The 17 Dreamiest Island Airbnbs Off the Coast of Florida
A short drive from Florida’s busiest cities -- but you’ll feel a world away.
Florida has more islands than you might think — thousands of keys, barrier islands, and tucked-away inlets stretch along its coastline — and while big-name destinations like Key West and Sanibel often steal the spotlight, the state is dotted with smaller, quieter islands that are just as inviting. From the pastel cottages of Anna Maria to the driftwood-strewn shores of Cedar Key, these are islands where the days move more slowly, the roads are narrow, and the beaches stretch for miles.
Some are close enough to make a last-minute weekend escape from cities like Miami, Tampa, or Orlando. Others, like North Captiva or Little Gasparilla, require a boat ride and a break from cell service. But whether you’re after Gulf views, sea turtle sightings, or a private dock to fish from at sunset, these islands offer a version of Florida that feels refreshingly out of step with the rest of the state.
I’ve rounded up some of Florida’s dreamiest Airbnbs scattered across the islands — from overwater bungalows in Key Largo to old Florida cottages that have been lovingly restored. Whether you’re traveling with kids, friends, or just yourself, there’s a place here that will make you want to unpack, unplug, and stay a little longer.
We hope you love the island Airbnbs we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
Amelia Island
Photo: Madison Y Photo / Shutterstock
Amelia Island lies at Florida’s northeastern edge, just below the Georgia border. It’s part of the Sea Islands chain, and while you’ll find the usual coastal rentals and golf carts, you won’t find the typical spring break chaos here. The island’s main town, Fernandina Beach, has a walkable historic district with late-1800s architecture, dive bars, and a few spots to grab fresh shrimp straight off the boat. Beyond town, you’ll find residential neighborhoods, state parks, and quiet stretches of beach. Amelia is laid-back, welcoming, and close enough to Jacksonville to make a last-minute weekend feel like a proper escape.
Private beachfront lighthouse seconds from the shoreline
If you’d like to be close to Fernandina Beach, check out this lighthouse Airbnb. Built in the 1980s by wooden-boat builders as a tribute to New England lighthouses, the three-bedroom home is perched on stilts, with parking for four cars underneath and private beach access through the dunes. It’s been featured in Dwell Magazine and on HBO’s Beach Cottage Chronicles, and it’s a well-known landmark on the island. The home has an open layout, a large dining table that seats eight, and a fully stocked kitchen. Outside, there’s a wrap-around deck with ocean views and a stash of essentials, including boogie boards and sandcastle tools.
Another great find near Fernandina is this three-bedroom family home ($650 per night) with an outdoor swimming pool. It also comes with extras like a golf cart and bikes for exploring the island, plus a private yard with a pool, firepit, grill, and spa.
Six guests, three bedrooms
Price: $670 per night
Anna Maria Island
Photo: UA-Visions / Shutterstock
Before you even cross the causeway, Anna Maria Island feels like a retreat. No high-rises or sprawling resorts — just pastel beach cottages, quiet neighborhoods, and the sound of palm fronds rattling in the breeze a few blocks from the Gulf. Situated along Florida’s Gulf Coast, this barrier island is just under an hour from Tampa and about two from Orlando, with the closest airport — Sarasota-Bradenton — around 30 minutes away. Most visitors stay in rented homes or apartments, a setup that keeps the vibe low-key and local. You’ll find plenty of small businesses, a strong focus on wildlife conservation, and island-wide resistance to overdevelopment. Just know that on long weekends or during high season, the narrow roads can back up quickly — your best bet is to park the car and soak it all in on foot or bike.
Updated old Florida cottage with beach access
This stunning rental, known as “The Surof House,” sits just across from the Gulf of Mexico, with wide-open water views and beach access only steps from the door. The house has two king bedrooms and a loft with three single beds — reachable only by ladder — which might not be ideal for younger kids or older adults. Inside, the space is bright and colorful, with large windows and an open layout that connects the kitchen, dining, and living areas. Outside, a wrap-around deck faces the Gulf, and there’s also an enclosed outdoor shower and a collection of seaside staples like chairs, umbrellas, and toys. The location is within walking distance of the shops and restaurants along Bridge Street, but still feels tucked away enough to unplug. The home is a modern reimagining of a 1915 beach cottage that once stood on the site, blending understated coastal style with updated finishes and fresh architecture.
Another option for groups is this four-bedroom house ($895 per night), located right on the water at the north end of Anna Maria Island, just a short walk from the city pier and Pine Avenue. Three of the bedrooms have king beds, the fourth has a queen, and there’s a pull-out sofa on the enclosed porch facing the sand. Inside, the house is bright and open, with a mix of updated appliances and vintage decor — like a pine dining table surrounded by old nautical chairs and a wall of mounted fish. The living room and porch both look out over the water, where you can spot boats, jet skis, and occasionally dolphins or manatees. Kayaks and paddleboards are provided, along with bikes for exploring the area, and there’s plenty of space outside to relax.
Seven guests, three beds
Price: $533 per night
Captiva Island
Photo: EQRoy / Shutterstock
Captiva Island lies off Florida’s southwest coast, connected to the mainland by the Sanibel Causeway and a small bridge from Sanibel Island. It’s about a three-hour drive from Tampa and just under two from Fort Myers, which is home to the nearest airport. The island is small, with narrow roads, a handful of local restaurants, and a blend of weathered beach cottages and breezy vacation rentals beneath palms. Even with the occasional group of day-trippers, the island rarely feels crowded. Shelling is a daily ritual here, sunsets are gorgeous, and it’s not uncommon to see dolphins playing just offshore or pelicans gliding low over the water. Captiva was hit hard by Hurricane Ian in 2022, and while some rebuilding is still in progress, much of the island has reopened and still feels like the same quiet escape.
Bright, family-friendly condo bear the beach in Captiva’s South Seas Area
This two-bedroom condo is set within the South Seas area on Captiva Island, just a short walk from the sand and the restaurants and shops in Captiva Village. It’s privately owned and separate from the resort, so while you won’t get resort perks, you’ll trade that for a little more peace and a lot more space to yourself. The property is drenched in light, with coastal art, updated furnishings, and a screened-in lanai that looks out toward the Gulf. It sleeps up to six with a king bed, two twins, and a sleeper sofa, making it a fit for small families or a couple who wants extra room to spread out.
If you’re traveling with a bigger crew, check out this four-bedroom home ($760 per night). Located on North Captiva Island — accessible only by boat or small plane — it sits seconds from the beach and is designed for easygoing living. The interior is cheerful and airy, with a spacious kitchen, casual dining area, and a screened-in wraparound porch perfect for catching the breeze. Outside, there’s a private pool, outdoor bar, grill, and everything from cornhole to paddleball ready to go. The rooftop lookout deck offers sweeping Gulf-to-Bay views, and the property includes a golf cart, bikes, and access to a shared dock. With room for up to ten guests and features like a kids’ loft with games and bunk beds, it’s ideal for multigenerational getaways or two families traveling together.
Six guests, two bedrooms
Price: $536 per night
Cedar Key
Photo: JRP Studio / Shutterstock
Time feels slower in Cedar Key. It’s the kind of place where cell service cuts out, but nobody seems to mind. This small island community on Florida’s Gulf Coast is about an hour southwest of Gainesville and two from Tampa. The town is tiny, and that’s exactly the appeal for those who keep coming back. Cedar Key has a long history tied to fishing, clamming, and weathering storms. There’s a main street with a handful of shops and restaurants, and the rest of the island is mostly old homes, stilted rentals, and boat docks. People come here to fish, kayak, watch birds, or simply sit by the water and let the day slip by.
Spacious Cedar Key home with a rooftop deck and water views
This three-story house is right by the water’s edge and set up perfectly for groups. It has three bedrooms, including a private top-floor master suite, plus a Murphy bed and an oversized couch to accommodate extra guests. The interior is light-filled and vibrant, with a recently updated kitchen and new furniture throughout. There are several indoor gathering spaces, and outside you’ll find a rooftop deck, a gas firepit, and an outdoor shower for rinsing off after a paddle in one of the house’s kayaks. It’s family-friendly, with gear like a high chair and pack-and-play, and there’s plenty of room for everyone to unwind without feeling on top of each other. Located in a quiet part of Cedar Key, surrounded by water and woods, the home has the feel of an old-school Florida getaway that’s been thoughtfully modernized.
Just down the road, this newer stilted home ($228 per night) offers panoramic Gulf views and a clean, modern design. The interior is open and bright, with high ceilings, large windows, and multiple decks that catch both sunrise and sunset. It’s a great fit for families or mixed groups, with bunk-style beds for kids or extra guests and plenty of space to gather without feeling crowded.
Eight guests, three bedrooms
Price: $379 per night
Hutchinson Island
Photo: FloridaStock / Shutterstock
There’s no boardwalk, no flashy resort strip, and no rush to be anywhere on Hutchinson Island — and that’s exactly the draw. About 40 minutes north of West Palm Beach and a little over two hours from Orlando, this long, slender barrier island stretches for 23 miles between the Atlantic Ocean and the Indian River Lagoon. Sleepy neighborhoods, public beach access points, and a scattering of low-rise condos line the coast. You’ll likely see more more herons on the island than hotels. On weekends, the water fills with boats, kayaks, and jet skis, especially near the Fort Pierce and St. Lucie inlets, where fishing is a favorite pastime. In summer, sea turtles nest along the sand, and birders scan the mangroves for egrets and spoonbills. There’s no real town center and not much nightlife to speak of — just sand, sky, and the feeling of being somewhere slightly out of step with the rest of Florida.
Side-by-side beach houses with room for the whole crew
Just south of Fort Pierce, this side-by-side pair of beachfront homes sits on a peaceful stretch of Hutchinson Island, with 100 feet of private shoreline and a shared dock on the Indian River. It’s an ideal setup for big groups — multi-generational families, retreats, or friend getaways — with two decked out houses that offer plenty of space. There’s room to cook, work, relax, and gather, all within earshot of the waves.
For something smaller and more relaxed, there’s a nearby studio ($225 per night) that’s ideal for couples or solo travelers looking for a unhurried stay with easy access to the ocean. It’s located on the second floor and offers views of both the ocean and the pool. Inside, there are two beds, a pullout couch, and a compact layout that’s simple but efficient. Beach basics are provided, and there’s a bar and restaurant downstairs if you’d rather skip cooking.
15 guests, 17 bedrooms
Price: $5,080 per night
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Gasparilla Island
Photo: Henryk Sadura / Shutterstock
Gasparilla Island sits between Sarasota and Fort Myers, but feels a world apart. The small town of Boca Grande is the island’s heart, where low-rise buildings, historic homes, and a handful of local restaurants line the main street. While Gasparilla has paved roads and modern amenities, nearby Little Gasparilla Island is even more off-grid: no motorized transport, no stores, and no way in or out except by boat. If you’re planning a stay there, you’ll need to bring your own groceries and arrange for a water taxi. Both islands are ideal for those content with long coastal walks, afternoon fishing, and chilled evenings on the porch.
Beachside Boca Grande Club rental with pool access and walkable location
Part of the private Boca Grande Club on the north end of Gasparilla Island, this stunning rental offers access to uncrowded beaches and breezy Gulf views. It’s just a short walk to the sand, with tropical landscaping providing privacy even though the club’s pool and on-site dining are close by. Inside, the space is bright and comfortable, with relaxed beach décor, a modern kitchen, and plenty of room to settle in after a day outdoors. During your stay, you’ll have temporary access to the club and you’ll also be within easy reach of local shops and restaurants, all set along a stretch of town that hasn’t changed much in decades.
If you’d prefer to stay on Little Gasparilla Island, this two-bedroom cottage ($250 per night) is a great pick for couples or small groups after a more peaceful base. Surrounded by sandy paths, stilted homes, and a nearly empty stretches, the place feels secluded without being remote. The cottage has been recently updated and features a screened porch, a full kitchen, and an outdoor shower — best used after dark, under the stars.
Six guests, three bedrooms
Price: $666 per night
Key Largo
Photo: Lucky-photographer / Shutterstock
Just an hour south of Miami, Key Largo is the gateway to the Florida Keys — and the shift in scenery is immediate. It’s best known for its diving and snorkeling, thanks to the coral reefs just offshore and the underwater trails at John Pennekamp Coral Reef State Park — the first of its kind in the US. The island leans outdoorsy, with boat tours, kayaking routes, and nature parks offering plenty to explore. On land, it’s all about seafood shacks and the occasional bar that still feels like the ’70s never left. It’s also a gateway to Everglades National Park, with tours and eco-adventures just across the bridge. Whether you’re a South Florida local on a weekend escape or road-tripping the full stretch to Key West, Key Largo is well worth the stop.
Elegant overwater bungalow just off the coast
For something a little different, this floating bungalow offers a low-key alternative to the typical island rental. Anchored off the coast and accessible only by boat, it’s best suited for couples or solo travelers looking for space, solitude, and time offline. Inside, it’s simple but cozy: a king bed, a compact kitchenette, and glass doors that open onto a private deck with uninterrupted water views. A captain ferries you in and shows you around, then you’re left to spend your days however you like — whether that means reading on the deck, snorkeling nearby, or simply looking out over the water.
Back on land, this classic Key Largo three-bedroom house ($950 per night) sits on one of the last large waterfront lots in the Upper Keys, with its own dock, boat ramp, and a wide stretch of private shoreline. The home blends older Keys architecture — think coral rock walls — with a focus on outdoor living, including a massive screened patio and hammocks strung near the water.
Two guests, one bedroom
Price: $932 per night
Key West
Photo: Mihai_Andritoiu / Shutterstock
Key West sits at the very end of the Overseas Highway, about a four-hour drive from Miami — depending on traffic and how often you stop to take in the views. It’s the southernmost point in the continental US, closer to Havana than to the mainland, and that geography shows up in the island’s cultural mix, food scene, and overall feel. Duval Street is where most of the action is — bars, restaurants, art galleries, and the usual tourist stops — but walk a few blocks in either direction and things start to quiet down. Inland, you’ve got pockets like Bahama Village and the Historic Seaport for local food and history, while the shoreline offers everything from snorkeling trips to sunset sails, most of which can be booked on a whim. For a small island, it packs in a lot without asking you to do much more than show up and go with the flow.
Secluded Key West stay with a private pool, steps from the art scene
If you’d like something private and relaxed without being remote, this two-bedroom cottage off Havana Lane hits the mark. Set behind a gate in a peaceful Old Town neighborhood, the house wraps around a pool and garden that feels more like a hidden compound than a backyard. Inside, it leans rustic, with Dade County pine walls, cathedral ceilings, and retro appliances that give the space character. It’s best for couples or close friends traveling together who want to spend their days drifting between the pool, neighborhood galleries, and local haunts, with the option to bike over to Duval Street when things pick up at night.
For more ideas on where to stay in Key West, check out Matador‘s full list of the best Airbnbs in Key West
Four guests, two bedrooms
Price: $1,117 per night
Santa Rosa Island
Photo: Trong Nguyen / Shutterstock
Santa Rosa Island stretches along Florida’s northwest Gulf Coast, about 15 minutes from Fort Walton Beach and easily reached by car from Pensacola or Destin. It’s one of the more family-friendly islands in the state, with calm, shallow waters and long stretches of protected shoreline within Gulf Islands National Seashore. A paved trail runs much of the island’s length, with stops like the Footprints in the Sand Eco Trail — a self-guided route with info points on sea turtles, native plants, and how the island’s sugar-white sand came to be. With a few casual seafood spots, some small historic sites, and plenty of open shoreline, Santa Rosa makes for an easy weekend trip — especially if you’re traveling with kids or looking for a quieter stretch of coast.
Five-bedroom Navarre Beach house with Gulf views and easy trail access
Navarre Beach sits near the eastern end of Santa Rosa Island, in a stretch of shoreline known for its quiet neighborhoods and wide-open sand. This five-bedroom house is set right on the Gulf, with a wide balcony facing the water and plenty of space for a group. Inside, the layout is simple and functional with an open kitchen, a big table for shared meals or board games, and a living area that looks out over the dunes. It’s an ideal rental for large families or multiple households traveling together, especially if the plan is to spend most of the time outside grilling, swimming, or walking the nearby trail that runs along the water. The house is close to places like the Navarre Beach Sea Turtle Conservation Center and the fishing pier, but the real draw is the space, the view, and a stretch of sand that somehow stays quiet, even when everything else is full.
Just down the beach, this three-bedroom cottage ($679 per night) offers direct access to the sand and views of the Gulf from nearly every room. An outdoor shower, firepit, and shaded picnic area make it easy to stay outside all day, whether you’re grilling, rinsing off, or just catching the breeze. It’s a solid option for smaller families or groups who want a more low-key setup with the same front-row access to the shoreline. 
13 guests, five bedrooms
Price: $859 per night
