Places to Stay

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.

The Hammocks at Marathon is a tropical resort offering spacious studios and 1- and 2-bedroom suites with full kitchens, balconies, and access to amenities like a heated pool, hot tub, tiki bar, and marina.

Historic Key West Vacation Rentals offers a curated selection of luxury vacation homes, cottages, and condos in the Key West Historic District.

Key Lime Sailing Club & Cottages offers a unique, all-inclusive waterfront retreat in Key Largo, featuring self-contained cottages with unlimited sailboat use, kayaks, snorkeling gear, and more.

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

RV on the Go — mobile home & RV vacation rentals in the Florida Keys, offering turnkey setups where you arrive and relax without hauling your own trailer.

Grassy Key RV Park & Resort offers waterfront RV sites with full hookups, a heated and chilled pool, a private sandy beach, and access to Gulf and Atlantic waters, all just 45 minutes from Key West.

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

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.

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.

Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering elegant rooms, a 9-hole golf course, multiple dining options, and a full-service spa. Ideal for couples and families seeking a tranquil Keys getaway.

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.

Bayfront Suites in Key West offers luxury waterfront condos with modern amenities, a rooftop veranda, and a private marina. Perfect for both relaxation and special events.

Ocean Key Resort & Spa in Key West offers luxury accommodations with Gulf views, a rooftop pool, three waterfront dining options, and a full-service spa, all located at the iconic Zero Duval Street.