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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Florida Keys vacation 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, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is AED 621
AED 802 total
includes taxes & fees
15 Nov - 16 Nov
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (98 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is AED 547
AED 1,594 total
includes taxes & fees
21 Oct - 22 Oct
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A wooden deck with a large tree, outdoor seating, and a marina in the background.

3. 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 AED 612
AED 1,104 total
includes taxes & fees
18 Oct - 19 Oct
Poolside Cottage #412
A coastal area with clear water, a sandy beach, and a small island with buildings.

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

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.4 out of 10, Exceptional, (53 reviews)
"We had a nice stay"
United States
Kevin M.
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
The price is AED 584
AED 1,632 total
includes taxes & fees
19 Oct - 20 Oct
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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
10.0 out of 10, Exceptional, (41 reviews)
"Awesome house, convenient to everything we needed. Super clean and everything was pretty modern. I would definitely stay again and would definitely recommend this property"
United States
JOHN P.
The price is AED 397
AED 1,337 total
includes taxes & fees
19 Oct - 20 Oct
Charming Home in Key Largo
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

7. 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, (55 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is AED 711
AED 2,772 total
includes taxes & fees
29 Oct - 30 Oct
Sea Esta Suite | Located On Iconic Duval w/ Pool
Pool

8. 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 AED 579
AED 1,689 total
includes taxes & fees
2 Nov - 3 Nov
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

9. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 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 AED 612
AED 1,119 total
includes taxes & fees
18 Oct - 19 Oct
Poolside Cottage #411
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

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 AED 727
AED 1,856 total
includes taxes & fees
17 Oct - 18 Oct
Kelly's Kabin - Adorable Private Summerland Key Cottage
A wooden deck with a railing, wicker chairs, and a view of greenery.

11. 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 AED 1,107
AED 2,518 total
includes taxes & fees
27 Oct - 28 Oct
Starlight Serenity - Hideaway w Stunning Views
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

12. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (137 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is AED 777
AED 1,906 total
includes taxes & fees
18 Oct - 19 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A waterfront patio with a view of the sunset, a pool, and lounge chairs.

13. 4. Cozy Key Largo Waterfront Studio | Dive

4. Cozy Key Largo Waterfront Studio | Dive
Key Largo
9.8 out of 10, Exceptional, (13 reviews)
"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "
United States
Brittany M.
The price is AED 733
AED 1,426 total
includes taxes & fees
9 Nov - 10 Nov
4. Cozy Key Largo Waterfront Studio | Dive
A clear swimming pool with lounge chairs and palm trees.

14. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
Slice of Paradise
An aerial view of a resort with a large pool, palm trees, and a pier.

15. Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Really nice unit, well equipped, and quiet.Would stay again for sure."
United States
Tom A.
The price is AED 1,286
AED 2,548 total
includes taxes & fees
26 Oct - 27 Oct
Spanish Queen @Venture Out, Cudjoe Key
Pool

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, (4 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is AED 829
AED 1,986 total
includes taxes & fees
9 Nov - 10 Nov
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Pool

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 AED 771
AED 1,910 total
includes taxes & fees
18 Oct - 19 Oct
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

18. Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
9.6 out of 10, Exceptional, (17 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is AED 829
AED 1,997 total
includes taxes & fees
26 Oct - 27 Oct
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

19. 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 AED 829
AED 1,982 total
includes taxes & fees
17 Oct - 18 Oct
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

20. 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)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AED 733
AED 1,873 total
includes taxes & fees
21 Oct - 22 Oct
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great location"
Dianne 5-night trip
Posted 5 hours ago
Chesapeake Beach Resort