Nothing truly says luxury like a vacation in the tropical paradise of the Florida Keys. Whether its sunbathing on the pristine white sandy beaches or basking in the turquoise waters of the Gulf of Mexico, true bliss awaits you in the Keys. Enjoy your accommodations at Tranquility Bay Beach Resort, a top-rated resort in Marathon, Florida. Their onsite Butterfly Cafe is award winning, and their beach houses are designed elegantly and with a modern touch in mind. The Parrot Key Resort lets you dip and dive in its four amazing swimming pools, and lets you rent equipment right onsite! Called the “Prettiest Hotel in Key West” by New York Times List and ranked as the best hotel in Key West by TripAdvisor, you know that you’re getting the most luxurious accommodations at The Gardens Hotel. True luxury can be found in paradise-- and it just so happens that paradise is in the Keys!
Showing 1-20 of 43 Luxury Resorts
Retreat to the lap of luxury at Westwinds Inn, where you'll experience world-class hospitality in an intimate setting—teeming with a tranquility... more
- Beach
- Romantic
- Luxury
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
Key West Bed & Breakfast
Key West Bed and Breakfast is everything you're looking for in a luxurious Florida vacation. The inn is located in the Old Town area of Key West and... more
- Romantic
- Luxury
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
- Island
Coco Plum Inn
Couples of all ages will love a vacation at the Coco Plum Inn. This incredible Key West destination is just a block from the famous Duval Street and... more
- Nature
- Romantic
- Luxury
- Honeymoon
- Bed & Breakfasts, Inns
- Island
The Inn on Fleming
The Inn on Fleming is an unforgettable Key West vacation destination. The inn features elegant accommodations that are all impeccably furnished with... more
- Nature
- Romantic
- Luxury
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
- Island
Imagine being all alone on a beautiful island--you'll feel like it when you stay at Coral Bay Resort. Enjoy breathtaking views of the island while you... more
- Beach
- Family
- Reunions
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Historical
- Honeymoon
- Diving
- Holiday
- Island
The spacious two-bedroom, two-bathroom condominiums at Sunrise Suites Resort ensure your complete comfort and convenience. These charming rentals are... more
- Beach
- Family
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
Escape to the beauty and serenity of Key West, Florida, where the water is turquoise blue and the sunsets are radiant. With its island inspired charm... more
- Beach
- Family
- Romantic
- Luxury
- Honeymoon
- Boutique
- Bed & Breakfasts, Inns
Savor the lavish surroundings at Chesapeake Beach Resort. Here, you can feel right at home in a spacious villa, relax on your private terrace or... more
- Beach
- Family
- Meetings
- Reunions
- Wedding
- Nature
- Fishing
- Romantic
- Luxury
- Historical
- Honeymoon
- Diving
- Holiday
- Island
- Villas and Condos
Vacation Homes of Key West prides themselves on offering travelers with an impressive selection of accommodations that are beyond all your... more
- Beach
- Family
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Honeymoon
- Cabins, Cottages, and Chalets
- Holiday
- Island
- Villas and Condos
Keys Holiday Rentals features a wide range of charming accommodations throughout the Upper Keys. These spacious rentals offer many modern amenities... more
- Beach
- Family
- Nature
- Fishing
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
- Holiday
- Island
- Villas and Condos
The Paradise Inn is just that--paradise. Located beside Duval Street in beautiful Key West, this is truly as close to paradise as you can get. Their... more
- Beach
- Family
- Fishing
- Romantic
- Luxury
- Honeymoon
- Cabins, Cottages, and Chalets
- Bed & Breakfasts, Inns
- Island
Here, you can customize your own room that will host up to six people and enjoy plenty of luxury comforts that you expect in a luxury hotel... more
- Beach
- Family
- Fishing
- Romantic
- Luxury
- Boutique
- Holiday
- Bed & Breakfasts, Inns
At Home in Key West strives to do exactly as their name suggests: make you feel right at home. Their impressive selection of Key West accommodations... more
- Beach
- Family
- Nature
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
- Holiday
- Island
- Villas and Condos
Tranquility Bay Beachhouse Resort's beautiful setting on the Gulf of Mexico offers you a truly luxurious beach vacation unlike any you've experienced... more
- Beach
- Family
- Reunions
- Nature
- Fishing
- Romantic
- Luxury
- Historical
- Honeymoon
- Diving
- Holiday
- Island
- Villas and Condos
Ranging from a variety of styles and sizes, Barefeet Rnetals offers everything you expect in a luxurious getaway. Choose from waterview rentals to... more
- Beach
- Family
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Honeymoon
- Diving
- Holiday
- Island
- Villas and Condos
From the four incredible swimming pools to delightful poolside dining at the Café Blue to an unbeatable oceanfront location, you'll find luxury... more
- Beach
- Family
- Reunions
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Honeymoon
- Holiday
- Island
- Villas and Condos
Built with city-chic luxuries and total comfort in mind, the La Concha Hotel & Spa has been updated to encourage relaxation, entertainment, and... more
- Family
- Nature
- Romantic
- Luxury
- Historical
- Honeymoon
- Island
- Spa
- Villas and Condos
The Garden House is an elegant retreat for your Key West vacation. Here, you will choose from twelve charming rooms, each with its own selection of... more
- Beach
- Family
- Romantic
- Luxury
- Honeymoon
- Island
Pier House Resort & Spa is a luxurious location to spend your next vacation. Indulge your palate at one of the three onsite award winning... more
- Beach
- Family
- Meetings
- Reunions
- Wedding
- Nature
- Fishing
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
- Health
- Diving
- Holiday
- Island
- Spa
Florida Keys Vacation Rentals has a wide range of luxury accommodations throughout the beautiful Florida Keys. Choose from accommodations located in... more
- Beach
- Family
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Honeymoon
- Holiday
- Island
- Villas and Condos