Places to Stay

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 Vacation Rentals offers a curated selection of vacation homes and cottages in the Florida Keys, providing travelers with diverse options for a memorable stay.

Fitch Lodge: Your cozy, bohemian Key West basecamp steps from the Historic Seaport.

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.

Casa Clara Condos in Key Colony Beach offers oceanfront 2-bedroom, 2-bathroom condos with private balconies, a heated pool, tennis courts, and beach access. Ideal for both short and long-term stays.

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.

Cozy, family-run motel in the heart of Islamorada, Florida Keys paradise.

Sugarloaf Key KOA Resort offers waterfront RV sites, deluxe cabins, and tent sites with resort-style amenities in the Florida Keys.

The Garden House is a charming bed & breakfast nestled in Old Town Key West, offering cozy accommodations, a tranquil garden pool, and personalized concierge services—all just steps from Duval Street.

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.

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.

Sugarloaf Key RV Resort & Cottages is a luxury waterfront retreat in the Florida Keys, offering premium RV sites, pet-friendly glamping options, and a variety of amenities including a heated pool, kayak and paddleboard rentals, and an on-site tiki bar.

Leo’s Campground offers full-hookup RV sites up to 42', vacation rentals, and water access for kayaks and paddleboards, just minutes from Key West.

RV on the Go — mobile home & RV vacation rentals in the Florida Keys, offering turnkey setups where you arrive and relax without hauling your own trailer.