Hillsborough County Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Top Cities in Hillsborough County

Top Holiday Rentals Destinations in Hillsborough County

Chase Suite Hotel Rocky Point Tampa

3.0 star property
7.6 out of 10, Good, (4618)
"I love the way the treat you . Very clean "
The price is AU$231
includes taxes & fees
28 Nov - 29 Nov
Chase Suite Hotel Rocky Point Tampa

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very good, (4321)
"Rooms are spacious and very nice. Staff at bar very friendly. Very clean"
The price is AU$252
includes taxes & fees
10 Dec - 11 Dec
Sailport Waterfront Suites

The Pointe Condos by Barsala

4.5 star property
9.2 out of 10, Wonderful, (126)
"It was in the same complex our daughter lives in. Convenient "
The Pointe Condos by Barsala

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

9.4 out of 10, Exceptional, (117)
"We love sail port and the host was fantastic the air was not Worthen we arrived o and got right on it and got it fixed"
The price is AU$363
includes taxes & fees
10 Dec - 11 Dec
❤Waterfront View, Amazing Sunsets, Heated Pool 3mins to Airport ☀🐬🏖

Renovated retreat with pool, firepit, balcony, & bikes - snowbird-friendly

9.6 out of 10, Exceptional, (23)
"It was quaint, peaceful, and felt right at home. Loved the animals and the owners on site were super friendly, respectful of our privacy and there to answer all our questions. The house supplied anything you would need including linens, towels, and kitchen supplies. The trees down the driveway made the perfect photo ops, too!"
Renovated retreat with pool, firepit, balcony, & bikes - snowbird-friendly

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

10.0 out of 10, Exceptional, (68)
"We loved our stay. Great home with lots of living space. Property manager is a great communicator and ensured we had everything we needed."
Tampa Bay Perfect location for a safe vacation! 5 bedrooms, ,3.5 bath ,sleeps14

Cozy home away from home

8.0 out of 10, Very good, (1)
"Our experience was terrible. I messaged the host 2 weeks before our arrival inquiring about reservation status because of the recent hurricane. No response. I messaged the house the night before and the morning of our reservation. No response. I contacted VRBO and they tried to contact the host . No response. On our way to the airport the host messaged me and cancelled our reservation due to no electricity. It would have been different if the host would have told us two weeks ago when I...
Cozy home away from home

A memorable, peaceful, and fun experience!

9.2 out of 10, Wonderful, (31)
"My wife and I rented a room to attend our friend's wedding. A few days before, I accessed the web site and asked for our check in instruction(s) and a "form letter" email informed me that another email with all our info would be forthcoming. That didn't happen. When we were on the property we are still trying to get someone to reply through the web site. We could not get access to the room so we had to get prepared for the wedding in the parking lot in the car. Suffice it to say my wife was not...
The price is AU$428
includes taxes & fees
10 Dec - 11 Dec
A memorable, peaceful, and fun experience!

Perfect Stay Studio

9.4 out of 10, Exceptional, (8)
"Nice and clean affordable place to stay"
The price is AU$253
includes taxes & fees
10 Dec - 11 Dec
Perfect Stay Studio

#1 Tampa Waterfront Private Resort, 11BR Sleeps 40+, Heated Pool, Gym, Theater

10.0 out of 10, Exceptional, (6)
"We are 5 couples, long-time friends, who enjoy gathering and enjoying each others company. We found this private resort after our 5 bedroom VRBO on Indian Rocks Beach sustained hurricane damage. The resort facility offered such terrific amenities, we were happy to make the discovery and change. We sure enjoyed the hot tub and swimming pool and there were many other amenities we that made the stay enjoyable. Although there are multiple kitchens, as a small group (for this facility) we used just...
#1 Tampa Waterfront Private Resort, 11BR Sleeps 40+, Heated Pool, Gym, Theater

The Adaline

4.0 star property
9.6 out of 10, Exceptional, (37)
"noisy"
The price is AU$644
includes taxes & fees
17 Dec - 18 Dec
The Adaline

The Hemingway

4.0 star property
7.2 out of 10, Good, (10)
"Room was as advertised. The communication was great. All questions answered promptly. "
The price is AU$460
includes taxes & fees
10 Dec - 11 Dec
The Hemingway

Aileen Camping Space

9.6 out of 10, Exceptional, (34)
"Location was great, living accommodation was great, when I needed something the hosts was right there, I would definitely recommend this location and will definitely visit this location next year"
The price is AU$218
includes taxes & fees
14 Dec - 15 Dec
Aileen Camping Space

Modern space in the heart of Tampa

5.0 out of 10, (18)
"It’s an older house in a neighborhood of older houses, but has been completely remodeled inside as a rental. Basic and clean. Plenty of places to eat nearby. Easy to get around. It is right beside I-275 but the roadway is elevated so you’re not really hearing traffic when in the house. I thought the beds were very comfortable. "
Modern space in the heart of Tampa

Beautiful 3 bedroom home w/Patio, BBQ Grill & Fire table. Steps from 7th Ave.

9.6 out of 10, Exceptional, (8)
"We had a great experience at this property! It was close to the Arena and a great overall location. We would love to stay again in the future!"
Beautiful 3 bedroom home w/Patio, BBQ Grill & Fire table. Steps from 7th Ave.

Spacious And Private Tampa Retreat 1 Bedroom Condo by Redawning

3.0 star property
10.0 out of 10, Exceptional, (5)
"This is a perfect air b and b for two. The property is so inviting. There is a seating area outside surrounded by gorgeous trees. The bed is so comfortable. Everything is clean. The shower is huge. Walmart, super markets, all fast food, waffle House is a 5 min drive or 10 min walk. 10/10 recommend to everyone. Super convenient and wonderful. The renter was super responsive and helpful. Thank you so much for a beautiful experience. "
Spacious And Private Tampa Retreat 1 Bedroom Condo by Redawning

Tranquil Oasis, Private Entrance & Kitchen

9.2 out of 10, Wonderful, (5)
"We stayed here for a bit over a month before moving out of the area. It’s a nice and clean place in a quiet neighborhood. The yard could use a little cleaning up but the view over the river is beautiful."
Tranquil Oasis, Private Entrance & Kitchen

Waterfront/Pet friendly-7 min walk to Beach-TikiBar-Pool-Boat rentals-Marina-Gym

9.4 out of 10, Exceptional, (133)
"."
Waterfront/Pet friendly-7 min walk to Beach-TikiBar-Pool-Boat rentals-Marina-Gym

Cozy One Bedroom Apartment!

8.6 out of 10, Excellent, (7)
"This property was perfect for my boyfriend and me. The location was perfect for morning walks along Bayshore Blvd. We were in town to work on our property and visit family and this place was perfect. For those wanting to see the signts it is central to any activity you want to participate in!"
Cozy One Bedroom Apartment!

Bayside Bliss - Bold & Bright - Central

9.0 out of 10, Wonderful, (8)
"Clean and comfortable, efficient space. The host is super responsive and genuinely cares about the quality of your stay. Perfect location if you’re receiving treatment at Moffitt Magnolia Campus. Highly recommend. "
Bayside Bliss - Bold & Bright - Central
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.
Don't see what you're looking for?
See all available properties in Hillsborough County
Save an average of 15% on thousands of hotels when you're signed in
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.