Summerland Key Vacation Rentals
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Vacation Rentals in Summerland Key
Private Secluded Ocean View & Pool Near Key West
Summerland Key FL
With a stay at this vacation home in Summerland Key, you'll be by the sea, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Pool
Hot Tub
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key FL
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Pool
Kitchen
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
Little Torch Key FL
Located in Summerland Key, this vacation home is by the ocean, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea Market.
Kitchen
Washer
Tranquility Bayview House-Ocean Front with boat basin and boat ramp
Little Torch Key FL
With a stay at this vacation home in Summerland Key, you'll be within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea Market.
Kitchen
Washer
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Cudjoe Key FL
With a stay at this vacation home in Summerland Key, you'll be by the sea, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Pool
Kitchen
Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key FL
$792 nightly
The price is $880 total per night
$880 total
Dec 26 - Dec 27
Total with taxes and fees
Located in Summerland Key, this vacation home is by the ocean, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea Market.
Kitchen
Washer
Ocean View 4/2 Estate with Private Pool 15 minutes from Key West
Cudjoe Key FL
With a stay at this vacation home in Summerland Key, you'll be within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Pool
Hot Tub
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key FL
$554 nightly
The price is $616 total per night
$616 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
Pool
Hot Tub
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key FL
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Pool
Kitchen
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key FL
$885 nightly
The price is $982 total per night
$982 total
Dec 8 - Dec 9
Total with taxes and fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Pool
Hot Tub
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key FL
$860 nightly
The price is $954 total per night
$954 total
Dec 6 - Dec 7
Total with taxes and fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Pool
Hot Tub
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.
Summerland Key Vacation Rentals essential information
Accommodation | 388 Vacation Rentals |
|---|---|
Lowest Price | $616 |
Highest Price | $982 |
Popular accommodation | Private Secluded Ocean View & Pool Near Key West, Cudjoe Cottages, swimming pool, just 20 miles from Key West, OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS, Tranquility Bayview House-Ocean Front with boat basin and boat ramp, JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!, Old Florida Style, wrap around porch, boat basin for dockage, open water, Ocean View 4/2 Estate with Private Pool 15 minutes from Key West, NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!, Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West, Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly, Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool, Canal front home @ Venture Out Resort in the Florida Keys! |