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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (145 reviews)
"It is an excellent place."
United States
Arianna
The price is ￥23,582
￥30,983 total
includes taxes & fees
Sep 27 - Sep 28
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A building with a red door, a covered porch, and a bamboo plant in the foreground.

2. 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, (24 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is ￥22,284
￥70,944 total
includes taxes & fees
Sep 26 - Sep 27
Road's End | Prime Old Town Location! Updated Home w/ Pool
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (96 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is ￥20,417
￥62,438 total
includes taxes & fees
Sep 27 - Sep 28
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A wooden deck with lounge chairs, a pool, and a dock with boats.

4. Waterfront Tiny House w Pool, Beach, and Boat Dock

Waterfront Tiny House w Pool, Beach, and Boat Dock
Key Largo
9.6 out of 10, Exceptional, (70 reviews)
"We were really impressed with the house - it had all the little things that made the stay so comfortable - reclining chairs in the living room, A/C in every room, a great outside deck complete with a big TV and clean, clean, clean."
United States
Ann
The price is ￥15,669
￥49,955 total
includes taxes & fees
Sep 30 - Oct 1
Waterfront Tiny House w Pool, Beach, and Boat Dock
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is ￥23,582
￥66,315 total
includes taxes & fees
Sep 28 - Sep 29
SAVE BIG $$$ SEPT/OCT. 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 ￥16,808
￥57,447 total
includes taxes & fees
Sep 28 - Sep 29
Charming Home in Key Largo
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

7. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 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 ￥26,352
￥46,957 total
includes taxes & fees
Sep 27 - Sep 28
Poolside Cottage #411
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

8. 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 ￥34,819
￥84,220 total
includes taxes & fees
Oct 3 - Oct 4
Kelly's Kabin - Adorable Private Summerland Key Cottage
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

9. 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)
"Very nice villa "
United States
Grace L.
The price is ￥26,914
￥79,203 total
includes taxes & fees
Sep 28 - Sep 29
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

10. 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, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is ￥33,474
￥81,658 total
includes taxes & fees
Sep 27 - Sep 28
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A wooden pier with a thatched roof, leading to a rocky beach area with clear blue water. Directional signs indicate nearby locations.

11. 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 ￥39,568
￥99,631 total
includes taxes & fees
Oct 14 - Oct 15
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

12. 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 ￥24,928
￥72,460 total
includes taxes & fees
Sep 26 - Sep 27
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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, (72 reviews)
"Great unit and wonderful host. We will be back!"
United States
Lauren S.
The price is ￥44,702
￥125,111 total
includes taxes & fees
Sep 30 - Oct 1
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, (37 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is ￥29,280
￥50,093 total
includes taxes & fees
Oct 18 - Oct 19
Poolside Cottage #412
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.

15. 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 ￥55,236
￥114,548 total
includes taxes & fees
Oct 23 - Oct 24
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

16. 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 ￥33,237
￥79,908 total
includes taxes & fees
Sep 27 - Sep 28
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A bedroom with a wooden headboard, a bed with white bedding, a small round table, and a view of a swimming pool through a door.

17. 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 ￥29,486
￥58,772 total
includes taxes & fees
Sep 28 - Sep 29
4. Cozy Key Largo Waterfront Studio | Dive
An aerial view of a beach with clear turquoise waters, a sandy shore, and a cluster of umbrellas.

18. 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 ￥30,863
￥89,858 total
includes taxes & fees
Sep 28 - Sep 29
Luxury two floor apartment in prime location of famous Duval Street
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, (5 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is ￥33,237
￥82,757 total
includes taxes & fees
Sep 26 - Sep 27
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

20. Kawama G12 Upscale OceansideVilla with Marina 2/2

Kawama G12 Upscale OceansideVilla with Marina 2/2
Key Largo
10.0 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay, well stocked! Our host was not easy to get a hold of, but we would definitely stay again! "
United States
Brooke B.
The price is ￥37,391
￥80,754 total
includes taxes & fees
Sep 26 - Sep 27
Kawama G12 Upscale OceansideVilla with Marina 2/2
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

8/10 Good
"The Hampton Inn had a lot to offer their guests like kayak rentals, can go fishing from their dock. The pool is nice as well. The Tiki Bar theme was great, had a chance to meet other guests staying there while enjoying some drinks. Even though the hotel is undergoing some renovations the staff made sure the guests are taken care of and willing to help if a need arises. It is a hidden gem you should give it a try and stay for a bit. The breakfast every morning was very good, the staff in charge of setting it up, getting it all prepared does a very great job!"
Ronald 7-night trip
Posted 2 hours ago
Hampton Inn Key Largo Manatee Bay

Find out more about Florida Keys

Florida Keys Vacation Homes information

Number of reviews
770
Accommodation
1057 Vacation Homes
Lowest Price
￥30,983
Highest Price
￥125,111