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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Keys Holiday Rentals
Keys Holiday Rentals offers vacation homes and condos in Islamorada, Florida Keys, perfect for waterfront stays, fishing trips, and family getaways.
Cocoplum on the Bay
Coco Plum on the Bay — luxurious 4-bedroom waterfront vacation home in Marathon, FL.
Hadley Resort and Marina
Hadley House Resort is a laid-back waterfront hotel in Islamorada, offering rooms with kitchenettes, a private beach, an outdoor pool, and complimentary breakfast, all just steps from the Atlantic Ocean.
Happy In The Keys
Luxury waterfront vacation rentals in Marathon & Key Colony Beach, FL. Private pools, docks, and dog-friendly accommodations. Sleeps 8–10.
Nest Villa at Holiday House
The Nest Villa in Islamorada is a private upper-level retreat with two bedrooms, panoramic Florida Bay views, and marina access with free dockage.
Casa Feliz Florida Keys
Elegant three-story oceanfront villa on Grassy Key with private beach, pool, and luxury amenities.
Azul Del Mar
Secluded Key Largo boutique resort with romantic suites, waterfront fun, and stunning sunsets.
Isla Bella Beach Resort & Spa
Isla Bella Beach Resort offers luxury oceanfront rooms and suites, five pools, a full-service spa & multiple dining options—all set on over a mile of private beachfront
Gilbert's Resort
Gilbert’s Resort & Marina is a laid-back waterfront resort in Key Largo, featuring waterfront rooms, a private beach, and the Keys’ largest tiki bar with live music and dining.
Island House
Island House Key West is a private, adults-only clothing-optional resort with a heated pool, sauna, gym, and 24/7 café/bar in Old Town.
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.
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.