Island holiday rentals in Florida

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!

Private Tropical Oasis Pool Spa Walkable to Beach

Live the island dream in your private tropical oasis 🌴 Walk to the beach & Sharky’s, then unwind in your own spa-style retreat designed for relaxation and outdoor living. This cozy micro escape features a Tommy Bahama queen, kitchenette, an expansive backyard with pool, 46-jet hot tub, outdoor kitchen and open-air shower. Just 1.2 miles to historic Venice downtown with dining, boutiques, and charm. Perfect for a romantic getaway or a peaceful solo reset. See photos for the full experience!

@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.

@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)

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.

Dolphin Watch | Beachfront on private Beach

Dolphin Watch Welcome to Dolphin Watch, an exquisite beachfront villa located in the serene Cape Haze, Florida. This stunning five-bedroom property offers breathtaking ocean views and is designed for unforgettable beach vacations. Spanning over 3,461 square feet, Dolphin Watch comfortably accommodates up to 10 guests, making it perfect for families or groups seeking relaxation and adventure. The villa features four well-appointed bathrooms, ensuring convenience and privacy for all.

'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!

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!❤️❤️

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.

Loggerhead - Private Pool + Golf Cart - AMI Oasis

Loggerhead 🐢 - Escape to your island oasis on Anna Maria Island — just a 4-minute walk to the beach! 🏝️ Unwind in your private heated pool, sip sunset drinks at the Tipsy Turtle bar, and cruise the island in your included 6-person golf cart. Perfect for families or couples seeking the ultimate beach getaway filled with sun, relaxation, and island charm.

Island Dream 2BR|Steps to Beach + Private pool/spa

Welcome to Island Breeze, your perfect beach getaway on Anna Maria Island! Located in the heart of Bradenton Beach, this charming 2-bedroom vacation rental is just a short walk to the beach, restaurants, shops, and local attractions, making it the ideal spot for couples, families, or small groups looking to experience the best of island living.