A beach with palm trees, people relaxing on chairs, and colorful kayaks.

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Florida Keys holiday homes

A resort with a pool, lounge chairs, and a view of the ocean.

1. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (144 reviews)
"Amazing stay "
United States
Anthony
The price is £125
includes taxes & fees
8 Sept - 9 Sept
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A waterfront property with a covered porch, a boat dock, and a clear sky.

2. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (111 reviews)
"$125.00 extra charge when arriving. Almost all the remotes needed batteries. Furniture was all shoved up against walls, everything needed to be set back up. Kayaks were under house buried under a massive amount of junk and covered with sand and debris. A/C worked on and off. A/c window unit drain poured water on steps down to sea wall making them very slippery all the time. May have been a very nice place years ago but really shows its age and poor maintenance. Did not feel like calling the...
United States
Ken
The price is £298
includes taxes & fees
8 Sept - 9 Sept
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

3. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (128 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
The price is £378
includes taxes & fees
2 Sept - 3 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage
A modern living room with a white sofa, a coffee table, and a TV. There are large windows with blinds, a ceiling fan, and a view of the outdoors.

4. Waterfront Tiny Home Pool Dock Kayaks Paddleboards

Waterfront Tiny Home Pool Dock Kayaks Paddleboards
Key Largo
9.6 out of 10, Exceptional, (131 reviews)
"We appreciated having our boat docked behind the house. The campground was well maintained."
United States
Barbara A K.
The price is £275
includes taxes & fees
15 Sept - 16 Sept
Waterfront Tiny Home Pool Dock Kayaks Paddleboards
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

5. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 reviews)
"We stayed here for our honeymoon and it was perfect. The place was clean and well appointed. The pool right outside was huge and we spent lots of time there. Highly recommend!"
United States
DeAnna Z.
The price is £222
includes taxes & fees
3 Sept - 4 Sept
Poolside Cottage #411
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

6. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (40 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is £269
includes taxes & fees
2 Sept - 3 Sept
Charming Home in Key Largo
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

7. SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is £317
includes taxes & fees
7 Sept - 8 Sept
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A wooden pier with a thatched roof, leading to a rocky beach area with clear blue water. Directional signs indicate nearby locations.

8. FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (67 reviews)
"The pool was clean and enjoying "
United States
Aaron G.
The price is £373
includes taxes & fees
25 Sept - 26 Sept
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A building with a red door, a covered porch, and a bamboo plant in the foreground.

9. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (23 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is £337
includes taxes & fees
2 Sept - 3 Sept
Road's End | Prime Old Town Location! Updated Home w/ Pool
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

10. Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (55 reviews)
"We loved our stay here! The home was exactly as listed in the photos. The home was clean, the beds were comfy and the view was beautiful! Frank was excellent at communicating with us whenever we had a question. I would recommend and def would stay again."
United States
Angie M.
The price is £390
includes taxes & fees
3 Sept - 4 Sept
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

11. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (71 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is £544
includes taxes & fees
2 Sept - 3 Sept
Sunrise Escape - Ocean Front Villa - Sleeps 10
A wooden deck with a hanging hammock and a view of a green landscape.

12. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is £430
includes taxes & fees
15 Sept - 16 Sept
Starlight Serenity - Hideaway w Stunning Views
An aerial view of a beach with clear turquoise waters, a sandy shore, and a cluster of umbrellas.

13. Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (103 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is £441
includes taxes & fees
2 Sept - 3 Sept
Luxury two floor apartment in prime location of famous Duval Street

14. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (11 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is £459
includes taxes & fees
7 Sept - 8 Sept
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

15. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is £430
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

16. Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (53 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is £532
includes taxes & fees
6 Sept - 7 Sept
Sea Esta Suite | Located On Iconic Duval w/ Pool
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

17. Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3
Key Largo
9.4 out of 10, Exceptional, (230 reviews)
"Love the place , only problem with out a gulf car the beach and fishing area is too far away"
United States
Dayanis
The price is £423
includes taxes & fees
2 Sept - 3 Sept
Key Largo Kawama Villa L1, 3/3
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

18. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.4 out of 10, Exceptional, (17 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is £450
includes taxes & fees
2 Sept - 3 Sept
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

19. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.6 out of 10, Exceptional, (4 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is £459
includes taxes & fees
2 Sept - 3 Sept
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A marina with boats docked, a wooden dock, and a building with a covered area.

20. Waterfront Retreat

Waterfront Retreat
Duck Key
10.0 out of 10, Exceptional, (37 reviews)
"Really enjoyed our stay at Casa Wahoo! Very clean! Beautiful community."
United States
Joseph C.
The price is £374
includes taxes & fees
10 Sept - 11 Sept
Waterfront Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Florida Keys Hotel Reviews

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

8/10 Good
"Loved the overall Resort! The beach thenchair"
Julie Marie 4-night trip
Posted 3 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Find out more about Florida Keys

Florida Keys Holiday Homes information

Number of reviews
1,241
Accommodation
1049 Holiday Homes
Lowest Price
£125
Highest Price
£544