Family-friendly holiday rentals in Harbour Island

We have stayed at this location for a few years now and is also a very nice place! Very clean, well furnished and close to the beach and our favorite places. Thanks Kenneth and Deborah!

Had a wonderful stay with my friends for the weekend! We were comfortable and not far from anything we wanted to be a part of. We did not use the hot tub, but the backyard set up with a table/chairs was great! Also had a keurig and pods that is a must! 🤪 Street parking, but was not an issue this time for us, we were always able to find a spot in front of the home. We really enjoyed our stay!

This place is amazing! Each bedroom has a full bath! Large kitchen with an island. The dinning room provides more dinning area. Living room is clean and comfortable. I kept falling asleep. The rooftop hot tub area is remarkable. Words can’t describe this place. If you’re in Tampa you have to book this place. You won’t be disappointed! Trust me.

when we were impacted from Hurricane Helene we needed a place to stay since our home was not accessible. Valarie and her husband Stu went over and above to accommodate us. I can't say enough about them and their hospitality, compassion, and amazing support. There are good people out there and we had the pleasure at such a difficult time meeting them. We would highly recommend their beautiful waterfront condo.

We loved this historic Ybor home so much that we decided to spend our last day in Tampa coming back to it! From the moment we arrived, we were captivated by the charm, character, and unique details that make this home so special. The hosts were absolutely wonderful—attentive, welcoming, and truly made our stay feel special. The backyard is a gem, an oasis that we could have spent endless hours enjoying. And inside, there are so many fascinating and unique pieces that we never felt like we had enough time to take it all in. This home is more than just a place to stay—it’s an experience. We can’t recommend it enough and would absolutely return in a heartbeat!

Sophie & Aaron’s place was perfect for our pre-cruise stay. We visited with my nephew, who lives nearby and went to a few escape rooms. Lo and behold, you may even find something similar to an escape room at Sophie & Aaron’s. If you solve the puzzle, you might even find a weee treasure. We loved the decor at the house. It’s beautiful and served as a sign, as we talked about our next adventure being an African safari. The pool is amazing. We will definitely book again for our next pre-cruise stay. Try KeKe’s (nearby restaurant) for breakfast.

This was a great place to stay with a toddler! The house was clean and had lots of infant and toddler amenities. Matthew set up a pack 'n play before our arrival, provided two sound machines, a changing pad, toddler-safe silverware and dishes, a high chair, pool floaties, and lots of toys and books. The house itself was clean and well-stocked, and the neighborhood was quiet and family-friendly, with a neighborhood playground less than a block away. We really enjoyed the pool, which was clean and warm. Matthew was also very responsive via messages, and even arranged an early check-in. I highly recommend this spot!

Have stayed at Boca ciega quite a few times and its always nice. Hot tub and pool are warm and clean. Russell was responsive and helpful. His place was clean and well stocked, lots of towels for swimming! Would definitely stay again.

I had an enjoyable visit to St. Petersburg while staying at Lisa's place. It was in a nice neighborhood and close to a large park that I took advantage of while walking my dog. It is in a convenient location for getting around town and frequenting local restaurants. Lisa was very communicative and easy to work with. I'll stay here again during any future visits to St. Petersburg.

Lovely cottage and a great location. Short walking distance to the restaurants and bars, but on a quiet street and secluded patio. Barbara was welcoming and the instructions were clear. The cottage itself was clean, functional and overall a lively place. We can’t wait to be back to this place!

Susan has a great place. If you're coming to Tampa you should check it out.

We really enjoyed our stay. The location was better than expected, we were very close to Craig Park, Pinellas trail, and very walkable to both the restaurants in town and in the sponge district. The house is small but very clean and has all the kitchen amenities you would need. The backyard condensed but very private and was perfect for us to sit out along with our small dogs. The front door was opened with a code which is nice so that you did not have to worry about keys. The host is proactive with easy arrival instructions and everything worked well so we did not have to contact her during our stay; she responded very quickly with a question about the checkout process. We would definitely stay here again.

great location, walkable to the Pier for great restaurants. Uber was always very responsive and on time.

My husband and I had a great stay at the bungalow. Nice, clean and homey. The location is good for downtown and neighboring restaurants. It was nice to walk my dog with such friendly neighbors. I recommend the bungalow if your in St. Petersburg. - Gayle & Rob

Josh and Joy’s place is immaculate and near everything downtown St Pete. If this place is available book without hesitation. I’ll be back!

Once again we had a wonderful time at Evie's place. We are never disappointed and look forward to our "Happy Place" every year!!

I had a fantastic stay at this conveniently located Airbnb in Tampa. I arrived a few days early for some golf with friends before my work commitments and found this place to be perfect. The accommodation matched the pictures and exceeded my expectations. The location is ideal for catching baseball games, heading to the beach, or exploring the local parks and attractions. Parking was a breeze, right across from the pool area, and your balcony view is just 15 steps up the stairs. Although I only had time for a quick lunch at the pool, the burger was exactly what I needed. The atmosphere was great, with a mix of families, business travelers, and snowbirds. I will definitely stay here again. The hosts were extremely responsive, making sure I had everything I needed as soon as check-in time arrived. 10/10.

We had an amazing stay at Mad Beach Cottage! The location is unbeatable—just 60 steps to the sand with no streets to cross. The cottage is cozy and perfect for families, with plenty of space. Everything in the cottage is well thought out for function and convenience. There are plenty thoughtful amenities like a well appointed kitchen, a pack-n-play, and beach toys. The heated pool and BBQ area were fantastic, and we loved being so close to John's Pass for dining and entertainment. The sunsets from the property were amazing! The host was the most responsive host I've ever communicated with on Airbnb. He was able to answer our questions in advance of the stay and provided almost immediate response when we had a question about parking at the property. There was a folder with clear instructions and information about the property, making check in and out a breeze! The host has clearly thought about everything, making this a stress-free, enjoyable stay. I highly recommend this property!

Stayed here for a couple nights with my boyfriend to help a friend get ready for her wedding! We loved the Airbnb and its location so much my boyfriend made a joke that we should come down once a month for a weekend. Although that’s not possible we will most definitely be back! Responsive hosts, and Airbnb is like the photos. Pool was heated and nice!

Wonderful condo! Beautiful view of the water and spectacular sunsets! Nice private beach, pool, and restaurant! Gated condo and from what I could tell, it is strictly enforced - I felt very safe staying here. Christine was very friendly and prompt in communications. Thank you for the relaxing week in this condo!

Ryan was an absolutely wonderful host. Super responsive, great tips on the city, and he even offers boat taxi rides. We didn’t get to this time but next time we 100% will. We came in town for Shane Gillis at Amalie and it was the perfect stay in terms of location and size. Bed was super comfy, it was only a 10-15min uber to downtown (leave early if during rush hour!!). We wish we had more time to spend with Spar the friendly kitty that greeted us right at our door, will definitely book here again. Thanks Ryan!!!

Thank you to Kenneth for being such a wonderful Host. I’ll definitely be back. We appreciated the location, cleanliness and charming aspects of this space.

A perfect place to stay with family of all ages. The kids always had something to do ages 3-17!

home was stocked well with all necessities, was for our wedding and we had all we needed there