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
Historic Hideaways/Key West Realty
Historic Hideaways offers a curated selection of private Key West vacation homes, including cottages, townhomes, and historic residences, many with private pools.
Key West
Ocean Key Resort & Spa
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.
Weddings Max
200
Meetings Max
50
Total Space
870 sq ft
Largest Room
850 sq ft
Marathon
American Coastal Vacation Rentals
Luxury Florida Keys rentals with ocean, gulf, and canal views—docks, pools, tennis!
Key Largo
Seafarer Resort
The Seafarer Resort and Beach is a waterfront cottage motel located directly on Florida Bay in Key Largo, Florida.
Key Largo
Dolphin Point Villas
Dolphin Point Villas is an adults-only, gated resort on Florida Bay offering six spacious, modern villas with private beach access, a freshwater pool, and complimentary kayaks and paddleboards. Guests enjoy exclusive dolphin encounters and sunset views.
Weddings Max
120
Meetings Max
120
Key West
Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & Cottages is a tranquil adults-only boutique inn in Old Town Key West, offering four outdoor pools, daily continental breakfast, bike rentals, and lush tropical gardens just steps from Duval Street.
The Lower Keys
Little Torch Cottages
Little Torch Cottages offers 2-bedroom townhomes with full kitchens, private balconies, and access to two tropical pools in the Florida Keys.
Islamorada
Tea Table Key Island Estate & Wedding Venue
Tea Table Key is a spectacular, car-accessible private island estate in Islamorada, spanning over 15 acres and offering complete exclusivity just off the Overseas Highway.
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
Islamorada
Hadley Resort and Marina
Hadley House Resort is a laid-back waterfront hotel in Islamorada, offering rooms with kitchenettes, a private beach, an outdoor pool, and complimentary breakfast, all just steps from the Atlantic Ocean.
Key West
La Pensione Inn
La Pensione Inn is an adults-only boutique guesthouse in Old Town Key West, featuring Victorian architecture, a pool, and complimentary breakfast.
Key West
Keys Caribbean Resorts
Explore KeysCaribbean: Expert hotel management and luxury vacation rentals.
The Lower Keys
Sea View Estate
Sea View Estate is a secluded, oceanfront retreat on Sugarloaf Key featuring two vacation homes, a private dock, pool, tiki bar, and stunning Atlantic views just 15 minutes from Key West.
Islamorada
Casa Morada
Casa Morada is a boutique resort in Islamorada offering 16 suites with private balconies or patios, complimentary kayaks and paddleboards, and access to yoga sessions.
