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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 44 Luxury Resorts

Oceans Edge Key West Resort & Marina

Key West, Florida, United States
$199
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
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Pet Friendly
  • 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

Keys Holiday Rentals, Inc.

Islamorada, Florida, United States
$170
tel:+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
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Coral Bay Resort

Islamorada, Florida, United States
$129
1-855-533-0216

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

Tranquility Bay Beach House Resort

Marathon, Florida, United States
$279
1-855-604-1305

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

Key West Bed & Breakfast

Key West, Florida, United States

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

Resort features:
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns
  • Island

The Inn on Fleming

Key West, Florida, United States
$250
1-305-294-4043

The Inn on Fleming is an unforgettable Key West vacation destination. The inn features elegant accommodations that are all impeccably furnished with... more

Resort features:
  • Nature
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns
  • Island

Westwinds Inn

Key West, Florida, United States
$135
1-305-296-4440

Come experience a Victorian-inspired getaway, complete with the comforts of a modern hotel. At Westwinds Inn, you'll experience the hospitality,... more

Resort features:
  • Beach
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

Coco Plum Inn

Key West, Florida, United States

ouples 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

Resort features:
  • Nature
  • Romantic
  • Luxury
  • Honeymoon
  • Bed & Breakfasts, Inns
  • Island

Preferred Properties Key West

Key West, Florida, United States
$200
1-305-294-3040

Preferred Properties Key West features an exclusive list of luxurious condominiums and homes around Key West. Private swimming pools, outdoor hot... more

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

Florida Keys Vacation Rentals Inc.

Key West, Florida, United States
$200
1 (305) 743-5181

Florida Keys Vacation Rentals has a wide range of luxury accommodations throughout the beautiful Florida Keys. Choose from accommodations located in... more

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

Luxury Rentals by At Home in Key West

Key West, Florida, United States
$175
1-305-296-6996

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

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

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

Vacation Homes of Key West

Key West, Florida, United States
$250
1-305-294-7358

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

The Cabana Inn

Key West, Florida, United States
$209
1-305-296-2323

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

Resort features:
  • Beach
  • Family
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

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

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

The Gardens Hotel

Key West, Florida, United States
$359
1-305-294-2661

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

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

Showing 1-20 of 44 Luxury Resorts

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