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
Fitch Lodge
Fitch Lodge: Your cozy, bohemian Key West basecamp steps from the Historic Seaport.
Islamorada
Amara Cay Resort
Escape to Amara Cay Resort for luxe island vibes, ocean views, and pure relaxation.
Meetings Max
65
Total Space
575 sq ft
Largest Room
575 sq ft
Islamorada
Osprey Bay Villa
Osprey Bay Villa is a luxurious 5-bedroom, 3-bathroom bayfront home in Islamorada, offering a private pool, hot tub, deep-water dock, and breathtaking sunset views, accommodating up to 10 guests.
Key West
Azul Key West
Historic Azul Key West offers a serene, romantic oasis just steps from vibrant downtown.
Key West
Ridley House
Bohemian luxury in a historic Key West mansion with pool and chef's breakfast.
Weddings Max
40
Meetings Max
40
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.
Key West
Island Time Hospitality Vacation Rentals
Premier short-term vacation homes and waterfront escapes in Key West and the Florida Keys with pool, beach access, pet-friendly stays, and local water activities.
Islamorada
Island Bay Resort
Island Bay Resort is an adults-only boutique escape with tropical cottages, a private beach, and free kayaks & SUPs.
Marathon
Blackfin Resort & Marina
Escape to Blackfin Resort & Marina in the Florida Keys—relax, fish, boat, and enjoy stunning sunsets!
Key West
Pier House Resort & Spa
Pier House Resort & Spa is a historic oceanfront retreat in Old Town Key West, featuring a private white sand beach, full-service spa, three dining venues, and the iconic Chart Room Bar
Weddings Max
120
Meetings Max
120
Total Space
2600 sq ft
Largest Room
2000 sq ft
Key Largo
John Pennekamp Coral Reef State Park
Discover Pennekamp Park: Nature, adventure, and fun await you!
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
The Lower Keys
Sugarloaf Key Hotel at KOA Resort
Tropical seaside stay with marina access and on-site dining.
Key West
Palms Hotel
The Palms Hotel – A charming historic guesthouse in Key West’s Old Town offering affordable boutique accommodations steps from Duval Street.
