Places to Stay

The Galleon Resort & Marina is a waterfront resort in Old Town Key West offering spacious studios and suites with full kitchens or kitchenettes, a private beach, pool, and on-site marina—all just steps from Duval Street.

The Capitana Key West is a boutique waterfront hotel offering coastal-chic accommodations, a heated pool with a tiki bar, private beach access, and pet-friendly cottages.

Kona Kai Oasis offers boutique guesthouse accommodations with a pool, complimentary bikes, and lush botanical gardens in Key West’s Old Town.

Lazy River Vacation — family-friendly waterfront vacation home in Marathon, where a private heated lazy river pool and 70-ft dock redefine Florida Keys relaxation.

KeysCations offers a curated selection of luxury vacation homes in Marathon, FL, featuring private pools, docks, and ocean views. Ideal for families and groups seeking a tranquil Keys getaway.

Sea Dell Motel: Old Keys charm, pool, near Sombrero Beach in Marathon.

White Gate Court is a charming, pet-friendly boutique resort nestled on three lush acres in Islamorada, offering seven unique cottages with old Keys-style charm.

The Oasis in Islamorada is a private 2.75-acre estate featuring two homes, a heated saltwater pool, 200 feet of Atlantic Ocean frontage, and a variety of water sports amenities.

Pier House Resort & Spa is a historic oceanfront retreat in Old Town Key West, featuring a private white sand beach, full-service spa, three dining venues, and the iconic Chart Room Bar

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

Escape to Seabird Key: private 10-acre island retreat in Marathon, FL.

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.

Matecumbe Resort is an oceanfront, family-friendly resort in Islamorada, offering fully equipped suites, a heated pool, private beach, and complimentary kayaks and bicycles.

Blue Flamingo Resort in Key West offers a reimagined getaway with tropical-style rooms, two lively pools with luxe cabanas, and poolside dining at Rum Row and Toasted Coconut.

Vacation Rentals Florida Keys — vacation homes, condos & waterfront retreats throughout the Florida Keys, where you’ll find turnkey island stays with amenities, docks and fully‑equipped kitchens.