Places to Stay

Oceanfront 3BR rental in gated community with panoramic views, boat slip, and top Islamorada location.

Ragged Edge Resort & Marina is a charming, family-owned oceanfront retreat in Islamorada, offering a nostalgic "Old Keys" experience with modern comforts.

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

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.

Coral Bay Resort is a waterfront resort in Islamorada offering spacious accommodations, private balconies, a heated pool, and direct access to the bay. Ideal for relaxation and water activities.

Oceanfront, family-owned Florida Keys escape—discover Sands of Islamorada.

La Jolla Resort: Classic Keys charm, beachfront views, family fun!

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.

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

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

Bayside Villas by Islander Resort offers fully renovated, two-bedroom townhouse-style accommodations in Islamorada, featuring a bayview pool, water sports access, and private boat slips. Ideal for families, friends, and extended stays.

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.

The Islands of Islamorada is a luxurious, boutique resort nestled in the Upper Florida Keys, offering a serene and upscale escape for travelers seeking both relaxation and adventure.

Escape to Three Waters Resort & Marina for island luxury, ocean views, and endless adventure.Three Waters Resort & Marina, a Tribute Portfolio Resort, is a newly reimagined oceanfront destination in Islamorada, Florida, blending island charm with modern luxury.

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