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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, (146)
The price is AED 1,102
AED 2,327 total
includes taxes & fees
20 May - 21 May

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, (139)

Private Secluded Ocean View & Pool Near Key West
Private Secluded Ocean View & Pool Near Key West
8.4 out of 10, Very Good, (90)

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
10.0 out of 10, Exceptional, (1)

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, (73)

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 AED 1,980
AED 4,833 total
includes taxes & fees
21 May - 22 May

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, (109)
The price is AED 826
AED 1,973 total
includes taxes & fees
12 May - 13 May
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

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, (136)

Direct Oceanfront Cottage-Sunrise View- #2,
Direct Oceanfront Cottage-Sunrise View- #2,
8.6 out of 10, Excellent, (175)

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, (146)
The price is AED 1,102
AED 2,327 total
includes taxes & fees
20 May - 21 May
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

Looe Key Reef Resort
5/5 Excellent
"great vibe and friendly staff"
A verified traveler from miami stayed at Looe Key Reef Resort
Posted 2 days ago