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
Wicker Guesthouse
Wicker Guesthouse is a charming, adults-only boutique inn in the heart of Old Town Key West.
Casa 325
Casa 325 is a charming boutique guesthouse in the heart of Key West’s Historic Old Town. Tucked just off lively Duval Street, it offers uniquely designed rooms, a pool, and easy access to shops, dining, and attractions.
Caribbean Soul Charters
Waterfront Florida Keys rental with sailboat included—perfect for sailors and nature lovers!
Rentals in Paradise Inc
Discover a curated selection of vacation homes in Marathon, FL, featuring private pools, docks, and waterfront views. Ideal for families and groups seeking a relaxing Keys getaway.
Mansion by the Sea
The Mansion on the Sea (Southernmost House) is an adults-only historic boutique hotel in Key West offering oceanfront rooms, a heated infinity pool, and complimentary breakfast.
Parrot Key Hotel & Villas
Parrot Key Hotel & Villas is a tropical oasis in Key West, offering spacious rooms, suites, and villas surrounded by lush gardens, four outdoor pools, and a complimentary shuttle to Old Town attractions.
Beachside Resort
Spacious Key West condos with private beach, marina, dining, and island adventures.
Blackfin Resort & Marina
Escape to Blackfin Resort & Marina in the Florida Keys—relax, fish, boat, and enjoy stunning sunsets!
Dragonfly Lite
Dragonfly Lite is a secluded 2-bedroom, 1-bathroom vacation home in Marathon, FL, featuring a private heated saltwater pool, outdoor shower, and lush tropical patio. Ideal for couples or small families seeking a tranquil retreat.
Sunset Key Cottages
Sunset Key Cottages is a luxury resort situated on a 27-acre private island just 500 yards off Key West, offering upscale one- to four-bedroom cottages with wraparound verandas and panoramic ocean views.
Key Largo Cottages
Key Largo Cottages — boutique self-catering cottages offering free sailing, kayaking, paddle board and bike use in the Florida Keys.
Siesta Motel
Siesta Motel is a clean, family-run property in Marathon offering affordable rooms and efficiencies with kitchenettes, a pool with bar, and a relaxed tropical garden setting.
Caribbean House Hotel
Caribbean House is a charming Bed & Breakfast located in historic Bahama Village, just two blocks from Duval Street.
Coco Plum Vacation Rentals & Real Estate
Luxury Florida Keys vacation rentals with private pools, beach access, and endless ocean adventures await!