Island Vacations in Florida - HomeToGo base64Hash Island Vacations in Florida - HomeToGo

Island Vacations in Florida

Florida
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Rating
4.5+
4+
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

House Englewood East
Jun 29 - Jul 6
$129 per night
House ∙ 6 guests ∙ 2 bedrooms
Lovely Vacation Home in Englewood East with Beautiful Pool
Englewood East, Englewood, Florida
Details
Vrbo
View deal
View deal
House Jensen Beach
Nov 25 - Dec 2
$99 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Jensen Beach
5.0
Outstanding (2 ratings)
Jensen Beach, Martin County, Florida
Details
Vrbo
View deal
View deal
House Indian Shores
Dec 9 - Dec 16
-30%
$304
$212 per night
House ∙ 6 guests ∙ 2 bedrooms
Wonderful Vacation Home in Indian Shores with Grill & Pool
5.0
Outstanding (1 rating)
Indian Shores, Pinellas County, Florida
Details
Vrbo
View deal
View deal
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

Villa Key West
Aug 3 - Aug 10
-46%
$2,260
$1,221 per night
Villa ∙ 15 guests ∙ 6 bedrooms
Wonderful Villa in Key West with Tropical Garden, Close to West Martello Tower + Window View
4.3
Very good (31 ratings)
Key West, Florida Keys, Florida, United States
Details
Vrbo
View deal
View deal
Condo Key West
May 24 - May 31
-23%
$300
$231 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Key West with Private Balcony + Exceptional View
4.6
Excellent (104 ratings)
Key West, Florida Keys, Florida, United States
Details
Vrbo
View deal
View deal
Condo Key West
Sep 14 - Sep 21
-29%
$327
$232 per night
Condo ∙ 3 guests ∙ 1 bedroom
Charming Condo in Key West with Large Balcony, Next to Mallory Square
5.0
Outstanding (146 ratings)
Key West, Florida Keys, Florida, United States
Details
Vrbo
View deal
View deal

Information about Island Vacations in Florida

📏 Average home size 198 m²
😎 Least busy month October
🛏️ Popular home types Apartment rental 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

Frequently Asked Questions

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

There is a lot of House rental and Apartment rental that are great for Island Vacations in Florida.

Island Vacations in Florida: How much does it cost to rent a vacation home in Florida?

You can get a great vacation rental from $305 and get discounts up to 56%!

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

The average size for a House rental is 198 m² and may fit 9 guests on average which is ideal for large groups.

The Weather in Florida

max.
Min.
75°
59°
5 days 5
max.
Min.
73°
55°
7 days 7
max.
Min.
77°
61°
6 days 6
max.
Min.
84°
66°
7 days 7
max.
Min.
88°
70°
9 days 9
max.
Min.
90°
75°
15 days 15
max.
Min.
90°
75°
19 days 19
max.
Min.
91°
77°
18 days 18
max.
Min.
88°
75°
14 days 14
max.
Min.
82°
70°
7 days 7
max.
Min.
77°
63°
6 days 6
max.
Min.
75°
59°
5 days 5
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Average Nightly Rental Prices in Florida

Click on any bar to see price and availability information

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

Show more

Explore More Vacation Ideas

Show more
image-tag