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Villa holiday rentals in Hillsborough County

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Top-rated villa rentals in Hillsborough County

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Top Guest favourite
A sandy pathway leads through palm trees and lush greenery toward a wide beach. The ocean's calm surface reflects a bright blue sky with scattered clouds. A beach umbrella is visible to the left, suggesting a serene, inviting atmosphere.
Villa in Redington Shores
4.92 out of 5 average rating, 139 reviews

1 House to beach! Peaceful beachside villa

Best kept secret on quiet street beachside away from busy condos. Only 1 house to wide pristine beach stretching for miles. 1 of 3 units 2nd story **May be some repair activity on the lower units thru November. None Nov 27-30 or wkends Beach supplies: towels, beach chairs, cooler. Walk to restaurants. W/D IN UNIT, Central AC, WIFI, park free Bedrooms: Comfortable mattresses. Black-out curtains. 2 bdrms with king beds. 3rd bdrm: large BONUS ROOM/laundry 2 twin beds, sliding door for privacy

Top Guest favourite
An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.
Villa in St. Petersburg
4.95 out of 5 average rating, 128 reviews

Heated Pool! Huge Walk In Shower! 5 min to beach!

Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

Top Guest favourite
A spacious living room features a large sectional sofa adorned with green pillows and a coffee table placed on a vibrant area rug with palm leaf designs. A flat-screen TV is mounted on the wall, complemented by decorative accents and artwork throughout.
Villa in Safety Harbor
5 out of 5 average rating, 144 reviews

Villa Key West "Villas by Christine"

Perfect location, Charming Villa Guests are loving the newly renovated Villa Key West. Christine's goal was to make guests to feel the charm of a Key West Villa while experiencing the amenities of a 5 star hotel The Living room and bedrooms have large smart TV’s with complementary Roku, Netflix, Prime and Hulu. Enjoy the view out back of one of Safety Harbors 150 year old Oak & nature pond. We are per friendly. Please let us know you will be bringing pet. Pet fee of $100.00 due upon arrival.

Guest favourite
The kitchen features modern cabinets with white finishes and granite countertops. A round dining table with four chairs is situated near a large window, allowing natural light to fill the space. Stainless steel appliances, including a full-size refrigerator, are arranged along the wall.
Villa in Tampa
4.91 out of 5 average rating, 210 reviews

Busch Gardens, Moffitt, USF Charming Villa

Cozy 1 bedroom and 1 bathroom unit, completely renovated in Live Oaks Square. 3 minutes away from Busch Gardens, Adventure island, MOSI and USF. It is about 21 minutes from Tampa Airport. The back yard has been accommodated so you can enjoy every minute of your stay. -Tampa International Airport 15MI -Tampa Bay Buccaneers Stadium 8.0MI -Aquarium8.3MI -Busch Gardens1.6MI -Clearwater32MI -Adventure Island2.2MI -Epperson Lagoon23MI -James Haley Veterans2.9MI -USF3.2MI -Moffitt3.5MI -Publix4.1MI

Top Guest favourite
The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.
Villa in Largo
4.97 out of 5 average rating, 146 reviews

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

Guest favourite
Villa in Largo
4.9 out of 5 average rating, 117 reviews

The Tropical Oasis, w/ Solar Heated Pool and Games

Welcome to your private, tropical escape! Unwind by the solar-heated pool in a screened, mosquito-free lanai. ​FUN & GAMES: Enjoy Billiards (Pool Table) 🎱, Foosball, Cornhole, board games, and 3 Smart TVs 📺. ​PRIME LOCATION: Only 5 min 🚗 to Indian Rocks & Bellaire Beach, FL Botanical Garden, and dining. ​ Essentials: ​🌞 Heated Swimming Pool (Private!) ​🎮 Billiard Table / Foosball Table / Cornhole / Boardgames and more! ​🛏️ 4 Queen/Full Beds ​🧺 Beach Amenities

Top Guest favourite
A saltwater pool is featured with a large yellow inflatable duck wearing sunglasses. Water splashes create a lively ambiance, while a shaded patio area is visible in the background. Roller coasters can be seen beyond the pool area, highlighting the proximity to attractions.
Villa in Tampa
4.91 out of 5 average rating, 125 reviews

Busch Gardens Deluxe Edition w/heatedpool

Accommodation that you choose can make a big difference to your trip. Busch Gardens Royal Experience offers an exciting villa taking your adrenaline limit to the next level. Get out of that overwhelming routine. Create extraordinary memories in this full renovated house 3bedrooms/2bathrooms located 3 minutes away of Busch Gardens Tampa Bay. From its cozy pool area with a majestic pergola you can see several roller coasters. Just a VIP experience so Put it slow motion.

Guest favourite
An outdoor space features a sparkling swimming pool surrounded by a screened enclosure. A hot tub is adjacent to the pool under warm string lights. Various games are available, including a ping pong table and a billiard table, providing entertainment options for guests.
Villa in Brandon
4.83 out of 5 average rating, 132 reviews

Tampa heat pool /hot tub lake view near airport

Welcome to home away from home! This beautiful 4 bedroom 2 bathroom house is new with modern decor and has everything you need for a comfortable and relaxing stay. The house features a sparkling swimming pool and a hot spa, perfect for unwinding after a long day. Located in brandon, you’ll be just 15 minutes away from downtown, where you can experience the city’s vibrant culture and attractions. Get ready to create some unforgettable memories in this charming abode.

Superhost
A bright kitchen features a cheerful, colorful wallpaper with a playful design. A traditional farmhouse sink is situated on a light blue countertop, accompanied by various kitchen utensils and knives mounted on the wall. A vibrant yellow door complements the lively aesthetic, inviting natural light.
Villa in Gulfport
4.87 out of 5 average rating, 98 reviews

Cozy funky duplex with KING bed

Escape to the charming town of Gulfport, Florida, and discover a hidden gem nestled in the heart of this vibrant community. Our eclectic studio offers a one-of-a-kind experience for those seeking comfort, style, and a touch of the extraordinary. The main highlight is the funky wallpaper and the luxurious king-sized bed, adorned with premium linens and plush pillows, ensuring a restful night's sleep after your Gulfport adventures.

Guest favourite
A modern kitchen area features sleek white cabinetry, gray countertops, and stainless steel appliances. An island with two black stools offers additional seating. Well-lit by overhead fixtures, the space includes a door leading to an entrance and a doorway to a small adjacent room.
Villa in Tampa
4.88 out of 5 average rating, 174 reviews

Boho -Minimalist villa

Welcome to our Boho Minimalist Villa 4311 unit B with a 2 bedroom and 1 bathroom. Conveniently located in the heart of Tampa, Florida. “Points of interest” to visit and enjoy while you are here: Raymond’s James Stadium, New York Yankees Training Camp, Hillsborough Community College, International Tampa Airport, Downtown Tampa, Midtown within less than 10-minutes’ drive enjoy a great afternoon eating at many local restaurants.

Top Guest favourite
A charming exterior of a townhome is presented, featuring a bright red front door. Lush greenery and colorful plants frame the pathway leading to the entrance, with a well-maintained lawn inviting guests to explore. The surrounding area is dotted with additional townhomes.
Villa in Palm Harbor
5 out of 5 average rating, 35 reviews

Coastal Cottage

Relax with the whole family or a peaceful couples get away. Great little Hideaway with a Large Pool, Club House, Playground for the little one. This cozy town home is 900 sq ft This is a fully furnished unit has everything you need to hide out or venture out to see all Tampa Bay has to offer. Completely renovated tin early 2023 everything was purchased new. Brands Like Macys, Crate and Barrel, My Pillow and others.

Superhost
A charming gazebo is positioned beside a serene pool, surrounded by vibrant greenery. The calm waters of Lake Seminole reflect the pastel colors of the sunset sky, while the gazebo offers shaded seating for relaxation.
Villa in Largo
4.96 out of 5 average rating, 102 reviews

Waterfront Heated Pool, Sleeps 20 - 4plex

? Welcome to LAKESIDE RETREAT 4-plex, situated on a ⅓ acre next to Lake Seminole. Enjoy the perks of a private resort with amenities like a lakefront pool, a gazebo, and a cozy fire pit. The property is a 15-min drive to popular beaches, John’s Pass, and the Lake Seminole Park boat ramp. ✨ Perfect place! Exceeded our expectations! thank you so much! ✨

Popular amenities for Hillsborough County villa rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Private villa rentals

Superhost
Two blue chaise lounges are positioned in a private outdoor area, each adorned with colorful towels. A white picket fence and vibrant greenery provide a serene backdrop, enhancing the inviting atmosphere of the space.
Villa in Temple Terrace
4.88 out of 5 average rating, 33 reviews

Pet Friendly-Pool Villa 2 miles from USF & Moffit

Guest favourite
A serene outdoor space features a circular fire pit surrounded by several adirondack chairs. Lush greenery and trees frame the area, while a vibrant sunset paints the sky in soft pastel hues. The lake is visible in the distance, enhancing the peaceful ambiance.
Villa in Thonotosassa
4.96 out of 5 average rating, 50 reviews

Lakeside Villa

Superhost
A charming entryway features a light-colored front door surrounded by large windows and lush tropical plants. The space is paved with square tiles and shaded by a wooden trellis adorned with vibrant flowering vines.
Villa in Dunedin

Unique Villas 3Plex in the Heart of Downtn Dunedin

An open-concept living area is shown, featuring two gray armchairs positioned around a round table. A decorative plant adds a touch of greenery, while framed artwork adorns the wall. The space is brightened by natural light, highlighting a seamless connection to the dining area and kitchen.
Villa in Tampa
5 out of 5 average rating, 3 reviews

The Bayside Retreat - Unit A

Superhost
A cozy living area features a light-colored sectional sofa adorned with decorative pillows. Natural light enters through multiple plantation-shuttered windows, highlighting the soft tones of the furnishings. An entertainment unit with a large television and a small decorative table adds functionality to the space.
Villa in Clearwater
4.78 out of 5 average rating, 23 reviews

Private Villa with Courtyard

Superhost
A modern kitchen features white cabinetry and a spacious granite countertop. Stainless steel appliances, including a microwave and oven, are visible. A sink with a sleek faucet is positioned near a window, and a coffee maker is placed on the counter.
Villa in Ruskin
4.75 out of 5 average rating, 16 reviews

*Modern 2/2 Cottage with Spacious Backyard*

Guest favourite
A waterfront patio features two yellow lounge chairs positioned to face the serene water. The view includes docked boats and distant buildings under a clear blue sky, creating a peaceful outdoor space for relaxation.
Villa in Clearwater Beach
4.93 out of 5 average rating, 101 reviews

Water Front Villa 2; 5 min walk to beach & dinning

Top Guest favourite
A modern living space is presented with a spacious sofa and armchairs, arranged around a central coffee table. A large flat-screen TV is mounted on the wall opposite the seating area, with light walls and wood-look flooring enhancing the open layout.
Villa in Largo
5 out of 5 average rating, 46 reviews

10 Minutes to Beaches! Mint House

Luxury villa rentals

Guest favourite
A covered outdoor area showcases a glowing blue pool, surrounded by sleek lounge chairs and a playful pool float. Glass sliding doors offer a view of the comfortable seating area, where a table and chairs provide an inviting space for relaxation.
Villa in Tampa
4.84 out of 5 average rating, 50 reviews

Serene Heated Pool Oasis Tampa Vacation

Guest favourite
A spacious heated saltwater pool is surrounded by a screened enclosure, featuring colorful inflatable floats. A playroom is visible with cheerful decor, while a cozy media room offers comfortable seating. The exterior showcases a welcoming home, with a yard perfect for children’s play.
Villa in Dunedin
4.96 out of 5 average rating, 24 reviews

Family Haven/Kid's Amenities Near Honeymoon Island

Top Guest favourite
An aerial view showcases a coastal neighborhood along the intracoastal waterway, featuring a single-story home with a gray roof and a landscaped front yard. Palm trees line the driveway, and nearby properties reflect a variety of architectural styles, emphasizing the serene waterfront setting.
Villa in Indian Rocks Beach
5 out of 5 average rating, 39 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

Guest favourite
A spacious outdoor area features a heated pool, surrounded by lounge chairs and tropical plants. A covered patio is seen nearby, with seating and a BBQ grill for outdoor gatherings. The pool glimmers under natural light, inviting relaxation.
Villa in Tampa
4.97 out of 5 average rating, 31 reviews

(HGR) Heated pool villa. Boat rental available

Top Guest favourite
A serene outdoor pool area is enclosed by a screened structure, allowing for a private retreat. Sun loungers are positioned beside the clear, inviting water, and lush greenery surrounds the pool, enhancing the tranquil setting.
Villa in Tampa
5 out of 5 average rating, 79 reviews

Luxury home in the heart of South Tampa & POOL!

Superhost
An open dining area features a wooden table set for six, with white plates and dark napkins. A stylish light fixture hangs above, illuminating the space. The adjoining kitchen area includes dark cabinetry and modern appliances, offering a seamless flow between dining and cooking.
Villa in Largo
4.86 out of 5 average rating, 64 reviews

Best deal in town!

Top Guest favourite
Villa in Clearwater
5 out of 5 average rating, 12 reviews

[TOP PlCK] 5BR Family Pool Villa By Eagle Park!

Guest favourite
A rooftop terrace is shown with two lounge chairs and a small table. A large umbrella provides shade, while a view of the waterfront and city skyline is visible in the background. The sky displays soft hues of purple and pink, enhancing the serene setting.
Villa in Clearwater
4.98 out of 5 average rating, 42 reviews

4 min Walk to Beach, Pool, Roof Deck

Villa rentals with a pool

Top Guest favourite
The dining area features a modern table with gold accents, surrounded by plush gray chairs. A stylish chandelier hangs above, illuminating the space. The open-concept layout offers a clear view of the adjacent kitchen and a spacious living area with a large television.
Villa in Palm Harbor
4.94 out of 5 average rating, 48 reviews

Villa Luxe~Heated Saltwater Pool~Near Beaches

Superhost
A large heated swimming pool is surrounded by lounge chairs and tiki huts, set against the backdrop of a sandy beach and the shimmering Gulf waters. Sunlight reflects off the water, creating a tranquil atmosphere for relaxation and leisure.
Villa in Indian Shores
4.68 out of 5 average rating, 65 reviews

Relax just steps from beach & Gulf of America

Guest favourite
A spacious saltwater pool stretches across the backyard, bordered by a paved area featuring lounge chairs. Lush greenery, including palm trees and a nearby canal, enhances the serene outdoor setting under a clear blue sky.
Villa in St. Petersburg
4.78 out of 5 average rating, 172 reviews

Dolphin Cove Waterfront St. Pete Beach w/ Pool

Guest favourite
A modern kitchen features wooden cabinetry and a granite countertop, complemented by stainless steel appliances. Red chairs are placed around a dining area visible in the background, with decorative wall art enhancing the space. Natural light filters through the windows, providing a bright atmosphere.
Villa in Treasure Island
4.89 out of 5 average rating, 19 reviews

Luxury waterfront in the heart of treasure island

A spacious living area is featured, showcasing a leather sofa facing a glass coffee table with a collection of books. The room is illuminated by pendant lights and has large windows dressed with sheer curtains that allow natural light to fill the space.
Villa in Riverview
4.78 out of 5 average rating, 50 reviews

Brand New house with pool and much more

Guest favourite
A spacious lawn surrounds the villa, featuring tropical landscaping and a patio area with seating. A pool is visible alongside the well-maintained pathway, leading to the water. The structure showcases large windows that invite natural light, presenting a warm outdoor setting.
Villa in Tampa
4.89 out of 5 average rating, 85 reviews

The Palm Island Villa Luxury 4 BDR Waterfront Home

A bright outdoor area features a sparkling pool surrounded by sun loungers and a patio with stylish landscaping. The property includes a composite dock and is bordered by greenery, offering a tranquil view of the Intracoastal waterfront.
Villa in Indian Rocks Beach
4.7 out of 5 average rating, 56 reviews

Intra coastal home with pool · Awesome Waterfront

Guest favourite
A private pool area is enclosed by a screened lanai, providing a sunny and spacious setting. Loungers are arranged beside the crystal-clear water, and the surrounding patio is finished in light-colored stone. Sliding doors lead to the interior of the house, enhancing the outdoor living experience.
Villa in Greater Northdale
4.84 out of 5 average rating, 75 reviews

Beautiful 4-Bedroom Villa with Private Pool

Destinations to explore