
Holiday rentals with a pool in Harbour Island
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Top-rated rentals with a pool in Harbour Island
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House rentals with a pool

Charming 4 bedroom home in the BEST location.
We had a fantastic stay at this home in Tampa! Everything was exactly as described in the listing. The house was very easy to access, and Heather was super responsive to all of our questions—great communication throughout. The pool was a highlight for our family—our kids had an absolute blast! There were plenty of rafts and pool toys to keep them entertained for hours. The kitchen was also a big plus—well-equipped with all the appliances, pots, and pans we needed. We were especially impressed by how clean the home was—it was spotless and clearly well cared for. If we're back in the area again, we’ll definitely try to stay here. Also, a little tip: be sure to check out the bakery just down the street—it’s within walking distance and the perfect way to start your morning!

Pool Oasis | Karaoke | 5G | Theater 135" | Grill
The hosts were extremely friendly and responsive with any questions we had. They followed up to make sure there was nothing we needed to make our stay more comfortable. The home exceeded our expectations. There was definitely more room than expected and the layout worked very well. It was also very nice seeing there was a kurieg and a regular coffee pot. There were plenty of dishes, pot and pans to stay in and cook. We also like to make sure to clean up behind ourselves and most places lock up any cleaning supplies but they made it accessible to us which was also a plus! We would absolutely stay there again! Thank you again for everything!

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.

Relaxing 3BR/2BA POOL Home w. Pond View & HOT TUB
I was very happy that the hone looked exactly like the photos. The home was very clean. I would definitely recommend Jose & Sara's home.

Heated In-Ground Pool w/ Whirlpool!
Really enjoyed this rental space as it had a dining room table that also served as a pool table for some family. Fun. Also enjoyed the artificial grass out back so if you wanted to walk around without shoes you could comfortably. The size of the bedrooms and amount of space was able to accommodate our family of six without us feeling cluttered or on top of each other. There were TVs in every room which made it easier when someone needed a break from the group. The pool is a good size as well where we had enough space to swim and play games. Definitely would rent this space again!

Luxurious "Riverfront Oasis" - Waterfront w/pool
Great house with plenty of space for a larger group - everything was very clean and the hosts were very responsive to any and all messages. The house is positioned right on the river and just a short walk to a local restaurant, which is very convenient. The backyard is private and has plenty of seating to relax with a view. We would return if we were to ever be in the area again!

Pool + Park + Private = Perfect Place
This is the second time we've been able to book this home and if it's available I will book it again when we return. There is a park and walking trails across the street. The trails go along the Hillsborough River where you can see all the fun Florida birds. The accommodations are fantastic. It is clear the hosts care about details, including fluffy towels and sample shampoos and conditioners in the bathroom. I also appreciate the water pressure and quickness of the hot water tank to heat the water in the shower. This kitchen has everything you need if you want to cook. There are beach towels to use for the pool, as well comfortable deck chairs and floats. The hosts were very responsive, and asked if they could come over to clean the pool after an unusually heavy rain. Our family would love to stay there again when we visit Tampa.

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.
Condo rentals with a pool

Waterfront Condo - Sunset View of Tampa Bay
GOOD VIBES!! This condo is amazing! Waterfront, had a bar and food, spots to lay out and tan, heated pool. Chris was an amazing host, let us check in early, super clean, smelt good inside, super responsive , accommodating and helpful. Will book again in the future. thank you!!! 5 stars:)

Beach Condo with water view!
We really enjoyed our stay at Simone's AirBNB. Simone's property was exactly as described. it's set a ways back in the middle of the property and we experienced little traffic and a quiet atmosphere. It was clean and had all our basic needs for a comfortable stay. The book of suggested things to do and places to eat was super helpful! Im excited to stay again when my travels take me back home to Fla.

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.

Waterfront condo with sunset views of Tampa Bay.
We really enjoyed relaxing by the pool and having the Big Bamboo bar / restaurant on the premises made it so convenient. The bed was comfortable and shower pressure good. We also appreciated the coffee bar.

Heron's Hideaway- Studio by the bay!
The stay was awesome! The condo has an incredible view of the water and my wife and I were able to see dolphins and other marine life. The amenity descriptions were accurate. The condo’s AC blew nice and cold and the shower water got very hot. There were a few minor hiccups upon arrival but the host communicated very well and we were able to get them handled. This place is very close to the beach and there’s a Doc Fords Rum Bar right next door that’s within walking distance and has a very nice outdoor patio overlooking the water. This was extremely convenient. My wife and I spent a lot of our mornings and evenings sitting on the balcony of the condo watching the boats exit and enter the marina area. The view is incredible and extremely peaceful. We will definitely be staying again in the future.

Lakeside 2- Bed Apartment Near Clearwater Beaches
This was our first time to Florida! It was a very quiet area! Everything was as pictured. very easy check in. We had no problems, Mark did check in before we arrived as he was going to be out of the country.

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!

Spectacular beach to bay views from this resort.
Our stay was great! The place and location were perfect! We had absolutely everything we needed. Communication was awesome! Thanks so much!! Lara and Thomas Boulder Co
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- Anna Maria Island
- Siesta Beach
- Weeki Wachee Springs
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
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- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
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- Amalie Arena
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- Gulfport Beach Recreation Area
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- Fort De Soto Park
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park