Search Holiday Homes in Florida Keys

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Florida Keys Holiday Homes

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

9.6 out of 10, Exceptional, (36)
"Beautiful place. Our stay was quiet and wonderful. Very clean and comfortable. "
The price is £207
includes taxes & fees
3 Sept - 4 Sept
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Snappers - King Room w/ Ocean View Wifi

The price is £77
includes taxes & fees
17 Aug - 18 Aug
Snappers - King Room w/ Ocean View Wifi

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"loved it!!"
The price is £298
includes taxes & fees
18 Aug - 19 Aug
Charming Home in Key Largo

Spec @107.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio

9.0 out of 10, Wonderful, (170)
"This was a great location and easy place to stay. We were able to walk to many locations in Old Town. The new updates are a nice addition to this location. Fresh paint, refrigerator, A/C and the patio is a great place to relax. "
Spec @107.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (73)
"The house is great, tidy little spot to start all your Keys adventures from!"
The price is £269
includes taxes & fees
20 Aug - 21 Aug
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (96)
"Good location, short drive to lots of activities. Had to leave a day early due to family crises, but had a great two nights there. Thanks!!"
The price is £329
includes taxes & fees
28 Aug - 29 Aug
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (81)
"Great location near Key West. Awesome property, will book again."
The price is £359
includes taxes & fees
20 Aug - 21 Aug
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is £442
includes taxes & fees
17 Aug - 18 Aug
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Poolside Cottage #411

9.8 out of 10, Exceptional, (51)
"Lovely home to stay in for a couple of nights on Key West"
The price is £231
includes taxes & fees
18 Aug - 19 Aug
Poolside Cottage #411

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (118)
"Clean property in a nice location."
The price is £393
includes taxes & fees
2 Sept - 3 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage

Villa 5053 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (44)
"We had a good stay. Nice place"
The price is £424
includes taxes & fees
17 Aug - 18 Aug
Villa 5053 on Duck Key BOAT SLIP available

Kingfish Keep | Lively Escape on Duval! Balcony!

10.0 out of 10, Exceptional, (17)
"Awesome location with excellent communication. "
The price is £276
includes taxes & fees
25 Aug - 26 Aug
Kingfish Keep | Lively Escape on Duval! Balcony!

Poolside Cottage #412

9.2 out of 10, Wonderful, (25)
"The property and our place was really nice. Would definitely stay again. "
The price is £231
includes taxes & fees
19 Aug - 20 Aug
Poolside Cottage #412

Paradise found

9.8 out of 10, Exceptional, (27)
"Clean, quiet and great location near Key West. "
Paradise found

Villa 5023 on Duck Key BOAT SLIP available

9.4 out of 10, Exceptional, (32)
"We had a few days on Duck key and were pleased with the property. The house was clean, no complaints. I didn’t see any pans for cooking, but overall the kitchen was functional. We were a bit short on bath towels, but we made it work. We would stay again. Thanks! "
The price is £417
includes taxes & fees
17 Aug - 18 Aug
Villa 5023 on Duck Key BOAT SLIP available

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (7)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is £469
includes taxes & fees
26 Aug - 27 Aug
Island Time #110 Ocean Views - Cudjoe Key

Sweet Caroline by Brightwild Pool Parking

2.0 star property
The price is £515
includes taxes & fees
25 Aug - 26 Aug
Sweet Caroline by Brightwild Pool Parking

Villa 5103 on Duck Key BOAT SLIP available

9.4 out of 10, Exceptional, (53)
"Our stay was great. The place had ampule room, a great view, the bath area had lots of towels that were a good quality. We enjoyed going to the "
The price is £424
includes taxes & fees
17 Aug - 18 Aug
Villa 5103 on Duck Key BOAT SLIP available

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

9.8 out of 10, Exceptional, (112)
"Very comfortable house in a great location. "
The price is £407
includes taxes & fees
18 Aug - 19 Aug
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Casa Largo

9.0 out of 10, Wonderful, (127)
"Victor’s place was as advertised. Great location, walk to water front restaurants and music. Lots for a family to do on the grounds.Thanks, Victor!"
The price is £416
includes taxes & fees
17 Aug - 18 Aug
Casa Largo
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Florida Keys Hotel Reviews