Places to Stay
Claim your corner of The Florida Keys & Key West. Waterfront resorts, tucked-away inns, vacation rentals with a dock out back, campgrounds under the palms...however you like to unwind, there's a place here that gets it. Filter by destination, amenities or whatever matters most and find the spot that turns your trip from planned to perfect. Checkout is the only thing that should stress you out.
Filters
Marathon
La Casa Habana Vacation Rental
La Casa Habana — private waterfront vacation home on Grassy Key with pool, dock, and gulf views.
Islamorada
Chesapeake Beach Resort
Escape to paradise at Chesapeake Beach Resort—luxury oceanfront stays in the Florida Keys.
Key West
Mansion by the Sea
The Mansion on the Sea (Southernmost House) is an adults-only historic boutique hotel in Key West offering oceanfront rooms, a heated infinity pool, and complimentary breakfast.
Key West
Havana Cabana
Cuban vibes meet Key West charm—discover Havana Cabana.Havana Cabana at Key West is a Cuban-inspired hotel featuring the largest pool in Key West, a poolside bar, and a food truck serving Cuban cuisine.
Weddings Max
150
Meetings Max
60
Total Space
1820 sq ft
Largest Room
1100 sq ft
Marathon
Caribbean Soul Charters
Waterfront Florida Keys rental with sailboat included—perfect for sailors and nature lovers!
Key Largo
Key Largo Vacation Home Rentals
Key Largo Vacay — family-friendly vacation rental and lodging service in Key Largo, where waterfront amenities and island comfort meet.
Key West
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront offers a newly renovated, resort-style experience with no resort or parking fees. Enjoy spacious rooms, a heated outdoor pool, Tiki Bar, and direct access to the Gulf of Mexico.
The Lower Keys
Deer Run on the Atlantic
Charming eco-lodge on Big Pine Key with oceanfront views and Key deer nearby.
Key West
The Cabana Inn
The Cabana Inn is an adults-only boutique hotel nestled just one block from Duval Street in Old Town Key West.
Islamorada
Caloosa Cove Resort
Caloosa Cove Resort & Marina offers 30 oceanfront suites with kitchens, balconies, and ocean views.
Key West
The Laureate Key West
The Laureate Key West is a luxury all-suite hotel offering serene bayfront views, coastal chic decor, and modern amenities.
Key West
New Orleans House
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.
Key Largo
Star Properties Destinations
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.
