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 West
Pegasus International Hotel
Stay in the heart of Key West with stylish rooms, rooftop pool, and free breakfast!
The Lower Keys
Captains Quarters
Captain’s Quarters #415 — stylish 2-bedroom waterfront rental in the gated Venture Out community on Cudjoe Key, Florida Keys.
Key West
Southernmost Beach Resort
Southernmost Beach Resort & Guesthouses is an oceanfront Key West escape featuring multiple heated pools, beachfront dining, a full-service spa, and lush tropical gardens just steps from Duval Street.
Weddings Max
200
Meetings Max
200
Total Space
1476 sq ft
Largest Room
800 sq ft
Key West
Andrew's Inn & Garden Cottages
Charming tropical boutique inn in historic Key West with pool, breakfast, and happy hour.
Key West
Center Court Key West
Center Court Key West offers boutique vacation rentals in Old Town, featuring 9 private suites with heated pools, lush gardens, and a central location just steps from Duval Street.
Islamorada
Coral Bay Resort
Coral Bay Resort is a waterfront resort in Islamorada offering spacious accommodations, private balconies, a heated pool, and direct access to the bay. Ideal for relaxation and water activities.
Key West
Opal Key Resort & Marina
Opal Key Resort & Marina is a luxury waterfront resort in the heart of Old Town Key West, offering 178 elegant rooms, Lolita’s Coastal Cocina, a 37-slip marina, and a sparkling pool just steps from Mallory Square and Duval Street.
Weddings Max
200
Meetings Max
300
Total Space
6800 sq ft
Largest Room
3850 sq ft
Islamorada
Caloosa Cove Resort
Caloosa Cove Resort & Marina offers 30 oceanfront suites with kitchens, balconies, and ocean views.
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
Ella's Cottages
Bohemian Key West charm awaits at Ella’s Cottages—stylish, cozy, and full of island spirit.
Key West
Blue Flamingo Resort
Blue Flamingo Resort in Key West offers a reimagined getaway with tropical-style rooms, two lively pools with luxe cabanas, and poolside dining at Rum Row and Toasted Coconut.
Islamorada
Mitchell's Islamorada Villas
Mitchell’s Keys Villa is a secluded waterfront vacation rental in Islamorada, offering a private beach, marina, and boat ramp, ideal for fishing and relaxation.
Key West
Seascape Tropical Inn
Seascape Tropical Inn is an adults-only, Conch-style bed & breakfast just steps from Duval Street, offering tropical charm, a heated pool and spa, and a complimentary breakfast with Champagne mimosas.
Key West
Bluewater Key RV Resort
Bluewater Key RV Resort offers luxury RV sites with private tiki huts, lush landscaping, and waterfront access.
