Cottage vacation rentals in Hillsborough County

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Top-rated cottage rentals in Hillsborough County

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.

Cottage in Gulfport

4.97 out of 5 average rating, 177 reviews

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

ValueFamilyOutdoor spaces

Guest favorite

The image captures the tranquil waterway with gentle ripples reflecting the sky. In the background, a charming beach cottage is framed by palm trees and boats docked nearby, creating a serene waterfront scene.

Cottage in St. Pete Beach

4.96 out of 5 average rating, 182 reviews

Pass-a-Grille Historic Cottage Unit 2

PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 2 - 2 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front and back patio area w/ BBQ grill. Private parking for 2 vehicles.

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Top guest favorite

A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.

Cottage in Dunedin

4.99 out of 5 average rating, 389 reviews

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away on a quaint prime downtown street. Private yard with grill in terrific location. Walk to restaurants, breweries, shops, and live music. Walk to Dunedin's stunning sunsets or drive minutes to award-winning beaches such as Honeymoon & Caladesi Island & Clearwater Beach. Sleeps 6. Two king bed suites and a luxury leather couch that sleeps 2 more. Loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today!

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Top guest favorite

The front exterior of Cooper Cottage features a welcoming porch with two black rocking chairs and potted plants. A pathway leads to the entrance, while large windows allow natural light to illuminate the space. Lush trees provide shade and a tranquil atmosphere.

Cottage in Tarpon Springs

4.99 out of 5 average rating, 191 reviews

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

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Guest favorite

The cottage features a welcoming front porch adorned with vibrant flowers and lush greenery. A stone pathway leads to the entrance, framed by well-maintained landscaping. Large windows allow ample natural light, enhancing the charm of the remodeled exterior.

Cottage in Tampa

4.95 out of 5 average rating, 170 reviews

Wonderful 2-Br, 2 Bath Cottage near the river.

Welcome to my little cottage in the city. The house was built in 1926 but has been fully remodeled with modern style, while keeping the charm of an older home. Even though it's close to everything Tampa has to offer, it still has the feeling of that little, quiet neighborhood near the river. This is my get away home. I love the front porch to sit on with a cold beverage and watch neighbors stroll by walking their dogs. The river park is very close by which is a nice walk from the cottage.

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Guest favorite

A cozy living area features a yellow sofa and two accent chairs flanking a wooden coffee table. A TV displays a calming fireplace scene, with decorative wall art and patterned accents adding character. Natural light filters through windows covered by white blinds.

Cottage in Tampa

4.91 out of 5 average rating, 101 reviews

River adjacent, Quiet neighborhood, King bed

Small and cozy, this Seminole Heights home sits among other adorable homes in a stellar neighborhood, just a block from the Hillsborough River, and is within walking distance to great places to eat and drink. The Seminole Heights part of Tampa is wildly convenient to all of this city’s must-see spots; downtown, bayshore boulevard, Hyde Park Village, Busch Gardens, The Tampa Riverwalk and more. Whether or not you book with me, I’m still thrilled to help you find things to do while here.

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Top guest favorite

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

4.98 out of 5 average rating, 268 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

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Top guest favorite

A comfortable living area is depicted, featuring a light-colored sofa accompanied by two side lamps on small tables. A ceiling fan is visible, and a round piece of wall art echoes a coastal theme. Natural light filters in through the window with white blinds.

Cottage in Indian Rocks Beach

4.94 out of 5 average rating, 233 reviews

Kooky Coconut Cottage, Indian Rocks Beach

Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.

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Top guest favorite

Cottage in Gulfport

4.98 out of 5 average rating, 122 reviews

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

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Top guest favorite

Cottage in St. Petersburg

4.91 out of 5 average rating, 171 reviews

Adorable Cottage, Pet friendly, near beach & DT

The Cottage is a beautiful, comfy, clean, peaceful home where you will feel just at home, in the hearth of St Pete. It is in a great location, safe & quiet neighborhood, easy-to-access, just a short drive or bike ride away (5-10 minutes) to many good restaurants, grocery stores, museums, library, coffee place, breweries, hospitals, bars and night clubs in downtown & sandy white beaches. Jumped in the sun runner or public transport to downtown or beaches. Perfect for long stay.

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Top guest favorite

The porch features a circular daybed with decorative cushions, accompanied by a small table and two chairs. Direct views of the bright blue sky and nearby palm trees are visible, enhancing the outdoor relaxation space.

Cottage in Indian Rocks Beach

4.97 out of 5 average rating, 199 reviews

𖤓Updated Stilt home: just steps to the beach!𖤓

Experience a stylish and relaxing beach vacation at our vacation retreat! We are a very popular spot for Honeymooners and anniversaries! As a 4-year Superhost, we offer a charmingly renovated home just steps away from the beach and local restaurants. Explore Indian Rocks Beach with our provided bikes and unwind in the bubbly spa. Escape the everyday and find paradise here! BTR #2292

ValueFamilyBiking

Top guest favorite

A private hot tub is positioned on a wooden deck, outfitted with two black chairs and a small table. The cottage features a light blue exterior with a white door framed by two towels. A pergola with climbing plants is visible in the background.

Cottage in Safety Harbor

4.92 out of 5 average rating, 114 reviews

Heart of Town Cottage with Hot Tub

Escape to a stylish designer cottage just one block from vibrant Main Street! Perfect for couples or small families, this private home offers a luxurious getaway. Enjoy a fully equipped kitchen, a dedicated workspace, and an incredible private backyard with a hot tub, fire pit, and gazebo. Experience upscale comfort in a prime, walkable location.

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