Places to Stay

Luxury waterfront vacation rentals in Marathon & Key Colony Beach, FL. Private pools, docks, and dog-friendly accommodations. Sleeps 8–10.

Kon Tiki Resort offers waterfront cottages with private boat dockage, heated pool, and a private lagoon in Islamorada, Florida Keys

Spacious 4-bedroom, 3-bathroom vacation homes in Marathon, FL, featuring private pools, boat slips, and access to a private beach.

Luxury beachfront resort in Key Largo with stunning bay views, spa, and watersports.

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

Coconut Cove Beach Resort & Marina is a family-friendly, waterfront resort in Islamorada, offering a zero-entry pool, private beach, and event spaces for weddings and private functions. Located on a 7-acre tropical estate, it's ideal for both relaxation and special events.

Big Pine Key RV Park in the Lower Florida Keys spans 10 acres between the Gulf of Mexico and Atlantic Ocean at Mile Marker 33, offering waterfront RV sites, rustic campsites, Airstream rentals, and a rooftop heated pool.

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.

Eden House Key West is a boutique hotel in the heart of Old Town, offering a heated pool, tropical gardens, and walking distance to Duval Street. Ideal for couples seeking a charming, relaxing retreat.

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

The Garden House is a charming bed & breakfast nestled in Old Town Key West, offering cozy accommodations, a tranquil garden pool, and personalized concierge services—all just steps from Duval Street.

Colocada Vacation Rentals specializes in upscale Key West accommodations, offering nightly, weekly, and monthly rentals with VIP-level guest services rooted in generations of local expertise.

Bayside Inn Key Largo: Waterfront hotel with private beach, pool, and stunning sunsets.

New Orleans House is a gay male-only guesthouse on Duval Street in Key West, featuring a clothing-optional pool, rooftop sundeck, and complimentary happy hour.