Summerland Key Vacation Rentals

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Vacation Rentals in Summerland Key

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

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 Key.

Pet friendly

Hot Tub

WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification

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 Key.

Pool

Pet friendly

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

With a stay at this vacation home in Summerland Key (Cutthroat Harbor Estates), you'll be within a 10-minute drive of Florida Keys Beaches and Venture Key.

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

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 Key.

Pool

Hot Tub

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

With a stay at this vacation home in Summerland Key, you'll be near the beach, within a 10-minute drive of Florida Keys Beaches and Venture Key.

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

$350

per night

May 29 - May 30

With a stay at this vacation home in Summerland Key, you'll be on the beach, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.

One of the very few beach houses with a daily, rental license in the Keys.

With a stay at this vacation home in Summerland Key, you'll be on the beach, just a 4-minute walk from Florida Keys Beaches and within a 5-minute drive of Crab Key.

Pool

Pet friendly

Old Florida Style, wrap around porch, boat basin for dockage, open water

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.

Pet friendly

Outdoor Space

Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

With a stay at this vacation home in Summerland Key, you'll be by the ocean, within a 10-minute drive of Florida Keys Beaches and Venture Key.

Enjoy Caribbean weather. Last minute opening beginning 5/2/24! Enjoy the Keys!

With a stay at this vacation home in Summerland Key, you'll be within a 10-minute drive of Florida Keys Beaches and Venture Key.

Island Therapy

With a stay at this vacation home in Summerland Key, you'll be within a 10-minute drive of Florida Keys Beaches and Venture Key.

Cozy, Perfect Conch Cottage!

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 Venture Key.

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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.