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

Florida Keys Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 CA $184
CA $247 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $199
CA $637 total
includes taxes & fees
Sep 29 - Sep 30
Road's End | Prime Old Town Location! Updated Home w/ Pool
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

3. 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 CA $204
CA $582 total
includes taxes & fees
Oct 1 - Oct 2
Charming Home in Key Largo
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (97 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is CA $182
CA $576 total
includes taxes & fees
Sep 29 - Sep 30
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

5. 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 CA $280
CA $723 total
includes taxes & fees
Oct 3 - Oct 4
Kelly's Kabin - Adorable Private Summerland Key Cottage
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is CA $211
CA $611 total
includes taxes & fees
Sep 29 - Sep 30
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A wooden deck with lounge chairs, a pool, and a dock with boats.

7. 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 CA $143
CA $455 total
includes taxes & fees
Sep 30 - Oct 1
Waterfront Tiny House w Pool, Beach, and Boat Dock
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, (70 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 CA $258
CA $458 total
includes taxes & fees
Oct 10 - Oct 11
Poolside Cottage #411
A wooden deck with a railing, wicker chairs, and a view of greenery.

9. 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 CA $326
CA $883 total
includes taxes & fees
Oct 5 - Oct 6
Starlight Serenity - Hideaway w Stunning Views
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

10. 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 CA $255
CA $809 total
includes taxes & fees
Sep 29 - Sep 30
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

11. 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 CA $299
CA $738 total
includes taxes & fees
Sep 29 - Sep 30
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

12. 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 CA $240
CA $709 total
includes taxes & fees
Sep 29 - Sep 30
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

13. 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 CA $223
CA $645 total
includes taxes & fees
Sep 29 - Sep 30
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.

14. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very good, (21 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is CA $350
CA $723 total
includes taxes & fees
Sep 29 - Sep 30
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A wooden deck with a large tree, outdoor seating, and a marina in the background.

15. 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 CA $257
CA $457 total
includes taxes & fees
Oct 10 - Oct 11
Poolside Cottage #412
A modern kitchen with a built-in microwave, stove, and dishwasher.

16. 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 CA $223
CA $476 total
includes taxes & fees
Sep 29 - Sep 30
4. Cozy Key Largo Waterfront Studio | Dive
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.

17. 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 CA $267
CA $742 total
includes taxes & fees
Sep 29 - Sep 30
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

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 CA $276
CA $843 total
includes taxes & fees
Oct 13 - Oct 14
Luxury two floor apartment in prime location of famous Duval Street

19. 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 CA $297
CA $737 total
includes taxes & fees
Sep 29 - Sep 30
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A modern kitchen with a dishwasher, a dining area with a glass coffee table, and a ceiling fan.

20. Charming 3-bedroom house in Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
8.4 out of 10, Very good, (15 reviews)
"This place was perfect for our family. Just the right distance between Marathon and Key West. Would definitely recommend it to anyone looking for a place to stay"
United States
Robert C.
The price is CA $317
CA $885 total
includes taxes & fees
Sep 29 - Sep 30
Charming 3-bedroom house in Big Pine Key near Beach and Key West
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Florida Keys Hotel Reviews

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

10/10 Excellent
"Place was great!! Can’t wait to go back!!"
Cory 1-night trip
Posted 3 hours ago
Hampton Inn Key Largo Manatee Bay

Find out more about Florida Keys

Florida Keys Vacation Homes information

Number of reviews
819
Accommodation
1052 Vacation Homes
Lowest Price
CA $247
Highest Price
CA $885

Explore a world of travel with Expedia