Family-friendly holiday rentals in Hillsborough County

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!

Our group had such a great stay. The location was great and it was the perfect spot for a beach weekend. Daniel was super helpful and responsive to any messages sent during our stay. We loved the spacious quirky layout of the apartment and would definitely stay here again!

All good, nice location with many options close by

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.

I had an amazing stay at this Airbnb in Ybor! The location was perfect—right in the heart of everything, with fantastic restaurants just steps away (both were absolutely delicious). The space itself was unique and filled with beautiful artwork everywhere, which added such a cool vibe. The pool and hot tub were incredible—perfect for relaxing after a day of exploring. I definitely plan to come back! Highly recommend this spot for anyone visiting Ybor.

Loved our stay. Neighborhood was so quiet and safe. We walked around the nearby golf course everyday. Folk were always waving and saying hi. Host were proactive and checked in regularly to see how our stay was. House was well stocked with kitchen, bathroom and laundry items. Pool was amazing as was the hot tub. Pool was a nice temperature- especially being winter months. While the bbq wasn’t propane, and used briquettes- it was manageable- just had to plan a bit ahead. The indoor furniture was super comfy. We absolutely loved our stay there and were a bit sad when our stay came to an end. In a heartbeat we would stay there again. Thanks for being a great host and caring about your guest.

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!

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.

We stayed a month and it felt like being at a real home; the house was very well equipped and full of character. On a daily basis, we had everything we needed, and the very few times we needed assistance/solving, Edie was very diligent to make sure we were happy. Extra points to the shaded parking space and the firmness of the mattress. We truly enjoyed our stay, as well as the location, the private fenced patio for our kitty, and our little casual encounters with Matt in the shared backyard/laundry area :)

Linda was amazing hostess. the home was as or better than expected. Linda gave my family privacy and was very responsive.

This was our 2nd stay at this property. Tom is a great host and we would recommend his property to anyone. The installation of the dishwasher since our last visit was a great addition. We will be trying to book another stay next year.

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!

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!

Great place to stay!! Great spot to walk around and hangout

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.

Jeff was very responsive and had a list of great recommendations prepared for guests. Home is within beautiful historic neighborhood and walking distance to local coffee shops and parks

Will definitely recommend this spot to others! Very convenient spot in Northeast St. Pete.

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!

We were all very happy with the house and pool. A lot of places to visit. Had a great time at the Tampa Zoo at Lowry Park. Still working on repairs to the Pavillions and trails at Honeymoon Island Park, but the beach was beautiful. Many wonderful restaurants. Love Frenchy's . Well worth the drive to eat at Doc Fords in St. Pete.

So glad we had the opportunity to experience the Historic Kenwood neighborhood and Ken's gem of a studio! Beautiful, comfortable, unique. Close to downtown, but homey and peaceful. His gardens and pool are totally Zen! Spent lots of time on the bike trail which is one of the best. In all, one of our favorite Airbnb experiences, thanks to Ken!

Their place was very clean and cozy. Host was very helpful on directions. Me and my girls had a wonderful time.

We had a wonderful stay in this beautiful house. Nothing to complaint about. Jess was very responsive. I got everything as mentioned except the wooden swing in the backyard which is probably damaged during the recent events. Also I just want to mention that the heated pool need many hours to reach the temperature. It took me almost 24 hrs to reach the temp from 69 ° F to 95° F. Again, Its not a complaint but just to plan accordingly. I highly recommend this place if you have vacation plans near clearwater.

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

Lindsay was very sweet and hospitable. Communication was very good. Her place is a very cute little Florida gem. You can tell she loves her home. Would definitely book again. The location is close to everything you need by car. Thank you Lindsay for a great stay!