A city skyline with modern buildings, a calm river reflecting the structures, and a sunset in the background.

Hillsborough County Holiday Rentals

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Our top choices for Hillsborough County holiday rentals

A beach with thatched umbrellas and lounge chairs, a sandy shore, and a sunset in the background.

1. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,199 reviews)
"Very attractive siting on water"
United States
David
Sailport Waterfront Suites
A beachside seating area with a fire pit and chairs, overlooking the ocean.

2. The Hemingway

The Hemingway
4.0 star property
Rocky Point
8.4 out of 10, Very good, (33 reviews)
"The location was amazing!"
United States
Amy
The Hemingway

3. Swann Ave Suite Walk to Bayshore Hyde Park

Swann Ave Suite Walk to Bayshore Hyde Park
2.0 star property
Hyde Park
7.6 out of 10, Good, (4 reviews)
"Very cozy, well appointed and conveniently located "
United States
Heather
Swann Ave Suite Walk to Bayshore Hyde Park
A white house with a porch, wooden steps, and a white picket fence.

4. Casa Julieta Luxury Ybor-themed Studio

Casa Julieta Luxury Ybor-themed Studio
2.0 star property
Ybor City
10.0 out of 10, Exceptional, (7 reviews)
"Love this place!! The bed was unbelievably comfortable. Will be booking again!"
United States
Raegan
Casa Julieta Luxury Ybor-themed Studio
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.
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Top Hillsborough County Hotel Reviews

Holiday Inn Tampa Westshore - Airport Area by IHG

Holiday Inn Tampa Westshore - Airport Area by IHG

10/10 Excellent
"The staff made checking in a breeze, they have friendly staff. My room was clean and cozy."
Sherelle 1-night trip
Posted 1 hour ago
Holiday Inn Tampa Westshore - Airport Area by IHG