Places to Stay

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.

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

Historic charm meets modern comfort at Duval Inn, steps from Key West's vibrant heart.

Star Properties Destinations is a vacation rental and property management company in the Florida Keys, offering a variety of accommodations across Key Largo, Islamorada, Marathon, Tavernier, and the Lower Keys.

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.

Keys Properties offers curated waterfront rentals and real estate in Key Colony Beach, including over 50 vacation homes with owner-managed care.

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.

Sunset Key Cottages is a luxury resort situated on a 27-acre private island just 500 yards off Key West, offering upscale one- to four-bedroom cottages with wraparound verandas and panoramic ocean views.

The Ocean View Inn & Sports Pub in Islamorada offers comfortable accommodations with a tropical flair, an outdoor pool, and a lively pub serving classic American fare and late-night bites.

Waterfront resort in Marathon offering coastal luxury, a full-service marina, spa, dining, four pools, and a sister property, Courtyard by Marriott.

Luxury 2-story townhome in Key West's premier Truman Annex, near Duval St.

The Nest Villa in Islamorada is a private upper-level retreat with two bedrooms, panoramic Florida Bay views, and marina access with free dockage.

La Te Da is an adults-only hotel, restaurant, bar, and cabaret located on Duval Street in Key West, offering live entertainment and gourmet dining.

Hyatt Centric Key West – Waterfront resort with spa, pool, and dining.