Places to Stay
Claim your corner of The Florida Keys & Key West. Waterfront resorts, tucked-away inns, vacation rentals with a dock out back, campgrounds under the palms...however you like to unwind, there's a place here that gets it. Filter by destination, amenities or whatever matters most and find the spot that turns your trip from planned to perfect. Checkout is the only thing that should stress you out.
Filters
Islamorada
Topsider Resort
Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.
Key West
Ridley House
Bohemian luxury in a historic Key West mansion with pool and chef's breakfast.
Weddings Max
40
Meetings Max
40
Marathon
Coco Plum Vacation Rentals & Real Estate
Luxury Florida Keys vacation rentals with private pools, beach access, and endless ocean adventures await!
Key West
Ibis Bay Beach Resort
Ibis Bay Resort offers a fun, colorful Key West escape with a private beach, pool, and onsite restaurant. Perfect for families, couples, and adventure seekers.
Islamorada
Sun Outdoors Islamorada
Sun Outdoors Islamorada: island-style RV sites and oceanview vacation homes.
Islamorada
Ragged Edge Resort & Marina
Ragged Edge Resort & Marina is a charming, family-owned oceanfront retreat in Islamorada, offering a nostalgic "Old Keys" experience with modern comforts.
Key Largo
Bay Harbor Lodge & Coconut Bay Resort
Bay Harbor & Coconut Bay Resort offers a tranquil waterfront escape in Key Largo, featuring 23 charming cottages, a private beach, and lush tropical gardens.
Islamorada
Nest Villa at Holiday House
The Nest Villa in Islamorada is a private upper-level retreat with two bedrooms, panoramic Florida Bay views, and marina access with free dockage.
Key West
Courtney's Place Historic Cottages
Charming historic cottages in the heart of Old Key West, steps from Duval Street!
Marathon
Happy In The Keys
Luxury waterfront vacation rentals in Marathon & Key Colony Beach, FL. Private pools, docks, and dog-friendly accommodations. Sleeps 8–10.
Marathon
Edgewater Lodge
Edgewater Lodge is a waterfront retreat in Long Key, Florida, offering direct access to the water, an on-site boat ramp, and a private beach area. Ideal for boating enthusiasts and those seeking a tranquil escape.
Key West
Casa Del Sol, a Key West Vacation
Luxury 2-story townhome in Key West's premier Truman Annex, near Duval St.
Key West
Fairfield Inn & Suites by Marriott
Fairfield Inn & Suites Key West at The Keys Collection is a newly renovated, family-friendly hotel near the airport offering a heated outdoor pool, fitness center, and complimentary breakfast—perfect for convenient island getaways
