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.

Marathon

Key By The Sea

Pet-friendly RV/mobile-home community with canal dock access, clubhouse, bathhouse, and oceanfront pavilion.

Marathon

Grassy Flats Resort & Beach Club

Eco-friendly boutique resort in the Florida Keys with oceanfront dining, water sports, and unique "olde Florida" charm.

Key West

Beachside Resort

Spacious Key West condos with private beach, marina, dining, and island adventures.

Weddings Max

600

Meetings Max

1075

Total Space

11500 sq ft

Largest Room

5675 sq ft

Key West

The Capitana Key West

The Capitana Key West is a boutique waterfront hotel offering coastal-chic accommodations, a heated pool with a tiki bar, private beach access, and pet-friendly cottages.

Key West

Heron House

Heron House Hotels offers two charming, adults-only properties—Heron House and Heron House Court—featuring lush gardens, an outdoor pool, rooftop sundeck, and complimentary continental breakfast.

Key West

The Bishop Key West

The Bishop Hotel in Key West offers a boutique guesthouse experience across five historic Conch-style properties, blending Old Town charm with modern comfort.

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.

Islamorada

Fisher Inn Resort and Marina

Fisher Inn Resort & Marina is an oceanfront boutique resort in Islamorada offering stylish rooms with kitchenettes, a heated pool with ocean views, and unique amenities like its own boat ramp and marina. Ideal for anglers, boaters, and families seeking waterfront comfort.

Key West

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.