Places to Stay

Luxury Florida Keys rentals with ocean, gulf, and canal views—docks, pools, tennis!

Coconut Cove Beach Resort & Marina is a family-friendly, waterfront resort in Islamorada, offering a zero-entry pool, private beach, and event spaces for weddings and private functions. Located on a 7-acre tropical estate, it's ideal for both relaxation and special events.

Southwinds Motel is a budget-friendly, adults-only hotel in Old Town Key West, offering two outdoor pools, complimentary continental breakfast, and convenient access to Duval Street and the Atlantic Ocean.

Waterfront hotel in the Florida Keys with pools, marina, and tropical dining.

Charming Key West oasis with private baths, heated pool, and prime location.

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

Hadley House Resort is a laid-back waterfront hotel in Islamorada, offering rooms with kitchenettes, a private beach, an outdoor pool, and complimentary breakfast, all just steps from the Atlantic Ocean.

Courtyard by Marriott Key West Waterfront offers a newly renovated, resort-style experience with no resort or parking fees. Enjoy spacious rooms, a heated outdoor pool, Tiki Bar, and direct access to the Gulf of Mexico.

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.

Coconut Palms of Key West offers spacious 2- and 3-bedroom beachfront condos at 1800 Atlantic Resort, adjacent to Smathers Beach. Enjoy ocean views, a heated pool, and easy access to water activities.

Waterfront resort in Marathon offering coastal luxury, a full-service marina, spa, dining, four pools, and a sister property, Courtyard by Marriott.

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.

Conch Key Cottages offers charming waterfront accommodations on Conch Key in the Florida Keys. Guests can enjoy private cottages with boat slips, ideal for fishing and exploring nearby attractions.

The Key West Hotel is a boutique retreat offering a blend of historic charm and modern comfort in the heart of Old Town Key West.

Dragonfly Lite is a secluded 2-bedroom, 1-bathroom vacation home in Marathon, FL, featuring a private heated saltwater pool, outdoor shower, and lush tropical patio. Ideal for couples or small families seeking a tranquil retreat.