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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 34 Luxury Resorts

Chesapeake Beach Resort

Islamorada, Florida, United States
$179
1-866-588-0250

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

Resort features:
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Oceans Edge Key West Hotel & Marina

Key West, Florida, United States
$299
1-877-250-3908

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

Resort features:
  • Beach
  • Family
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island

Coral Bay Resort

Islamorada, Florida, United States
$129
1-888-328-0454

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

Resort features:
  • Beach
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island

Keys Holiday Rentals, Inc.

Islamorada, Florida, United States
$170
1-866-967-3004

Keys Holiday Rentals features a wide range of charming accommodations throughout the Upper Keys. These spacious rentals offer many modern amenities... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

The Gardens Hotel

Key West, Florida, United States
$359
1-866-806-8810

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

Resort features:
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island

Rent Key West Vacations

Key West, Florida, United States
$150
1-866-980-7608

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

Resort features:
  • Beach
  • Family
  • Golf
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Historical
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Barefeet Rentals

Key Largo, Florida, United States
$175
1-866-599-3095

Ranging from a variety of styles and sizes, Barefeet Rnetals offers everything you expect in a luxurious getaway. Choose from waterview rentals to... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Diving
  • Holiday
  • Island

Luxury Rentals by At Home in Key West

Key West, Florida, United States
$175
1-877-695-2791

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

Resort features:
  • Beach
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Vacation Homes of Key West

Key West, Florida, United States
$250
1-866-241-1140

Vacation Homes of Key West prides themselves on offering travelers with an impressive selection of accommodations that are beyond all your... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Holiday
  • Island
  • Villas and Condos

Florida Keys Vacations Inc.

Marathon, Florida, United States
$251
1-855-478-7640

A trip with Florida Keys Vacations Inc will help you redefine the idea of luxury travel. Lavish vacation homes feature oversized private decks and... more

Resort features:
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Island
  • Villas and Condos

Parrot Key Resort

Key West, Florida, United States
$179
1-866-939-3715

From the four incredible swimming pools to delightful poolside dining at the Café Blue to an unbeatable oceanfront location, you'll find luxury... more

Resort features:
  • Beach
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Tranquility Bay Beach House Resort

Marathon, Florida, United States
$279
1-866-452-5369

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

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Curry House

Key West, Florida, United States
$138
1-305-294-6777

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

Resort features:
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Island

Garden House Bed & Breakfast

Key West, Florida, United States
$168
1-305-296-5368

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

Resort features:
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Island

Key West Vacation Rentals

Key West, Florida, United States
$169
1-305-296-9292

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

Resort features:
  • Beach
  • Family
  • Golf
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Sunrise Suites Resort

Key West, Florida, United States
$169
1-305-296-6661

The spacious two-bedroom, two-bathroom condominiums at Sunrise Suites Resort ensure your complete comfort and convenience. These charming rentals are... more

Resort features:
  • Beach
  • Family
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon

Pier House Resort & Spa

Key West, Florida, United States
$330
1.305.296.4600

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

Resort features:
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Health
  • Diving
  • Holiday
  • Island
  • Spa

La Concha Hotel & Spa

Key West, Florida, United States
$213
1-305-296-2991

Built with city-chic luxuries and total comfort in mind, the La Concha Hotel & Spa has been updated to encourage relaxation, entertainment, and... more

Resort features:
  • Family
  • Nature
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Island
  • Spa
  • Villas and Condos

Sunset Key Guest Cottages, a Luxury Collection Resort

Key West, Florida, United States
$251
1-800-937-8461

Imagine yourself sipping your morning coffee as you relax in a comfortable Adirondack chair on the private porch of a charming cottage as a basket of... more

Resort features:
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Romantic
  • Luxury
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Island
  • Spa

1800 Atlantic Condominiums

Key West, Florida, United States
$195
1-800-433-2819

Each interior space at 1800 Atlantic Condominiums is designed for convenience and stylish comfort. Features include living room wet bars, oversized... more

Resort features:
  • Beach
  • Family
  • Luxury
  • Romantic
  • Villas and Condos

Showing 1-20 of 34 Luxury Resorts

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