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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Islamorada
Condos in the Keys.com
Oceanfront condos in Islamorada with stunning views, pool, tennis, and beach fun!
Islamorada
Mermaid's Bay Boutique Estate
Mermaid’s Bay is a secluded boutique estate in Islamorada, offering three private waterfront homes with resort-style amenities, ideal for group getaways
Islamorada
Kon Tiki Resort
Kon Tiki Resort offers waterfront cottages with private boat dockage, heated pool, and a private lagoon in Islamorada, Florida Keys
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
Coconut Cove Resort & Marina
Coconut Cove Beach Resort & Marina is a family-friendly, waterfront resort in Islamorada, offering a zero-entry pool, private beach, and event spaces for weddings and private functions. Located on a 7-acre tropical estate, it's ideal for both relaxation and special events.
Islamorada
Scuba Town USA
Scuba Town USA in Islamorada offers an all-in-one dive and vacation experience with lodging, dining, pools, a private beach, and access to multiple dive-related businesses, all set within Three Waters Resort & Marina.
Islamorada
Beach House at Tarpon Point
Luxury oceanfront home with stunning views, private beach, and pool.
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.
Islamorada
La Siesta Resort & Marina
La Siesta Resort & Villas offers beachfront cottages, suites, and villas with pools, complimentary watersports, and access to three sister resorts in Islamorada.
Islamorada
Oceanview Inn & Sports Club
The Ocean View Inn & Sports Pub in Islamorada offers comfortable accommodations with a tropical flair, an outdoor pool, and a lively pub serving classic American fare and late-night bites.
Islamorada
Angler's Reef
Oceanfront 3BR rental in gated community with panoramic views, boat slip, and top Islamorada location.
Islamorada
Chesapeake Beach Resort
Escape to paradise at Chesapeake Beach Resort—luxury oceanfront stays in the Florida Keys.
Islamorada
Mangrove Marina
Full-service marina in Tavernier offering wet slips, dry storage, houseboat rentals & resort amenities in a protected mangrove setting.
Islamorada
Fisher Inn Resort and Marina
Fisher Inn Resort & Marina is an oceanfront boutique resort in Islamorada offering stylish rooms with kitchenettes, a heated pool with ocean views, and unique amenities like its own boat ramp and marina. Ideal for anglers, boaters, and families seeking waterfront comfort.
