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
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
Marathon
Captain Pip's Marina & Hideaway
Captain Pip’s Marina & Hideaway offers waterfront accommodations in Marathon, FL, featuring cozy rooms and 1- and 2-bedroom apartments with kitchenettes.
Key West
Marrero's Guest Mansion
Marrero’s Guest Mansion is an adults-only boutique B&B in Old Town Key West, offering unique rooms in a restored Victorian mansion with a saltwater pool.
Islamorada
Topsider Resort
Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.
Key Largo
Florida Keys Luxury Rentals
Florida Keys Luxury Rentals offers high-end vacation homes throughout the Keys, pairing luxury accommodations with personalized concierge, private boating, fishing, gourmet meals, and diving experiences.
Key Largo
Key Largo Vacation Home Rentals
Key Largo Vacay — family-friendly vacation rental and lodging service in Key Largo, where waterfront amenities and island comfort meet.
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 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
Key Largo Vacation Rental Villas
Experience resort-style fun with the largest pool in the Florida Keys, ocean-view lounging, a speakeasy game room, marina access, and exclusive tennis and pickleball courts—including the Keys’ only indoor pickleball court.
The Lower Keys
KOA Sugarloaf
Sugarloaf Key KOA Resort offers waterfront RV sites, deluxe cabins, and tent sites with resort-style amenities in the Florida Keys.
Key West
Old Town Suites
Old Town Suites is a boutique hotel in Key West featuring self-catering apartments with full kitchens, a coffee shop, and a prime location just steps from Duval Street and the Ernest Hemingway Home and Museum.
Islamorada
Caloosa Cove Resort
Caloosa Cove Resort & Marina offers 30 oceanfront suites with kitchens, balconies, and ocean views.
