
Vacation 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

NEW Cozy Family Retreat, Tampa: Private Pool Oasis
This adorable house was perfect and so comfortable to stay in for a few days, will absolutely stay again next time I come to Tampa.

The Coastal Casita- Private Pool Home in Tampa, FL
Greatly enjoyed our stay. Very quiet, peaceful, safe neighborhood. House was exactly as described. Spotless and comfortable. Would highly recommend. I would stay here again if ever back in Tampa!

5BR Serenity Tampa: Pool/Hot tub
Such a beautiful home, so sparkly clean throughout and very well stocked with all the essentials. We felt right at home. Grilling by the pool was so fun and our dog had a blast just lounging in the sun. They even had a crib set up for our baby, as well as a high chair available which was great. The washing machine was broken upon our arrival but Adam and his team were immediately on it, they sent a tech asap and reimbursed us for the inconvenience. The attention to detail and communication was amazing! Keep in mind if you visit in the summer like us, the mosquitos were absolutely crazy. Make sure you bring some spray or stay covered! Overall this was such a great stay. Would absolutely recommend staying here for a fun time with family or friends.

The white lagoon Relaxing waterfront home w/ pool
My family and I stayed here about a week and had an amazing time! Eva was always quick to respond, the house was nice and clean and the neighborhood was quiet. We hope to return in the future!

Chic Chalet in Tampa Bay with Heated Pool
Great stay, very close to my sisters & the games we were going to. The pool and outside area was very nice & relaxing.

your home close to everything
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 :)

Fun Oasis! Private Pool, Hammock, Golf & Grill!
Dean was the perfect host and the house was clean and comfortable. The pool area was so enjoyable for my family and friends and the couch was so comfy and the perfect place to wind down. The open kitchen made it easy to cook and talk to those in the living room so we never felt left out of the conversation. Would highly recommend staying.

1915 Bayshore Bungalow w/ Pool House
Our needs were different than most as we were there for a surgery at a local hospital for our child. We needed to be close by but still have a place we felt safe and able to relax. Peter's place was perfect for that and you simply cannot beat the quiet and lovely neighborhood. Plenty of local restaurants nearby and the locally famous Yogurt Natually shop is within walking distance if you do not mind a little hike. One caution is the street is fairly narrow and parking is common on the opposite side so navigating a large vehicle up the driveway can be a bit tedious. Having said that, we had a large minivan and had zero issues during our stay. Would 100% stay here again and based on the record collection on display, I'm certain Peter and I would be friends in real life. :) Thanks for the stay Peter!
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:)

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

Bright and Spacious 1Bed/1Bath condo.
Daniel is a pro and his place is awesome in every way! Highly recommend!

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES
we really enjoyed our stay! the condo was in a very nice and quiet area. about a 15 minute drive to clearwater beach. everything was exactly as pictured/described. we got a lot of use out of the provided beach chairs, umbrellas, etc. and were very happy that was available for use. the only issue we ran into during our whole stay was we were unable to find a can opener in the kitchen when we went to cook dinner and it was too late to go out and buy one. besides that, we were beyond pleased with the location, price, cleanliness, and amenities. would recommend to anyone and we are looking forward to coming back!

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209
Cozy little place, well decorated and clean. Bed was comfy. The pull out bed was good enough for my 6 yr old, but would recommend bringing a pillow for it if you’re going to use it. There isn’t one in the room for it unless you use the main bedroom pillows. We beached most of the time and didn’t watch TV, but if we wanted to the couch wasn’t comfy for lounging around. We loved the balcony though! The only “complaint” would be all the coffee supplied was decaf and it was a shock the first morning after getting in super late. So, bring your own coffee just in case. Host was super helpful when there was any other issues. Very kind and accommodating! Plus they supplied plenty of TP and PT, beach towels and towels. Can’t wait to come back!

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

1145 Sqft! - 2 Bedroom 2 Bath (GULF FACING!) Condo
This condo was hands down one of the best places I’ve ever stayed! It was clean, spacious, and beautiful. Best of all, the view of the ocean was absolutely amazing. We enjoyed sunsets over the ocean right from our balcony every night. We are thrilled to have found this gem by our favorite beach spot and plan to return each time we visit St. Pete!

Modern Waterfront Condo - Captivating Sunset Views
Rosana was an excellent host- very responsive, kind, and accommodating. Fun location on the bay with a great view, pool with towel service, and bar/grill with great burgers. Fire pit on the little beach at night with great view of sunset. The unit is in a quiet location within the complex with a view of the beach and bay. The trade-off is that the unit is a bit far from the elevator (though close to stairs). Great experience overall.
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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
- Lido Key Beach
- Cortez 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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