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
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- Luxury
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
Key West Bed & Breakfast
Key West Bed and Breakfast is everything you want in a luxurious Florida vacation. The inn is located in the Old Town area of Key West and features... more
- Romantic
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- 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
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- Luxury
- Honeymoon
- Bed & Breakfasts, Inns
- Island
Named "The Best in the World" by Conde Nast Traveler, rated #1 of 42 hotels in Key West by TripAdvisor, and called "The Prettiest Hotel in Key West"... more
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- Romantic
- Luxury
- Honeymoon
- Holiday
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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
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
Rent Key West Vacations offer numerous options that will have you feeling like you're in the lap of luxury. Choose properties with granite... more
- Beach
- Family
- Golf
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Historical
- 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
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
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
Keys Holiday Rentals features a wide range of charming accommodations throughout the Upper Keys. These spacious rentals offer many modern amenities... more
- Beach
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- Nature
- Fishing
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
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- Villas and Condos
Preferred Properties Key West features an exclusive list of luxurious condominiums and homes around Key West. Private swimming pools, outdoor hot... more
- Beach
- Family
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
- Holiday
- Island
- Villas and Condos
Originally a historic conch estate, the Cabana Inn now features charming cottages and an elegant inn that offers everything you're looking for in a... more
- Beach
- Family
- Fishing
- Romantic
- Ecotourism
- Luxury
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
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
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
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
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
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
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
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