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
Key West
Winslow's Bungalows
Discover Winslow’s Bungalows: a vibrant, historic Key West oasis with pools, charm, and local tales.
Weddings Max
40
Meetings Max
40
Key West
La Te Da
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.
Key Largo
Holiday Inn Key Largo
Holiday Inn Key Largo is a tropical hotel featuring two heated outdoor pools with a waterfall, a poolside Tiki bar, and an on-site marina.
Weddings Max
140
Meetings Max
140
Total Space
3070 sq ft
Largest Room
2400 sq ft
Marathon
Rainbow Bend Resort
Rainbow Bend Resort is a family-friendly, oceanfront retreat in Marathon, Florida, offering a private beach, saltwater pool, and hot tub with ocean views.
Islamorada
Matecumbe Resort
Matecumbe Resort is an oceanfront, family-friendly resort in Islamorada, offering fully equipped suites, a heated pool, private beach, and complimentary kayaks and bicycles.
Marathon
Monte Christo Condos
Monte Christo Condominiums is a luxury oceanfront retreat in Key Colony Beach, offering two- and three-bedroom condos with resort-style amenities.
Key West
Weatherstation Inn
The Weatherstation Inn is an adults-only, historic Key West bed & breakfast tucked away in the gated Truman Annex, offering charming, island-inspired rooms, a sunny terrace, outdoor pool, free continental breakfast, and easy walking access to Duval Street and Mallory Square.
Key West
Heron House Court
Heron House Hotels offers two charming, adults-only properties—Heron House and Heron House Court—featuring lush gardens, an outdoor pool, rooftop sundeck, and complimentary continental breakfast.
Key Largo
Kawama Yacht Club Vacation Rental
Key Largo Rentals offers premier vacation homes—from oceanfront condos to spacious townhouses and luxury villas—ideal for families and water lovers.
Marathon
Banana Bay Resort Marathon
Banana Bay Resort & Marina in Marathon is a laid-back tropical retreat featuring 59 charming guestrooms, a private marina, and complimentary breakfast. Nestled on ten serene Gulf Coast acres, it's the perfect blend of coastal comfort and Florida Keys adventure.
Total Space
1000 sq ft
Marathon
American Coastal Vacation Rentals
Luxury Florida Keys rentals with ocean, gulf, and canal views—docks, pools, tennis!
Key West
The Key West Hotel
The Key West Hotel is a boutique retreat offering a blend of historic charm and modern comfort in the heart of Old Town Key West.
Weddings Max
100
Marathon
Happy In The Keys
Luxury waterfront vacation rentals in Marathon & Key Colony Beach, FL. Private pools, docks, and dog-friendly accommodations. Sleeps 8–10.
Key West
Wicker Guesthouse
Wicker Guesthouse is a charming, adults-only boutique inn in the heart of Old Town Key West.
