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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Island Villa Rental Properties
Discover Island Villa: Luxury Florida Keys getaways await.
Sun Outdoors Islamorada
Sun Outdoors Islamorada: island-style RV sites and oceanview vacation homes.
Matecumbe Resort
Matecumbe Resort is an oceanfront, family-friendly resort in Islamorada, offering fully equipped suites, a heated pool, private beach, and complimentary kayaks and bicycles.
Casa Morada
Casa Morada is a boutique resort in Islamorada offering 16 suites with private balconies or patios, complimentary kayaks and paddleboards, and access to yoga sessions.
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.
Breezy Palms Resort
Breezy Palms Resort offers a family-friendly, oceanfront experience with accommodations including poolside apartments, two-bedroom units, beach cottages, oceanfront apartments, and bungalows.
Pines & Palms Resort
Pines & Palms Resort — a boutique, ocean-front retreat in Islamorada offering a peaceful Keys-style village with cottages and suites.
Cheeca Lodge & Spa
Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering elegant rooms, a 9-hole golf course, multiple dining options, and a full-service spa. Ideal for couples and families seeking a tranquil Keys getaway.
Islander Resort
Escape to Islander Resort: vibrant Florida Keys stays, beachside dining, and endless adventures!
Long Key State Park
Long Key State Park offers kayaking, hiking, birdwatching, and tent camping along the Atlantic Ocean in the Florida Keys.
Topsider Resort
Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.
Condos in the Keys.com
Oceanfront condos in Islamorada with stunning views, pool, tennis, and beach fun!
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.
Mar-Key Islamorada
Mar‑Key Islamorada is an exclusive oceanfront private estate in the Florida Keys blending historic Old Florida charm with modern luxury.