Places to Stay

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.

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.

Opal Key Resort & Marina is a luxury waterfront resort in the heart of Old Town Key West, offering 178 elegant rooms, Lolita’s Coastal Cocina, a 37-slip marina, and a sparkling pool just steps from Mallory Square and Duval Street.

Florida Keys Vacations offers family-friendly vacation rental homes and condos in Marathon and Key Colony Beach, FL—with beachfront and canal-front properties that deliver easy access to boating, snorkeling, and island living.

Seascape Resort & Marina: serene oceanfront escape with pool, marina, and tropical charm.Seascape Resort & Marina is a tranquil oceanfront retreat in Marathon featuring a private beach, marina access, an outdoor pool, and complimentary kayaks, paddleboards, bicycles, and grilling facilities.

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

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.

Bohemian luxury in a historic Key West mansion with pool and chef's breakfast.

55+ pet-friendly manufactured home community with 23 homes, laundry, fishing, and picnic spaces.

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.

El Patio Motel is a nostalgic 30-room motel in Old Town Key West, featuring original Cuban tile floors, a rooftop deck, and a ground-floor pool. Located just 2 blocks from the beach and 3 blocks from Duval Street, it's ideal for travelers seeking simplicity and charm.

Waterfront Florida Keys rental with sailboat included—perfect for sailors and nature lovers!

Conch Key Landing — waterfront vacation-rental cottages with private dockage and stunning Florida Bay views on Conch Key.

Caribbean House is a charming Bed & Breakfast located in historic Bahama Village, just two blocks from Duval Street.

Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.