Looking for the best cottages 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!
These cottages to rent in Florida 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!
15 Cutest Cottages in Florida To Escape To
Chick-A-Pea Cottage (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. Plus this property is dog friendly, making it perfect get-a-way for family vacations. It is worth noting guests must be over 25 years of age.
This Key West cottage is 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 luxury 4 bedroom 3-bathroom cottage that sleeps 8 sits on a shared property with a private pool! Chick-A-Pea Cottage is a tropical oasis where indoor living flows into the outdoor patio and pool that fully opens to the outdoor space. You will find a cabana, grill and chairs.
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 Flamingo’s Nest (White Springs)
One of the perfect Florida cottages located north of Gainesville, this is perfect spot for those visiting the North Florida springs! In White Springs you will want to visit Big Shoals State Park, to visit some of the prettiest waterfalls in Florida!
An idyllic brightly colored cottage, with a white picket fence and flower pots on the deck, porch swing, a large wooden deck with table, chairs and large umbrella welcome guests before even stepping foot inside the 2 bedroom, 1 bath The Flamingo’s Nest .
The home is decorated in pink tones, and the owners welcome guest with complimentary cold drinks, a full breakfast and everything else you could need.
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Secluded Island Luxury Retreat (Placida)
Secluded Island Luxury Retreat 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 Beach Cottage (Siesta Key)
This is one of two Siesta Key Beach Cottage on our list located right on beach road across from the one best beaches in the United States! And just minutes to 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 beachside Siesta Key cottage in Florida that sleeps 2. The owners have thought of everything in this remolded beach front cottage. From the complimentary beach cruiser bikes to explore, a large back paved deck, granite counter with a full kitchen, a comfortable king bed guest rave about, outdoor shower and more ! 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!
This beachfront cottage rentals has beautiful gardens, koi ponds, and a poo ! Use it as your personal escape from the busy beaches of Siesta Key! This Siesta Key Cottage is on two-acres of your own .
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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Paradise Found Florida (Melbourne Beach)
The Paradise Found Florida is one of the best luxury private oceanfront cottages in Florida located on Melbourne Beach. This bright pink cottage sits beachfront making it perfect spot to relax with friends or family.
Sleeping 4 this 2-bedroom 1-bath cottage, can be combined with smaller cottage next door to accommodate 6. From the open living space and bedrooms, a modern kitchen, relaxing backyard with deck, outdoor shower and hammock this is perfect for those wanting the ultimate luxury of walking out the door to the beach.
Located on the Florida Space Coast this Melbourne Beach cottage on the beach is the perfect place to return after exploring Kennedy Space Center, the beaches, or downtown Melbourne!
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Ibis Cottage (Sanibel lsand)
This gorgeous cottage is located in the heart of Sanibel Island. Whether you are in town to visit the beaches, or just relax on the island this beach chic renovated cottage awaits you. Be on the lookout for wildlife right outside your cottage.
The Ibis Cottage is one of the Sanibel Island cottages just minutes from the beach! The old Florida charm inside this quaint cottage is decorated In a coastal theme. It is a 1 bed 1 bath that sleeps 4.
Make sure of the beach parking permit, bicycles, outdoor grill, as well as the outdoor sewer and shelling station. Sanibel is known for its amazing shelling!
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Castaway Cottage (Anna Maria Island)
Castaway Cottage is a 2-bedroom 1-bath mint green cottage that sleeps 5 guests. Located on the Florida Gulf Coast on Anna Maria Island. This is the one of the cottages in Tampa area that offer guests the complete package. Renovated accommodations, a private pool, stand up paddle boards, a golf cart, bikes and more.
Located near Bean Point, this cottage has everything you need for a vacation. Just need to bring yourself! From bikes, beach chairs, heated or cooled pool and hot tub and outdoor shower plus ample seating around pool.
Inside you will find an open floor plan with comfy living space, renovated bathroom and bedrooms where you will find a welcome basked with wine, chocolate, coffee and waters! If looking for restaurants or breakfast spots check out our suggestions.
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White Beach Cottage (Clearwater Beach)
This White Beach Cottage is a 2 bedroom 2 bath standalone beach cottage located less than 100 steps to the beach in Clearwater. It sleeps 6 with two bedrooms and a pull out sofa bed in the living room.
It is another one of our choices for cottages in Clearwater perfect for a beach weekend! Step out the door of this beachfront oasis onto the white sand beach of the Gulf of Mexico. And it has a free parking spot, and close to restaurants.
This charming cottage is located in one of the most popular beach destinations in Florida. Decorated in a nautical theme with open floor plan in natural colors. IF traveling with others there are a total of 3 cottages.
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Cavalier Cottage (St. Augustine)
Cavalier Cottage is one of the cottages in Florida located in St. Augustine. This 2 bedroom, 1-bath cottage sleeps 5 guests. Located on Ruth B street a private spot in the heart of St. Pete beach, where you are just steps form the beach!
This is one of the cottages in St. Augustine that features a fenced back yard, perfect if traveling with you pet! The open floor plan features a renovated kitchen, large living area, lofted bedroom all decorated in a modern beach decor. The hosts even provide coffee, tea, snacks and welcome drinks!
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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Boat House Row (Mount Dora)
Boat House Row is one of our picks for romantic cottages in Florida. Located in Mount Dora , just 35-minute northwest of Orlando. Mount Dora is a one of the cutest small towns for its antique shops and the best festivals in Florida.
This studio cottage was converted from a old boat house and is now an 800 sq foot romantic oasis, with a full kitchen, bathroom and more. Sit on the large front porch and enjoy the sunsets over the lake. Or relax on the back screened in porch.
The decor is antiques and dark colors with large sliding doors that let in lots of light. Just steps to downtown Mount Dora where you explore all this small town has to offer. Guests rave about the owners, the cottage and the proximity to town.
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The Jesse (Pensacola)
The Jesse is a renovated vintage 1903 cottage. This is one of the cottages in Florida located just one block from Seville square in Pensacola. This one-bedroom one-bath cottage sleeps 4.
This Pensacola 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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Leaning Palms (Santa Rosa Beach)
Leaning Palms is one of the chic designer cottages in Florida located on the Panhandle. Located on the popular 30A, between Destin and Seaside you will have access to some of the best Gulf Coast beaches.
This Santa Rosa Beach cottage has 3 bedrooms, 2 baths and sleeps 7. Located just one block from the beach you are welcomed by two oversized porch swing beds, a large deck, and an open floor plan on the first level. From the relaxing living room, gourmet kitchen, large bedrooms you will find plenty of space here.
Head out back to the large grass yard, with decks outback as well or take a quick walk to enjoy the beautiful white sand beaches. Make use of the bikes, beach chairs, umbrellas, beach games and more housed in the garage for guest use!
This is another of the cottages in Destin that requires guests to be over 25 years of age.
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