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Our top choices for Florida Keys vacation 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 ¥28,477
¥36,494 total
includes taxes & fees
Nov 18 - Nov 19
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

2. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is ¥22,465
¥66,102 total
includes taxes & fees
Nov 13 - Nov 14
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

3. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (38 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is ¥29,319
¥49,525 total
includes taxes & fees
Dec 1 - Dec 2
Poolside Cottage #412

4. 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 ¥24,710
¥68,786 total
includes taxes & fees
Nov 11 - Nov 12
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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

SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is ¥23,614
¥68,305 total
includes taxes & fees
Nov 11 - Nov 12
SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is ¥31,538
¥78,012 total
includes taxes & fees
Nov 21 - Nov 22
SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

7. 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)
"Excellent property and the communication with the hosts was excellent. Love that they offered complimentary pickup from the airport to the property too."
United States
Mike C.
The price is ¥23,511
¥66,816 total
includes taxes & fees
Nov 15 - Nov 16
Road's End | Prime Old Town Location! Updated Home w/ Pool

8. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (72 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is ¥29,319
¥49,525 total
includes taxes & fees
Dec 1 - Dec 2
Poolside Cottage #411

9. 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 ¥14,586
¥45,450 total
includes taxes & fees
Nov 10 - Nov 11
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

10. 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 ¥30,666
¥75,963 total
includes taxes & fees
Nov 14 - Nov 15
Kelly's Kabin - Adorable Private Summerland Key Cottage

11. 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 ¥29,953
¥75,161 total
includes taxes & fees
Nov 10 - Nov 11
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

12. 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 ¥29,121
¥74,066 total
includes taxes & fees
Nov 20 - Nov 21
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

13. 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 ¥29,203
¥74,157 total
includes taxes & fees
Nov 14 - Nov 15
Canal-Front Retreat with Dock, Pool & Open Ocean Views

14. 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 ¥29,953
¥75,161 total
includes taxes & fees
Nov 10 - Nov 11
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

15. 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 ¥17,401
¥55,631 total
includes taxes & fees
Nov 15 - Nov 16
Charming Home in Key Largo

16. 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 ¥28,455
¥73,318 total
includes taxes & fees
Nov 11 - Nov 12
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

17. 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 ¥28,455
¥73,318 total
includes taxes & fees
Nov 10 - Nov 11
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

18. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (24 reviews)
"Perfect rental, can’t say enough about it. The host was fantastic. Would definitely stay here again."
United States
Tammy C.
The price is ¥30,428
¥74,321 total
includes taxes & fees
Nov 18 - Nov 19
Tiny Villa, Big Ocean Views| Breathtaking Sunsets

19. 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 ¥32,198
¥75,151 total
includes taxes & fees
Nov 12 - Nov 13
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

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

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.6 out of 10, Exceptional, (59 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is ¥30,618
¥114,299 total
includes taxes & fees
Nov 11 - Nov 12
Sea Esta Suite | Located On Iconic Duval w/ Pool
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

Find out more about Florida Keys

Florida Keys Vacation Homes information

Number of reviews
682
Accommodation
1076 Vacation Homes
Lowest Price
¥36,494
Highest Price
¥114,299