
Find hotels in Summerland Key, FL from ¥34,287
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Our top choices for Summerland Key hotels

Atlantic View Luxury Villa with Pool
Atlantic View Luxury Villa with Poolcleanliness Unwind in the Florida Keys with a choice of 10 outdoor pools and a hot tub.

Sugar Loaf Lodge
Sugar Loaf Lodge
Parmer's Resort
Parmer's Resort
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning Views
The Laureate Key West
The Laureate Key Westcleanliness Enjoy serene poolside mornings at a coastal hideaway near Hemingway's estate.

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Fairfield by Marriott Inn & Suites Key West at The Keys Collectioncleanliness Peaceful Key West retreat with poolside bar and easy beach access.

Hampton Inn Key West FL
Hampton Inn Key West FLcleanliness Stay near Smathers Beach with poolside drinks and free breakfast in Key West.

Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collectioncleanliness Experience the best of Key West with a pool, hot tub, and quick drive to beaches.

DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West
Hyatt Vacation Club at Beach House, Key West
Hyatt Vacation Club at Beach House, Key Westcleanliness Serene oceanfront retreat in Key West with poolside lounge and tropical relaxation.

Ibis Bay Beach Resort
Ibis Bay Beach Resort
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfrontcleanliness Poolside paradise near Smathers Beach, with inviting hot tub and full-service bar.

Blue Flamingo Resort Key West
Blue Flamingo Resort Key Westcleanliness Experience island-style relaxation at a resort with 2 pools near Duval Street.

Barnacle Resort
Barnacle Resortcleanliness Wake up to serene beach views at this Key West B&B with a relaxing rooftop terrace.

Margaritaville Beach House Key West
Margaritaville Beach House Key Westcleanliness Coastal haven with pool retreat, steps from Smathers Beach in Key West.

Fairfield Inn and Suites by Marriott Key West
Fairfield Inn and Suites by Marriott Key Westcleanliness Serene escape just minutes from Duval Street with a peaceful pool oasis.

Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key Westcleanliness Unwind at this oceanfront Key West getaway with a pool and sunset views.

Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and Marinacleanliness Waterfront escape on Big Pine Key with a pool, marina, and scenic hiking trails.

Parrot Key Hotel & Villas
Parrot Key Hotel & Villascleanliness Soak in Key West's charm with four outdoor pools and kayaking adventures.
Where to stay in Summerland Key

Cutthroat Harbor Estates
Cutthroat Harbor Estates offers a tranquil slice of Florida Keys living with private boat docks and crystal-clear waters. This residential waterfront neighborhood provides an authentic escape from tourist crowds. Homes on stilts with weathered wood docks create a classic Keys atmosphere. The neighborhood's canals connect directly to the Gulf, making it perfect for fishing and boating enthusiasts. Gentle waves lap against private docks while tropical birds call at dawn. Nearby Venture Out Keys and Summerland Key provide dining options and additional sights.

Sugarloaf Shores
Sugarloaf Shores offers a tranquil escape on the Florida Keys waterfront. Private homes line peaceful canals where turquoise waters invite fishing, kayaking, and boating adventures. This residential haven sits away from tourist crowds yet provides easy access to stunning ocean views. The neighborhood's charm lies in its authentic Keys lifestyle with homes on stilts and tropical landscaping. Nearby Sugarloaf Beach and Lower Sugarloaf Sound provide perfect spots for swimming and snorkeling. Visitors appreciate the quiet streets for evening strolls and stargazing.
Cudjoe Gardens
Cudjoe Gardens offers a peaceful waterfront retreat in the Florida Keys. This quiet residential haven features canal-front properties with private docks for easy boat access. Travelers can enjoy fishing, wildlife watching, and stargazing from their vacation rentals. The neighborhood's tropical charm comes alive with pastel homes on stilts surrounded by palm trees and native plants. A rental car is essential for exploring nearby Summerland Key attractions and dining options. Water enthusiasts will appreciate direct canal access to open waters and nearby beaches.

Breezeswept Beach Estates
Escape to the peaceful shores of Breezeswept Beach Estates on Summerland Key. This residential haven offers private waterfront properties with boat docks and direct access to crystal-clear Florida waters. The neighborhood's charm lies in its quiet streets lined with pastel homes and tropical landscaping. Outdoor enthusiasts will love exploring nearby Newfound Harbor Keys by kayak or boat. Fish in the shallow waters, spot native birds, or simply relax under swaying palms. With minimal commercialization and abundant natural beauty, this peaceful retreat captures authentic Keys living without the tourist crowds.
Bay Point
Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.
Learn more about Summerland Key
Snorkel the vibrant coral reefs at Looe Key, where rangers can direct you to spots with fewer boats. Rent kayaks to explore the mangrove trails, then ask locals about their favorite seafood shacks serving fresh-caught Keys lobster.

More cheap stays in Summerland Key

Sugar Loaf Lodge
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