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Island Vacations in Florida

Florida
Anytime
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Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Island Vacations in Florida: Top Destinations

Enjoy Island Vacations in Florida

Many families, couples and friends love to escape to the Sunshine State on their vacation. Florida promises great weather, Southern hospitality and natural beauty, across the peninsula. If you want to experience a different side of Florida next time you're in the South, head to one of the state's islands. They're the perfect way to enjoy a romantic experience of the Sunshine State.

Island Vacations in Florida: Top Accommodations

Resort Ocean Walk Resort Condo
Oct 7 - Oct 14
-27%
$291
$214 per night
Resort ∙ 8 guests ∙ 2 bedrooms
Resort in Ocean Walk Resort Condo with Free Parking + Intercostal Views
Ocean Walk Resort Condo, Daytona Beach, Florida
Free cancellation
Details
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Condo Okaloosa Island
Nov 4 - Nov 11
-73%
$450
$120 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Condo in Okaloosa Island with Pool + Amazing Views
Okaloosa Island, Okaloosa County, Florida
Details
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House Davenport
Dec 9 - Dec 16
-61%
$218
$86 per night
House ∙ 10 guests ∙ 3 bedrooms
Pleasant House in Davenport with Pool & Grill
Davenport, Polk County, Florida
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Top 5 Romantic Islands to Visit in Florida

Top 5 Romantic Islands to Visit in Florida

Florida promises the second-largest number of islands anywhere within the United States and you better believe there are many romantic hotspots among them! Florida's islands promise beaches of white sand and quiet relaxation for couples looking to get away from it all.

  • 1. Key West

    Key West is one of Florida's most famous islands and the reason why is no secret. This historic paradise is the most Southernmost island in Florida and the closest to Cuba. Expect to see pine trees, multicolored houses, and sandy beaches aplenty. Key West is a popular hotspot for foodies, with the island's restaurants acclaimed for their wines and farm to table cuisine. Visit the historic house of Ernest Hemingway for an interesting day out. A trip to Key West is a step back into a simpler time.

  • 2. Destin

    Visit Destin and relax on white sandy beaches on neighboring Crab Island. Crab Island is popular among tourists and is a hotspot for local wildlife; many tourism providers offer dolphin watching trips from here. Destin is well-known for its raucous Spring Break celebrations at Crab Island, making this the perfect destination for couples who like to party.

  • 3. Orlando

    Lovers of luxury will absolutely adore Little Boat Island, in Orlando. Escape the rides and discover Little Boat Island by boat; choose a small taxi boat for the most romantic ride. Little Boat Island Resorts provides secluded bungalows for couples, which are just set back from the beach. Only a minutes stroll will take you from the bungalow to the beach.

  • 4. Panama City Beach

    Just off the coast of Panama City Beach is the beautiful Shell Island. Shell Island​ is the perfect island to get away from it all. Discover unspoiled sandy beaches and wildflowers. Snorkeling enthusiasts adore visits to Shell Islands because of the wide variety of tropical fishes seen in its waters. ​If you're lucky, you may see dolphins!

  • 5. Clearwater

    Most people believe Clearwater Beach is in Mainland Florida, but it is, in fact, an island, connected to the mainland by a bridge. Over 2.5 extensive miles of beach stretch across Clearwater, making it the perfect place for sunseekers looking to improve their tan. Activity lovers will enjoy a trip to Clearwater, as companies providing snorkeling, dolphin watching, and water-skiing excursions are open on the beach.

Best Places to Stay for Island Vacations in Florida

Condo Key West
Sep 23 - Sep 30
-20%
$250
$200 per night
Condo ∙ 3 guests ∙ 1 bedroom
Charming Condo in Key West with Large Balcony, Next to Mallory Square
5.0
"Excellent" (112 ratings)
Key West, Florida Keys, Florida, United States
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Condo Key West
Sep 2 - Sep 9
-41%
$374
$219 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Key West with Private Balcony + Exceptional View
4.6
"Outstanding" (99 ratings)
Key West, Florida Keys, Florida, United States
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Condo Key West
Sep 16 - Sep 23
-36%
$350
$224 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Key West with Yard, Pool & Grill, Near Southernmost Point
5.0
"Excellent" (196 ratings)
Key West, Florida Keys, Florida, United States
Details
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Frequently Asked Questions

Island Vacations in Florida: What is the vacation rental cost in Florida?

On average, you can get a great vacation home for somewhere between $309 and $519 and find discounts up to 55%!

Can I find a vacation rental for a large group for Island Vacations in Florida?

Usually the size of a House rental is 201 m² and can fit 9 people on average which is ideal for large groups.

What kinds of vacation rentals can I find for Island Vacations in Florida?

There are many Apartment rental and House rental that are perfect for Island Vacations in Florida.

The Weather in Florida

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Average Nightly Rental Prices in Florida

Vacation Rental Price Information in Florida

Vacation Rental Availability in Florida

Rental Availability Information in Florida

Island Vacations in Florida Inspiration

Top Vacation Ideas in Florida

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