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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 29 Island Resorts

Oceans Edge Key West Hotel & Marina

Key West, Florida, United States
$299
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
  • Fishing
  • Romantic
  • 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! You'll feel completely secluded in the best way possible when you stay at Rent Key West Vacation.... more

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

Luxury Rentals by At Home in Key West

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

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

The Gardens Hotel

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

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

Keys Holiday Rentals, Inc.

Islamorada, Florida, United States
$170
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
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Barefeet Rentals

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

Located in the Upper Florida Keys, Barefeet Rentals occupies the island of Key Largo and is just a short drive to Islamorada. Affectionately known as... more

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

Coral Bay Resort

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

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

Florida Keys Vacations Inc.

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

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
  • Romantic
  • Luxury
  • Honeymoon
  • Island
  • Villas and Condos

Vacation Homes of Key West

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

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

Parrot Key Resort

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

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

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:
  • Family
  • Nature
  • Romantic
  • Honeymoon
  • Island

Tranquility Bay Beach House Resort

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

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

Garden House Bed & Breakfast

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

Beautiful Key West is a year-round destination for anyone looking to experience the tranquil and tropical island life. At Garden House, you'll... more

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

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

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

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

Chesapeake Beach Resort

Islamorada, Florida, United States
$179
1-305-664-4662

As part of the Florida Keys, Islamorada is the Sport Fishing Capital of the World. But if you're not into fishing, there are plenty of other things to... more

Resort features:
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • 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

Sunset Key Guest Cottages, a Luxury Collection Resort

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

The Sunset Key Guest Cottages resort is located on the magnificent Sunset Key, a 27-acre Florida island. Cars are not allowed on the island, and you... more

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

Ocean Key Resort & Spa

Key West, Florida, United States
$459
1.800.328.9815

Ocean Key Resort & Spa is an intimate world-class resort in Key West, where sunny days glide naturally into moonlit nights and every sunset is a... more

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

Showing 1-20 of 29 Island Resorts

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