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Island Vacations in Florida

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Island Vacations in Florida: Recommended rentals

Island Vacations in Florida: find your perfect rental from just $61 per night!

House Pensacola Beach
-82%
Feb 23 - Mar 2
House ∙ 8 guests ∙ 3 bedrooms

Child-Friendly Charming Vacation Home with Barbecue | Beach Nearby | Pet-Friendly

Pensacola Beach, Escambia County, Florida
$677$168
per night
Excellent
$677$168
per night
View deal
House Destin
-68%
Nov 8 - Nov 15
House ∙ 14 guests ∙ 5 bedrooms

House with Pool

Destin, Okaloosa County, Florida
$1,329$498
per night
Excellent
$1,329$498
per night
View deal
House Miramar Beach
Nov 10 - Nov 17
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home with Heated Pool, Garden & Terrace | Perfect for Remote Work

Miramar Beach, Walton County, Florida
$379
per night
Outstanding(14 ratings)
$379
per night
View deal
Villa Siesta Key
Jul 12 - Jul 19
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with BBQ, Terrace & Heated Pool

Siesta Key, Sarasota County, Florida
$388
per night
Outstanding(7 ratings)
$388
per night
View deal
House Miramar Beach
Jun 21 - Jun 28
House ∙ 10 guests ∙ 5 bedrooms

House with Heated Pool, Patio & BBQ | Nature View

Miramar Beach, Walton County, Florida
$469
per night
Excellent(30 ratings)
$469
per night
View deal
House Marathon
-39%
Sep 6 - Sep 13
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Terrace, Grill & Private Pool | Nature View

Marathon, Monroe County, Florida
$594$385
per night
Excellent(63 ratings)
$594$385
per night
View deal
Condo Pensacola Beach
-77%
Nov 22 - Nov 29
Condo ∙ 10 guests ∙ 4 bedrooms

Condo with 4 Rooms for 10 Persons

Pensacola Beach, Escambia County, Florida
$896$255
per night
Excellent(113 ratings)
$896$255
per night
View deal
Condo Bel Air
-70%
Nov 22 - Nov 29
Condo ∙ 10 guests ∙ 5 bedrooms

Condo with Heated Pool, Terrace & Barbeque | Nature View

Bel Air, Panama City Beach, Florida
$710$329
per night
Good(182 ratings)
$710$329
per night
View deal
Condo Eledadolla
-54%
Oct 18 - Oct 25
Condo ∙ 10 guests ∙ 4 bedrooms

Beautiful Condo with Heated Pool, Sauna & Garden | Close to the Beach

Eledadolla, Pensacola Beach, Florida
$560$411
per night
Excellent(30 ratings)
$560$411
per night
View deal
House St. Augustine
-64%
Feb 22 - Mar 1
House ∙ 6 guests ∙ 3 bedrooms

Family-Oriented Spacious Vacation Home with Barbeque & Pool | Dogs Allowed

St. Augustine, St. Johns County, Florida
$417$157
per night
Very good
$417$157
per night
View deal
Condo Bradenton
-29%
Apr 26 - May 3
Condo ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Wonderful Condo | Nature View

Bradenton, Manatee County, Florida
$229$179
per night
$229$179
per night
View deal
Villa Beaches
Apr 5 - Apr 12
Villa ∙ 10 guests ∙ 4 bedrooms

Fully Equipped Villa with Yard & Grill | Next to the Beach | Perfect for Remote Work | Dogs Allowed

Beaches, Jacksonville, Florida
$285
per night
Outstanding(5 ratings)
$285
per night
View deal
House Indian Rocks Beach
-34%
Sep 6 - Sep 13
House ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Lovely Vacation Home with Barbeque & Patio | Nature View | Next to the Beach | Pets Are Welcome

Indian Rocks Beach, Pinellas County, Florida
$347$241
per night
Excellent(78 ratings)
$347$241
per night
View deal
House ChampionsGate
-48%
Mar 29 - Apr 5
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home with Private Pool, Patio & BBQ

ChampionsGate, Four Corners, Florida
$522$292
per night
Very good(5 ratings)
$522$292
per night
View deal
House Miramar Beach
-62%
Mar 8 - Mar 15
House ∙ 17 guests ∙ 7 bedrooms

Child-Friendly Ample House with Terrace, Private Pool & Barbeque

Miramar Beach, Walton County, Florida
$1,704$894
per night
Excellent(18 ratings)
$1,704$894
per night
View deal

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.
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

House Key West
May 18 - May 25
-35%
$889
$623
per night
House ∙ 6 guests ∙ 3 bedrooms

House with Yard, Private Pool & Barbecue | Close to Mallory Square

5.0
Outstanding(12 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Aug 9 - Aug 16
-25%
$482
$364
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-Oriented House with Barbecue, Terrace & Pool | Close to Mallory Square | City View

4.8
Outstanding(63 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
Sep 6 - Sep 13
-25%
$737
$562
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home with Barbecue, Terrace & Private Pool | Close to Southernmost Point

4.9
Outstanding(12 ratings)
Key West, Monroe County, Florida, United States
View deal

Information about Island Vacations in Florida

📏 Average home size 211 m²
😎 Least busy month May
🛏️ Popular home types Condo and House rental
🌡️ Hottest months August and June
❄️ Coldest months 55 °F in February and January
🌧️ Rainiest months 19 rainy days in July and August

Island Vacations in Florida: frequently asked questions

Island Vacations in Florida: What is the cost per night?

The average price for a vacation rental in Florida is usually around $348 and $502 per night.

Island Vacations in Florida: is there a good selection of vacation rentals for groups of guests?

Usually the average House rental size is 211 m² and can fit 9 people on average which is ideal for large groups.

Island Vacations in Florida: what types of vacation homes can I find?

We would suggest browsing our selection of House rentals and Condos in Florida.

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

Vacation rentals near Florida with popular amenities

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