Places to Stay

Gulf View Waterfront Resort offers a laid-back, Old Florida experience with spacious rooms featuring kitchenettes, an oceanfront pool, complimentary kayaks and paddleboards, and pet-friendly accommodations.

Experience resort-style fun with the largest pool in the Florida Keys, ocean-view lounging, a speakeasy game room, marina access, and exclusive tennis and pickleball courts—including the Keys’ only indoor pickleball court.

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

Islamorada Vacation Rentals offers a curated selection of vacation homes and cottages in the Florida Keys, providing travelers with diverse options for a memorable stay.

La Casa Habana — private waterfront vacation home on Grassy Key with pool, dock, and gulf views.

Osprey Bay Villa is a luxurious 5-bedroom, 3-bathroom bayfront home in Islamorada, offering a private pool, hot tub, deep-water dock, and breathtaking sunset views, accommodating up to 10 guests.

Key Largo Rentals offers premier vacation homes—from oceanfront condos to spacious townhouses and luxury villas—ideal for families and water lovers.

The Casablanca Hotel is a historic bed & breakfast located on Duval Street in Key West. Guests enjoy private balconies, complimentary breakfast, and an outdoor pool.

The Reach Key West, Curio Collection by Hilton, is a luxurious beachfront resort situated on the island's only private natural sand beach.

Dolphin Vacations offers a curated selection of vacation rentals in Key West and Marathon, FL, including historic homes and modern condos. Properties like Casa Rosa provide private pools and prime locations near Duval Street.

Heart of Morada — luxury 3-bed vacation home with private pool, boat dock & kayaks in the heart of Islamorada, Florida Keys.

Caloosa Cove Resort & Marina offers 30 oceanfront suites with kitchens, balconies, and ocean views.

Hampton Inn Key West is an oceanfront hotel located just 2 minutes from Key West International Airport, offering free hot breakfast, an outdoor pool with a poolside bar, and complimentary shuttle service to downtown attractions.

Escape to Amara Cay Resort for luxe island vibes, ocean views, and pure relaxation.

Sugarloaf Lodge is a waterfront retreat located at Mile Marker 17 on the Overseas Highway, offering 31 rooms with private patios or balconies overlooking the serene Lower Sugarloaf Sound.