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 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.
Islamorada
Casitas at Cheeca Lodge
Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering upscale accommodations, a 9-hole golf course, spa services, and a private beach with water sports activities. Ideal for couples and families seeking a tranquil Keys getaway.
Islamorada
Key Lantern
Key Lantern Motel & Blue Fin Inn offers clean, budget-friendly rooms in Islamorada, ideal for Keys adventurers.
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.
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.
Islamorada
Freewheeler Vacations
Freewheeler Vacations is the Upper and Middle Keys’ largest and longest-running vacation rental company, offering everything from cozy condos to grand estates, backed by 30+ years of expert service.
Islamorada
Keys Holiday Rentals
Keys Holiday Rentals offers vacation homes and condos in Islamorada, Florida Keys, perfect for waterfront stays, fishing trips, and family getaways.
Marathon
Terra Marine Park
55+ pet-friendly manufactured home community with 23 homes, laundry, fishing, and picnic spaces.
Key Largo
Key Largo Kampground and Marina
Key Largo Kampground: oceanfront escape with 40 acres of adventure.
Key West
Colors on White Apartments
Colors on White offers vibrant, apartment-style accommodations in Old Town Key West. Each unit features a private entrance, kitchenette, and access to a pool with a cascading waterfall.
Marathon
Florida Keys Villas
Spacious 6-bedroom waterfront villa in Marathon with private pool, spa, dock, and outdoor kitchen. Sleeps 14.
Key Largo
Stay Ombi
Escape to Stay Ombi in Key Largo, where private floating bungalows offer a one-of-a-kind luxury stay on the turquoise waters of the Florida Keys.
Key Largo
Tarpon Flats Inn & Marina
Tarpon Flats Inn & Marina is a boutique waterfront retreat in Key Largo, offering five spacious, air-conditioned rooms with kitchenettes, private beach access, and complimentary kayaks for exploring the surrounding waters.
Marathon
Florida Keys Vacations, Inc.
Florida Keys Vacations offers family-friendly vacation rental homes and condos in Marathon and Key Colony Beach, FL—with beachfront and canal-front properties that deliver easy access to boating, snorkeling, and island living.
