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
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.
Meetings Max
675
Total Space
16000 sq ft
Largest Room
10000 sq ft
Islamorada
Mermaid's Bay Boutique Estate
Mermaid’s Bay is a secluded boutique estate in Islamorada, offering three private waterfront homes with resort-style amenities, ideal for group getaways
Key West
Marquesa Hotel
The Marquesa Hotel is a boutique adults-only retreat in Key West’s historic district, offering lush garden setting, three pools, and the award-winning Café Marquesa.
Marathon
Key Colony Beach Rental
KCB Motel offers vintage charm, just steps from a private sandy beach, with simple rooms and a laid-back atmosphere.
Islamorada
Freewheeler Vacations
Freewheeler Vacations is the Upper and Middle Keys’ largest and longest-running vacation rental company, offering everything from cozy condos to grand estates, backed by 30+ years of expert service.
Key Largo
Drift Hotel
Drift Hotel is a boutique waterfront retreat in Key Largo offering modern, eco-chic rooms with bay views, complimentary kayaks, paddleboards, and bicycles, plus a private dock and fire pit. Ideal for couples and small groups seeking a tranquil, adventure-filled escape.
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.
Key West
Aqua Lodges At Hurricane Hole Marina
Stay in unique dual stateroom houseboats with full kitchens, A/C, and waterfront views!
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.
Marathon
Terra Marine Park
55+ pet-friendly manufactured home community with 23 homes, laundry, fishing, and picnic spaces.
Key West
Lighthouse Hotel
Historic charm meets vibrant Key West life steps from Hemingway House and the iconic lighthouse.
Weddings Max
60
Meetings Max
60
The Lower Keys
Parmer's Resort
Parmer's Resort is a tranquil, waterfront retreat on Little Torch Key, offering a variety of accommodations, a 90-foot private beach, boat slips, and easy access to the natural beauty of the Florida Keys.
Marathon
Coco Plum Beach and Tennis Club
Charming family-friendly beachfront resort in Marathon featuring tennis, marina access, and relaxing coastal villas.
Marathon
La Casa Habana Vacation Rental
La Casa Habana — private waterfront vacation home on Grassy Key with pool, dock, and gulf views.
Key West
Atlantis House
Luxurious Key West stays with ocean views, private suites, and island charm.
