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.

Key Largo

Waterside Suites & Marina

Waterside Suites & Marina offers spacious, two-floor townhouse-style suites with full kitchenettes and waterfront balconies on a tranquil marina—perfect for extended stays, family getaways, or fishing enthusiasts.

Islamorada

Chesapeake Beach Resort

Escape to paradise at Chesapeake Beach Resort—luxury oceanfront stays in the Florida Keys.

Marathon

Safe Harbor Marathon

Experience the ultimate Florida Keys marina with luxury amenities and stunning views.

Key West

Grand Guesthouse

The Grand Guesthouse is an adults-only bed and breakfast in Key West, offering tropical-themed rooms with private entrances, complimentary continental breakfast, and a central location near Duval Street.

Marathon

Gulf View Waterfront

Gulf View Waterfront Resort offers a laid-back, Old Florida experience with spacious rooms featuring kitchenettes, an oceanfront pool, complimentary kayaks and paddleboards, and pet-friendly accommodations.

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

Conch House Heritage Inn

The Conch House Heritage Inn is a historic adult-only bed and breakfast located in Old Town Key West. Guests enjoy elegant accommodations, a pool, daily breakfast with mimosas, and a prime location just steps from Duval Street.

Key West

Alexander's Guesthouse

Charming adult-only Key West retreat with pool, jacuzzi, and vibrant vibes.

Key West

Pegasus International Hotel

Stay in the heart of Key West with stylish rooms, rooftop pool, and free breakfast!

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.