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Family-friendly holiday rentals in Wesley Chapel

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Wesley Chapel family-friendly rentals

Family-friendly home rentals with a hot tub

Top Guest favourite
Home in Tampa
5 out of 5 average rating, 188 reviews

Multi-Award Winning & Top 5% Rated on Airbnb 2025

TheresaRating, 5 stars2 weeks ago
Great location, Jason’s eye to detail was perfect. He was responsive to every call. The house was absolutely beautiful. It was a peaceful time and minutes from the stadium and Ybor
Top Guest favourite
Home in Clearwater Beach
4.98 out of 5 average rating, 120 reviews

THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.

LaurenRating, 5 stars6 days ago
We had a great time staying here in Clearwater. SO close to the beach. Their place was clean and was ready for a family to stay. We look forward to coming back.
Superhost
Home in Largo
4.79 out of 5 average rating, 425 reviews

Spacious Home Solar-Heated Pool and Spa

ValerieRating, 5 stars2 months ago
Great value!! We loved the pool area and very quiet neighborhood!
Guest favourite
Home in Ybor City Historic District
4.97 out of 5 average rating, 404 reviews

Ybor Roost - Cozy, Urban Farmhouse Retreat

YardenRating, 5 stars1 month ago
Great location for the enthusiasts! Really enjoyed my work trip and stay away time.
Guest favourite
Bungalow in Ybor City Historic District
4.77 out of 5 average rating, 321 reviews

Historic Bungalow with Private Pool in Ybor City

StephenRating, 5 stars3 weeks ago
Great location, great character, great value. Pool was an excellent space to hang out at during the day and nice central location for everything else. Would stay again.
Top Guest favourite
Condo in St. Petersburg
4.98 out of 5 average rating, 269 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

KathrynRating, 5 stars2 days ago
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!
Guest favourite
Apartment in St. Petersburg
4.9 out of 5 average rating, 171 reviews

The Oasis

CherieRating, 5 stars1 week ago
Russell’s place was just as described. The bay of the bay was beautiful! This condo was within short driving distances of many great local beaches and restaurants. It had all the amenities, linens, and other items needed to make our stay perfect. Russell checked in with us prior to our stay, during and after.
Guest favourite
Condo in Indian Shores
4.94 out of 5 average rating, 105 reviews

Bay Shores Yacht & Tennis Club Indian Shores FL

AndreaRating, 5 stars4 weeks ago
Great location! Easy walk to the beach. Property has desired amenities. Inside had everything we needed.

Family- and pet-friendly home rentals

Top Guest favourite
Home in Largo
4.97 out of 5 average rating, 131 reviews

Crescent Beach House Pet friendly

HeatherRating, 5 stars1 month ago
This was the perfect location for our family. We loved the proximity to the beach and restaurants. The place was clean and well stocked. Would love to come back.
Superhost
Home in Dunedin
4.78 out of 5 average rating, 129 reviews

House of Relaxation

GracieRating, 5 stars1 month ago
Great home with everything we needed, we really enjoyed our stay!!
Top Guest favourite
Home in Seminole
4.97 out of 5 average rating, 196 reviews

4BR/3BA Pool Home 7mins to Madeira Beach-Sleeps 14

KerriRating, 5 stars2 days ago
This house was great and we would stay here again! We even had a 6 month old with us and one of the bungalows was big enough for mom/dad and a pack n play! The air was perfect and cold like we liked it and the extra bed in the room with the king was perfect to kick the snoring husband to after a full day in the sun. Such a great idea, that I came home and instantly thought about doing the same set up to our master bedroom nook, lol! Just brilliant! Everything was supplied, TV’s everywhere, enough beach chairs for everyone and the chairs were in great shape also! Easy to find, close to beach and shopping! We will definitely stay in one of Stephanie’s homes in the future. Thanks for a lovely weeks vacation! Had a blast!
Guest favourite
Home in Tarpon Springs
4.93 out of 5 average rating, 133 reviews

Our Gemini Place: Comfort & Charm in Old Tarpon

MahlonRating, 5 stars1 week ago
Gemini place was a real gem. Home was as described. Very roomy, very clean, decor top notch, very comfy and home like feel. Easy walking distance to Spring Bayou, Sponge Docks, shops and restaurants. Less than 50 years to a very spiritual moving shrine, St Michael’s. Very clean and safe neighborhood too. We absolutely loved the home and location.
Superhost
Apartment in Palma Ceia
4.84 out of 5 average rating, 183 reviews

Pet Friendly | 5min Downtown | Safe+Parking | Apt1

KeithRating, 5 stars2 months ago
Perfect place and location for small group on short stay visiting Tampa and the local area!
Superhost
Home in St. Petersburg
4.88 out of 5 average rating, 184 reviews

Baby Bungalow close to Downtown!

EmilyRating, 5 stars1 month ago
This adorable bungalow was perfect for a long weekend getaway! They have all of the amenities, it is centrally located, it's clean, and they communicated very well. I will definitely come again and recommend your place!!
Guest favourite
Bungalow in Indian Shores
4.9 out of 5 average rating, 205 reviews

Private Beach Bungalow 1BR *Heated POOL**PETS ok

Josh and Sarah Rating, 5 stars3 weeks ago
We recently wrapped up an AMAZING stay at The Lobster Beach Bungalow. Everything was as described- charming ‘old Florida’ feel and close proximity to the beach (50 steps). It felt like a miniature resort. We got to meet other vacationers staying at the other bungalows, which was pretty cool. We were even able to enjoy the pool on a day where the gulf waters were a little rougher. There are a lot of eateries within walking distance. We tried a different coffee shop every morning- yum! The bungalow itself was comfortable and had everything we needed for a great stay. The kitchen had we could have desired should we have decided to eat in. Too many yummy local eateries for that for us though! We also loved being able to have our fur babies with us, as no vacation is complete without our whole family. We look forward to returning next year with some extended family to experience this peaceful paradise. Thank you, Liz, for creating a place that feels like home away from home!
Guest favourite
Guesthouse in Pinellas Park
4.87 out of 5 average rating, 270 reviews

pet friendly on an equestrian farm

RoslynRating, 5 stars2 months ago
As a solo 74 year old gal with an English cocker, safety is most important. I was very comfortable and felt safe. there. Just a lovely place and nice people

Family-friendly home rentals with a pool

Guest favourite
Condo in Redington Beach
4.9 out of 5 average rating, 164 reviews

SWEET BEACH RETREAT - REDINGTON BEACH FLORIDA

KimRating, 5 stars2 weeks ago
The condo has everything you need to have a great holiday and not spend a fortune doing it. The cooker works well and the hob is very fast. We prepared our own meals most nights and ate outside overlooking the pool. The bathroom is well set out and the shower hot and powerful. What really appealed to us when booking was the access to a pool and not having to drive to, or pay for parking at a beach. It’s less than a five minute walk across Gulf Boulevard and Joy supplies chairs and an umbrella. The pool was clean and not at all busy. The area is safe and pleasant with easy access to Indian Rocks beach too. We had a day out to Universal Studios, an easy two hour dive away. Locally there are a few restaurants and cafes within walking distance, the Conch Grill is particularly good with a very generous happy hour from 11am - 7pm. We would like to return and highly recommend this accommodation.
Guest favourite
Condo in Indian Rocks Beach
4.96 out of 5 average rating, 116 reviews

Renovated Condo! Across the Street From The Beach

RachaelRating, 5 stars1 month ago
being 7 months pregnant this place was perfect for a quick baby moon! the beach is just a walk across the street, plenty of restaurants less than a 5 minute drive and had everything we needed for the beach as well.
Guest favourite
Home in St. Petersburg
4.91 out of 5 average rating, 111 reviews

Cozy Dream FL Vacation Home Pool is heated!

ColleenRating, 5 stars1 month ago
We stayed at this wonderful home for my daughter’s graduation from Eckerd College, and it couldn’t have been more perfect! The location is unbeatable—literally right across the street from the Eckerd College, which made everything so convenient. The house itself was spotless and incredibly comfortable. It truly felt like a home away from home. The pool was a highlight—clean, refreshing, and such a relaxing space for our family to enjoy some downtime. Nan, our host, was absolutely amazing. She was kind, responsive, and went out of her way to make sure we had everything we needed. She made us feel so welcome, and by the end of our stay, I truly felt like I had made a friend. Highly recommend this place for anyone visiting Eckerd or looking for a relaxing and well-cared-for stay in the St. Pete area!
Guest favourite
Bungalow in Indian Rocks Beach
4.88 out of 5 average rating, 121 reviews

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

GregRating, 5 stars2 weeks ago
We were looking for a quick family vacation at the Gulf of America and we found this little gem at Indian Rocks Beach. The location was perfect and only 30 min from the airport. With all equipment provided to be at the beach and only a short walk across the street, it was just what we needed. There's a cool little ice cream and sandwich shop right across the street Kooky Coconuts offering the best Cuban sandwich in Florida and great ice-cream. Sleeps 4 comfortably and has a great tiki bar in the back. If your looking for relaxation, great restaurants and beach, this is the place. Owners are awesome and where always available if we needed anything. Definitely will be back!
Top Guest favourite
Home in Spring Hill
4.94 out of 5 average rating, 113 reviews

3BR Roman Oasis: Caesar's Place + Heated Pool

JosephRating, 5 stars1 week ago
Gorgeous property, my friends and I loved it. They have automatic lights outside that help you find it easily at night and the outdoor cameras are an additonal sense of safety. We were all very impressed with the extras, greeted with a welcome package and plenty of stuff in the kitchen/bedrooms/lanai to make it a home. The beds and sofas are incredibly comforable as well as clean. It was amazing to be able to adjust the temp to our liking being new englanders, definitely our oasis in the summer heat. This place is worth a stay and we will certainly be back!
Superhost
Apartment in Belleair Beach
4.7 out of 5 average rating, 461 reviews

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

MichelleRating, 5 stars1 month ago
Mathew's place was exactly what I needed. Calm, quiet and very peaceful. I didn't hear the neighbors the whole time I was there. The beach was literally right out the window. So getting down there was very easy. Having a beach chair, cooler and bag in the condo was very convenient. The condo was very clean and homey. I liked being able to cook for myself and never having to leave the complex. I will definitely stay here again!!
Superhost
Condo in Clearwater
4.81 out of 5 average rating, 153 reviews

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES

ElliotRating, 5 stars1 week ago
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!
Guest favourite
Condo in Clearwater
4.93 out of 5 average rating, 120 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

CassandraRating, 5 stars3 weeks ago
We loved our stay! The hosts were great at communicating with us. Very clear instructions. Place was just like the photos. Very enjoyable stay!

Quick stats about holiday rentals that are family-friendly in Wesley Chapel

  • Total rentals

    140 properties

  • Total number of reviews

    2.7K reviews

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    60 properties have a pool

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    140 properties include access to Wi-Fi

Destinations to explore