Vacation Rentals on Florida Islands

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Island Vacation Rentals in Florida

Discover the largest selection of Florida Island vacation rentals. Book a dreamy island getaway reminiscent of the Caribbean islands through our list of properties for rent by owner below.

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From/Per night^$205

Oceanside, pet friendly, 2/2 smart home with paddle equip.-SUPs, kayaks Property

Marathon Vacation Rentals

2/BR 2/BA SLEEPS 5

From/Per night^$235

Private Villa Paradise! Just steps to #1 Beach 2br/2ba private lanai and Patio!

Siesta Key Vacation Rentals

2/BR 2/BA SLEEPS 6

From/Per night^$571

Renovated 4 bedroom directly on #1 Siesta Beach. Unobstructed views of gulf.

Siesta Key Vacation Rentals

4/BR 2.5/BA SLEEPS 8

From/Per night^$250

Key Largo Ocean Front / Marina Front Condominium

Key Largo Vacation Rentals

2/BR 2/BA SLEEPS 6

From/Per night^$170

SeaDuction of Anna Maria Island

Holmes Beach Vacation Rentals

2/BR 2/BA SLEEPS 6

From/Per night^$160

Gorgeous Updated Condo in Oceanfront Building

Islamorada Vacation Rentals

2/BR 2/BA SLEEPS 6

From/Per night^$550

CASA CAYO BY THE SEA ~ Waterfront Paradise

Key Largo Vacation Rentals

2/BR 3/BA SLEEPS 6

From/Per night^$400

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo Vacation Rentals

3/BR 3/BA SLEEPS 6

From/Per night^$340

Your own private resort - Mockingbird Pointe - Waterfront, pool and dockage

Marathon Vacation Rentals

2/BR 2/BA SLEEPS 6

From/Per night^$1428

Islamorada - Oceanfront - Private 1 acre Estate | Heated Pool - 4000 sq.ft

Islamorada Vacation Rentals

4/BR 5/BA SLEEPS 12

From/Per night^$643

Luxury High End Islamorada Private Sandy Beach Access Hammocks, Kayaks, & More!

Islamorada Vacation Rentals

3/BR 2/BA SLEEPS 6

From/Per night^$183

TRADEWINDS Premium Beach Location & Gulf View - 11th Floor Renovated Condo

Marco Island Vacation Rentals

2/BR 2/BA SLEEPS 4

From/Per night^$300

Paradise Cozy Home

Marathon Vacation Rentals

3/BR 2/BA SLEEPS 8

From/Per night^$510

Large Heated Pool, 2 Master-Bedroom suites, Very Close to Gulf Beach

Anna Maria Vacation Rentals

4/BR 3.5/BA SLEEPS 8

From/Per night^$575

Luxury Private Vacation Estate on Sanibel

Sanibel Island Vacation Rentals

4/BR 2.5/BA SLEEPS 10

From/Per night^$230

AMI North End Private Heated Pool. Great location to the Beach

Anna Maria Vacation Rentals

2/BR 2/BA SLEEPS 6

From/Per night^$249

Backyard Bliss

Holmes Beach Vacation Rentals

2/BR 2/BA SLEEPS 4

From/Per night^$350

Diving, Fishing, Snorkeling, Kayaking Paradise - Golf Cart Included!

Key Largo Vacation Rentals

2/BR 2/BA SLEEPS 6

From/Per night^$156

Sandy's Siesta Key Condo

Siesta Key Vacation Rentals

2/BR 1.5/BA SLEEPS 4

From/Per night^$250

Nacho Condo

Perdido Key Vacation Rentals

3/BR 2/BA SLEEPS 7

From/Per night^$400

Family vacation on AMI w/pool 4BR, 2.5BA, 8 guests

Holmes Beach Vacation Rentals

4/BR 2.5/BA SLEEPS 8

From/Per night^$450

Key Largo Ocean Front Villa on the Beach with Incredible views

Key Largo Vacation Rentals

3/BR 3/BA SLEEPS 6

From/Per night^$400

Seaside Inn

Anna Maria Vacation Rentals

3/BR 2/BA SLEEPS 6

From/Per night^$1100

Gypsy Wind Island Retreat

North Captiva Island Vacation Rentals

5/BR 4.5/BA SLEEPS 14

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Are there Many Vacation Rentals on Florida Islands to Rent?

Florida has many beautiful islands with vacation rentals available for visitors. Florida Rental By Owners has over 570 island vacation rentals to browse and book. However, some of the most popular islands for vacation rentals include:

1. Anna Maria Island: Located on Florida's Gulf Coast, Anna Maria Island is a charming barrier island with plenty of vacation rental options. Visitors can choose from beachfront homes, condos, and cottages, all within walking distance of the island's many restaurants and shops.

2. Sanibel Island: Known for its beautiful beaches and world-class shelling, Sanibel Island is a top vacation rental destination. Visitors can choose from a variety of vacation rentals, including beachfront homes, condos, and cottages.

3. Siesta Key: This barrier island near Sarasota is known for its beautiful, powdery white sand beaches. Vacation rental options on Siesta Key include beachfront homes and condos, as well as smaller cottages and apartments.

4. Key West: Located at the southernmost point of the Florida Keys, Key West is a popular vacation rental destination with a laid-back vibe and plenty of attractions. Visitors can choose from a variety of vacation rentals, including historic homes, condos, and guesthouses.

5. St George Island: Nestled along Florida's Gulf Coast, beckons travelers with its pristine beaches, vibrant wildlife, and laid-back atmosphere. Escape the hustle and bustle as you immerse yourself in the island's natural beauty, where white sands meet turquoise waters. Whether you're craving a serene retreat or exciting outdoor adventures like fishing or kayaking, St. George Island promises an unforgettable getaway for all.

6. Marco Island: A paradise off Florida's southwest coast, boasts luxurious resorts, stunning beaches, and a myriad of outdoor activities. With its lush tropical surroundings and upscale amenities, it's the perfect destination for relaxation and indulgence. Explore the island's pristine shores, indulge in world-class dining, or embark on a thrilling eco-tour through the mangroves — Marco Island offers a slice of paradise for every traveler.

7. Longboat Key: An enchanting barrier island on Florida's Gulf Coast, captivates visitors with its serene beaches, upscale resorts, and championship golf courses. Discover a haven of tranquility where swaying palm trees and gentle ocean breezes set the scene for relaxation. Whether you're lounging on the sand, teeing off on the greens, or savoring fresh seafood at waterfront restaurants, Longboat Key promises a luxurious retreat immersed in natural beauty.

8. Siesta Key: A gem along Florida's Gulf Coast, is renowned for its powdery white sands and crystal-clear waters. Experience laid-back island life as you unwind on the beach, explore charming villages, or embark on thrilling water sports adventures. With its vibrant atmosphere and stunning sunsets, Siesta Key offers the perfect blend of relaxation and excitement for a memorable tropical escape.

9. Key Largo: The "First of the Florida Keys," entices visitors with its captivating underwater world, vibrant coral reefs, and lush tropical landscapes. Dive into adventure as you explore the John Pennekamp Coral Reef State Park, indulge in fresh seafood cuisine, or simply relax and soak in the island's serene atmosphere. Whether you're snorkeling through colorful marine life or basking in the sun on its pristine shores, Key Largo promises an unforgettable island getaway filled with natural beauty and relaxation.

10. Cudjoe Key: Nestled amidst the tranquil Florida Keys, offers a secluded paradise for travelers seeking a serene escape. Embrace the laid-back island lifestyle as you unwind in waterfront accommodations, explore pristine nature trails, or embark on unforgettable fishing expeditions. With its breathtaking sunsets and pristine waters, Cudjoe Key invites you to relax, recharge, and create cherished memories in a picturesque tropical setting.

To find the best vacation rental for your needs, it's recommended to start with a reputable vacation rental website or agency like FLARBO who verifies hosts before they are permitted to publish their rentals. Be sure to read reviews from past guests to ensure you choose a rental that meets your expectations

Are Keys considered Islands too?

Yes, the Florida Keys are a chain of islands located off the southern coast of Florida, extending from Key Largo in the north to Key West in the south. The Keys are a popular vacation destination known for their stunning beaches, clear waters, and laid-back atmosphere. There are many vacation rental options available throughout the Florida Keys, including beachfront homes, condos, and cottages. Visitors can enjoy a variety of activities, including snorkeling, diving, fishing, and exploring the many shops and restaurants on the islands.

What do I need to know to rent a beach house rental on a Florida island or Key?

Renting a beach house vacation rental on a Florida island or Key can be a great way to enjoy a relaxing and memorable vacation. Here are some things you should know before booking your rental:

1. Start your search early: Florida is a popular vacation destination, so it's best to start your search for a vacation rental as early as possible, especially if you're looking to visit during peak travel seasons.

2. Consider transportation: Depending on where you're staying, you may need to rent a car or plan for other transportation options. Some islands and keys have limited public transportation, so it's important to plan ahead to ensure you can get around easily.

3. Research the area: Before booking a rental, research the area to make sure it's the right fit for you and your travel companions. Consider things like proximity to the beach, nearby attractions, and local restaurants and shops.

4. Check for any restrictions: Some vacation rentals may have restrictions on things like pets, smoking, or noise levels, so it's important to read the rental agreement carefully and ask questions if anything is unclear. For example pets may not be permitted on the beach.

5. Check the amenities: Make sure the rental has all the amenities you need, such as a fully equipped kitchen, air conditioning, and Wi-Fi. Check the listing for details on what's included and what you'll need to bring with you.

6. Read reviews: Read reviews from past guests to get an idea of what to expect from the rental and the property management company. Look for reviews that mention the cleanliness of the rental, the responsiveness of the management team, and any issues that guests encountered during their stay.

7. Understand the rental agreement: Be sure to carefully review the rental agreement before booking. Understand the terms and conditions, cancellation policy, and any additional fees that may apply.

8. Prepare for your stay: Once you've booked your rental, make sure you're prepared for your stay. Pack appropriately for the weather and activities you have planned, and bring any essentials you'll need during your stay.

By following these tips, you can find the perfect beach house vacation rental on a Florida island or Key for a relaxing and enjoyable vacation.

What are the Typical Stay Periods for Island rentals?

The way in which Florida beach house vacation rentals can be rented varies depending on factors such as the location of the rental (city zone) and the preferences of the host.

nightly
weekly
monthly
seasonally (3 or more months)

What is the Typical Turnover Day for Island rentals?

During high season, Florida beach house vacation rentals typically have a Friday or Saturday turnover date in accordance with local standards, although this may vary depending on the preferences of the individual host.

Friday or Saturday during high season and holidays
Any day during low season

How much is rent for Beach House Vacation Rentals on Florida Islands?

Low range from $83 per night
High range from $2,500 per night

Beachfront Rentals on Florida Islands

There are many beachfront vacation rentals on islands in Florida. With over 8,000 miles of coastline and numerous islands, Florida offers a wide range of beachfront vacation rental options. From cozy cottages to luxurious villas, there are vacation rentals to suit every taste and budget. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, you're sure to find the perfect beachfront vacation rental on a Florida island. Using the beachfront filter there are 142 beachfront rentals on Florida islands on FLARBO

Vacation Rentals with Boat Docks on Florida Islands

There are many boat-friendly vacation rentals on islands in Florida. With its abundant waterways and numerous islands, Florida is a popular destination for boaters. Many vacation rentals in Florida offer convenient access to boating and water sports activities, and some even have their own docks or boat slips. Whether you're looking to explore the local waterways or enjoy a day of fishing, you're sure to find a boat-friendly vacation rental on a Florida island that meets your needs. Using the boat friendly filter there are 129 boat friendly rentals on Florida islands on FLARBO

Luxury Vacation Rentals on Florida Islands

There are many luxury vacation rentals on islands in Florida that offer high-end amenities and services. From luxurious villas with private pools and beach access to high-end condos with stunning ocean views, there are many options for those seeking a luxury vacation rental experience in Florida. Some of the most popular luxury vacation rental destinations in Florida include the Florida Keys, Anna Maria Island, Sanibel Island, Captiva Island, and Amelia Island. Keep in mind that luxury rentals typically come with a higher price tag, but they can be worth it for those seeking a truly special and indulgent vacation experience. Using the luxury filter there are 176 luxury rentals on Florida islands on FLARBO

Florida Rentals on Islands for Monthly Stays - Snowbird Rentals

There is a high demand among winter travelers for long-term, extended stays and monthly beach house rentals. By selecting the long-term suitability filter, you can find 277 island monthly or seasonal rental options that cater to the needs of snowbirds.

Florida Island Rentals with Pools and Hot Tubs

Florida Islands are popular vacation destinations, known for their temperate weather and outdoor activities. Many travelers are seeking beach house rentals for their stay, and amenities such as pools and hot tubs are important factors in their decision. Fortunately, there are numerous options for rentals with pools and hot tubs, making this an ideal year-round vacation spot.

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Florida Rentals by Owner

Island Vacation Rentals in Florida