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
Southernmost Beach Resort
Southernmost Beach Resort & Guesthouses is an oceanfront Key West escape featuring multiple heated pools, beachfront dining, a full-service spa, and lush tropical gardens just steps from Duval Street.
Weddings Max
200
Meetings Max
200
Total Space
1476 sq ft
Largest Room
800 sq ft
Marathon
Conch Key Cottages
Conch Key Cottages offers charming waterfront accommodations on Conch Key in the Florida Keys. Guests can enjoy private cottages with boat slips, ideal for fishing and exploring nearby attractions.
Islamorada
Angler's Reef
Oceanfront 3BR rental in gated community with panoramic views, boat slip, and top Islamorada location.
Marathon
La Casa Habana Vacation Rental
La Casa Habana — private waterfront vacation home on Grassy Key with pool, dock, and gulf views.
Islamorada
Coastal Vacation Rentals of the Florida Keys
Discover unforgettable Florida Keys vacations with cozy condos to oceanfront estates!
Islamorada
Island Bay Resort
Island Bay Resort is an adults-only boutique escape with tropical cottages, a private beach, and free kayaks & SUPs.
Key West
Marrero's Guest Mansion
Marrero’s Guest Mansion is an adults-only boutique B&B in Old Town Key West, offering unique rooms in a restored Victorian mansion with a saltwater pool.
Key West
Keys Vacation Rentals
Curated Florida Keys vacation homes and island escapes in Key West, Key Largo, Marathon, and beyond — combining comfort, local charm, and personalized service for every traveler.
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.
Marathon
Coco Plum Vacation Rentals & Real Estate
Luxury Florida Keys vacation rentals with private pools, beach access, and endless ocean adventures await!
The Lower Keys
Veterans Dive Center & Retreat
Veterans Dive Center & Retreat — dive shop and veteran-friendly retreat in Summerland Key, Florida.
Key Largo
Drift Hotel
Drift Hotel is a boutique waterfront retreat in Key Largo offering modern, eco-chic rooms with bay views, complimentary kayaks, paddleboards, and bicycles, plus a private dock and fire pit. Ideal for couples and small groups seeking a tranquil, adventure-filled escape.
Marathon
Keys Ocean Vacation Rentals
Florida Keys escapes—discover, book, plan with Keys Ocean Vacation Rentals.
Islamorada
Scuba Town USA
Scuba Town USA in Islamorada offers an all-in-one dive and vacation experience with lodging, dining, pools, a private beach, and access to multiple dive-related businesses, all set within Three Waters Resort & Marina.
