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Compare 357 Vacation Homes in Summerland Key with updated reviews, rates, and availability.

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
8.8 out of 10, Excellent, (144)
The price is SAR 1,126
SAR 2,352 total
includes taxes & fees
25 Apr - 26 Apr

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key West
8.8 out of 10, Excellent, (137)
The price is SAR 1,032
SAR 2,261 total
includes taxes & fees
20 Apr - 21 Apr

Private Secluded Ocean View & Pool Near Key West
Private Secluded Ocean View & Pool Near Key West
8.4 out of 10, Very Good, (88)

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, (32)

Old Florida Style, wrap around porch, boat basin for dockage, open water
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.6 out of 10, Exceptional, (72)

One of the very few beach houses with a daily, rental license in the Keys.
One of the very few beach houses with a daily, rental license in the Keys.
8.8 out of 10, Excellent, (59)
The price is SAR 2,249
SAR 5,223 total
includes taxes & fees
22 Apr - 23 Apr

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very Good, (105)
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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Other property types in Summerland Key

Direct Oceanfront Cottage-Sunrise View- #2,
Direct Oceanfront Cottage-Sunrise View- #2,
8.6 out of 10, Excellent, (174)
The price is SAR 845
SAR 1,549 total
includes taxes & fees
21 Apr - 22 Apr

Cottage with Pool and Boat Dockage just minutes to Key West!
Cottage with Pool and Boat Dockage just minutes to Key West!
8.6 out of 10, Excellent, (133)

Cottage with Pool and Dockage, just minutes to Key West
Cottage with Pool and Dockage, just minutes to Key West
9.2 out of 10, Wonderful, (136)
The price is SAR 657
SAR 1,297 total
includes taxes & fees
17 Apr - 18 Apr
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.
Recent reviews of Summerland Key hotels
Recent reviews of Summerland Key hotels

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
5/5 Excellent
Exactly what we wanted for a Florida Keys vacation
"We truly enjoyed our 5 day stay at this rental. The pool on site was super clean and warm. Our granddaughter loved it! We especially enjoyed riding their bikes around the neighborhood. We met many nice neighbors who gave us great tips on beaches, restaurants and other things to do in the area. Highly recommend this as the perfect Keys getaway!"
A verified traveler stayed at Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Posted 2 days ago