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
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
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
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
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
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
Luxury is around every corner when you stay at the Oceans Edge Key West Hotel & Marina. From the full-service marina to the six oceanfront... more
- Beach
- Family
- Meetings
- Reunions
- Wedding
- Nature
- Fishing
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
- Holiday
- 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
Regardless of group size, you'll experience unparalleled luxury at Key West Vacation Rentals. For example, the The Curry House is a nine bath/nine bed... more
- Beach
- Family
- Golf
- Nature
- Fishing
- Romantic
- Luxury
- Honeymoon
- Diving
- 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
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
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
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
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
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
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
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
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
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
The Curry House is a charming retreat that's welcomed guests since the mid-1900s. It's nine bedrooms each offer its own unique style and amenities... more
- Beach
- Family
- Romantic
- Luxury
- Honeymoon
- Island