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.

Hawks Cay Resort is a luxury resort on Duck Key offering five pools, a saltwater lagoon, a full-service marina, and a spa.

Little Basin Villas offers 3-bedroom, 3.5-bathroom waterfront townhomes with private balconies, a heated pool, and boat dockage in Islamorada’s Art District.

Premier short-term vacation homes and waterfront escapes in Key West and the Florida Keys with pool, beach access, pet-friendly stays, and local water activities.

Baker’s Cay Resort Key Largo — boutique waterfront resort with beach access, watersports, dining and family-friendly amenities in Key Largo, FL.

Vacation Homes of Key West is a locally owned boutique vacation rental company offering a curated collection of authentic island-style homes.

Luxury beachfront escape with stunning views and top amenities awaits you!

Bayside Villas by Islander Resort offers fully renovated, two-bedroom townhouse-style accommodations in Islamorada, featuring a bayview pool, water sports access, and private boat slips. Ideal for families, friends, and extended stays.

The Conch House Heritage Inn is a historic adult-only bed and breakfast located in Old Town Key West. Guests enjoy elegant accommodations, a pool, daily breakfast with mimosas, and a prime location just steps from Duval Street.

Stay at the iconic Southernmost House, an oceanfront boutique hotel blending historic charm with unforgettable Atlantic views.

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.

Leo’s Campground offers full-hookup RV sites up to 42', vacation rentals, and water access for kayaks and paddleboards, just minutes from Key West.

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.

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.