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
Key Largo
Gilbert's Resort
Gilbert’s Resort & Marina is a laid-back waterfront resort in Key Largo, featuring waterfront rooms, a private beach, and the Keys’ largest tiki bar with live music and dining.
Key West
Winslow's Bungalows
Discover Winslow’s Bungalows: a vibrant, historic Key West oasis with pools, charm, and local tales.
Weddings Max
40
Meetings Max
40
Key West
Vacation Homes of Key West
Vacation Homes of Key West is a locally owned boutique vacation rental company offering a curated collection of authentic island-style homes.
Key Largo
Baker's Cay Resort
Baker’s Cay Resort Key Largo — boutique waterfront resort with beach access, watersports, dining and family-friendly amenities in Key Largo, FL.
Meetings Max
400
Total Space
14706 sq ft
Largest Room
3522 sq ft
Key West
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.
The Lower Keys
Sugarloaf Key Hotel at KOA Resort
Tropical seaside stay with marina access and on-site dining.
Key Largo
Rock Reef Resort
Luxury beachfront escape with stunning views and top amenities awaits you!
Weddings Max
100
Meetings Max
100
Key Largo
Holiday Inn Key Largo
Holiday Inn Key Largo is a tropical hotel featuring two heated outdoor pools with a waterfall, a poolside Tiki bar, and an on-site marina.
Weddings Max
140
Meetings Max
140
Total Space
3070 sq ft
Largest Room
2400 sq ft
Key West
Island City House Hotel
Island City House Hotel blends historic charm with lush gardens, pool, and three unique guesthouse styles in Old Town Key West. Perfect for families, wedding groups, or history lovers.
The Lower Keys
Sunshine Key RV Resort & Marina
RV on the Go — mobile home & RV vacation rentals in the Florida Keys, offering turnkey setups where you arrive and relax without hauling your own trailer.
Key West
Seashell Motel & Key West Youth Hostel
Seashell Motel & Key West Hostel is a budget-friendly, centrally located lodging offering private rooms and dorms, free Wi-Fi, on-site bike rentals, and proximity to Duval Street.
Islamorada
Chesapeake Beach Resort
Escape to paradise at Chesapeake Beach Resort—luxury oceanfront stays in the Florida Keys.
Key West
Speakeasy Inn
The Speakeasy Inn is a historic adults-only guesthouse in Old Town Key West, offering tropical-themed suites, a wraparound porch, and a Rum Bar featuring over 350 rums.
Key West
Caribbean House Hotel
Caribbean House is a charming Bed & Breakfast located in historic Bahama Village, just two blocks from Duval Street.
