Holiday houses 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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Top Guest favourite
Home in Tampa
5 out of 5 average rating, 10 reviews

Allison Palms Luxury Tampa Townhome + Pool

This beautifully furnished home comfortably hosts up to 6 adults and is perfectly located at the I-4 and I-75 junction for easy access to Tampa’s top attractions. Enjoy a spacious open layout with stylish designer décor, luxury beds, fully equipped kitchen, and ample storage. The community pool with shaded seating is just across the street. Airports, Disney, beaches, Busch Gardens, and Tampa’s stadiums and arenas are all within an hour or less, making this the ideal hub for your Florida getaway.

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, 173 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
The tiny home is set amidst a lush forest backdrop, featuring a welcoming entrance that is framed by large windows. A spacious wooden deck is adorned with comfortable seating, including two bright blue chairs and two red chairs. A black hammock hangs between trees, inviting relaxation.
Campsite in Thonotosassa
4.99 out of 5 average rating, 295 reviews

The Palm Tree Getaway

Ever stayed the night in the woods? Cross it off the bucket list with our ‘tiny-house’ style stay near the Hillsborough State Park. Rated #7 on PureWow as one of the 20 Best Airbnb Cabins. This brand new luxury tiny home was thoughtfully crafted to capture the natural beauty of its old Florida virgin forest surroundings. Glamping at its finest with the best modern conveniences like a full gourmet kitchen, spa like shower, 1G FiberWi-Fi Internet, TV, and a super quiet Mini SplitAC & Heating.

Top Guest favourite
The exterior of a charming half duplex is shown, featuring a light-colored facade and white door. A path leads to the entrance, bordered by manicured grass and flower beds. Comfortable outdoor chairs are positioned on the side yard, inviting relaxation in the sun.
Apartment in Tampa
4.96 out of 5 average rating, 26 reviews

Tranquil Davis Islands duplex overlooking water

Discover an inviting Davis Island apartment. This cozy unit offers both comfort and fully stocked for everyday convenience. Explore nearby beaches, a vibrant dog park, and Main Street's diverse dining options. Rest assured with a hospital just moments away. Embrace city life with downtown just a short bike ride away, providing an array of entertainment, shopping, and dining choices. Enjoy seamless access to essential amenities and markets in downtown, Ybor, Hyde Park, and the wider Tampa area.

Top Guest favourite
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, 248 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.

Top Guest favourite
Apartment in Tampa
4.99 out of 5 average rating, 209 reviews

Tampa Bay Gem: 2BR Modern Apartment Hideaway

Welcome to your stylish oasis in Tampa Bay. Our thoughtfully designed apartment combines modern sophistication with the comforts of home, making it the perfect base for your next adventure. Minutes away from your desired Tampa Bay attractions plus more. Don't miss the chance to experience a stay from the comfort of this Hidden gem. Whether you're here for business or leisure, our apartment is your home away from home. Book your stay now and make memories that will last a lifetime.

Top Guest favourite
An open-concept living area is shown, featuring a comfortable seating arrangement that includes a sofa and two armchairs. A dining table with chairs is visible. Large glass doors lead to a private outdoor patio, allowing natural light to fill the space.
Home in Clearwater
5 out of 5 average rating, 25 reviews

Townhouse in Clearwater

Enjoy a stylish experience at this completely remodeled centrally-located Townhouse Spacious LR with 65" TV 100% Sanitized New SS kitchen appliances. New vinyl flooring throughout Beautiful 2 BR/1.5 bath Large primary bedroom with reach thru closet and a slider to an enclosed balcony. Both Bedrooms located on the 2nd floor along with Washer/dryer Near Golf Courses Clearwater Beach (8 mi) Pinellas Trail TPA Phillies Baycare Park Blue Jays TD Park Honeymoon Island Food/Shopping

Guest favourite
A rustic tiny house stands within a lush garden, featuring a wooden deck adorned with comfortable seating. The entrance showcases large glass doors, framed by greenery, while a charming pathway of stones leads toward the entrance. Subtle decorative elements enhance the inviting outdoor space.
Tiny home in Tampa
4.99 out of 5 average rating, 567 reviews

Cozy AF Tiny-House Oasis

Awarded a *Unique Stay* by Airbnb, welcome to the **Cozy AF Tiny-House Oasis**, a rustic tiny home that started its journey as a world-traveling storage container. Now transformed into a charming cottage, it’s filled with unique and fun details waiting to be discovered. Enjoy the entire backyard, complete with a hot tub, koi pond, fire pit, hammocks, greenhouse, and even a bunny garden! Our goal is not just to offer you a place to stay but an experience you’ll cherish forever

Guest favourite
A comfortable seating area features a large, brown leather sectional couch, accompanied by a wooden coffee table and a sleek side table. A flat-screen TV is mounted on the wall, and natural light enters through two large windows, adding brightness to the space.
Apartment in Tampa
4.99 out of 5 average rating, 73 reviews

Riverside Heights Guesthouse

Enjoy a stylish experience at this centrally-located Guest House. The guest house was built in November 2022. It has its own free private parking area off street and it's own private entrance. The guest house is conveniently located in the heart of Tampa. Just a short half mile walk to the Riverwalk and Armature Works. Just minutes from downtown Tampa, Ybor city, Raymond James Stadium, University of Tampa, Tampa airport, and close to major highways and interstates.

Top Guest favourite
A serene sleeping area is defined by a wooden bed frame draped with sheer white fabric. The plush bedding features a subtle pattern. A vibrant green plant wall provides a backdrop, and a decorative neon sign reading 'Tiny Tulum' adds a modern touch.
Guest suite in Tampa
4.98 out of 5 average rating, 215 reviews

Tiny Tulum | Tropical Oasis in Tampa’s Heart!

Welcome to Our Romantic Tulum-Inspired Retreat! Escape to a tropical paradise at our enchanting Tulum-inspired oasis, designed with romance and relaxation in mind. Nestled in a serene neighborhood, our beautifully decorated retreat offers the perfect blend of luxury, comfort, and bohemian charm, creating an idyllic getaway for couples seeking a memorable experience. Why book a generic Airbnb when you can book a hand crafted Tropical Paradise?

Top Guest favourite
Home in Tampa
4.95 out of 5 average rating, 19 reviews

Sunny Tampa Gem, Has It All!

Welcome to this charming Tampa bungalow, perfectly located near the vibrant Seminole Heights shops and restaurants. Just minutes from Armature Works, this home offers both comfort and convenience. With 2 cozy bedrooms, 1 bathroom, and a fully equipped kitchen, it has everything you need for a perfect stay. The beautiful backyard is a true oasis, with plenty of seating to relax and enjoy the sunny Tampa weather. Your ideal getaway awaits!

Top Guest favourite
The living area features a spacious layout with a comfortable gray sofa and a decorative wooden coffee table. A flat-screen TV is mounted on the wall, while a well-equipped kitchen with modern fixtures is visible in the back. Natural light enters through the windows, creating a bright atmosphere.
Home in Tampa
4.97 out of 5 average rating, 131 reviews

Charming House 2B/2B Centrally Located Tampa Bay

Come and enjoy our house, 2Bedroom/2Bathroom with a clean full kitchen is the perfect place for your next vacation! This is an entire 1200sqft, AC, dryer/ washer, huge parking space, Smart TVs, internet/Wi-Fi, First AID and closet spaces. It fits up to 6 adults. This premium location offers small driving distance to restaurants and Super Walmart, is about 3 minutes to Westfield Citrus Park Mall. Busch Gardens (9 miles away).

Popular amenities for Hillsborough County holiday rentals

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