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Island Vacations in Florida

Florida
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Florida
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Popular Filters to find the Perfect Home Rental in Florida

Pool
2 Adults
1 Bedroom
House
Pets allowed
4 Adults

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

House Cutler Bay
May 7 - May 14
-41%
$313
$185 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Cutler Bay with Private Pool + Pool Views

4.8
Outstanding (5 ratings)
Cutler Bay, Miami-Dade County, Florida
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House Panacea
Feb 1 - Feb 8
-49%
$495
$250 per night
House ∙ 12 guests ∙ 4 bedrooms

Lovely Vacation Home in Panacea with Grill & Patio + Unobstructed Views

4.7
Excellent (131 ratings)
Panacea, Wakulla County, Florida
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House Barefoot Beach
Aug 3 - Aug 10
-41%
$600
$352 per night
House ∙ 10 guests ∙ 5 bedrooms

Beautiful House in Barefoot Beach with Spacious Pool + Beach Nearby

4.9
Outstanding (65 ratings)
Barefoot Beach, North Naples, 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
Oct 11 - Oct 18
-71%
$606
$173 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Pleasant Condo in Key West with Private Parking, Next to Southernmost Point

4.5
Excellent (66 ratings)
Key West, Monroe County, Florida, United States
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House Key West
Sep 8 - Sep 15
-71%
$2,368
$677 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Key West with Lagoon-Style Pool

4.8
Outstanding (199 ratings)
Key West, Monroe County, Florida, United States
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Accommodation Key West
Jun 15 - Jun 22
-39%
$365
$225 per night
Accommodation ∙ 2 guests ∙ 1 bedroom

Rental in Key West with Private Balcony, Next to Southernmost Point

4.2
Very good (272 ratings)
Key West, Monroe County, Florida, United States
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Information about Island Vacations in Florida

💳 Highest rates in March
🥳 Busiest month December
🛏️ Popular home types House rental and Apartment rental
🌡️ Hottest months 91 °F in August and June
❄️ Coldest months February and January
🌧️ Rainiest months 19 rainy days in July and August

Frequently Asked Questions

Island Vacations in Florida: What is the price per night for a stay?

The average price for a vacation rental in Florida is usually between $325 and $509 per night.

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

The size of a House rental is 209 m² and can fit 9 guests on average which is great for large groups.

What types of vacation homes can I find for Island Vacations in Florida?

You can find 24,064 Apartment rental and 110,688 House rental for Island Vacations in Florida on HomeToGo.

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Average Nightly Rental Prices in Florida

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Vacation Rental Price Information in Florida

Vacation Rental Availability in Florida

Rental availability information in Florida

Island Vacations in Florida: Top Destinations

Island Vacations in Florida Inspiration

Top Vacation Ideas in Florida

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