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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 36 Island Resorts

1800 Atlantic, All Florida Keys Property Management

Key West, Florida, United States
$300
1-844-334-0106

Enjoy the ultimate island experience when you stay with 1800 Atlantic! Ideally located on the beautiful Florida Keys, this exciting destination offers... more

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

Island City House Hotel

Key West, Florida, United States

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 of the Florida Keys archipelago located off the southern tip of Florida. Surrounded by the Gulf of Mexico and... more

Resort features:
  • 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

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

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

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

Rent Key West Vacations

Key West, Florida, United States
$150
1.800.833.7368

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

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

Barefeet Rentals

Key Largo, Florida, United States
$175
1-305-394-9787

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
  • 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

Keys Holiday Rentals, Inc.

Islamorada, Florida, United States
$170
1-305-664-8808

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

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

Tranquility Bay Beach House Resort

Marathon, Florida, United States
$279
1-(844)-489-9665

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
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Rock Reef Resort

Key Largo, Florida, United States
$115
1-305-852-2401

The Florida Keys are a stretch of beautiful tropical islands along the southern tip of Florida. Surrounded by the Atlantic Ocean and the Gulf of... more

Resort features:
  • Beach
  • Family
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Holiday
  • Island

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

Coral Bay Resort

Islamorada, Florida, United States
$129
1.305.664.5568

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 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

The Paradise Inn

Key West, Florida, United States
$269
1-305-293-8007

Key West, Florida is everything you're looking for in a magical island retreat! Part of the Florida Keys archipelago, Key West is also Florida's most... more

Resort features:
  • Beach
  • Family
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Bed & Breakfasts, Inns
  • Island

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

Showing 1-20 of 36 Island Resorts

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