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.

Discover a historic Key West icon blending vintage flair with modern luxury.

Heron House Hotels offers two charming, adults-only properties—Heron House and Heron House Court—featuring lush gardens, an outdoor pool, rooftop sundeck, and complimentary continental breakfast.

KCB Motel offers vintage charm, just steps from a private sandy beach, with simple rooms and a laid-back atmosphere.

Adult-only Key West inn with lush gardens, pool, spa, and cozy rooms.

Spacious 4-bedroom, 3-bathroom vacation homes in Marathon, FL, featuring private pools, boat slips, and access to a private beach.

The Hammocks at Marathon is a tropical resort offering spacious studios and 1- and 2-bedroom suites with full kitchens, balconies, and access to amenities like a heated pool, hot tub, tiki bar, and marina.

Historic charm meets modern comfort at Duval Inn, steps from Key West's vibrant heart.

Coconut Cay RV Resort is a boutique family-operated RV park in Marathon, Florida, featuring 25 spacious sites with electric, water, and sewer hookups. Enjoy a heated pool, private sunset beach, and easy access to boat dockage.

Bluewater Key RV Resort offers luxury RV sites with private tiki huts, lush landscaping, and waterfront access.

Charming beachfront condos in Key Colony Beach, perfect for a relaxing Florida Keys getaway.

Escape to paradise at Conch Key Fishing Lodge—prime fishing, stunning views, and cozy waterfront rooms!

Ocean Key Resort & Spa in Key West offers luxury accommodations with Gulf views, a rooftop pool, three waterfront dining options, and a full-service spa, all located at the iconic Zero Duval Street.

Luxury Florida Keys vacation rentals with ocean views, private pools, and 24/7 support.

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.