Best Vacation Homes in Hillsborough County
RV Rental
10.0(6 Reviews)
1 Bedroom
1 Bath
4 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $102/Night
7 Nights - US $715
House
10.0(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
602.78 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $76/Night
7 Nights - US $532
House
1 Bedroom
1 Bath
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $738/Night
7 Nights - US $5,168
New
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
2000 ft²
Private Pool
Oceanfront
Hot Tub- Fireplace/Heating
US $335/Night
7 Nights - US $2,344
Apartment
10.0(14 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $102/Night
7 Nights - US $712
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
9 Guests
- Private Pool
- Fireplace/Heating
Pool
Ocean View
US $656/Night
7 Nights - US $4,593
Apartment
10.0(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
1100 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $349/Night
7 Nights - US $2,443
House
10.0(1 Review)
6 Bedrooms
3 Baths
12 Guests
3600 ft²
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
US $897/Night
7 Nights - US $6,276
Hillsborough County Luxury Rentals
House
1 Bedroom
1 Bath
1 Guest
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
Unlock the Best Price
Boat Rental
4 Bedrooms
5 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
Unlock the Best Price
Apartment
2 Bedrooms
1 Bath
6 Guests
Pet Friendly- Air Conditioner
- Internet
- Child Friendly
US $9,100/Night
7 Nights - US $63,700
US $6,503/Night
7 Nights - US $45,518
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
1173.27 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $5,667/Night
7 Nights - US $39,669
House
1 Bedroom
2 Baths
8 Guests
1270.14 ft²
- Pool
- Balcony/Terrace
- Parking
- Air Conditioner
US $5,000/Night
7 Nights - US $35,000
Apartment
7.6(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $4,553/Night
7 Nights - US $31,873
Apartment
1 Bedroom
1 Bath
- Balcony/Terrace
- Pet Friendly
- Parking
- Internet
US $4,461/Night
7 Nights - US $31,228
Hillsborough County Pet Friendly Vacation Rentals
New
House
10.0(1 Review)
4 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $279/Night
7 Nights - US $1,953
Apartment
10.0(9 Reviews)
1 Bedroom
1 Bath
4 Guests
818.06 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $81/Night
7 Nights - US $567
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
- Pet Friendly
- Parking
- Internet
- Child Friendly
US $330/Night
7 Nights - US $2,307
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1367 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $228/Night
7 Nights - US $1,597
Villa
10.0(5 Reviews)
4 Bedrooms
4 Baths
10 Guests
5005.22 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $494/Night
7 Nights - US $3,458
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $196/Night
7 Nights - US $1,375
House
9.4(3 Reviews)
1 Bedroom
1 Bath
3 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $98/Night
7 Nights - US $684
New
House
6 Bedrooms
4 Baths
15 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $851/Night
7 Nights - US $5,955
Hillsborough County Large Vacation Homes
New
House
4 Bedrooms
3 Baths
10 Guests
1710 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $758/Night
7 Nights - US $5,303
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
12 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
US $210/Night
7 Nights - US $1,469
Villa
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $1,319/Night
7 Nights - US $9,231
New
House
5 Bedrooms
4 Baths
11 Guests
38750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $601/Night
7 Nights - US $4,206
House
10.0(2 Reviews)
1 Bedroom
5 Baths
16 Guests
2830.91 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $722/Night
7 Nights - US $5,054
New
House
4 Bedrooms
4 Baths
10 Guests
2400 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $542/Night
7 Nights - US $3,794
New
House
4 Bedrooms
4 Baths
10 Guests
2400 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $542/Night
7 Nights - US $3,794
New
Villa
3 Bedrooms
2 Baths
8 Guests
1400 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $331/Night
7 Nights - US $2,317
Why Choose Rent By Owner for your Hillsborough County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Hillsborough County
When should you plan your Vacation Rentals stay?
Timing your visit to this destination can greatly enhance your experience, as certain seasons offer ideal weather and events, making it the perfect time to book your vacation rentals in Hillsborough County's vibrant region.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences warm daytime temperatures, making it an ideal escape from colder climates.
Average Temperature Daytime: Average daytime temperatures range from 70°F to 75°F - Nighttime: Nighttime temperatures typically fall between 50°F and 55°F
Spring (March to May)
Spring brings pleasant weather with less rainfall, attracting visitors seeking outdoor activities in the area.
Average Temperature Daytime: Daytime temperatures hover around 75°F to 85°F - Nighttime: Evenings are comfortably cool, with lows around 60°F to 65°F
Off-Season Highlights
Summer (June to August)
In summer, you can expect higher humidity and consistent warmth, perfect for enjoying the area's outdoor attractions.
Average Temperature Daytime: Temperatures often exceed 90°F - Nighttime: Nights tend to stay above 70°F
Fall (September to November)
Fall sees slightly cooler temperatures and fewer tourists, offering a peaceful retreat within the region.
Average Temperature Daytime: Daytime temperatures range from 80°F to 85°F - Nighttime: Nighttime lows usually fall between 60°F and 65°F
Weekly Weather Forecast for Hillsborough County
How to Book Your Hillsborough County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Hillsborough County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool to relax and cool off during your stay.
- Take advantage of spacious patios or decks perfect for outdoor dining and gatherings.
- Explore beautifully landscaped gardens that enhance the outdoor ambiance.
- Use the barbecue grills available for preparing delicious meals outside.
- Benefit from outdoor seating areas ideal for lounging and socializing under the sun.
- Find convenient parking spaces with easy access to outdoor amenities.
- Experience outdoor recreational features such as tennis courts or walking trails, common in the area’s vacation rentals.
Top Attractions Around Hillsborough County
What attractions are nearby?
In the area, you'll find a variety of outdoor activities and cultural attractions to explore, making it an ideal destination for those seeking both adventure and relaxation during their stay.
Family Activities
- Busch Gardens Tampa Bay: Experience thrilling rides, captivating wildlife exhibits, and live entertainment at this popular theme park in the area, perfect for a fun-filled family day out.
- Florida Aquarium: Discover diverse marine life and interactive exhibits here, making it an educational and engaging activity suitable for children and adults alike in this region.
- Lettuce Lake Park: Enjoy scenic nature walks, birdwatching, and picnicking in this peaceful park, offering a great outdoor escape for families visiting here.
- Museum of Science & Industry (MOSI): Engage with hands-on science exhibits and IMAX movies that inspire curiosity and learning, ideal for family explorations in the area.
Adult Activities
- Visit Busch Gardens Tampa Bay: Experience thrilling roller coasters and exotic animal encounters at this renowned amusement park nestled in the region.
- Explore the Florida Aquarium: Discover vibrant marine life and engaging exhibits that showcase the area's aquatic ecosystems, perfect for an educational outing.
- Enjoy outdoor activities at Hillsborough River State Park: Paddle along scenic river routes, hike through lush nature trails, or simply unwind in the tranquility of this natural preserve.
- Dine at local culinary hotspots: Savor diverse flavors and regional specialties at the area's acclaimed restaurants, ideal for a relaxed evening after your day’s adventures.
Other Places to Stay in Hillsborough County, FL
Florida Gulf Coast
Northwest Tampa
Tampa Bay
Downtown Tampa
Ybor City
Ruskin
Southside Rural Community
Tampa Heights
Rocky Point
East Tampa
Apollo Beach
Hillsborough County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit During Off-Peak Seasons: Visiting during less busy times can help you enjoy popular attractions and accommodations with more comfort and better rates.
- Explore Local Dining and Markets: Take advantage of nearby eateries and markets to experience authentic regional flavors and support local businesses.
- Utilize Public Transportation or Rideshare Services: Making use of the area's transit options can simplify your travel between attractions and your vacation rental.
- Research Nearby Activities and Events: Check for local events or outdoor activities that align with your interests to enrich your stay here.
Transportation Options
- Public Transit (HART Bus System): You can conveniently explore the area using the local bus system, which provides affordable and reliable transportation options around this region.
- Skyway Trolley: This free trolley service connects key destinations within the city, making it easy to get around without a car during your stay here.
- Rental Cars: Renting a car offers the flexibility to visit popular attractions and scenic spots in the area at your own pace.
- Airport Shuttle Services: Dedicated shuttle services are available for quick and comfortable transfers between the airport and your vacation rental here.
Local Customs Options
- Southern Hospitality: You will experience the warm and friendly nature of locals, who take pride in welcoming visitors to the region with open arms.
- Respect for Nature: Here, environmental conservation is valued, and you'll find locals practicing eco-friendly habits that preserve the area's natural beauty.
- Community Events: Participating in local festivals and gatherings offers insight into the region’s cultural traditions and strong community spirit.
- Casual Dress Code: Visitors often observe a laid-back dress style, reflecting the relaxed lifestyle embraced by residents of this destination.
Hillsborough County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Hillsborough County?
There are a lot of options in Hillsborough County. If you plan on staying in the Hillsborough County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hillsborough County:
- Secluded Lakefront House short drive to Beaches, Busch Gardens, Stadium, Disney
- The Palm Tree Waterfront - Pool Home - Free Heated pool- Pool Table - kayaks
- SOUTH TAMPA, HYDE PARK, BAYSHORE, UNIV TAMPA, TAMPA GENERAL, RIVERWALK- 5 STARS!
- Immaculate & Cozy Entire Heated Pool House
- Stunning Key West Style Waterfront Home with Exceptional Views!
- Waterfront Retreat in the Heart of Tampa. Close to TPA, RayJay and Steinbrenner
- Stunning Heated Pool House Close to Tampa & Casino
- Apollo Beach Waterfront 3BR — Private Dock, Heated Saltwater Pool & Kayaks
- Seminole Heights River Retreat - Central Tampa location
- Tampa Bay Perfect location for a safe vacation! 5 bedrooms, ,3.5 bath ,sleeps14
2. How many vacation rentals have private pools in Hillsborough County?
There are 1048 vacation rentals with private pools near Hillsborough County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Hillsborough County are best for families?
If you are looking for a family-friendly vacation home in Hillsborough County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hillsborough County:
4. How many Rentbyowner vacation rentals are available in Hillsborough County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 9594 in the Hillsborough County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Hillsborough County.
5. What is the cancellation policy for vacation rentals in this area?
The cancellation policies vary by listing, so it’s important to review the specific terms on each property’s details page. Many listings offer flexible options, but some may have strict policies. For clarity, contact the property owner directly if you have particular concerns about your booking.
6. How do I ensure the vacation rental meets my needs before booking?
You should carefully read the property description, amenities, and house rules listed online. Checking recent reviews can also provide insight into the quality and accuracy of the listing. If you have specific requirements, don’t hesitate to reach out to the host for confirmation.
7. Are there any additional fees I should be aware of when booking a property here?
Additional fees such as cleaning, service charges, or local taxes might apply depending on the property. These details are usually outlined during the booking process, but it’s advisable to review the total cost breakdown before confirming your reservation.
8. What is the check-in and check-out process for vacation rentals in this region?
Check-in and check-out times are specified in each listing, often with flexible options available. Contact the property owner if you need special arrangements or have questions about the process to ensure a smooth arrival and departure.
9. How can I contact the property owner if I encounter issues during my stay?
Contact information for the property owner is typically provided within the booking platform or on the listing page. If you experience any problems, reach out to them directly through the messaging system or contact support for assistance.
Hillsborough County Top Rated Vacation Rentals
House
10.0(148 Reviews)
4 Bedrooms
2 Baths
10 Guests
1850 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $402/Night
7 Nights - US $2,813
House
10.0(138 Reviews)
4 Bedrooms
2 Baths
14 Guests
2053 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $345/Night
7 Nights - US $2,412
House
10.0(124 Reviews)
4 Bedrooms
2 Baths
8 Guests
1806 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $450/Night
7 Nights - US $3,152
House
10.0(123 Reviews)
4 Bedrooms
2 Baths
12 Guests
1309 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $300/Night
7 Nights - US $2,099
House
10.0(122 Reviews)
3 Bedrooms
2 Baths
6 Guests
1950 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $304/Night
7 Nights - US $2,128
House
10.0(118 Reviews)
5 Bedrooms
3 Baths
14 Guests
3000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $408/Night
7 Nights - US $2,856
House
10.0(117 Reviews)
3 Bedrooms
2 Baths
5 Guests
1200 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $345/Night
7 Nights - US $2,417
House
10.0(115 Reviews)
3 Bedrooms
2 Baths
6 Guests
2072 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $346/Night
7 Nights - US $2,421
