
Holiday rentals with a pool in Hillsborough County
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Top-rated rentals with a pool in Hillsborough County
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Popular amenities for Hillsborough County rentals with a pool
House rentals with a pool

The Jungalow SOHO - Pool/Hot Tub
A private paradise! This was the best part of our family vacation. The house was immaculate and organized. The outside area was amazing. I loved enjoying morning coffee in the hot tub everyday and listening to all the birds. I will be back.

Insta Worthy Retreat - Heated pool-putt putt | Bar
What a beautiful home! Never a dull moment in this home. We appreciated the vintage arcade, the awesome pool, and the mini golf in the backyard, as well as the ample space to watch our shows and movies. Super clean and lots of room. This is a great stay either if you by yourself, your partner or family and friends. Also it was great to be able to have the laundry machines at our disposal. 100 out of 10.

Beach Vacation Dream Pool Home-5 Mins to Beach
We had a great stay. House had everything we needed and more. Good location to local restaurants and beach access. Loved having beach chairs and cooler/beach bags for use!

tu hogar cerca de todo
Absolutely loved this booking! Alan was a great and responsive host. We had no issues the whole weekend and felt right at home. Will definitely be booking again :)

Tropical Getaway, Perfect Home & Great Location
If i could give 100 stars I would. This place is such a vibe. the house is absolutely stunning and they take care of you like you are family. There was coffee in the pantry, they have shampoo, conditioner and body wash if you want to use. The beds are very comfortable and the place is so clean. The outside was great for the kids. The house is located in a really good place close to everything. We felt like we were in our own home. Thank you so much for providing such a great experience for us.

Lakeview Retreat with Private Pool Perfect Getaway
This was an excellent stay for me and my family. The house has been completely remodeled on the inside, it’s extremely nice. There’s a pool and you can fish off the back of the property into the lake, so if you love fishing, it’s a great spot for you. The hosts were incredible and communicated very well at all times. I have nothing bad to say about our experience with this host or their home. Two thumbs up

Coastal Escape: heated saltwater pool & beaches
We had an amazing time at Benji and Kathleen's spot. Our kids, age 6, 3 and 2 were overjoyed with the amenities and toys available. The pool was lovely and I felt confident that my children were safe with the gate around the pool as well as the closed living space on the outdoor patio. We spent a morning at the beach and another morning at the Tampa Zoo but getting back to the house, swimming, relaxing and playing were certainly the memorable highlights of the trip. Benji was also extremely responsive and made sure to check in. We arrived very late from our flight and had no problem finding the house and getting inside. We highly recommend this home for a trip to Palm Harbor/Tampa if you have small children. It was perfect and a great family escape.

North Ybor escape with Private POOL and POOL TABLE
We loved this place!! My family and I stayed for the weekend for my oldest son's college graduation and were so happy to have found this gem! The pool was fantastic. They went crazy for the pool table! The kitchen is much bigger than expected and the couch is amazingly comfortable. Jeannette and Nathaniel are very proactive and fast with their communication. We loved this place! Highly recommend and will be back for sure!
Apartment rentals with a pool

SWEET BEACH RETREAT - REDINGTON BEACH FLORIDA
The condo has everything you need to have a great holiday and not spend a fortune doing it. The cooker works well and the hob is very fast. We prepared our own meals most nights and ate outside overlooking the pool. The bathroom is well set out and the shower hot and powerful. What really appealed to us when booking was the access to a pool and not having to drive to, or pay for parking at a beach. It’s less than a five minute walk across Gulf Boulevard and Joy supplies chairs and an umbrella. The pool was clean and not at all busy. The area is safe and pleasant with easy access to Indian Rocks beach too. We had a day out to Universal Studios, an easy two hour dive away. Locally there are a few restaurants and cafes within walking distance, the Conch Grill is particularly good with a very generous happy hour from 11am - 7pm. We would like to return and highly recommend this accommodation.

Seasalt Breeze private unit No cleaning fee
Amazing! Enjoyed the apartment along with the pool! Great location and loved the recommendations

Very cozy quality condo close to Clearwater Beach
Marta is a pro host, she is attentive and quick to address any issues. Things happen and how those things are handled is what makes the difference between an ok experience and a great experience. I would absolutely stay at Marta's place again. Her place is equipped with all that you need to be comfortable and to feel right at home. The place is an excellent value!

Tampa Bay Near by Airport & Stadium
This place was perfect! We found that whatever we needed or forgot was provided in the condo. The beds were comfy, lots of pillows, and loved sitting with our coffees (lots of varieties) on the balcony. Definitely be returning.

Heron's Hideaway- Studio by the bay!
What a treasure!! Though small, it completely met our needs. Was clean and homey. Ideal location between downtown Saint Pete and the beaches. Loved the view of the water from the balcony. Kids loved the pool.

Rocky Point paradise
It was a very clean place and a great location. We were there to attend an event at Raymond James which was only a short drive, and close enough to the beach to enjoy that as well. The balcony was nice and private. We loved being able to just sit and enjoy the peaceful water view!

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views
Great area. Great view. Awesome pool/ bar area!

Waterfront condo on top floor @ Boca Ciega Resort
The condo was just what we were looking for. The kitchen was equipped with the basics and the view was wonderful. Tamara was friendly, responsive, and a great host. Would stay at her place again!
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- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Public Beach
- Dunedin Beach
- John's Pass
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Reunion West
- Gulfport Beach Recreation Area
- ChampionsGate Golf Club
- North Beach
- Fort De Soto Park
- Island H2O Water Park
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park
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