So much nicer than a hotel, in our opinion. Thanks for sharing your paradise with us Holly and Javier!
Molly Barth, Fort Thomas, KY USA

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Big Pine Key Florida Vacation Rentals - Home
1 / 8

Big Pine Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$187

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$187 - $197
Per week:$1,307 - $1,377
Pets allowed:Yes
Internet:Yes

Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts décor by an award winning Key West decorator. Includes fast access Internet for you to surf the internet quickly in addition to a large screen TV. Enjoy a swim in the new,...

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Island Wind
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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Cudjoe Key Florida Vacation Rentals - Home
1 / 8

Cudjoe Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$84

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$84 - $92
Per week:$584 - $642
Pets allowed:Yes
Internet:Yes

Everything about this wonderful 2 bed/2 bath home is exceptional. Located just 23 miles from Key West to explore all the great activities the southernmost city has to offer. The home is decorated in tropical island style with soothing colors by one of our famous local artists....

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Living Room with 42" SONY LED, BOSE surround sound and screened deck
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 8 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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Key Largo Florida Vacation Rentals - Home
1 / 16

Key Largo Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$107
Per week:$747
Pets allowed:Yes
Internet:Yes

This is a beautiful 2 bedroom / 2 full bathroom home for rent in Key Largo, Florida located within a gated community. You have a gorgeous ocean front property with beach access. If you have a boat this property is just for you, you have water access to anchor boat with water...

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Sugarloaf Key Florida Vacation Rentals - Home
1 / 8

Sugarloaf Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 14

from

$167

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:14
Type:Home
Per night:$167 - $184
Per week:$1,167 - $1,284
Pets allowed:No
Internet:Yes

You and your family will absolutely love Bow Channel Manor! Situated on a very private 4- acre parcel on Upper Sugarloaf Key, you, your family and your friends will create wonderful memories here. It's like having your own private resort! There are 3, separate homes on this...

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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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Cudjoe Key Florida Vacation Rentals - Home
1 / 8

Cudjoe Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 5

from

$74

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:5
Type:Home
Per night:$74 - $84
Per week:$514 - $584
Pets allowed:No
Internet:Yes

Come and enjoy the wonderful Florida Keys lifestyle at Tropical Bay. Located at mile marker 23, close to Key West and Marathon for great day trips around the islands. This spacious 3 bedroom, 2 bathroom ground level home is cozy and comfortable. Extra large screened porch overlooks...

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Key West Florida Vacation Rentals - Townhouse
1 / 21

Key West Townhouse
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Townhouse
Per night:$225 - $343
Per week:$1,575 - $2,400
Pets allowed:No
Internet:Yes

CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, ...

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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 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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Backside of Mar Azul
1 / 16

Marathon Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”12 Reviews

from

$350

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$350 - $408
Per week:$2,450 - $2,850
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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Cudjoe Key Florida Vacation Rentals - Home
1 / 6

Cudjoe Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$160

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$160
Per week:$1,120
Pets allowed:No
Internet:No

This beautiful, vacation home is tropical, bright and comfortable. You'll wish it was your own! Kitchen is fully equipped with all the luxuries of home (and more! ). Tiki Hut and hammock dockside, overlook a great deepwater boating and swimming canal and 50' seawall. Enjoy...

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1 / 8

Marathon Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$329

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$329
Per week:$2,300
Pets allowed:No
Internet:Yes

The Sombrero Pool Home A great Vacation spot! Pool, Spa, Dockage and only a 1/2 Mile from Sombrero Beach! This 3 bedroom, 3 bath home has a refreshing feel to it the moment you walk in the door. Full of color to make your vacation days start and end on a happy note. The ...

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Marathon pool home

“ Excellent ”
July 1, 2013
Beautiful home with a great location. Good ocean access. Inside of home was fairly well kept the only disappointment was the 3rd bedroom located on the bottom floor isolated from the rest of the home. The pool was great ...dock was perfect. All things considered it was a good vacation home!
susan atwell, Florida USA

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1 / 8

Cudjoe Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$150

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$150 - $160
Per week:$1,050 - $1,120
Pets allowed:No
Internet:No

Relax and enjoy this light and tropical, like- new vacation home with a private heated swimming pool. Step onto the large open porch and soak in the warm Island breezes while overlooking the sweeping canal views and pool. Concrete dock, shore power and fish cleaning station are ...

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Summerland Key Florida Vacation Rentals - Home
1 / 8

Summerland Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$184

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$184 - $200
Per week:$1,284 - $1,400
Pets allowed:Yes
Internet:No

This spacious, Caribbean- style vacation home comes equipped with its own private swimming pool and great deep- water canal. This beautiful home has three stories including a super play room off the pool area with a ping- pong table and a big screen TV for the kids. The 2nd floor...

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Summerland Key Florida Vacation Rentals - Home
1 / 8

Summerland Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$94

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$94 - $104
Per week:$654 - $724
Pets allowed:Yes
Internet:Yes

This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining areas for ...

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Key Largo Florida Vacation Rentals - Condo
1 / 16

Key Largo Condo
2 Bedrooms / 2 Bathrooms / Sleeps 5

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Condo
Per night:$97 - $110
Per week:$677 - $770
Pets allowed:No
Internet:Yes

As one of Buttonwood Bays highly sought after condo units this 2 bedroom 2 bathroom home will charm you and warm you! With easy elevator access you are located on the third floor with spectacular views overlooking the entrance to Buttonwood Bay's private coral rock harbor. Only...

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Penthouse
#1 of 2 pools with waterfall
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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Summerland Key Florida Vacation Rentals - Home
1 / 8

Summerland Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$230

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$230 - $240
Per week:$1,610 - $1,680
Pets allowed:Yes
Internet:No

Surrounded by lush, tropical landscaping, this gated open- water vacation home comes equipped will all the thoughtful touches of home and so much more. Choose the fantastic top floor master bedroom with Jacuzzi tub and sitting room or one of the other fantastic rooms! Enjoy...

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1 / 10
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Townhouse
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

Escape to Islamorada and enjoy this beautifully updated 2 bedroom / 2 bath townhouse located in Executive Bay Club a bay front property. This is a private gated community with 24 hour security. The property features 2 tennis courts, a full size pool with bay views, private beach,...

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Very Satisfied

“ Excellent ”
April 2, 2013
The property is in excellent condition. It was a pleasure staying at Executive Bay Club. We were fortunate to have good weather, the pool is very nice, as well as the beach and dock facilities . WE WILL BE BACK !
Fred Lipp, Highland Hts. Ohio

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Ocean View Elevated 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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Newly repainted 2013 Note: safety gate to restrict access to dock if needed.
1 / 30

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 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 is located adjacent...

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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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Marathon Florida Vacation Rentals - Home
1 / 15

Marathon Home
4 Bedrooms / 4 Bathrooms / Sleeps 10

“ Excellent ”5 Reviews

from

$470

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Home
Per night:$470
Per week:$3,290
Pets allowed:No
Internet:Yes

At Ocean Breezes, enjoy relaxing Atlantic breezes from either of the verandas at this spacious waterfront home. For your enjoyment there is a private pool and hot tub with gorgeous ocean views. Relax on the patio and watch the brilliant orange sunrise over the Atlantic. Splash in...

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Marathon Key

“ Excellent ”
December 6, 2014
Really need to provide beach towels, cushions for all the pool furniture and useable kitchen knives. Dull kitchen knives are more dangerous than sharp ones.
Nils Albert, Colorado

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Welcome to Paradise Rental Retreats new vacation home rental Villa Breeze!
1 / 28

Islamorada Home
4 Bedrooms / 3 Bathrooms / Sleeps 12

from

$550

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:12
Type:Home
Per night:$550 - $750
Per week:$3,850 - $5,250
Pets allowed:No
Internet:Yes

Great house in desirable Venetian Shores. This 4 bedroom/3 bath home is roomy and has great porches. Lovely master suite on the top floor with it's own balcony. Modern house with stylish, comfortable furnishings. 90 feet of excellent deep water dockage on a wide canal leading directly...

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Summerland Key Florida Vacation Rentals - Home
1 / 7

Summerland Key Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$187

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$187 - $197
Per week:$1,307 - $1,377
Pets allowed:No
Internet:No

Looking for that perfect vacation spot in the Keys? This is the one. Luxury waterfront accommodations await for the whole group. This stately home has all the best of everything. The large great room has lots of seating. 42” Flat screen Sony hi- def TV with surround sound makes...

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1 / 21

Key West Home
1 Bedroom / 1.5 Bathrooms / Sleeps 4

“ Excellent ”2 Reviews

from

$210

/ night

Email Owner
Bedrooms:1
Bathrooms:1.5
Sleeps:4
Type:Home
Per night:$210 - $342
Per month:$6,300 - $10,260
Pets allowed:No
Internet:Yes

TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back...

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A heart-warming and tranquil oasis

“ Excellent ”
August 1, 2013
We truly enjoyed our stay at Tranquility on Olivia Street. The neighbourhood is charming and very peaceful. There are many interesting restaurants to discover in the surroundings and many other services easily accessible at walking and biking distance. We enjoyed relaxing in the swimming pool at the end of the day and meeting many of the interesting folks renting other cottages at the Colony. I highly recommend Tranquility for its location, the peaceful neighbourhood, the physical setting at the Colony, and the charming interior decoration of the cottage. The colors are fresh, bright and full of joy. Our only recommendation would be to provide vacationers with a binder presenting essential information on things to do, to see and, especially, a list of surrounding service providers such as: grocery store, fish market, pharmacy, bike rental, local restaurants, and hospital in case of emergency. The sofa-bed mattress would need to be changed. It’s really not comfortable. And finally, the master bedroom air conditioner is quite noisy. Should we plan to visit the Keys in the near future, Tranquility would be our place to stay. What a great place to call home for a week on vacation. Thanks!
Paul Turpin, Key West, FL, USA

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Ramrod Key Florida Vacation Rentals - Home
1 / 8

Ramrod Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$100

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$100 - $117
Per week:$700 - $817
Pets allowed:Yes
Internet:Yes

The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile marker 27. Close to all the choice restaurants and services that the Florida Keys have to offer. This home is beautifully decorated in island style with attention...

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1 / 7

Key Largo Home
2 Bedrooms / 2 Bathrooms / Sleeps 10

from

$400

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:10
Type:Home
Per night:$400
Per week:$2,000
Pets allowed:No
Internet:Yes

Gorgeous views in this recently remodeled elegant home. Features 2/2 upstairs and 2/1 downstairs available for rent also. Swim, fish or go boating from your private dock and/beach. Once you visit you won't wan to leave. All the comforts of home are provided. Visit for a vacation...

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Views of Vaca Cut and the Gulf from the home
1 / 22

Marathon Villa
3 Bedrooms / 3 Bathrooms / Sleeps 7

from

$243

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:7
Type:Villa
Per night:$243 - $315
Per week:$1,700 - $2,200
Pets allowed:No
Internet:Yes

Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2, 000 square feet on 2 levels with under cover parking....

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2 bed & 2 bath Villas Pool & Atlantic Ocean Beach. Full Kitchen, Laundry Room
1 / 17

Marathon Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 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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5 night stay in marathon

“ Excellent ”
January 15, 2015
Very enjoyable; nicely refurbished older facility. The only real issue for us was that you must climb stairs to enter unit. This puts you on kitchen/dining level. You then climb internal circular stairs to reach bedrooms, bathrooms and living room. The second set of stairs are nearly impossible to make with a larger suitcase. We finally left ours on the first level.The beach area was very nice and the pool and hot tub were great after a long day. We would consider this again for the future.
ray rose, Tulsa, OK

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1 / 21

Key West Home
3 Bedrooms / 4 Bathrooms / Sleeps 8

from

$572

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
Per night:$572 - $1,029
Per week:$4,000 - $7,200
Pets allowed:No
Internet:Yes

EASY LIVIN' - - The name says it all! This lovely private home with pool is located in a secluded cul- de- sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. ...

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Little Torch Key Florida Vacation Rentals - Home
1 / 8

Little Torch Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$117

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$117 - $127
Per week:$817 - $887
Pets allowed:Yes
Internet:Yes

Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 people in this 3 bedroom, 2 bath, Little Torch Key home. Located down a private lane and overlooking the crystal blue waters of Pine Channel, gulf side. All the rooms are spacious...

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1 / 26

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$236

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Townhouse
Per night:$236 - $420
Per week:$1,650 - $2,940
Pets allowed:No
Internet:Yes

KEY WEST FOUND – A striking 2 bedroom, 2. 5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The first floor features...

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Wonderful

“ Excellent ”
October 16, 2014
Perfect location...reasonable rent
Judy Kolbe, Okauchee,Wi usa

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1 / 36

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”37 Reviews

from

$199

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$199 - $269
Per week:$1,393 - $1,883
Pets allowed:Yes
Internet:Yes

Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun- filled days pampered by our warm and friendly...

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Great Location

“ Excellent ”
January 20, 2015
This property was very clean and had everything we needed for our stay. The condo was 4 miles from the downtown area and duval street which was very convenient. The property was located in a nice area. I will definitely stay there again!!!
Alexandra Wilson, Stuart Florida

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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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