Holiday Rentals in Hillsborough County

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Top Cities in Hillsborough County

Featured Holiday Rentals in Hillsborough County

Our top choices for Hillsborough County holiday rentals

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very good, (4715)
"Very beautiful property staff was excellent "
The price is €124
includes taxes & fees
7 Sept - 8 Sept
Sailport Waterfront Suites

Happy Travelers RV Resort

3.0 star property
9.4 out of 10, Exceptional, (254)
"Great little place. Awesome little cabins with excellent roads and parking. Well worth the price "
The price is €62
includes taxes & fees
29 Sept - 30 Sept
Happy Travelers RV Resort

The Adaline

4.5 star property
9.6 out of 10, Exceptional, (48)
"Great property in a great location "
The price is €315
includes taxes & fees
2 Sept - 3 Sept
The Adaline

Landing Tampa Westshore

4.5 star property
9.0 out of 10, Wonderful, (155)
"GREAT!"
Landing Tampa Westshore

#1 Tampa Waterfront Private Resort, 13BR Sleeps 40+, Heated Pool, Theater

8.8 out of 10, Excellent, (11)
"We had a great time with a large group. The backyard was beautiful and the communication was very quick!"
#1 Tampa Waterfront Private Resort, 13BR Sleeps 40+, Heated Pool, Theater

Welcome to our charming studio, perfectly located near Tampa Bay's attractions.

2.0 star property
9.2 out of 10, Wonderful, (34)
"We enjoyed our time in Tampa and would stay at this VRBO again. Thank you "
The price is €87
includes taxes & fees
5 Sept - 6 Sept
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.

Landing Apartments near Sun City Center and Riverview

4.0 star property
6.0 out of 10, (1)
"It was a bad experience, no entry code and spent 3hrs and didn’t get in until 8am next day. Lost a night, had book a room down the street. No refund for the night lost. Wife was screaming when we got in as a live roach was in the sink of the master suite bathroom. Place is brand new😒never again!!!!!!"
Landing Apartments near Sun City Center and Riverview

Highland Down Town Tampa

3.5 star property
6.0 out of 10, (2)
"I booked this place bc it was advertised as 3 bedrooms house that can sleep up to 7 people , with beautiful pictures of the house, but when arrived , it was a separate in law apartment in the back with a 1 bedroom , was very disappointed… the place wasn’t clean, dirty dishes and stuff in kitchen cabinets , and 2 overflowed trash barrels out front door. We had to clean the place up before settling in… I wish they have advertised correctly , it was false advertisement I believe …"
The price is €414
includes taxes & fees
1 Sept - 2 Sept
Highland Down Town Tampa

❤Waterfront View, Amazing Sunsets, Heated Pool 3mins to Airport ☀🐬🏖

9.2 out of 10, Wonderful, (145)
"My daughter, granddaughter and I stayed for 3 nights after a cheerleading competition and greatly enjoyed the condo and chance to relax around the pool and in the sandy beach area with tiki torches and fire pit. The pool restaurant bar was also enjoyed!!"
The price is €210
includes taxes & fees
2 Sept - 3 Sept
❤Waterfront View, Amazing Sunsets, Heated Pool 3mins to Airport ☀🐬🏖

Small But Pleasant Studio

8.4 out of 10, Very good, (57)
"Very good wouldn't want to go nowhere else "
The price is €104
includes taxes & fees
1 Sept - 2 Sept
Small But Pleasant Studio

*Your Large 2nd Home in Tampa Bay* **Thoroughly Sanitized**

9.8 out of 10, Exceptional, (70)
"Very spacious Easy to locate Amble space "
*Your Large 2nd Home in Tampa Bay* **Thoroughly Sanitized**

The Hemingway

4.0 star property
7.4 out of 10, Good, (16)
"The place was beautiful wondering service and very welcoming I definitely would recommend this place amd would come again. "
The price is €194
includes taxes & fees
24 Sept - 25 Sept
The Hemingway

⭐️BEST⭐️ SOUTH TAMPA MANSION- REMODELED- MOVIE THEATER- 🔥POOL-HOTTUB HUGE 5000 sqf

9.4 out of 10, Exceptional, (30)
"The house was perfect for our needs. The kitchen was large and the open layout made hanging in the living room/kitchen really fun with our group of friends. "
The price is €1,090
includes taxes & fees
26 Sept - 27 Sept
⭐️BEST⭐️ SOUTH TAMPA MANSION- REMODELED- MOVIE THEATER- 🔥POOL-HOTTUB HUGE 5000 sqf

Paradise Waterfront Resort! Pool &Spa with swim-up bar, Dock Kayaks, Pet Welcome

9.6 out of 10, Exceptional, (81)
"The pool was excellent! The pool deck was large for all to enjoy. The only downside of our stay was the neighbor across the canal that clearly did not want anyone enjoying the outdoors. "
Paradise Waterfront Resort! Pool &Spa with swim-up bar, Dock Kayaks, Pet Welcome

Tampa Bay Perfect location for a safe vacation! 5 bedrooms, ,3.5 bath ,sleeps14

10.0 out of 10, Exceptional, (95)
"This property was absolutely perfect for our family to stay at for a few days just prior to our carnival cruise! The place was immaculate and the pool was just the icing on the cake! I highly recommend this house for your stay in Tampa! "
Tampa Bay Perfect location for a safe vacation! 5 bedrooms, ,3.5 bath ,sleeps14

Chestnut Villas Down Town Tampa

3.0 star property
4.8 out of 10, (38)
"My family loved the clean and spacious rooms. The staff were so kind and made us feel right at home. The breakfast was amazing!"
Chestnut Villas Down Town Tampa

Escape to The Marine – Cozy Studio with a Touch of Nautical Elegance

2.0 star property
9.0 out of 10, Wonderful, (2)
"Check-in was a little confusing. "
The price is €112
includes taxes & fees
7 Sept - 8 Sept
Escape to The Marine – Cozy Studio with a Touch of Nautical Elegance

Bush Gardens, USF, Hard Rock group stay!

8.8 out of 10, Excellent, (43)
"It was great and close to everything!"
The price is €298
includes taxes & fees
1 Sept - 2 Sept
Bush Gardens, USF, Hard Rock group stay!

Resort style pool with lazy river, grotto, and hot tub! Dog-Friendly!

9.8 out of 10, Exceptional, (102)
"Great place, great location. "
Resort style pool with lazy river, grotto, and hot tub! Dog-Friendly!

Home Paradise, Cozy guest suite in Ruskin POOLS HIGH SPEED WIFI BEACH MINUTES!!!

10.0 out of 10, Exceptional, (24)
"Very nice property "
Home Paradise, Cozy guest suite in Ruskin POOLS HIGH SPEED WIFI BEACH MINUTES!!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Hillsborough County Hotel Reviews

Find out more about Hillsborough County

Find out more about Hillsborough County

Holiday Homes in Hillsborough County

Search for holiday homes in Hillsborough County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Hillsborough County using one of the methods below: 

  • View our selection of featured holiday homes in Hillsborough County
  • Use the map to find apartments and other holiday rentals in the Hillsborough County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Hillsborough County while they last

Look no further and take a look at our great range of rental properties in Hillsborough County!

Explore a world of travel with Expedia