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
Long Key State Park
Long Key State Park offers kayaking, hiking, birdwatching, and tent camping along the Atlantic Ocean in the Florida Keys.
Key West
Coconut Mallory Resort & Marina
Coconut Mallory Marina + Resort is a laid-back, family-friendly retreat in Key West, offering studio, one-bedroom, and two-bedroom condos with full kitchens.
Key West
Cayo Hueso Resorts
Cayo Hueso Resorts offers tropically elegant vacation rentals in Old Town Key West. Choose from private 1–3 bedroom bungalows, cottages, and homes, just steps from Duval Street.
Islamorada
Mar-Key Islamorada
Mar‑Key Islamorada is an exclusive oceanfront private estate in the Florida Keys blending historic Old Florida charm with modern luxury.
Meetings Max
20
Key West
New Orleans House
New Orleans House is a gay male-only guesthouse on Duval Street in Key West, featuring a clothing-optional pool, rooftop sundeck, and complimentary happy hour.
Key Largo
Snappers Oceanfront Restaurant & Bar
Snappers Oceanfront Restaurant & Bar in Key Largo serves vibrant waterfront dining with a casual Tiki Bar, live music, dockside seating, boat dockage, and a “Keysy” island vibe.
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
Key West Hideaways
Key West Hideaways: premier Key West vacation rentals with full service.
The Lower Keys
Sugar Loaf Lodge
Sugarloaf Lodge is a waterfront retreat located at Mile Marker 17 on the Overseas Highway, offering 31 rooms with private patios or balconies overlooking the serene Lower Sugarloaf Sound.
Key Largo
Star Properties Destinations
Star Properties Destinations is a vacation rental and property management company in the Florida Keys, offering a variety of accommodations across Key Largo, Islamorada, Marathon, Tavernier, and the Lower Keys.
Key West
Smallest Bar Inn
The Smallest Bar Inn is an eclectic Duval Street lodging that’s home to Key West’s famously tiny 72 sq ft “Smallest Bar,” offering six cozy accommodation units steps from Old Town’s top attractions.
Key West
Courtney's Place Historic Cottages
Charming historic cottages in the heart of Old Key West, steps from Duval Street!
