Search Vacation Homes in Florida Keys

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Florida Keys vacation homes

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (103 reviews)
"Great location. "
United States
Davian k.
The price is AED 1,355
AED 2,595 total
includes taxes & fees
8 Mar - 9 Mar
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (30 reviews)
"Great location. Very clean very nice, stay there again"
United States
Mark B.
The price is AED 830
AED 1,983 total
includes taxes & fees
12 Mar - 13 Mar
Charming Home in Key Largo

Relax by Florida Keys Beaches, just a 7-min drive away

Relax by Florida Keys Beaches, just a 7-min drive away
Cudjoe Key
9.8 out of 10, Exceptional, (201 reviews)
"The cottage was clean and the location was nice and quiet. "
United States
Jaconica B.
The price is AED 1,010
AED 2,430 total
includes taxes & fees
27 Feb - 28 Feb
Relax by Florida Keys Beaches, just a 7-min drive away

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (123 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is AED 1,010
AED 2,233 total
includes taxes & fees
1 Mar - 2 Mar
Kelly's Kabin - Adorable Private Summerland Key Cottage

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Key Largo
9.6 out of 10, Exceptional, (124 reviews)
"Great stay!! Location was perfect view of the canal and close to the pool. Unit was very clean and would definitely stay again!!"
United States
Brad T.
The price is AED 1,095
AED 2,201 total
includes taxes & fees
1 Mar - 2 Mar
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

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

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.6 out of 10, Exceptional, (88 reviews)
"It was a perfect getaway. Great location. "
United States
Anonymous traveler
The price is AED 932
AED 1,974 total
includes taxes & fees
2 Mar - 3 Mar
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Close to all & beach with your own full front porch ,full kitchen good rates

Close to all & beach with your own full front porch ,full kitchen good rates
Old Town Key West
9.6 out of 10, Exceptional, (242 reviews)
"Great locationPlace looked like picsGreat host"
United States
derek a.
Close to all & beach with your own full front porch ,full kitchen good rates

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
7.6 out of 10, Good, (13 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is AED 909
AED 1,868 total
includes taxes & fees
11 Feb - 12 Feb
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is AED 2,000
AED 4,204 total
includes taxes & fees
20 Feb - 21 Feb
Private and Exclusive Florida Keys Getaway

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is AED 1,286
AED 2,485 total
includes taxes & fees
16 Feb - 17 Feb
Spanish Queen @Venture Out, Cudjoe Key

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, (47 reviews)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is AED 1,098
AED 2,411 total
includes taxes & fees
11 Feb - 12 Feb
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Great Family Vacation Rental.

Great Family Vacation Rental.
Stock Island
8.8 out of 10, Excellent, (15 reviews)
"Enjoyed staying here super clean and well stocked!"
Canada
Kirsty E.
Great Family Vacation Rental.

Overlooking Saltwater Lagoon Free Kayaks Renovated

Overlooking Saltwater Lagoon Free Kayaks Renovated
Key Largo
9.6 out of 10, Exceptional, (46 reviews)
"Absolutely perfect trip. The house was clean and had everything we needed. Its a great location too!"
United Kingdom
Jill D.
The price is AED 1,370
AED 3,325 total
includes taxes & fees
11 Mar - 12 Mar
Overlooking Saltwater Lagoon Free Kayaks Renovated

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is AED 1,429
AED 2,689 total
includes taxes & fees
5 Mar - 6 Mar
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West
Stock Island
The price is AED 1,256
AED 2,073 total
includes taxes & fees
12 Mar - 13 Mar
3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveler
The price is AED 2,567
AED 5,679 total
includes taxes & fees
17 Feb - 18 Feb
Capmar House at Lunara Bay

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is AED 2,318
AED 3,835 total
includes taxes & fees
11 Mar - 12 Mar
Starlight Serenity - Hideaway w Stunning Views

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is AED 1,377
AED 2,674 total
includes taxes & fees
21 Feb - 22 Feb
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Stock Island
9.6 out of 10, Exceptional, (120 reviews)
"Great location, close to everything family had a great time."
United States
rafael m.
The price is AED 1,506
AED 2,840 total
includes taxes & fees
27 Feb - 28 Feb
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
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