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 holiday homes

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)
"Will definitely stay here again "
United States
Jeannine R.
Relax by Florida Keys Beaches, just a 7-min drive away

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

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
"Great location. "
United States
Davian k.
The price is HK$1,555
HK$3,871 total
includes taxes & fees
25 Feb - 26 Feb
SAVE BIG $$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, (31 reviews)
"Great location. Very clean very nice, stay there again"
United States
Mark B.
The price is HK$1,491
HK$3,895 total
includes taxes & fees
23 Feb - 24 Feb
Charming Home in Key Largo

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 HK$2,150
HK$4,753 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, (125 reviews)
"We had a wonderful time host was responsive and the property was perfect for our needs"
United States
Mike C.
The price is HK$2,482
HK$4,761 total
includes taxes & fees
2 Mar - 3 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)
"Great location! Super quiet and relaxing area! "
United States
Devin H.
The price is HK$1,908
HK$4,107 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.
The price is HK$1,559
HK$4,725 total
includes taxes & fees
11 Mar - 12 Mar
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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 HK$2,040
HK$4,140 total
includes taxes & fees
25 Feb - 26 Feb
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Feb 3-10 $245 off the rates close beach full kitchen & patio

Feb 3-10 $245 off the rates close beach full kitchen & patio
Old Town Key West
9.6 out of 10, Exceptional, (243 reviews)
"Great locationPlace looked like picsGreat host"
United States
derek a.
The price is HK$2,259
HK$4,101 total
includes taxes & fees
11 Mar - 12 Mar
Feb 3-10 $245 off the rates close beach full kitchen & patio

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 HK$4,256
HK$8,939 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 HK$2,736
HK$5,287 total
includes taxes & fees
16 Feb - 17 Feb
Spanish Queen @Venture Out, Cudjoe Key

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 HK$2,139
HK$3,780 total
includes taxes & fees
22 Feb - 23 Feb
3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

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.
The price is HK$2,736
HK$4,892 total
includes taxes & fees
3 Mar - 4 Mar
Great Family Vacation Rental.

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is HK$4,199
HK$7,505 total
includes taxes & fees
12 Mar - 13 Mar
Starlight Serenity - Hideaway w Stunning Views

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 HK$2,915
HK$7,076 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 $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (83 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is HK$3,040
HK$5,721 total
includes taxes & fees
5 Mar - 6 Mar
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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 traveller
The price is HK$8,989
HK$16,685 total
includes taxes & fees
11 Mar - 12 Mar
Capmar House at Lunara Bay

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, (151 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 HK$2,931
HK$5,689 total
includes taxes & fees
22 Feb - 23 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, (122 reviews)
"Great location, close to everything family had a great time."
United States
rafael m.
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is HK$2,667
HK$6,081 total
includes taxes & fees
6 Mar - 7 Mar
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
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

Find out more about Florida Keys

Florida Keys Vacation Homes information

Number of reviews
1,290
Accommodation
972 Vacation Homes
Lowest Price
HK$3,871
Highest Price
HK$16,685

Explore a world of travel with Expedia