
Holiday rentals with a pool in Harbour Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Harbour Island
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Harbour Island rentals with a pool
House rentals with a pool

Pool Oasis | Karaoke | 5G | Theater 135" | Grill
Lots of different areas to hang out. Movie room was my fav and the video games. The house could be a little updated but it was perfect for what we needed. Thanks again!

Upscale Tampa Dream Home Pool, Golf, Pool Table
Had a great stay at Angel’s place for my bachelor party. The location was central and just a short drive from everything we wanted to do in Tampa, including golf, spring training, and exploring downtown. The house was exactly as described with tons of fun activities and a great outdoor space. Angel was an excellent host—very communicative and flexible, which made the trip even smoother. The only small comment was that the beds weren’t the most comfortable, but that didn’t take away from the overall experience. Would definitely recommend this place for anyone visiting Tampa!

Private Pool |Child Friendly|Near Clearwater beach
Our stay was absolute perfection! The house was stunning, a total jewel! The living areas were open and spacious, but also cozy. Great kitchen area, lots of seating. The bedrooms were large, closets were great and the beds/bedding were beautiful and comfortable. The pool and yard were so relaxing and beautiful. The house had all the amenities you could want. Everything was very new and super clean!!! The location was near to a lovely park, the beach, and major roads for dining and traveling. Oanh the host was lovely, was so communicative before and during our stay. We are so grateful that she shared this gem with us, and are looking forward to next year!

Ultimate Getaway: w/ Pool, Patio, Pool Table & BBQ
Our stay at Mark's place was great, the home is centrally located in Tampa, safe and a good value. We had a couple minor issues and Mark was very responsive and fixed them within a day. Highly recommend.

Heated pool-Hot tub-Close to Beaches-Pet Friendly
Barry & Alisha's place was just as described and they sent out a variety of fun things to do and places to go prior to check in. I did ask a question about the places where we had reservations and never received a response - I think their texts/reminders are just generated. We did have a problem with the water temperature and Barry came out within a 4 hour period to make sure it was great. Excellent response time. We didn't find the couch in the living room to be comfortable. And that's a thing for us. And the toilet rocks when you sit on it. That probably could stand to be replaced. But the pool was incredible and the hot tub was the reason we booked. Well maintained and cared for. They also asked for us to do laundry and sweep on the way out which was strange considering we have a cleaning fee - he said it was to honor other guests with early check in requests. We thought it was 5/5 and would stay again.

Beautiful house with pool, fire pit, billiard room
This home is beautiful, in a quiet neighborhood! The thoughtful owners have really gone the extra mile to include everything to make your stay fun for all ages, with lots of games for younger and older kids. The property inside and out is spotless and super organized to make everything easy for you! The best part is you can walk to local town centers with great restaurants, cafes, parks, bike and walking trails!

Spacious House w/ Pool & Hot Tub near Tampa
Loved it ! Would definitely book again. Conveniently located 8-10 minutes to tons of restaurants and activities. Everything was super smooth.

Private 3 Bedroom House w/ Heated SaltWater Pool
Kacper was always super helpful and responsive with any needs or small issues we had. We felt right at home. Definitely recommend this place.
Condo rentals with a pool

Upham Beach #1 Location Heated Pool Stylish Studio
Kristin was an amazing host! Very friendly and communicative. The place was immaculate and perfect for two people. Patio and pool area were very well organized and clean.

Tiki Themed Waterfront Condo on Tampa Bay
I stayed in the Tiki condo for 2 nights when I came into town for a wedding with my husband and two young kids. Chris is an excellent host! He was very responsive and provided the most clear information regarding the condo that we have ever experienced! The condo was clean and cute and met our needs well. The pool area was full of friendly vacationers, music and a bar with tasty treats. The pool was very warm even on a chilly day (68 and windy). Construction due to hurricane damage was minimal and did not impact our stay at all. Laundry facilities are extremely easy to access on the same floor as the condo. The drive into downtown Tampa was about 15 minutes. Overall we had a great stay. Chris is a top of the line host and did everything he could to make our stay convenient and comfortable! Highly recommend the tiki condo!

Waterfront Condo - Dolphin sightings-Walk to beach
Had a great stay. Convenient location for supermarket, restaurants and beach. Apartment was comfortable and had everything we needed. Would stay again.

Beautiful and spacious condo centrally located
We loved this place and the location was great. We initially had problems with the WiFi but Alexandra and her husband fixed them right away with a new router. We didn’t have any problems at all after that. We would definitely stay here again! Highly recommend.
2 bedroom in great location
Our family with small children had a brief but wonderful stay in Treasure Island. The condo was extremely nice and clean, the building felt safe, and the beach was only a very short walk away. We loved being able to see sunsets over the Gulf from the condo!

Waterfront condo on top floor @ Boca Ciega Resort
Tamara was very accommodating with our requests. Got right back to us when we had questions. Place was perfect for our quick weekend trip. Restaurant next door was great. Food was awesome and live music on the water.

Waterfront quiet condo w Pool by Madeira Beach
Stayed for a week in February. The condo was as advertised and the perfect size for a couple. Appreciated the cleanliness, comfortable bed, availability of beach towels and washer & dryer. Waterfront balcony offered viewing of dolphins and gorgeous sunsets. Owner was a great communicator. Can’t go wrong with this Airbnb.

PondView/Pool/Pickleball/Dryer/Washer/Ground Floor
This is our third time staying at Rick‘s place. It is perfect! It is beyond spotlessly clean. And, it has everything you could possibly need for a wonderful stay. Rick is an incredible host. He either picked up the phone when I called or he got back to me immediately! We are going to book soon for a fourth stay. love this place!.
Destinations to explore
- Tampa Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Central Florida Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Rentals with pools United States
- Rentals with pools Florida
- Rentals with pools Central Florida
- Rentals with pools Orlando
- Rentals with pools Tampa
- Rentals with pools Hillsborough County
- Rentals with a patio Harbour Island
- Fitness-friendly rentals Harbour Island
- Apartment rentals Harbour Island
- Family-friendly rentals Harbour Island
- Rentals with a hot tub Harbour Island
- Monthly Rentals Harbour Island
- Rentals with a washing machine and dryer Harbour Island
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom