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Best Vacation rentals and Airbnb offers in Hillsborough County, FL

1 Bed 1 Bath Condo, Quiet And Clean, Hidden Gem - Hillsborough County, FL
9.5 187 reviews
Hillsborough County, FL
2 1
$193/nighttotal: $386 (2 )

1 Bed 1 Bath Condo, Quiet And Clean, Hidden Gem

apartment - Brandon
This Brandon apartment is conveniently located near Brandon Regional Hospital and AdventHealth Medical Group Primary Care, making it ideal for medical travelers. It's also within a short drive of Bloomingdale Square and Westfield Brandon, offering plenty of shopping and dining options. The apartment consistently receives excellent ratings for location, cleanliness, and user experience.
This one-bedroom, one-bathroom apartment comfortably sleeps four guests and offers 700 square feet of living space. Guests can enjoy amenities such as a fitness center, tennis court, swimming pool, and a spa, as well as a fully equipped kitchen and a private patio.
New Luxury Casita W/hot Tub, Fire Pit, Backyard️ - Hillsborough County, FL
9.7 421 reviews
Hillsborough County, FL
2 1
$161/nighttotal: $322 (2 )

New Luxury Casita W/hot Tub, Fire Pit, Backyard️

house - St. Petersburg
This St. Petersburg casita offers a central location, minutes from St. Pete Beach and close to nature trails, shopping, and downtown St. Petersburg, providing easy access to Tampa.
This one-bedroom, one-bathroom house sleeps four guests and features a private tropical backyard with a fire pit, hot tub, heated outdoor shower, granite countertops, stainless steel appliances, a washer/dryer, and on-site massage services.
Lovely Rental Unit With Independent Entrance Apt # 1 - Hillsborough County, FL
9.6 26 reviews
Hillsborough County, FL
2 1
$103/nighttotal: $206 (2 )

Lovely Rental Unit With Independent Entrance Apt # 1

apartment - Tampa
This Tampa apartment rental is conveniently located near Tampa International Airport, approximately 3.7 miles away, offering easy access to Busch Gardens, Raymond James Stadium, and other major attractions.
The one-bedroom, one-bathroom unit sleeps five guests and features a fully equipped kitchen with a dishwasher and microwave, a private terrace, free Wi-Fi, and complimentary wine or champagne.
"Luxury Casita/jacuzzi/bush Gardens/usf/casino" - Hillsborough County, FL
9.9 171 reviews
Hillsborough County, FL
2 1
$147/nighttotal: $294 (2 )

"Luxury Casita/jacuzzi/bush Gardens/usf/casino"

house - Tampa
This Tampa casita is located within walking distance of Busch Gardens, offering easy access to the theme park and other Tampa Bay attractions. This one-bedroom, one-bathroom house sleeps two guests and features a private jacuzzi, putting green, and modern amenities including a fully equipped kitchen with a fridge, freezer, and microwave.
Ybor City Bungalow W/casita & Backyard Oasis - Hillsborough County, FL
9.6 60 reviews
Hillsborough County, FL
6 4
$164/nighttotal: $4428 (27 )

Ybor City Bungalow W/casita & Backyard Oasis

apartment - Tampa
This Tampa apartment is conveniently located just a few blocks from Ybor City, a historic district known for its vibrant nightlife, Cuban culture, and easy access to the free trolley.
This 1-bedroom, 3-bathroom home sleeps 8 guests and features a spacious outdoor area with a covered pergola, seating, dining, BBQ grill, and fire pit, perfect for relaxing and entertaining.
Gambino Getaway Shotgun Style Apt In The Heart Of Ybor City - Hillsborough County, FL
9.4 920 reviews
Hillsborough County, FL
2 1
$155/nighttotal: $310 (2 )

Gambino Getaway Shotgun Style Apt In The Heart Of Ybor City

apartment - Tampa
This shotgun-style apartment is located in Tampa's Ybor City district, just a short distance from the Amalie Arena and Tampa International Airport. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment features a separate bedroom, living room, fully equipped kitchen, and bathroom. Amenities include free Wi-Fi, a patio, and a kitchen with a dishwasher and oven.
Mercis Apartment - Hillsborough County, FL
9.8 419 reviews
Hillsborough County, FL
2 1
$106/nighttotal: $212 (2 )

Mercis Apartment

apartment - Town 'n' Country
This Town 'n' Country apartment rental boasts convenient access to Tampa International Airport and major expressways, offering easy travel to area attractions and shopping malls.
The one-bathroom unit sleeps two guests and features a private outdoor seating area, on-site parking, and a bidet; occasional nearby celebrations may be audible.
Updated Ybor City House W/ Fenced Yard - Hillsborough County, FL
9.0 106 reviews
Hillsborough County, FL
6 2
$187/nighttotal: $5049 (27 )

Updated Ybor City House W/ Fenced Yard

house - Tampa
This Tampa house is located in Ybor City, a historic district known for its lively nightlife and diverse restaurants, within a short drive to the Amalie Arena and Raymond James Stadium. The house has received very good ratings for its location, user experience, and cleanliness, with an excellent cleanliness rating.
This two-bedroom house offers 620 square feet of space, comfortably accommodating up to six guests. Enjoy a private yard, a fully equipped kitchen, air conditioning, a swimming pool, a spa, a fitness center, and free Wi-Fi.
The Chill Spot W/outside Patio Near Armature Works - Hillsborough County, FL
9.6 189 reviews
Hillsborough County, FL
6 3
$227/nighttotal: $6129 (27 )

The Chill Spot W/outside Patio Near Armature Works

apartment - Tampa
This Tampa home is located in Old West Tampa, within walking distance of Armature Works, the Tampa Riverwalk, and the University of Tampa. Guests rave about the location, cleanliness, and overall experience.
The home has three bedrooms and three bathrooms, comfortably accommodating up to six guests. Enjoy amenities like a balcony, a barbecue grill, free Wi-Fi, and a fully equipped kitchen.
The Fold Hotels Indian Shores - Hillsborough County, FL
9.1 2368 reviews
Hillsborough County, FL
6 2
$373/nighttotal: $10071 (27 )

The Fold Hotels Indian Shores

resort - Indian Shores
Legacy Vacation Resorts-Indian Shores is located on the Intracoastal Waterway in Indian Shores, just across from the beach and 10 miles from the shops and restaurants of Pier 60 and Clearwater Beach. This resort consistently receives excellent ratings for location, cleanliness, and overall user experience.
The resort offers a variety of accommodations, including suites with fully equipped kitchens, seating areas, and sofa beds. Guests can enjoy an outdoor pool, hot tub, shuffleboard court, a game room with billiards, a fitness center, and a business center.
Charming Beachside Retreat #2 - Steps To The Beach - Hillsborough County, FL
9.3 3 reviews
Hillsborough County, FL
6 2
$276/nighttotal: $7452 (27 )

Charming Beachside Retreat #2 - Steps To The Beach

house - Indian Rocks Beach
This beach house in Clearwater Beach offers unbeatable proximity, located just a 2-minute walk to Indian Rocks Beach and 7.8 miles from Pier 60.
This 750 sq ft rental accommodates up to 8 guests with 2 bedrooms and 1 bathroom, featuring a full kitchen with a dishwasher and microwave, complimentary WiFi, free parking, and outdoor seating, with cycling activities available nearby and John's Pass Village and Boardwalk 8.9 miles away.
Cozy Bungalow Just 8 Min To Indian Rocks Beach! - Hillsborough County, FL
9.9 167 reviews
Hillsborough County, FL
6 2
$286/nighttotal: $7722 (27 )

Cozy Bungalow Just 8 Min To Indian Rocks Beach!

apartment - Largo
This family-friendly vacation home in Largo is located just a short distance from the beach and within 2 miles of Largo Mall and Pinellas Trail, offering easy access to shopping, dining, and recreation. The property has received excellent ratings for its location, cleanliness, and overall experience.
The 880 square foot house has two bedrooms, one bathroom, and can comfortably accommodate up to six guests. Amenities include a swimming pool, jacuzzi, fitness center, and a fully equipped kitchen with a refrigerator, oven, and microwave.

Best family friendly Hillsborough County, FL vacation rentals

Among the 33226 accommodations in Hillsborough County, FL, here are the 4 best family friendly rentals

Guest House Located Walking Distance From Downtown - Hillsborough County, FL
9.9 177 reviews
Hillsborough County, FL
2 2
$187/nighttotal: $374 (2 )

Guest House Located Walking Distance From Downtown

house - Tampa
This Tampa Heights apartment is just a short distance from Armature Works, the Tampa Riverwalk, and the University of Tampa, offering easy access to popular attractions and a vibrant neighborhood atmosphere. With excellent ratings for location, cleanliness, and user experience, you can be sure of a comfortable and enjoyable stay.
The two-bedroom apartment comfortably sleeps six guests and features a fully equipped kitchen, a cozy living area, and a private balcony. Enjoy free Wi-Fi, a relaxing garden, and a refreshing Jacuzzi, perfect for unwinding after a day exploring Tampa.
Heated Pool Oasis | Family Retreat | Sleeps 8 - Hillsborough County, FL
9.8 56 reviews
Hillsborough County, FL
6 3
$284/nighttotal: $7668 (27 )

Heated Pool Oasis | Family Retreat | Sleeps 8

apartment - Zephyrhills
This apartment in Zephyrhills is ideally located for travelers seeking convenience and tranquility. Situated just 45 minutes from both Clearwater Beach and Walt Disney World Resort, it offers easy access to major tourist attractions. With excellent user, location, and cleanliness ratings, this apartment guarantees a comfortable and memorable stay.
The spacious apartment features three bedrooms, each with an ensuite bathroom, ensuring privacy for multiple guests. It boasts a fully equipped kitchen, air conditioning, and a private entertainment space for relaxation. Guests can also enjoy the outdoor swimming pool, garden, spa, and parking facilities. The apartment's serene atmosphere and convenient location make it an ideal choice for families, pet owners, and those seeking a relaxing getaway in Zephyrhills.
Bahia Vista 9-521 - Hillsborough County, FL
9.3 179 reviews
Hillsborough County, FL
6 2
$572/nighttotal: $15444 (27 )

Bahia Vista 9-521

apartment - St. Petersburg
Bahia Vista 8-115 is located in St. Petersburg, Florida, just steps from Isla del Sol Beach and a short drive from St. Pete Beach, offering a peaceful retreat with easy access to local attractions. This apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment has two bedrooms, a dining area, and a living room, comfortably accommodating families or groups of friends. It features modern amenities like air conditioning, a dishwasher, a satellite TV, free Wi-Fi, and access to a swimming pool, Jacuzzi, fitness center, spa, and parking.
Plush Sheets, Games!, Huge Backyard, Massage Chair - Hillsborough County, FL
9.9 232 reviews
Hillsborough County, FL
6 4
$240/nighttotal: $6480 (27 )

Plush Sheets, Games!, Huge Backyard, Massage Chair

house - Tampa
This Tampa vacation rental is conveniently located just a short drive from Busch Gardens and Adventure Island, offering easy access to popular attractions. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
This 4-bedroom, 3-bathroom home spans 2300 square feet. Guests can enjoy a fully equipped kitchen, a private patio, a massage chair, a pool table, table tennis, and a garden, along with free Wi-Fi, parking, and laundry service.

Top cities

Best Hillsborough County, FL vacation rentals with a pool

Among the 33226 accommodations in Hillsborough County, FL, here are the 4 best rentals with a pool

Madeira Bay Resort 509 - Hillsborough County, FL
9.3 556 reviews
Hillsborough County, FL
6 2
$367/nighttotal: $9909 (27 )

Madeira Bay Resort 509

house - Madeira Beach
Madeira Bay Resort 509 is located just steps from the white sands of Madeira Beach and a short walk from the lively John's Pass Village and Boardwalk. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
The resort offers comfortable rooms with air conditioning, TVs, and private bathrooms. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, sauna, spa, fitness center, restaurant, bar, and free Wi-Fi.
619 Studio- Little Harbor Pool & Canal View! - Hillsborough County, FL
8.9 507 reviews
Hillsborough County, FL
2 1
$209/nighttotal: $418 (2 )

619 Studio- Little Harbor Pool & Canal View!

apartment - Ruskin
Pirates Bay U3270, also known as "Florida At It's Finest!", is a smoke-free vacation home located just over a mile from Cockroach Bay Preserve State Park and two and a half miles from Tampa Bay, offering easy access to nature and outdoor activities. It's a popular choice for travelers, with very good user ratings and an excellent location rating.
The vacation home is equipped with a fully equipped kitchen, a washer and dryer, and three bathrooms. Guests can enjoy a range of amenities including a fitness center, swimming pool, jacuzzi, spa, bar, and a garden.
Little Harbor Resort #207 Tampa Bay Fl, Paradise - Hillsborough County, FL
8.1 19 reviews
Hillsborough County, FL
2 1
$158/nighttotal: $316 (2 )

Little Harbor Resort #207 Tampa Bay Fl, Paradise

apartment - Ruskin
Little Harbor Resort #207, a Ruskin, Florida apartment rental, is located a 4-minute walk from Bahia Beach and 25 miles from both Amalie Arena and the 1-800 Ask Gary Amphitheatre.
This 310-square-foot condo sleeps five guests in one bedroom and one bathroom and boasts amenities including a pool, hot tub, fitness center, tennis court, free Wi-Fi, and parking, plus nearby snorkeling and bicycle rentals.
Forever Beach View Sailport Resort Condos Tampa - Hillsborough County, FL
8.9 41 reviews
Hillsborough County, FL
2 1
$263/nighttotal: $526 (2 )

Forever Beach View Sailport Resort Condos Tampa

house - Tampa
This Tampa vacation rental is located in the Harbor district, just a short drive from Ben T Davis Beach and Raymond James Stadium. The house has received excellent ratings for cleanliness, location, and overall experience.
This one-bedroom, one-bathroom house features a private pool, balcony, fully equipped kitchen, and fitness center. Enjoy a relaxing stay with amenities like a hot tub, garden, and elevator access.

Frequently Asked Questions about vacation rentals in Hillsborough County, FL

  • What are the must-see sights in Hillsborough County, Florida?

    For must-see sights in Hillsborough County, you've got plenty of options! The Florida Aquarium is a fantastic place to spend the day, especially if traveling with kids. Busch Gardens Tampa Bay offers thrilling rides and animal encounters. Ybor City, Tampa's historic Cuban district, is a must-see for its architecture, cigar shops, and vibrant nightlife. Then there's the Henry B. Plant Museum, housed in a stunning Victorian hotel, and the Tampa Riverwalk, perfect for a stroll.
  • What are the best Airbnb and vacation rentals in Hillsborough County, FL?

    Private Apartment Near The Airport, Davis Islands Gem: Cozy/quiet And Pet Friendly and 303 - New Listing Waterfront - Heated Pool 2 Min To Airport are the most popular Airbnb and vacation rentals in Hillsborough County, FL among travelers.

  • Are there unique natural phenomena in Hillsborough County, Florida?

    While Hillsborough County doesn't have, say, geysers, its unique natural beauty lies in its diverse ecosystems. The beaches along the Gulf Coast offer stunning sunsets and opportunities for shelling. Hillsborough River State Park provides hiking trails and glimpses of Florida's natural landscape, including diverse birdlife. Exploring the many parks and preserves reveals the area's rich biodiversity.
  • What are the most popular Airbnbs in Hillsborough County, FL?

  • What essentials should you bring along for a trip to Hillsborough County, Florida?

    Pack light, breathable clothing suitable for warm, humid weather. Sunscreen, sunglasses, and a hat are absolute necessities, especially during peak sun hours. Comfortable walking shoes are a must, given the amount of walking you'll likely do. Don't forget insect repellent, especially if you plan on spending time outdoors, and a reusable water bottle to stay hydrated.
  • What are the best vacation rentals with a pool in Hillsborough County, FL?

  • What famous events or festivals are happening in Hillsborough County, Florida?

    Hillsborough County hosts many events throughout the year. The Gasparilla Pirate Festival is a huge, well-known event featuring a parade and a pirate invasion. The Florida State Fair is another popular annual event with rides, food, and entertainment. Check local listings for smaller, neighborhood festivals and events happening during your visit.
  • What are the best rentals for families and kids in Hillsborough County, FL?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Hillsborough County, Florida?

    A daily budget will vary greatly depending on your travel style. For a mid-range budget, you could plan on $150-$300 per day. This covers a moderate hotel, meals at a mix of restaurants and cafes, local transportation like ride-sharing or public transit, and entry fees to attractions. Luxury travel will obviously be significantly more expensive.
  • What are the best rentals or Airbnbs with a jacuzzi in Hillsborough County, FL?

  • Where can you find the best restaurants serving local dishes in Hillsborough County, Florida, and what are the must-try specialties?

    For authentic Cuban cuisine, head to Ybor City. Columbia Restaurant is a historic landmark serving traditional dishes. Bern's Steak House is a Tampa institution known for its exceptional steaks and extensive wine cellar. Many restaurants along the Riverwalk offer fresh seafood. You should definitely try Cuban sandwiches, fresh seafood, and key lime pie.
  • What are some less-famous attractions in Hillsborough County, Florida that are worth a visit?

    The Tampa Bay History Center offers a fascinating look at the area's past. The Glazer Children's Museum is a great option for families. The University of Tampa campus is architecturally beautiful and worth a wander. Check out smaller, local museums and art galleries for a more unique experience.
  • What are the best activities for engaging with locals and understanding their culture in Hillsborough County, Florida?

    Visiting local farmers' markets allows you to interact with vendors and sample local produce. Attending a community event or festival provides a chance to mingle with residents. Exploring Ybor City and engaging with the local businesses and residents can offer insight into the area's rich Cuban heritage. Simply striking up conversations with people you meet shows genuine interest.
  • What unique natural landscapes and terrain features can travelers explore in Hillsborough County, Florida?

    Hillsborough County boasts a variety of landscapes. The beaches along the Gulf Coast offer sandy shores and calm waters. Hillsborough River State Park features diverse flora and fauna, including cypress swamps and hardwood forests. Exploring the various parks and preserves reveals the county's natural beauty, from coastal areas to inland wetlands.
  • How many days are ideal for visiting Hillsborough County, Florida, and what are some itinerary suggestions?

    Three to five days is a good amount of time to experience Hillsborough County. A possible itinerary could include one day for the Florida Aquarium and Riverwalk, one day for Busch Gardens, and one day exploring Ybor City and the historic districts. You could add a day trip to a beach or state park, depending on your interests.

Nearby regions

Best Hillsborough County, FL vacation rentals with a balcony

Historic Bungalow W/game Room By Downtown Tampa! - Hillsborough County, FL
9.8 283 reviews
Hillsborough County, FL
6 3
$168/nighttotal: $4536 (27 )

Historic Bungalow W/game Room By Downtown Tampa!

apartment - Tampa
This charming bungalow is located in Seminole Heights, a historic neighborhood in Tampa, just a short walk from Florida Avenue and a quick drive to downtown Tampa, Hyde Park, and Armature Works. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The bungalow offers 1,250 square feet of space with three bedrooms, one bathroom, and can comfortably accommodate up to seven guests. This home features a fully equipped kitchen, a dedicated workspace, a game room, a shared backyard, and free parking.
Tampa Bay 1br - Pool, Balcony & Beach Access - Hillsborough County, FL
9.2 41 reviews
Hillsborough County, FL
2 1
$151/nighttotal: $302 (2 )

Tampa Bay 1br - Pool, Balcony & Beach Access

apartment - Tampa
This Tampa condo rental in the Rocky Point neighborhood offers easy access to Westshore Plaza Mall and the Tampa Riverwalk, with ZooTampa and the Florida Aquarium a short drive away.
The 600-square-foot, one-bedroom, one-bathroom unit sleeps four and features a private balcony with pool views, plus access to a geothermal pool, fitness center, and free airport shuttle.
Modern Waterview 2br Condo Mins From Airport - Hillsborough County, FL
9.4 44 reviews
Hillsborough County, FL
6 2
$198/nighttotal: $5346 (27 )

Modern Waterview 2br Condo Mins From Airport

apartment - Town 'n' Country
This Town 'n' Country condo rental is minutes from Tampa International Airport, Busch Gardens Tampa Bay, area beaches, and Raymond James Stadium, offering easy access to major interstates.
The 1600-square-foot, two-bedroom unit sleeps six and features a fully equipped kitchen, air conditioning, a swimming pool, and two balconies with waterfront views, perfect for a family vacation or extended stay.
Sea Shell 14 - Premier - Hillsborough County, FL
9.0 153 reviews
Hillsborough County, FL
6 2
$363/nighttotal: $9801 (27 )

Sea Shell 14 - Premier

house - Indian Shores
Sea Shell 14 - Premier is located just a 4-minute walk from Indian Shores Beach, offering easy access to the beautiful white sands and turquoise waters. The property has consistently received very good ratings for location, cleanliness, and overall user experience.
The 1230 square foot house features two bedrooms and a well-equipped kitchen with a dishwasher, oven, and microwave. Enjoy the private balcony, free Wi-Fi, a swimming pool, a tennis court, and a garden.

Neighborhoods and points of interest in Hillsborough County, FL

Best Hillsborough County, FL vacation rentals with parking

Walk To Beaches & Gulf: Indian Rocks Beach Duplex! - Hillsborough County, FL
9.6 56 reviews
Hillsborough County, FL
6 2
$403/nighttotal: $10881 (27 )

Walk To Beaches & Gulf: Indian Rocks Beach Duplex!

apartment - Indian Rocks Beach
This Indian Rocks Beach duplex is a five-minute walk from Indian Rocks Beach, 1.1 miles from Indian Shores Beach, and within 12 miles of Clearwater Beach attractions like Pier 60 and John's Pass.
This 1300-square-foot vacation rental boasts two bedrooms, one bathroom, a fully equipped kitchen with oven and microwave, in-unit laundry, free Wi-Fi, cable TV, and a patio; it sleeps up to four and allows pets.
Historic & Cozy Bungalow By Downtown - Hillsborough County, FL
9.4 39 reviews
Hillsborough County, FL
6 3
$155/nighttotal: $4185 (27 )

Historic & Cozy Bungalow By Downtown

house - Tampa
This Tampa bungalow, near downtown and within 5-7 miles of Busch Gardens, Adventure Island, Amalie Arena, and Raymond James Stadium, offers convenient access to major attractions.
This 1350-square-foot house features three bedrooms, one bathroom, sleeps 13 guests, and includes a fully equipped kitchen, free Wi-Fi, free parking, and a garden.
Resort-style Avalon Condo In Clearwater - Hillsborough County, FL
9.3 76 reviews
Hillsborough County, FL
6 2
$252/nighttotal: $6804 (27 )

Resort-style Avalon Condo In Clearwater

apartment - Clearwater
This Clearwater apartment is conveniently located near Morton Plant Hospital and Pinellas County Primary Care and Hospitalists, within walking distance of these medical facilities and a short drive from the Church of Scientology and Clearwater Country Club. The apartment has excellent user, location, and cleanliness ratings, making it a great option for travelers. This 2-bedroom, 2-bathroom apartment can comfortably accommodate up to 6 guests. The apartment comes equipped with a kitchen, a washing machine, a fitness center, a swimming pool, a garden, and parking, ensuring a comfortable and enjoyable stay.
Madeira Bay Resort I By Travel Resort Services - Hillsborough County, FL
9.1 64 reviews
Hillsborough County, FL
6 3
$409/nighttotal: $11043 (27 )

Madeira Bay Resort I By Travel Resort Services

house - Madeira Beach
This Madeira Beach vacation rental is just a 3-minute walk from John's Pass Village and Boardwalk, offering easy access to shops, restaurants, and entertainment. The home has earned excellent ratings for its location, cleanliness, and overall experience.
The house features a fully equipped kitchen, a private balcony, and a relaxing outdoor pool and hot tub. Enjoy free Wi-Fi, private parking, and a prime location that puts you close to the beach, snorkeling, and fishing.
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