15 Cutest Cottages in Florida To Escape To

Looking for the best Airbnb in Florida for your next vacation? We have you covered with our list of the cutest cottages in Florida!

Florida makes for a great destination year round. With warm weather and year round sunshine we have picked the cutest cottages in Florida for the perfect get-a-way!

Whether you want to head to some of the best beaches in the United States, hit up historical sites in the oldest city in America, have your own private island, or just enjoy a relaxing weekend we have you covered!

Airbnb’s are a great option as they are often unique and provide a more homey stay! Take a look some of our favorite from around the state! Perfect if looking to take a road trip, attend a festival, hit up the beaches, or a fall getaway!

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15 Cutest Cottages in Florida To Escape To

Old Town Luxury Oasis (Key West)

This is one of the amazing cottages in Florida located in the heart of downtown Key West one block from the famous Duval Street.

A short walk to Hemingway house, and all the restaurants, bars and shops on Duval street. Duval street is known as the heart of Key West and you will find everything you need here! This Luxury Key West cottage is perfect to relax after a day spent exploring Key West or enjoying the beach.

Fully renovated this 3 bedroom 2-bathroom cottage that sleeps 6 sits on a shared property with access to a pool! Old Town Luxury Oasis is a tropical oasis with bright decor perfect for families or friends.

This is the perfect Key West cottage if looking for fun things to do in Key West!

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Vacasa Key West ( Key West)

If looking for a dog friendly place to stay in Key West is one of the cottages in Florida that is pet friendly! A perfect Key West cottage located 5 blocks from Higgs Beach Pier, and a short walk to Duval Street.

This is one of the Key West Cottages made for relaxing! There is a shared pool and BBQ area perfect for relaxing after visiting the beach, taking a fishing charter, or exploring Key West! The perfect destination for year round travel!

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SkyBlue Cottage Oasis (Lake Worth)

This Sky Blue Oasis is another one of the cottages in Florida that is pet friendly! Lake Worth is located only a 5 minutes drive to the beach, and an 8-minute walk to downtown this is the perfect cottage location!

Lake Worth is located in Palm Beach about an hour north of Miami. The host goes above and beyond providing fresh fruit, coffee and tea that you can enjoy on a beautiful upstairs balcony. This 2 bedroom 1 bath is the perfect weekend getaway.

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The Sunny Shell Basket Cottage (Sanibel)

One of the perfect Sanibel Island cottages located near the beach! Sanibel is only 25-minute drive from Fort Meyers it is a place people come to unwind! The Sunny Shell Basket Cottage is perfect for “sunshine, seclusion, and the sound of the sea!”

Only a few minute walk to the beach this 2 bedroom 2-bathroom is one of the bright and cozy cottages in Florida! A complete separated upstairs cottage is all yours! Perfect those bird watchers who after often greeted by Heron or Ibis right off the deck!

Visit Captiva island one of the most secluded islands just a short drive away from Sanibel!

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Bellissima by the Beach (Placida)

Bellissima by the beach is a cottage for those wanting to escape and unplug! This beach-chic beachfront high-end home is one of the cottages in Florida known for luxury and panoramic views of the Gulf of Mexico. Placida is located about an hour south of Sarasota and provides a relaxing outdoor escape.

Enjoy dinner on the outdoor deck while watching a sunset, kayak in the turquoise waters, dolphin watch from the dock or take a boat ride from the marina.

The home is accessible by only boat or water taxi and perfect for those visiting Little Gasprilla Island and Don Island State Park. The home even has a sauna in the master room! Just a few steps from the cottage to the beach!

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Siesta Key Cozy Cottage (Siesta Key)

This is one of two Siesta Key Cottages on our list located one block from the beach in the iconic Siesta Key Village on the north side of the island.

Siesta Key is located in Sarasota south of Tampa and St. Petersburg. Known for its white sand beaches, year round warm weather this is one of the cottages in Florida near the beach!

Known to have the top beaches in the United States, Siesta Key has tons of dining spots, canoe or kayak tours, or fishing charters.

It is one bedroom one-bathroom cottage in Florida that sleeps 3 with a pull out sofa bed! Here is our suggestion for things to do in Sarasota!

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Enchanted Cottage on the Beach (Siesta Key)

Enchanted Cottage on the Beach is our second of the cottages in Florida located in Siesta Key! This secluded paradise is a 1 bedroom, 1 bath Siesta Key cottage that sleeps 2!

With beautiful gardens, koi ponds, and a pool this Siesta Key Cottage is on two-acres of beachfront property! Use it as your personal escape from the busy beaches of Siesta Key!

With a sand walkway to the beach, you can relax under the gazebo with chairs and shade, or take a short walk to Siesta Key Village for restaurants and nightlife!

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The Gull House at Azure Estate (Melbourne Beach)

The Gull House at Azure Estate is one of the best luxury oceanfront cottages in Florida located on Melbourne Beach. This beautiful home sits on a private beach, with a shared pool, relaxing outdoor oasis and beautifully decorated.

Sleeping 4 this 2-bedroom 2-bath cottage has oceanfront views from the living space and bedrooms. Perfect for those wanting the ultimate luxury of walking out the door to your own private beach.

Located on the Florida Space Coast this Florida cottage on the beach is the perfect place to return after exploring Kennedy Space Center, the beaches, or downtown Melbourne!

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Artsy Cottage (St. Petersburg)

This gorgeous cottage is located in the heart of downtown St. Petersburg. Whether you are in town to visit the beaches, the Dali or Fine Arts Museum, art murals, or Sunken Gardens this is one of the best cottages in Florida.

Just a short drive from Tampa we have some great suggestions for day trips around the area!

The Artsy Cottage is one of the St. Petersburg cottages that is beautifully decorated in a quiet neighborhood 10 minutes from downtown! This is a 2-bedroom, 1.5 baths with a private garden! Relax inside or on the deck overlooking the garden! This property was fully renovated in January 2020!

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Paralia House (Clearwater Beach)

Paralia House is a 2-bedroom 1.5-bath cottage located in Florida on Clearwater Beach. This Clearwater Beach cottage is a renovated 1920s property that has been complete transformed into a modern oasis.

On the Gulfside of Mandala avenue, this cottage is located only one block off the beach, the name in Greek means beach or seaside! If looking for a Greek restaurant take a trip to nearby Tarpon springs just a 30-minute drive!

This cottage is close to all the downtown Clearwater Beach restaurants, bars, shops and attractions.

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Historic Florida Beach Cottage (Indian Rocks Beach)

This Historic Florida Beach Cottage is a 2 bedroom 1 bath standalone beach cottage located right on Indian Rocks Beach. It sleeps 6 with bunk beds in the second room and a pull out sofa bed in the living room.

It is another one of our choices for cottages in Florida perfect for a beach weekend! Step out the door of this beachfront oasis onto the white sand beach of the Gulf of Mexico.

This charming cottage is located in a small 4000 person relaxing beach town. Head to the nearby Indian Rocks Nature Preserve for bird watching if you want to escape the beach for a little.

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Bluefish Bungalow (St. Augustine)

Bluefish Bungalow is one of the cottages in Florida located in St. Augustine. This 3 bedroom, 2-bath cottage sleeps 6 guests. Located near Treasure Island beach, it is a 10-minute walk via a private walkway to Butler Beach.

This St. Augustine cottage is brightly decorated with funky outdoor colors. There is a spa bathroom in the master bedroom, two twin beds in the second bedroom, and pullout couch in the living room, and outdoor patio.

If you want to try out something unique, St. Augustine is known for some of the best ghost tours in Florida. St. Augustine is the oldest city in the United States, after the beaches visit Castillo San Marcos Fort or Lightner Museum.

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Cane Cottage (Ponte Vedra Beach)

Cane Cottage is one of our picks for luxury cottages in Florida. Located on Ponte Vedra Beach, this 1940s beachfront cottage has gone through a full renovation.

There is a large kitchen that opens up to the deck facing the beach with an outdoor dining area. Or relax on one of the hammocks under the palm trees. This 2 bedroom 2-bathroom cottage sleeps 7.

The second bedroom features four beds – three twins and a queen in a bunk set up, while the other bedroom features a queen room. The bathrooms are large and beautifully decorated.

Ponte Vedra is the perfect place to visit the beaches, playing golf, wild oaks and palmetto trees, and natural lagoons.

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Pelican Retreat (Pensacola)

Pelican Retreat is a renovated vintage 1943 cottage. This is one of the cottages in Florida located in a quiet neighborhood in Pensacola. This one-bedroom one-bath cottage sleeps 4.

This cottage is walking distance to restaurants, bars and a locally owned grocery store. Pensacola Beach is located 15 minutes away and downtown Pensacola is only 10 minutes away.

Enjoy the large deck, or backyard hammock after hanging at the beach all day. If visiting during the fall don’t miss Pensacola Seafood Festival! IF interested in museums check out the Naval Aviation Museum, Fort Pickens or head to the Pensacola pier to do some fishing or watch a sunset.

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Paradise Island (Jacksonville)

Paradise Island is one of the unique cottages in Florida located on a private island. This Jacksonville Beach cottage is located 10 minutes from Jacksonville airport, 15 minutes to downtown and 6 miles from the beach.

This Jacksonville cottage is surrounded by water, has kayaks, a fire pit, 2 docks and is your own slice of paradise. Head to Big or Little Talbot Island, the Kinglsey Plantation or Huguenot Memorial all located close by.

Head out to the Jacksonville Riverwalk for a fun activity, or visit some museums or restaurants on the St. Johns River. You can even take a day trip to nearby Amelia Island!

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