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Our top choices for Florida Keys vacation homes

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, (46 reviews)
"We absolutely loved it! "
United States
Emily B.
The price is ¥17,141
¥49,606 total
includes taxes & fees
May 19 - May 20
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

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)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
Kelly's Kabin - Adorable Private Summerland Key Cottage

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, (17 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is ¥31,310
¥72,099 total
includes taxes & fees
May 13 - May 14
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

4. Cozy Waterfront Apartment in Key Largo!

4. 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 ¥26,292
¥56,993 total
includes taxes & fees
May 3 - May 4
4. Cozy Waterfront Apartment in Key Largo!

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

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.4 out of 10, Exceptional, (93 reviews)
"Clean and cute tiny house. Simple and easy check in at campground, very nice staff there . "
United States
Tami B.
The price is ¥26,318
¥66,302 total
includes taxes & fees
May 5 - May 6
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Casa Largo

Casa Largo
Key Largo
9.2 out of 10, Wonderful, (133 reviews)
"The unit was clean and beautiful. The entire complex was very nice, too. We had everything needed to enjoy our stay."
United States
Rhonda D.
The price is ¥37,996
¥85,672 total
includes taxes & fees
May 3 - May 4
Casa Largo

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is ¥31,254
¥95,163 total
includes taxes & fees
May 14 - May 15
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is ¥39,008
¥88,121 total
includes taxes & fees
May 12 - May 13
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is ¥46,998
¥95,975 total
includes taxes & fees
May 5 - May 6
Paradise found

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (63 reviews)
"This was a beautiful property, great location and awesome amenities. We loved it and will highly recommend it! "
United States
Kim H.
The price is ¥40,105
¥65,700 total
includes taxes & fees
May 29 - May 30
Poolside Cottage #411

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (66 reviews)
"Nice location with 5 min walk to ocean view. "
United States
Trevor P.
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

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
10.0 out of 10, Exceptional, (12 reviews)
"Location, friendly neighbors, calming courtyard."
United States
Jim C.
The price is ¥36,522
¥91,210 total
includes taxes & fees
May 5 - May 6
Road's End | Prime Old Town Location! Updated Home w/ Pool

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (53 reviews)
"Had a great stay. Being so close to the lagoon we were able to launch the kayaks for our kids multiple times a day no problem. We saw tarpon, lobster, parrot fish and tons of other sea life right out the front door. And the pool was just as close. Also being on this side of the property it is a quick walk to the beach to watch the sunset. The unit seemed as if we were the first ones staying there after it had been renovated. Grew up in south Florida and had stopped coming back to visit but we...
United States
Jonathan D.
The price is ¥51,944
¥105,250 total
includes taxes & fees
May 4 - May 5
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (147 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is ¥49,058
¥102,324 total
includes taxes & fees
May 3 - May 4
Beautiful Kawama Townhouse

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

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (107 reviews)
"Janet and Jerry were excellent hosts and the property was perfect for our trip "
United States
Shayne H.
The price is ¥23,342
¥67,990 total
includes taxes & fees
May 5 - May 6
SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
10.0 out of 10, Exceptional, (21 reviews)
"Loved the quiet, well equipped, easy ride to all the activity in Key West. Enjoyed the French bakery and Italian restaurants within walking distance. Would most definitely return to this private townhouse....Thank you!"
United States
David M.
The price is ¥49,348
¥154,859 total
includes taxes & fees
May 14 - May 15
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

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
8.0 out of 10, Very Good, (10 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is ¥47,471
¥111,503 total
includes taxes & fees
May 4 - May 5
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Key Largo
9.6 out of 10, Exceptional, (137 reviews)
"My family and I had a great time. The place was very comfortable. Location was great and we enjoyed all the amenities. Great experience over all."
United States
Raul e.
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (166 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is ¥49,348
¥102,359 total
includes taxes & fees
May 8 - May 9
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from 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.
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Top Florida Keys Hotel Reviews

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Florida Keys Vacation Homes information

Number of reviews
1,320
Accommodation
983 Vacation Homes
Lowest Price
¥49,606
Highest Price
¥154,859