Family-friendly holiday 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

Superhost
Flat in Orlando
4.75 out of 5 average rating, 591 reviews

Luxury condo in Orlando 1 br/1 ba

RabindraRating, 5 stars1 month ago
good place to stay, close to all attractions and MCO airport.
Top guest favourite
Home in Kissimmee
4.92 out of 5 average rating, 143 reviews

Disney Playhouse, Private Pool & Spa, Near Disney

AnyelisRating, 5 stars3 weeks ago
The house was absolutely gorgeous and was exactly like in the pictures. The hosts were extremely friendly and communicative through our entire stay and even before. It was very clean, had everything one needs during a vacation, and very peaceful. We will be booking again soon!
Superhost
Apartment in Kissimmee
4.76 out of 5 average rating, 255 reviews

King Bed Small Studio Disney World Universal

CharlieRating, 5 stars2 weeks ago
Good location, restaurants 10 mins to walk and most of all a kind host ever and provided me useful information. Thank you.
Guest favourite
Apartment in Florida Center
4.9 out of 5 average rating, 126 reviews

The Point Hotel & Suites - 705H Luxury - Pool View

CarlosRating, 5 stars1 week ago
Ronaldo’s place was amazing, everything was as described, all the main attractions are nearby and he was always responsive to all our questions since day 1, definetely a great place to stay in Orlando
Superhost
Home in Kissimmee
4.89 out of 5 average rating, 182 reviews

Luxurious Private Retreat w/Spa & Saltwater Pool

JessicaRating, 5 stars1 month ago
Carrie thank you so much for hosting our family! This was so much better for our family than a hotel! Our kids never said they were bored! The next time we are in the Orlando area we will book again for sure!
Top guest favourite
Apartment in Davenport
4.98 out of 5 average rating, 206 reviews

Disney Orlando Bahama Bay Resort Theme Parks &More

CandidaRating, 5 stars5 days ago
We really liked staying here during our Disney vacation. It’s about 20-25 minutes from the parks. Condo was clean, well stocked, and very quiet in the area. Bed was very comfortable. We would definitely stay here again. 2 pools/hot tubs close to unit as well as splash pad.
Top guest favourite
Townhouse in Kissimmee
4.94 out of 5 average rating, 177 reviews

Updated Pics | 5 Miles to Disney | Themed bunkroom

LindseyRating, 5 stars1 week ago
This was our second stay in the Windsor Hills community townhouses. Last year we paid about the same amount as we did for Heather’s place this year, and I would say that was worth the price, but Heather’s place was a step above our place last year! Everything is new, hard flooring throughout, nice furniture, linens, and blankets. My kids loved the ocean/character themed room. The house was very clean and had baby gates available to use, a stroller, and more for those with small kids. You can tell a lot of care has gone into making this house special!
Top guest favourite
Apartment in Kissimmee
4.94 out of 5 average rating, 354 reviews

Disney World Condo w/ Full Kitchen, Balcony & Pool

AnaRating, 5 stars2 weeks ago
Adam is a great host. We really appreciate the extra amenities that most airbnbs skimp out on like extra toilet paper rolls, my kids adored the extra Disney touches, and although having to wait for 3 toddlers to make it up to the 3rd floor was challenging for me they had no complaints! We very much enjoyed our stay and took advantage of what the resort had to offer! Thank you Adam for helping me find the airbnb when I accidentally put in the wrong directions. Your communication was greatly appreciated. Would stay again.

Family- and pet-friendly home rentals

Guest favourite
Apartment in Orlando
4.95 out of 5 average rating, 127 reviews

Vista Cay Luxury Vision Walk to EPIC and OCCC

ReneeRating, 5 stars2 weeks ago
Great place to stay and certainly a great price for what you get .
Top guest favourite
Home in Kissimmee
4.83 out of 5 average rating, 109 reviews

5 Stars Vacation Home with Private Pool/Jacuzzi

JasonRating, 5 stars2 months ago
We booked this airbnb with 5 guests. The home has plenty of space, in a very welcoming and peaceful neighborhood. The house was spotless, and check in was a breeze. Tons to do around the house with a little games room in the garage, and a beautiful backyard with a pool, netted to keep the bugs away. Great communication with the host. Will definitely be coming back.
Top guest favourite
Villa in Kissimmee
4.86 out of 5 average rating, 411 reviews

OMG! Disney Area, Movie Theater, Game Room & Pool!

ShamayaRating, 5 stars2 weeks ago
We had a wonderful stay !! It was very roomy and exactly like the pictures! Definitely would recommend and stay again !
Guest favourite
Home in Orlando
4.84 out of 5 average rating, 212 reviews

Waterside Pet Friendly Lakefront

KennethRating, 5 stars3 weeks ago
Place was exactly as described. Virginia was a great host. Would stay here again.
Superhost
Home in Kissimmee
4.79 out of 5 average rating, 526 reviews

Private Pool Villa near Disney & Orlando sleeps 12

Girish KumarRating, 5 stars3 weeks ago
I had a wonderful experience staying at Sam’s place. The house was very clean, well-maintained, and located in a quiet, safe, and family-friendly neighborhood. It truly felt like a home away from home. Sam was an exceptional host—very responsive, friendly, and helpful throughout our stay. He made sure we had everything we needed and offered great local tips that made our Disneyland trip even more enjoyable. The house was spacious, comfortable, and perfect for our family of six. The kitchen was fully equipped, and the beds were cozy. One of the highlights for us was the swimming pool—my kids absolutely loved it and spent hours enjoying themselves! We especially appreciated the smooth check-in and check-out process. I highly recommend Sam’s home to anyone visiting the area. Thank you once again, Sam, for your warm hospitality!
Superhost
Home in Kissimmee
4.8 out of 5 average rating, 104 reviews

View the Disney fireworks from your pool!

MeganRating, 5 stars3 weeks ago
We enjoyed our stay at Judy’s house. We found that it was very close to the magic and a nice and comfortable escape from the parks. We didn’t have much luck seeing the full fireworks show (the trees across the way have gotten a bit tall), but enjoyed the pool and outdoor space.
Top guest favourite
Home in Orlando
5 out of 5 average rating, 120 reviews

Stay in the best neighborhood in downtown Orlando!

ChrisRating, 5 stars2 days ago
We were helping to move our daughter to Orlando area from out of state and needed a home base for a few days while we got everything set up for her. David’s place fit the bill perfectly - clean, lots of space, quiet, quick responses to any questions. It was exactly what we needed.
Top guest favourite
Home in Sanford
4.95 out of 5 average rating, 190 reviews

Historic Sanford Sunshine Cottage w/ Treetop suite

RachelRating, 5 stars3 months 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.

Family-friendly home rentals with a pool

Top guest favourite
Houseboat in Sanford
4.98 out of 5 average rating, 191 reviews

Floating Cottage - Summer/Fall Rates Reduced

MarilynRating, 5 stars1 month ago
We loved feeding the turtles 🐢. You have to check out downtown Sanford, walk the Riverwalk & go to the Central Florida Zoo & Botanical Gardens. Don't forget to try the Jailhouse Restaurant - in a real old jailhouse, great food! She was an amazing host.
Guest favourite
Flat in Sorrento
4.93 out of 5 average rating, 343 reviews

Quiet Neighborhood in the Country

ShaeRating, 5 stars2 days ago
Great area to stay! Chuck was great to deal with and gave us some recommendations on local things to do! Loved the area and the neighbourhood was very peaceful. Enjoyed the pool many days of our stay here. Would highly recommend and would definitely stay again! Thanks Chuck:)
Guest favourite
Cottage in Kissimmee
4.95 out of 5 average rating, 482 reviews

Bright & Cozy Cottage Near Disney

KellyRating, 5 stars1 week ago
this is my second time staying here and I loved it. we had a peaceful, enjoyable week, walking the grounds and enjoying the pool. The space is so close to so many attractions and awesome restaurants. The house had everything that we need including laundry so our stay was extra relaxing.
Guest favourite
Cottage in Kissimmee
4.94 out of 5 average rating, 471 reviews

Entire cottage for 5, close to Disney, Universal!

RaishRating, 5 stars1 week ago
Very peaceful and beautiful! Had an excellent trip. Will try to stay here every time I go to Orlando.
Guest favourite
Townhouse in Kissimmee
4.88 out of 5 average rating, 316 reviews

B-Gated Resort-5 miles to Disney-2 FREE Water Park

JessRating, 5 stars3 weeks ago
James’ place was the perfect hub to make our family vacation seamless. The unit was as described and very family friendly. We appreciated having multiple pack-n-play’s and a high chair- Overall we would recommend this place and would rent from James again.
Superhost
Guest suite in Kissimmee
4.83 out of 5 average rating, 590 reviews

Private 2 bedroom w/bathrm in portion of POOL home

JessicaRating, 5 stars1 week ago
This place was so nice for my daughter and I. We were welcomed with open arms and the place was just as described. We met the grounds keeper CC who was a joy to meet. It was quiet and conveniently located. We will definitely stay again.
Top guest favourite
Home in Orlando
4.95 out of 5 average rating, 325 reviews

*HALF HOME* (read desc) Pool/Disney/Universal

AmberRating, 5 stars1 month ago
this family is beyond accommodating. I don't typically do airbnbs with the in home post this was the first for me. They are very accommodating and welcoming. They made me feel right at home and like part of the family. Their home is clean and very well decorated. If I am ever in the area again I would stay there without hesitation. They do have dogs which for me was great. But if you are uncomfortable with them I am sure they would make sure that you do not have to interact with them. But for me the dogs made it feel more like home. I cannot say enough nice things about this family and how accommodating and friendly they are. If you're unsure about staying with an in home host I would urge you to stay with this family. You won't regret it. Just like their ad says you will be staying with friends you just haven't met yet. Cannot recommend this location enough.
Guest favourite
Apartment in Orlando
4.91 out of 5 average rating, 116 reviews

VC7 306 - Lake and Pool view by Universal Studios

ShellyRating, 5 stars3 weeks ago
My family and I had a wonderful stay! The unit was spacious, pretty, and well-appointed. We wanted to stay close to Universal’s Epic Universe and we were within five minutes from it. The pool area was great and my husband enjoyed the workout facility. We’ll definitely be back!

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

  • Total rentals

    70 properties

  • Nightly prices starting at

    ₹2,597 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

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