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.
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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.
Key West
Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & Cottages is a tranquil adults-only boutique inn in Old Town Key West, offering four outdoor pools, daily continental breakfast, bike rentals, and lush tropical gardens just steps from Duval Street.
The Lower Keys
Veterans Dive Center & Retreat
Veterans Dive Center & Retreat — dive shop and veteran-friendly retreat in Summerland Key, Florida.
The Lower Keys
Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages is a luxury waterfront retreat in the Florida Keys, offering premium RV sites, pet-friendly glamping options, and a variety of amenities including a heated pool, kayak and paddleboard rentals, and an on-site tiki bar.
Marathon
Casa Clara Condominium
Casa Clara Condos in Key Colony Beach offers oceanfront 2-bedroom, 2-bathroom condos with private balconies, a heated pool, tennis courts, and beach access. Ideal for both short and long-term stays.
Marathon
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.
Key West
Westwinds Inn
Westwinds Inn is a charming, adults-only Victorian-style boutique hotel located in the Historic Seaport District of Old Town Key West.
Marathon
Keys Ocean Vacation Rentals
Florida Keys escapes—discover, book, plan with Keys Ocean Vacation Rentals.
The Lower Keys
Big Pine Fishing Lodge & Campground
Big Pine Key RV Park in the Lower Florida Keys spans 10 acres between the Gulf of Mexico and Atlantic Ocean at Mile Marker 33, offering waterfront RV sites, rustic campsites, Airstream rentals, and a rooftop heated pool.
Marathon
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.
Key Largo
Dream Bay Resort
Dream Bay Resort is a private, gated resort and wedding venue in Key Largo, offering five charming cottages, a small marina, and breathtaking sunset views over Florida Bay. Ideal for romantic getaways and intimate weddings.
Key West
Garden House Hotel
The Garden House is a charming bed & breakfast nestled in Old Town Key West, offering cozy accommodations, a tranquil garden pool, and personalized concierge services—all just steps from Duval Street.
Key West
Oceans Edge Resort & Marina
Oceans Edge Key West Resort & Marina is a luxury waterfront resort on Stock Island, featuring six heated saltwater pools, a 165-slip marina, an on-site restaurant, and complimentary shuttle service to Old Town Key West.
