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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Florida Keys vacation homes

Outdoor pool, pool umbrellas, sun loungers

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, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is AED 724
AED 918 total
includes taxes & fees
1 Jul - 2 Jul
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Beach

Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras

Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras
Old Town Key West
9.6 out of 10, Exceptional, (251 reviews)
"Loved our stay here!"
United States
Kristin E.
Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras
Shower, hair dryer, towels, soap

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"The condo is extremely clean and has everything you need for your stay. "
United States
hillary w.
The price is AED 529
AED 1,493 total
includes taxes & fees
30 Jun - 1 Jul
Charming Home in Key Largo
Exterior detail

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is AED 843
AED 2,349 total
includes taxes & fees
29 Jun - 30 Jun
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
On the beach

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (49 reviews)
"We had a great time. Loved the kayaks!!"
United States
Laurie S.
The price is AED 375
AED 1,265 total
includes taxes & fees
24 Jun - 25 Jun
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Dining

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (71 reviews)
"Host was very responsive, location safe and wuiet."
United States
Tracey C.
The price is AED 1,411
AED 3,320 total
includes taxes & fees
21 Jul - 22 Jul
Sunrise Escape - Ocean Front Villa - Sleeps 10
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
The price is AED 826
AED 1,960 total
includes taxes & fees
12 Jul - 13 Jul
Kelly's Kabin - Adorable Private Summerland Key Cottage
Terrace/patio

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, (16 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is AED 607
AED 1,779 total
includes taxes & fees
24 Jul - 25 Jul
Road's End | Prime Old Town Location! Updated Home w/ Pool
Outdoor dining

Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (31 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is AED 874
AED 1,459 total
includes taxes & fees
10 Jul - 11 Jul
Poolside Cottage #412
Property grounds

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, (53 reviews)
"Very nice villa "
United States
Grace L.
The price is AED 904
AED 2,182 total
includes taxes & fees
24 Jun - 25 Jun
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Miscellaneous

Cozy Waterfront Apartment in Key Largo!

Cozy Waterfront Apartment in Key Largo!
Key Largo
9.8 out of 10, Exceptional, (12 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 687
AED 1,416 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Waterfront Apartment in Key Largo!
Property grounds

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, (159 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is AED 992
AED 2,188 total
includes taxes & fees
28 Jun - 29 Jun
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Outdoor dining

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (66 reviews)
"We had a wonderful stay. The house was very clean, the area was quiet and peaceful, and the pool was incredibly relaxing. We enjoyed it so much that we have already booked another stay."
United States
Tiara B.
The price is AED 874
AED 1,459 total
includes taxes & fees
10 Jul - 11 Jul
Poolside Cottage #411
Exterior

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

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (91 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is AED 841
AED 1,965 total
includes taxes & fees
26 Jun - 27 Jun
SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
TV

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, (15 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is AED 974
AED 2,267 total
includes taxes & fees
24 Jun - 25 Jun
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor pool, a heated pool

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
7.8 out of 10, Good, (20 reviews)
"Everything was perfect location house amenities Really enjoyed our time there"
United States
Matt S.
The price is AED 770
AED 1,715 total
includes taxes & fees
6 Jul - 7 Jul
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A heated pool

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, (10 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 694
AED 2,184 total
includes taxes & fees
24 Jun - 25 Jun
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Exterior

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (108 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
The price is AED 841
AED 1,965 total
includes taxes & fees
28 Jun - 29 Jun
SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Smart TV, DVD player, books, printers

Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (28 reviews)
"Left to go to key west decided to stay here on our drive back up because we enjoyed it so much!"
United States
Regan C.
The price is AED 992
AED 2,406 total
includes taxes & fees
24 Jun - 25 Jun
Charming 3-bedroom house featuring a heated private pool.
Pool

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is AED 1,062
AED 2,197 total
includes taxes & fees
24 Jun - 25 Jun
Paradise found
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

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"The best hotel in key largo everything is good excellent"
johana 1-night trip
Posted 3 hours ago
Playa Largo Resort & Spa, Autograph Collection

Explore a world of travel with Expedia