Places to Stay

Historic Hideaways offers a curated selection of private Key West vacation homes, including cottages, townhomes, and historic residences, many with private pools.

Florida Keys Rental Store offers curated short-term and seasonal vacation home rentals in Key Largo and Islamorada, focused on luxury residences with ocean-front views and seamless guest services.

Historic Key West Vacation Rentals offers a curated selection of luxury vacation homes, cottages, and condos in the Key West Historic District.

Historic Key West B&B: adult-only charm, with no resort fees.

Casa 325 is a charming boutique guesthouse in the heart of Key West’s Historic Old Town. Tucked just off lively Duval Street, it offers uniquely designed rooms, a pool, and easy access to shops, dining, and attractions.

Edgewater Lodge is a waterfront retreat in Long Key, Florida, offering direct access to the water, an on-site boat ramp, and a private beach area. Ideal for boating enthusiasts and those seeking a tranquil escape.

Scuba Town USA in Islamorada offers an all-in-one dive and vacation experience with lodging, dining, pools, a private beach, and access to multiple dive-related businesses, all set within Three Waters Resort & Marina.

Locally owned vacation rental company offering a variety of homes and condos in Marathon, FL. Features include private pools, pet-friendly options, and concierge services.

The Marker Key West Harbor Resort is a luxury hotel located in Old Town Key West, offering a blend of classic Florida Keys elegance and modern amenities.

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.

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

La Pensione Inn is an adults-only boutique guesthouse in Old Town Key West, featuring Victorian architecture, a pool, and complimentary breakfast.

Old Wooden Bridge Resort & Marina in Big Pine Key offers charming houseboat-style accommodations, a marina, an outdoor pool, and a prime location near the No Name Key Bridge and the National Key Deer Refuge.

Historic charm meets vibrant Key West life steps from Hemingway House and the iconic lighthouse.

Breezy Palms Resort offers a family-friendly, oceanfront experience with accommodations including poolside apartments, two-bedroom units, beach cottages, oceanfront apartments, and bungalows.