Places to Stay

Discover Winslow’s Bungalows: a vibrant, historic Key West oasis with pools, charm, and local tales.

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 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.

Glunz Ocean Beach Hotel & Resort offers a beachfront retreat with spacious suites and villas, two oceanfront pools, a private sandy beach, and complimentary water sports equipment—all just steps from Havana Jack’s Oceanside Restaurant.

Old Town Manor is a historic Victorian bed and breakfast in the heart of Key West, offering 14 unique rooms, a lush tropical garden, and an organic continental breakfast, just steps from Duval Street.

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.

Banana Bay Resort & Marina in Marathon is a laid-back tropical retreat featuring 59 charming guestrooms, a private marina, and complimentary breakfast. Nestled on ten serene Gulf Coast acres, it's the perfect blend of coastal comfort and Florida Keys adventure.

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

Marina Del Mar Resort & Marina is a waterfront resort in Key Largo featuring pet-friendly rooms, deep-water marina slips, pools, and on-site dining.

Stay inspired in a charming Key West guesthouse honoring literary legends.

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.

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.

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.

Ragged Edge Resort & Marina is a charming, family-owned oceanfront retreat in Islamorada, offering a nostalgic "Old Keys" experience with modern comforts.