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When it comes to a vacation on an island surrounded by tropical vistas and white, sandy beaches, the Florida Keys has everything for a perfect beach vacation. The Parrot Key Resort has five acres of gorgeous landscaped grounds and palm groves, the idyllic beachside resort contains beautiful beaches with the famous Florida Key sunsets. For those that want a more private island retreat, the Florida Keys Vacations Inc offers a variety of gorgeous rentals right on the islands, able to accommodate a wide variety of folk for their own luxury island retreat. Located within the heart of Islamorada, the La Jolla Resort Hotel gives you a taste of a true “Old Florida” style resort! Their docks give you a chance to cast a line or explore the waters along the shores, while the resort has a taste of historical luxury. The island vacation of your dreams awaits you in the Florida Keys!

Showing 1-20 of 35 Island Resorts

Oceans Edge Key West Resort & Marina

Key West, Florida, United States
$199
1-877-250-3908

Historic Stock Island is an unforgettable retreat in Florida's beautiful Key West. Oceans Edge Key West Hotel & Marina rests along the shores... 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

Head to Key West for a picturesque island retreat! The Florida Keys are a thin stretch of island archipelago off the southern tip of Florida and is... 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

The Florida Keys are an exciting island vacation experience that doesn't necessarily break the bank. When you plan your getaway with Keys Holiday... 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

Islamorada is comprised of six islands including Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key and the offshore islands of... 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

Experience a beautiful and relaxing island vacation when you plan your next Florida vacation at Tranquility Bay Beach House Resort. Located on... more

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

Island City House Hotel

Key West, Florida, United States
$185
1-305-294-5702

The Island City House Hotel is located in Key West. In the Gulf of Mexico, Key West is an island of 7.4 square miles, with an average temperature of... more

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

Key West Bed & Breakfast

Key West, Florida, United States

Key West is a stunning island retreat that's part of the Florida Keys archipelago located off the southern tip of Florida. Surrounded by the Gulf of... 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 located on the beautiful island of Key West, located among the Florida Keys off the southern tip of Florida. Surrounded by the... more

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

Coco Plum Inn

Key West, Florida, United States

Coco Plum Inn is located along the breathtaking coast of the Gulf of Mexico as part of the Florida Keys archipelago. Bask in the incredible ocean... 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

Key West is a beautiful island city in Florida's stunning Florida Keys, a collection of islands off the coast of Florida's southern tip. Key West is... 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

The beautiful Florida Keys are a group of tropical islands that stretch around 120 miles from the southern tip of Florida. Surrounded by the Gulf of... 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

Discover the magic of beautiful Key West, Florida, when you stay with At Home in Key West. This beautiful island retreat lets you unwind and take... 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

When staying at La Concha Hotel & Spa, you'll be on the beautiful Island of Key West. See views of the Atlantic Ocean and beautiful city from our... 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

Thanks to being a small island, wherever you are in Key West you're never too far away from everything else. From enjoying the island on a bicycle or... 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

Beautiful Key West is the perfect destination for when you're craving the laid-back, sunny island lifestyle. With Vacation Homes of Key West, you can... more

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

Pier House Resort & Spa

Key West, Florida, United States
$330
1.305.296.4600

While in the Keys, you'll be secluded on your own island! Enjoy views of the Gulf of Mexico while staying at Pier House Resort & Spa. Take... 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

There are few places better to experience the laid-back wonders of an island vacation than Key West. This famous Florida retreat welcomes guests from... more

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

The Gardens Hotel

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

Key West, Florida welcomes travelers from all over the world to discover it's majestic white sand beaches, stunning natural wonders, and relaxing... more

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

Florida Keys Vacations Inc.

Marathon, Florida, United States
$125
1-305-395-4370

Planning your next island getaway has never been easier than with Florida Keys Vacations Inc. Spend your days splashing around your own private... more

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

Parrot Key Resort

Key West, Florida, United States
$179
1-888-211-0348

Located on the beautiful island of Key West, a getaway at Parrot Key Resort is the tropical vacation you've been looking for. Here, you can feel... more

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

Showing 1-20 of 35 Island Resorts

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