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Family-friendly vacation rentals in Casselberry

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Casselberry family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A spacious living area features a large mounted television above a stone fireplace. Reclining sofas provide comfortable seating for relaxation. Soft, ambient lighting is present, creating a cozy setting that is complemented by dark curtains framing a large window.
Home in Davenport
4.88 out of 5 average rating, 16 reviews

The Orlando Oasis 1

ReynaldoRating, 5 stars9 months ago
This was our 3rd summer booking Robert’s place. Robert is the best host. His home is Beautiful and what’s great about him is that he puts back into the house. He doesn’t just sit back collecting money and leave the house the same. Every year there has been renovations done. Always clean and feels like home. Thanks Robert for everything. And we’re already looking forward to next summer.
Superhost
An outdoor pathway lined with lush green grass extends along a gated area of the home, leading to a patio with a table and chairs. The neighboring water body is visible, enhancing the serene atmosphere of the environment.
Townhouse in Kissimmee
4.8 out of 5 average rating, 127 reviews

Comfy Lake View Jacuzzi Terra Verde Resort

AndréRating, 5 stars2 weeks ago
The house is very good, exactly as in the listing. The location is also good, there is a Walmart nearby and it is not far from Disney. Communication with the owner was good, always responding very quickly.
Top guest favorite
Home in Kissimmee
4.89 out of 5 average rating, 198 reviews

Private Jacuzzi-Heated ResortPool-BBQ-7 mls Disney

AngelRating, 5 stars2 weeks ago
Tetyana's place made my stay in Orlando easy and fun, easy because checking in and out was simple and fun because there is so much to do on location. Wish I had more time to challenge my son at the pool table and ping pong table. Avoid the overpriced small hotel rooms and do yourself and your family a favor and stay at this wonderful place.
Superhost
A playground area features colorful play structures with slides and climbing elements, surrounded by well-maintained grass and shade from nearby trees. The equipment is designed for various age groups, encouraging outdoor play and exploration in a welcoming environment.
Home in Kissimmee
4.67 out of 5 average rating, 57 reviews

Disney 3 bed 2 bath pool hot tub RR

DavidRating, 5 stars26 months ago
We thoroughly enjoyed your lovely home. It was perfect for our needs. Everything was very well-kept and clean. We especially enjoyed the hot tub after long days walking through the Disney and Universal parks! It saved our aching feet. We felt right at home immediately!
Superhost
Villa in Kissimmee
4.81 out of 5 average rating, 229 reviews

Veranda Palms Luxurious Home w/Pool & NEAR DISNEY

DerrickRating, 5 stars3 weeks ago
What a fantastic trip! Thank you so much for making our vacation stay easy and relaxed! We will def be back!
Top guest favorite
A well-appointed bathroom features a countertop with dual sinks and a light-colored wooden vanity. A shower-tub combination is enclosed with a tropical patterned curtain, while plush towels hang neatly on a bar. Natural light filters in, highlighting the inviting space.
Home in Davenport
4.91 out of 5 average rating, 126 reviews

The Shire -Private Pool & Hot Tub, Close to parks!

DanaRating, 5 stars2 weeks ago
Monica was very responsive when we had an issue with one of the bathrooms and got it promptly fixed! We have stayed at this house previously and love the location and amenities. We will be back!
Superhost
A spacious hot tub, enclosed in a screen room, is positioned on a patio. It features a wooden surround, steps for easy access, and is set against a backdrop of lush greenery from the forest preserve.
Home in Kissimmee
4.89 out of 5 average rating, 175 reviews

Luxurious Private Retreat w/Spa & Saltwater Pool

Ashleigh JaneRating, 5 stars2 weeks ago
Carrie was great! The house was beautiful and had more than what could even do with! We had a hiccup with the AC which led to a warm night after a hot day at Disney, however Carrie was so quick to resolve the issue and even allowed us to heat the pool for a night free of charge for the inconvenience. It was a lovely home that we will be staying in again our next visit to Disney! The neighborhood was easy to find and navigate. The perfect distance from the main interstates that had all food locations. The house was clean and comfortable! Carrie even made check out so seamless we had to confirm with her she didn’t want anything more for us to do! Would recommend staying here and would stay here again in a heart beat.
Guest favorite
Townhouse in Kissimmee
4.89 out of 5 average rating, 189 reviews

Adorable 2 bdr lakefront w/jacuzzi 5 min *Disney*

MichaelRating, 5 stars3 months ago
Location, cleanliness, ease of check in and check out, instructions from the owner were all great. Just one minute south of 192, it was easy to get to the Disney Parks or Universal. It is closer to Disney but we did venture to Universal one day and it was right up I-4. It is just south of Old Town but you couldn't hear anything from there. The place was exactly like the pictures. Two bedrooms, 2 1/2 baths, 2 full on the upper floor and 1/2 on the main floor. Although we didn't use any of it, the kitchen came complete with silverware, dishes, pots and pans. A shower only in one bathroom and a bath/shower in the other. I only had a couple of questions along the way and they were answered quickly. I would absolutely stay here again.

Family- and pet-friendly home rentals

Superhost
A well-appointed bathroom features a light granite countertop with a sink and a wall-mounted mirror. A floral shower curtain and fresh flowers in a vase add a subtle touch. Soft towels are neatly arranged on the black shelf beside the toilet.
Townhouse in Kissimmee
4.8 out of 5 average rating, 143 reviews

Compass Bay 5164 AD - Beautiful and Near Disney

JessicaRating, 5 stars1 week ago
The house was clean and inviting, the neighborhood was quiet, and it was great being so close to Disney! The hosts were quick to respond. All in all, we had a wonderful stay!
Superhost
Apartment in Kissimmee
4.79 out of 5 average rating, 211 reviews

Fantastic Award Winning Renovated 2+2 Near Disney

FredericRating, 5 stars1 month ago
Great place to stay
Guest favorite
The exterior of the house is characterized by a light gray facade with a covered front porch. Lush greenery and colorful plants adorn the landscape, while a well-maintained lawn extends to the driveway. The surrounding trees provide a sense of tranquility.
Home in Orlando
4.85 out of 5 average rating, 206 reviews

Waterside Pet Friendly Lakefront

SkylaRating, 5 starstoday
This will be my second time staying at Virginia’s Orlando location. My husband and I truly love it so much and will continue to stay here. Virginia is very responsive and is always checking up on you. Her description of the place is accurate. The location is lovely and is extremely safe! I have only good things to say and would recommend this Airbnb to anyone. :)
Superhost
Home in Kissimmee
4.8 out of 5 average rating, 519 reviews

Private Pool Villa near Disney & Orlando sleeps 12

JordanRating, 5 stars2 weeks ago
Sam was always responding to my questions and inquiries, was quick to respond, and very helpful. House was within minutes of Disney, nice pool, and plenty of grocery stores nearby, and other stores as well. The family had a great time and hope to be able to book again when we make another trip to Disney! Thanks Sam!
Superhost
The exterior of the home features a spacious driveway, paved in light-colored bricks, leading up to an attached garage with an ornate door. A well-maintained lawn with green grass and palm trees is visible, complemented by a clear blue sky filled with clouds.
Home in Kissimmee
4.79 out of 5 average rating, 102 reviews

View the Disney fireworks from your pool!

AlexRating, 5 stars4 months ago
This is the second time I've stayed at Mrs. Judy's and both times have been wonderful. I can't say enough good things about the house or our hosts. I plan on staying here every time I'm in the area. I would highly recommend this place to anyone traveling to the Kissimmee Orlando area. Plus you can't beat hosts like Mrs Judy and Mr Harlan.
Top guest favorite
A large screened-in porch features a wood floor and is furnished with a comfortable swing and two wicker chairs. Warm string lights are draped overhead, enhancing the serene ambiance. Lush greenery is visible outside, creating a peaceful, nature-infused retreat.
Home in Sanford
4.95 out of 5 average rating, 190 reviews

Historic Sanford Sunshine Cottage w/ Treetop suite

RachelRating, 5 stars1 month ago
This was a really fun, unique place to stay while we were in town for a family wedding. We particularly enjoyed hanging out on the screened porch upstairs. Sara was really accommodating with an early check-in when we ended up on a very early morning flight, which was SO appreciated. We’d definitely stay again.
Top guest favorite
A spacious kitchen area is highlighted by modern appliances and a light wood dining table. Natural light floods the space through large glass doors, with greenery visible outside. Decor includes vases of dried flowers and framed wall art, adding a touch of warmth.
Home in Altamonte Springs
4.97 out of 5 average rating, 315 reviews

A Home Where Eclectic Luxury Meets Affordability

ChristineRating, 5 stars1 week ago
We have stayed multiple times and it’s always perfect. Great host!
Top guest favorite
A cozy living area is displayed, featuring a wooden bookshelf filled with books and decorative items. Natural light filters through blinds on multiple windows. A comfortable leather chair and a small table with a lamp provide a welcoming reading space.
Home in Maitland
4.94 out of 5 average rating, 163 reviews

Orlando area pool home in Maitland

MiaRating, 5 stars1 month ago
Had a great week at Lisa’s place! The pool was a bit too chilly to use but still enjoyed the backyard and amenities. It’s very peaceful and quiet and just a short drive to anywhere you would need to go! Also, almost anything you would need in the kitchen and bedrooms. One thing- the bedroom doors are not sound proof whatsoever so keep that in mind if traveling with young kids and etc.

Family-friendly home rentals with a pool

Top guest favorite
Home in Kissimmee
4.92 out of 5 average rating, 105 reviews

Hidden Treasure Very Comfy! Pool Home - Sleeps 6

MarcusRating, 5 stars3 months ago
Wonderful place to stay!! Neighborhood was quiet, house was just as pictured. Pool heat worked out very well for our stay. Property management team stopped by to make sure the trash made it to the road, had the pleasure of speaking with him for a while he seemed to take real pride in the property all the way around a great home for a wonderful price wouldn’t mind to stay again at all!!
Superhost
A community area features a colorful playground with a yellow slide and climbing frame, surrounded by fresh green grass. Nearby, a basketball hoop stands on a concrete surface, with a clear sky and fluffy clouds in the background.
Home in Davenport
4.8 out of 5 average rating, 153 reviews

Welcoming fully equipped villa in Davenport

AngelaRating, 5 stars2 weeks ago
We have rented Jane and Brian’s villa now for several years in a row and it is our home away from home! The villa is always clean and welcoming! Although the villa is self serving, it also comes with an abundance of items to start you off and keep you comfortable during your stay. The beds are comfortable, and there are plenty of seating options inside and out. The lanai and pool area is always clean and very spacious. The location is perfect in a quaint neighborhood with access to everything you can think of. Communications with the hosts are quick and pleasant! Once again we have no complaints and can’t wait to return next year. Thank you Jane and Brian for sharing your villa with us!
Guest favorite
A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.
Home in Clermont
4.92 out of 5 average rating, 108 reviews

Spacious Bungalow with Private Pool and Courtyard

RobinRating, 5 stars3 days ago
We had the best time. We loved the sun room. we stayed in there the most. Would definitely rent again
Superhost
A water play area is seen beside a resort-style pool, featuring colorful slides, interactive water features, and a large water bucket. Brightly colored structures are surrounded by palm trees and lounge chairs, creating a fun environment for families.
Townhouse in Kissimmee
4.84 out of 5 average rating, 110 reviews

Majorca Paradise: Townhome Near Magic Disney

Justin KyleRating, 5 stars1 month ago
Beautiful location, felt safe, plenty of space and the kids enjoyed the pool
Top guest favorite
A welcoming entrance area includes a small table with a lamp and two white chairs adorned with orange cushions. A framed artwork adds a touch of color, leading towards a spacious dining area visible in the background.
Home in Kissimmee
4.89 out of 5 average rating, 129 reviews

Remy's Refuge: Stylish 4BR - 10 min to Disney!

AnastasiaRating, 5 stars7 months ago
This was our second time staying at Trevor and Amanda’s place and it was just as good as the first time. The place is in a great location very close to the Disney parks. The pool area is beautiful especially looking over the lake. Their home is clean, comfortable and has everything that you need. We really enjoyed our stay and are looking forward to visiting again soon.
Superhost
A vibrant splash pad features colorful water features, including buckets and fountains. Surrounding palm trees and sun loungers create a refreshing environment. The clear blue sky complements the serene water area, designed for family fun and relaxation.
Townhouse in Kissimmee
4.83 out of 5 average rating, 173 reviews

Spacious home with private pool in gated resort

MiguelRating, 5 stars3 weeks ago
We loves the space but didn't realize that we have to pay extra to use the grill.
Superhost
A guest bathroom is presented with a neutral color palette, featuring a single vanity with a sink and ample counter space. A large mirror reflects the area, while green towels hang neatly on a rack. A shower is visible through a glass door.
Townhouse in Kissimmee
4.79 out of 5 average rating, 169 reviews

Amazing family home with pool near Disney

ElizabethRating, 5 stars2 months ago
We had a great time, it is prepared considerately for guests and was close (20 min drive) to disney world where we went every day.
Superhost
Home in Davenport
4.79 out of 5 average rating, 139 reviews

Beautiful 4 bed home, south-facing pool,games room

LisaRating, 5 stars1 month ago
This home was fabulous! We had college athletes in the area playing their sports for 8 days … this was the perfect getaway after long days in the sun! The home is very nice and well stocked. We will come back again next year!

Quick stats about vacation rentals that are family-friendly in Casselberry

  • Total rentals

    70 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    2.9K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore