Places to Stay

Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.

Breezy Palms Resort offers a family-friendly, oceanfront experience with accommodations including poolside apartments, two-bedroom units, beach cottages, oceanfront apartments, and bungalows.

Drop Anchor Resort & Marina offers oceanfront accommodations with full kitchens, a heated pool, complimentary kayaks, paddleboards, and bicycles, all set in a tropical garden atmosphere. Ideal for couples and families seeking a relaxing Florida Keys getaway.

La Siesta Resort & Villas offers beachfront cottages, suites, and villas with pools, complimentary watersports, and access to three sister resorts in Islamorada.

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.

Mitchell’s Keys Villa is a secluded waterfront vacation rental in Islamorada, offering a private beach, marina, and boat ramp, ideal for fishing and relaxation.

Escape to Amara Cay Resort for luxe island vibes, ocean views, and pure relaxation.

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.

Heart of Morada — luxury 3-bed vacation home with private pool, boat dock & kayaks in the heart of Islamorada, Florida Keys.

Long Key State Park offers kayaking, hiking, birdwatching, and tent camping along the Atlantic Ocean in the Florida Keys.

Fifteen acres on the ocean at mile marker 73.5, with 30 suites that all have kitchens, balconies and water out the front door, plus a heated pool and a sandy beach. Tie your boat up out back, walk over to Habano's for Cuban food, and never move the car.

Sun Outdoors Islamorada: island-style RV sites and oceanview vacation homes.

Florida Keys Vacation Rentals makes finding your perfect Keys getaway easy, featuring a wide selection of beachfront homes and condos from Key Largo to Key West—book securely with a trusted local provider.

Key Lantern Motel & Blue Fin Inn offers clean, budget-friendly rooms in Islamorada, ideal for Keys adventurers.

Relax in paradise at Atlantic Bay Resort with private beach, waterfront views, and tropical cottages.