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
Old Town Manor B&B
Old Town Manor is a historic Victorian bed and breakfast in the heart of Key West, offering 14 unique rooms, a lush tropical garden, and an organic continental breakfast, just steps from Duval Street.
Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages is a luxury waterfront retreat in the Florida Keys, offering premium RV sites, pet-friendly glamping options, and a variety of amenities including a heated pool, kayak and paddleboard rentals, and an on-site tiki bar.
Weatherstation Inn
The Weatherstation Inn is an adults-only, historic Key West bed & breakfast tucked away in the gated Truman Annex, offering charming, island-inspired rooms, a sunny terrace, outdoor pool, free continental breakfast, and easy walking access to Duval Street and Mallory Square.
Coral Bay Resort
Coral Bay Resort is a waterfront resort in Islamorada offering spacious accommodations, private balconies, a heated pool, and direct access to the bay. Ideal for relaxation and water activities.
Historic Key West Vacation Rentals
Historic Key West Vacation Rentals offers a curated selection of luxury vacation homes, cottages, and condos in the Key West Historic District.
Courtyard by Marriott Key Largo
Courtyard by Marriott Key Largo — comfortable Key Largo hotel with full-service marina, pool, fitness center and easy access to Florida Keys adventures.
La Pensione Inn
La Pensione Inn is an adults-only boutique guesthouse in Old Town Key West, featuring Victorian architecture, a pool, and complimentary breakfast.
Wicker Guesthouse
Wicker Guesthouse is a charming, adults-only boutique inn in the heart of Old Town Key West.
Island House
Island House Key West is a private, adults-only clothing-optional resort with a heated pool, sauna, gym, and 24/7 café/bar in Old Town.
Hawks Cay Resort
Hawks Cay Resort is a luxury resort on Duck Key offering five pools, a saltwater lagoon, a full-service marina, and a spa.
Artist House
Stay in a charming Victorian Key West inn with unique rooms, pool, and breakfast.
Silver Palms Inn
Silver Palms Inn is a chic, eco-certified boutique hotel in Old Town Key West, featuring lush tropical décor, an outdoor saltwater pool, complimentary breakfast, and bicycle rentals just steps from Duval Street.
Cheeca Lodge & Spa
Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering elegant rooms, a 9-hole golf course, multiple dining options, and a full-service spa. Ideal for couples and families seeking a tranquil Keys getaway.