Island holiday rentals in Florida

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Top-rated island rentals in Florida

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A coastal beach house is observed from the water, displaying a vibrant color scheme and surrounded by palm trees. An American flag and a black flag are seen flying nearby. The scene captures the serenity of an evening sky with a hint of blue.

Home in Grant-Valkaria

Island Getaway in Grant, FL

Welcome to the Island! Located on a private island (*boat access only) in the intracoastal waterway, VIP Island is minutes from Melbourne & only a 1.5 hr drive from Orlando. The perfect spot for fishing, paddling or just to relax and enjoy seaside living. The home is 2 story Cape Cod style beach house located on the northern tip of the island. Surrounded by water and plenty of beach, it's the perfect spot to enjoy the sunrise and sunset. Kick off your shoes, bring your bathing suit and enjoy!

Guest favourite

An aerial view showcases a private island surrounded by water, featuring lush greenery and two tiny homes. A manicured lawn is visible with seating areas, umbrellas, and pathways that create a serene outdoor environment.

Tiny home in Sarasota

4.87 out of 5 average rating, 235 reviews

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

Top guest favourite

Tiny home in Sarasota

4.96 out of 5 average rating, 378 reviews

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

A comfortable living space features light green leather sofas arranged around a central ottoman. Above the seating area, large windows provide natural light, while wall art adds interest to the room. The hardwood floors reflect the inviting atmosphere of the home.

Townhouse in Lee County

5 out of 5 average rating, 12 reviews

Amazing Harbor Views! Waterfront Property w/ Dock!

Steps from the water and right next to the bay, located on a barrier island. Get to the island by a short hourly water ferry ride or private charter. No cars, no roads...nothing but sandy trails with electric golf carts as transportation (included). Launch your kayak (provided) steps from the front door on the private bay beach. Dock is available. Heated pool, tennis courts, private beach access with beach-front gazebo minutes from the property. 3 minute golf cart ride to Gulf beaches.

Guest favourite

Two tall palm trees frame a serene beach scene, their fronds gently swaying in the breeze. The turquoise water stretches toward the horizon under a bright blue sky, providing a tranquil atmosphere that invites relaxation.

Flat in Venice

4.92 out of 5 average rating, 37 reviews

Venice Island Tropical Oasis w Pool & Spa

Come explore Island life! Walkable to beach & Sharky's. Great outdoor fun, paddle board/kayak/snorkel/surf/fish/boat/hike/bike/beach yoga/tennis/pickle ball/basket ball/golf. Historic & quaint little downtown is 1.2 miles, w/ boutiques, cafes, fine dining, art festivals, theatre, market. The studio offers comfortable Tommy Bahama queen bed/tv/fridge/kitchenette/sofa/backyard, 46 jet hot tub, NEW POOL, "open air walk in shower", outdoor kitchen, bbq grill, 2 burner gas stove.

Top guest favourite

The spacious studio features high wood-beam ceilings and a mix of natural materials. A large, comfortable bed is positioned beside a vibrant seating area made of driftwood. A dining space with bar stools complements the serene atmosphere, enhancing the overall warmth and charm.

Loft in Merritt Island

5 out of 5 average rating, 38 reviews

'Bali House' Tranquil Merritt Island Oasis!

At this vacation rental, you won’t need to travel overseas to feel as though you’re immersed in a waterfront Balinese paradise. The picturesque views and tropical huts will beckon you to opt outside and enjoy your surroundings, while a gorgeous 1-bath studio awaits your return. Just a few miles away, wander white-sand beaches along the coast or tee off for the day on one of the many local golf courses. Either way, the Merritt Island getaway of your dreams awaits!

Top guest favourite

A vibrant graphic showcases the property's amenities and themed rooms, including a relaxing lake view, a game room, and a heated pool. Images of colorful decor, a spa, and entertainment options highlight the family-friendly atmosphere, accompanied by text emphasizing the house's spaciousness and features.

Villa in Kissimmee

4.97 out of 5 average rating, 115 reviews

Luxury Themed Villa 9 BR | Close to Disney

🏖️☀️🏄‍♀️Experience the heart of Orlando in this luxurious house! Perfect for an unforgettable time with family, this new house has 9 stylish bedrooms and can house 22 people! This house is incredibly close to Disney World, Universal, Sea World, and the Orlando Airport! Located in Storey Lakes, Orlando's premier resort, we have wonderfully themed bedrooms (perfect for kids!), a game room, and a patio and pool.🌴👙🩳🥽🩴 We'd love to welcome you here!❤️❤️

Guest favourite

The entrance showcases a charming front porch with two comfortable chairs and decorative green shutters on either side of the door. A welcoming white door is framed by ornamental trim, complemented by a tasteful wreath. Lush greenery adds to the tranquil atmosphere.

Cottage in Key West

4.86 out of 5 average rating, 65 reviews

Eyebrow Suite @ Eyebrow House

Eyebrow Suite – Spacious Two-Bedroom Retreat with Private Outdoor Oasis Located in the heart of Old Town Key West, just half a block from Duval Street, the Eyebrow Suite offers historic charm, modern comfort, and one of the most desirable addresses on the island. Set in a lovingly restored turn-of-the-century eyebrow house, this spacious two-bedroom suite is perfect for families, couples, or friends traveling together.

Top guest favourite

Home in Holmes Beach

4.98 out of 5 average rating, 44 reviews

Loggerhead - Private Pool + Golf Cart - AMI Oasis

Escape to the tranquility of Anna Maria Island in this charming 2-bedroom, 2-bathroom home nestled on a peaceful, secluded street. -6-Person Golf Cart included! -Private heated Pool & backyard -4-minute walk to the beach