Holiday rentals in Hillsborough County

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Top-rated holiday rentals in Hillsborough County

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

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Superhost
A serene riverside cabin is surrounded by lush greenery, with ample trees and open grass areas leading to the water's edge. A wooden deck extends towards the river, providing access to the water for leisure activities. Kayaks can be seen nearby, enhancing the tranquil setting.
Home in Ruskin
4.76 out of 5 average rating, 197 reviews

Riverbend Retreat on the Little Manatee River

Discover the peace and serenity of Old Florida here on the Little Manatee River. This very comfortable 2 bedroom getaway is enhanced by a big wrap-around screened porch. You can't see another house from here! Enjoy the kayaks and fire pit with friends and family, or have a romantic escape. Nature is all around and it's impossible to feel stress here. This is a unique, remote spot where you really feel the essence of wild Florida, a disappearing treasure! Close to civilization but feels so far...

Guest favourite
An inviting backyard space features a covered grill area, a warm-toned outdoor seating arrangement, and a relaxing hot tub. Lush green artificial turf enhances the ambiance, while palm trees provide a tropical touch. Soft lighting allows for enjoyment during evening hours.
Home in Tampa
4.96 out of 5 average rating, 176 reviews

46 Jet hot Tub |Downtown Tampa Palmetto Paradiso

NO DAMAGE & FULL POWER POST-MILTON centrally-located Tampa Stunner w/ hot tub! Modern style home located very close to Downtown Tampa, Riverside, Amateur Works, Amalie arena and more! Indulge in the lush interior featuring tropical forest inspired 3 bedroom/ 2.5 baths. Enjoy family and friends in a cozy yet spacious open living area . Bask in the sun or enjoy the gentle breeze as you grill in the Backyard Paradiso cuddled in palm trees. Your own "lil palms" peaceful escape. Hablamos Español.

Top guest favourite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.98 out of 5 average rating, 164 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Guest favourite
The exterior of the guesthouse features a charming blue façade with unique hexagonal windows. A covered entrance is highlighted by a black awning, while well-maintained landscaping adds a welcoming touch. The surrounding area is characterized by gravel and lush greenery.
Guest house in Tampa
4.88 out of 5 average rating, 181 reviews

Hyde Park Cottage - The Ultimate Location

Originally built as a barn in the 1920's, the Hyde Park Cottage was lovingly restored into a chic 2-story guesthouse. Centrally located between SOHO and Hyde Park Village. Walk to Restaurants, Shops, Parks, & Bayshore Blvd. Minutes to downtown, 15 min. from Airport, 30 min. to Beaches. Historic Hyde Park is beautiful and the 1100sqft cottage is outfitted to reflect the character and class of the neighborhood. Private Guest Access - Parking - TV/Internet - Full Kitchen - Washer/Dryer -

Superhost
An outdoor patio area is enclosed by a wooden fence, featuring a fire pit surrounded by two white adirondack chairs. Lush greenery and small shrubs border the space, which is accentuated by a stone path and grassy patches under a clear blue sky.
Guest house in Tampa
4.84 out of 5 average rating, 263 reviews

La Casa Azul - Private Detached Guest House

Please note the Hot tub has been removed. Charming, detached guest house in South Tampa. Just a short stroll to scenic Bayshore Blvd and stunning views of Tampa Bay. Shopping, dining and more. This guest house has lots of windows, providing a lot of natural light! It has off street parking and a gated patio/yard area. It's stylishly furnished, has an LED TV, surround sound, the Amazon Fire stick and Alexa. FREE Wifi. Bedroom has Tempur-Pedic Bed and inflatable mattress.

Top guest favourite
A welcoming porch area is seen, featuring two white rocking chairs and a small side table. Lush greenery and blooming flowers surround the space, while a door leads inside. Light reflects off the stone flooring, complementing the vibrant green walls.
Home in Largo
4.98 out of 5 average rating, 108 reviews

Walk to beach shops food drinks “The Inbetween”

This is one of Island Rum Suites collection! Stay with us to see why we are one of the best family owned and operated around! We are in a quiet and safe neighborhood, walking distance to the beach, shopping, restaurants, nature parks, water park, pizza, pubs and ice cream! All guests must be listed on the reservation in order to be on the property and accounted for, even children. Zoning allows 2 people per bed and 2 cars No pets allowed Florida State License # DWE6215889

Top guest favourite
A cozy living room features a sectional sofa and two accent chairs with colorful pillows. A round coffee table centers the space, while a large flat-screen television is mounted on the wall. Natural light streams through glass doors leading to the patio.
Apartment in Tampa
4.98 out of 5 average rating, 212 reviews

Location! 1 Block from Bayshore / SOHO / Hyde Park

Enjoy the best of South Tampa in this spacious 2-bedroom, 2-bath ground-floor condo just steps from Bayshore Boulevard. Features include a comfortable living space, large private patio, updated kitchen, and dedicated covered parking. Located three blocks from South Howard Ave with quick access to downtown, Amalie Arena, Ybor City, UT, and the Convention Center. Bay views included. Not available during Children’s or Adult Gasparilla Parade weekends per HOA policy.

Guest favourite
Bungalow in Tampa
4.92 out of 5 average rating, 184 reviews

Boutique Bungalow with Private Saltwater Pool

Relax in a crisp Florida bungalow with a private saltwater pool set in a fully private backyard oasis. Whether you are coming to Tampa for an event, extending your cruise vibe, or coming to Tampa for work, this home has got you covered. You’ll be 15 minutes from the Tampa Convention Center and the Port Tampa Bay Cruise Terminal, close to South Tampa dining and nightlife, 10 minutes to TPA, and an easy drive to award-winning Gulf beaches.

Guest favourite
Townhouse in Tampa
5 out of 5 average rating, 6 reviews

Tampa 3BR Townhome I Family-Friendly | Garage

Welcome to a Coastal-themed 3 Bed / 2.5 Bath townhome with a 2-car covered garage. Enjoy bright décor, 2 inviting living areas, a fully equipped kitchen, perfectly curated for style, comfort, and convenience. Upstairs offers three serene bedrooms with plush bedding. Perfect for families, couples, or long stays—just 20 mins to the Tampa airport and close to Tampa’s top shopping, dining, and beautiful world class Gulf Coast beaches.

Top guest favourite
A serene pool area is framed by lush greenery, with a clear blue pool inviting relaxation. Gentle steps lead into the water, and a wooden deck extends nearby, offering additional seating. The tranquil view of the lake canal enhances the peaceful atmosphere of the space.
Home in Tampa
4.97 out of 5 average rating, 107 reviews

Lakeview Retreat with Private Pool Perfect Getaway

Welcome to our charming Tampa retreat! This newly renovated house has been carefully designed with an open layout, it features 2 bedrooms and 2 full bathrooms. The highlight of this home is undoubtedly the patio area, beautiful outdoor furniture, and an amazing pool with a stunning and unique view of the lake canal. The location is perfect, everything is nearby with quick access to major highways such as I-4, I-75, and I-275.

Superhost
A compact bedroom is highlighted by a full-size bed made with a white quilt and accented with two checkered pillows. Light blue walls enhance the space, complemented by framed artwork on the wall. Natural light filters through a partially covered window.
Home in Tampa
4.89 out of 5 average rating, 159 reviews

Private Studio near MacDill Base

Quiet and peace full Studio. This new 195 square feet Studio has everything you need, full size bed, fridge, microwave, coffee table, compact kitchen, TV, Wi Fi, Patio and a private entrance with parking spot. Excellent location, 2 miles from MacDill Airforce Base, 1 block away from bobby Hicks Park and within 5 minutes to Picnic Island, Gandy Beach and Selmon Expressway.

Top guest favourite
The charming cottage features a bright yellow front door, flanked by potted plants. A welcoming porch is screened with white framing. The well-maintained yard is adorned with manicured grass and a path leading to the entrance, with a white picket fence visible in the background.
Cottage in Oldsmar
4.96 out of 5 average rating, 310 reviews

Louisa's Cottage

This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmar’s main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants .This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.

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