Places to Stay

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.

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.

Escape to Blackfin Resort & Marina in the Florida Keys—relax, fish, boat, and enjoy stunning sunsets!

Oceanfront 2-bedroom, 2-bath condos in Key Colony Beach, FL, offering private beach access, heated pool, and stunning Atlantic views. Ideal for couples and families seeking a tranquil Keys getaway.

Key Largo Cottages — boutique self-catering cottages offering free sailing, kayaking, paddle board and bike use in the Florida Keys.

Premier short-term vacation homes and waterfront escapes in Key West and the Florida Keys with pool, beach access, pet-friendly stays, and local water activities.

Dolphin Point Villas is an adults-only, gated resort on Florida Bay offering six spacious, modern villas with private beach access, a freshwater pool, and complimentary kayaks and paddleboards. Guests enjoy exclusive dolphin encounters and sunset views.

Stay in the heart of Key West with stylish rooms, rooftop pool, and free breakfast!

Oceanlivin offers luxury vacation rentals in Key West, featuring oceanfront properties with private pools, gourmet kitchens, and concierge services. Ideal for travelers seeking a tranquil island retreat.

Gilbert’s Resort & Marina is a laid-back waterfront resort in Key Largo, featuring waterfront rooms, a private beach, and the Keys’ largest tiki bar with live music and dining.

Breezy Pines RV Estates — peaceful Big Pine Key community offering full-service RV sites and easy access to the Lower Keys’ best attractions.

Escape to paradise at Sunset Cove Beach Resort—your perfect getaway awaits!

Big Pine Key Motel on Overseas Highway offers clean and comfortable rooms with free Wi-Fi, parking, and an on-site café. Nestled between Marathon and Key West, it’s minutes from Bahia Honda State Park and the famous Key Deer refuge.

The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.

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.