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

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Our top choices for Florida Keys holiday homes

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, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is £170
includes taxes & fees
2 Dec - 3 Dec
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

2. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is £210
includes taxes & fees
9 Nov - 10 Nov
Poolside Cottage #412

3. SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is £310
includes taxes & fees
10 Nov - 11 Nov
SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

4. SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is £387
includes taxes & fees
29 Nov - 30 Nov
SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

5. Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (54 reviews)
"We had a nice stay"
United States
Kevin M.
The price is £236
includes taxes & fees
5 Nov - 6 Nov
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

6. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
9.0 out of 10, Wonderful, (2 reviews)
"This was a sweet little modular home that gave us a clean and comfortable place to stay… away from the tourist scene."
United States
Nora Kay F.
The price is £335
includes taxes & fees
5 Nov - 6 Nov
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

7. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (72 reviews)
"I loved having the pool right outside the door! It was extremely clean and perfectly located for our needs. I really enjoyed sitting outside in the evenings. I would absolutely stay here again and recommend it to others!"
United States
Cristy D.
The price is £234
includes taxes & fees
1 Dec - 2 Dec
Poolside Cottage #411

8. 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
9.6 out of 10, Exceptional, (28 reviews)
"Charming, clean accommodations in a conveniently located area of Key West for walking to sites and renting bicycles"
United States
BARBARA Y.
The price is £316
includes taxes & fees
15 Nov - 16 Nov
Road's End | Prime Old Town Location! Updated Home w/ Pool

9. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.6 out of 10, Excellent, (4 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is £317
includes taxes & fees
11 Nov - 12 Nov
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

10. Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.8 out of 10, Excellent, (3 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is £351
includes taxes & fees
9 Nov - 10 Nov
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

11. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is £290
includes taxes & fees
17 Nov - 18 Nov
Charming Home in Key Largo

12. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
9.6 out of 10, Exceptional, (7 reviews)
"Clean and excellent water access"
United States
Chris P.
The price is £348
includes taxes & fees
12 Nov - 13 Nov
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

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

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (129 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is £360
includes taxes & fees
5 Nov - 6 Nov
Kelly's Kabin - Adorable Private Summerland Key Cottage

14. 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, (18 reviews)
"Perfect location, great price."
United States
Suzanne T.
The price is £337
includes taxes & fees
9 Nov - 10 Nov
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

15. Canal-Front Retreat with Dock, Pool & Open Ocean Views

Canal-Front Retreat with Dock, Pool & Open Ocean Views
Cudjoe Key
9.0 out of 10, Wonderful, (13 reviews)
"This property is convenient to food and fun. It was very clean, comfortable and we felt safe to walk around the resort. We had a wonderful stay here."
United States
Catherine C.
The price is £362
includes taxes & fees
14 Nov - 15 Nov
Canal-Front Retreat with Dock, Pool & Open Ocean Views

16. Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is £361
includes taxes & fees
12 Nov - 13 Nov
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

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 £351
includes taxes & fees
9 Nov - 10 Nov
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

18. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
The price is £368
includes taxes & fees
13 Nov - 14 Nov
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

19. 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, (58 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is £538
includes taxes & fees
10 Nov - 11 Nov
Sea Esta Suite | Located On Iconic Duval w/ Pool

20. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (24 reviews)
"This was without a doubt one of the nicest places we have ever stayed! Our hostess was PHENOMENAL and went above and beyond to be sure we were comfortable and had everything we needed for our stay. Literally the best vacation we’ve had!!!’ I suggest this place to everyone!"
United States
Stephanie
The price is £341
includes taxes & fees
19 Nov - 20 Nov
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
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

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Florida Keys Holiday Homes information

Number of reviews
621
Accommodation
1013 Holiday Homes
Lowest Price
£170
Highest Price
£538