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

Holiday Homes in Florida Keys

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 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, (143 reviews)
"Amazing stay "
United States
Anthony
The price is €159
includes taxes & fees
2 Sept - 3 Sept
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A kitchen with a refrigerator, stove, and two bar stools.

2. Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!

Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
The price is €250
includes taxes & fees
31 Aug - 1 Sept
Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
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 €442
includes taxes & fees
31 Aug - 1 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage
A building with a red door, a covered porch, and a bamboo plant in the foreground.

4. 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 €407
includes taxes & fees
31 Aug - 1 Sept
Road's End | Prime Old Town Location! Updated Home w/ Pool
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (110 reviews)
"Stay was great. We met the hosts and they were wonderful people."
United States
James B.
The price is €346
includes taxes & fees
31 Aug - 1 Sept
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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.

6. 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.
Waterfront Tiny Home Pool Dock Kayaks Paddleboards
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

7. 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 €413
includes taxes & fees
31 Aug - 1 Sept
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

8. 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 €260
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.

9. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (40 reviews)
The price is €351
includes taxes & fees
31 Aug - 1 Sept
Charming Home in Key Largo
A wooden deck with a hanging hammock and a view of a green landscape.

10. 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 €525
includes taxes & fees
15 Sept - 16 Sept
Starlight Serenity - Hideaway w Stunning Views
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

11. 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 €507
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A wooden pier with a thatched roof, leading to a rocky beach area with clear blue water. Directional signs indicate nearby locations.

12. 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 €437
includes taxes & fees
25 Sept - 26 Sept
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
A modern kitchen with a large island, wooden ceiling, and a view of the pool.

13. 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.
Sunrise Escape - Ocean Front Villa - Sleeps 10
A wooden deck with a large tree, outdoor seating, and a marina in the background.

14. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (36 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is €260
includes taxes & fees
1 Sept - 2 Sept
Poolside Cottage #412
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is €368
includes taxes & fees
31 Aug - 1 Sept
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A living room with a sofa, two armchairs, a coffee table, and a ceiling fan. There is a large window with a view of the beach and a patio area with outdoor furniture.

16. Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.0 out of 10, Wonderful, (16 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is €449
includes taxes & fees
31 Aug - 1 Sept
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

17. 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 €532
includes taxes & fees
31 Aug - 1 Sept
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A beach setting with white chairs arranged around a fire pit, a thatched-roof structure, and a view of the ocean.

18. 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 €479
includes taxes & fees
31 Aug - 1 Sept
Key Largo Kawama Villa L1, 3/3
A beach with white Adirondack chairs, a clear pool, and a building with blue and white exterior walls.

19. NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (62 reviews)
"Especially enjoyed the private lagoon."
United States
Tom W.
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
An aerial view of a beach with clear turquoise waters, a sandy shore, and a cluster of umbrellas.

20. 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 €510
includes taxes & fees
31 Aug - 1 Sept
Luxury two floor apartment in prime location of famous Duval Street
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

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

10/10 Excellent
"Beach, tiki bar and pool area were a tropical paradise. Breakfast was better than some other Hampton Inns where I have stayed."
Robin 4-night trip
Posted 4 hours ago
Hampton Inn Key Largo Manatee Bay

Find out more about Florida Keys

Florida Keys Holiday Homes information

Number of reviews
1,331
Accommodation
1049 Holiday Homes
Lowest Price
€159
Highest Price
€532