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Family-friendly holiday rentals in Maitland

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Maitland 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

DaianeRating, 5 stars2 weeks ago
Amei o lugar, tudo muito limpo, roupas de cama impecáveis, com certeza voltarei, o Ricardo é ótimo anfitrião e responde rápido as mensagens, a localização é ótima, tem um ponto de ônibus na entrada no condomínio que é super prático pra andar pela Internacional Drive, o atendimento na recepção do condomínio também foi excelente. Só tenho elogios.
Guest favourite
Apartment in Orlando
4.81 out of 5 average rating, 164 reviews

INTERNATIONAL dr/UNIVERSAL 2 BEDROOMS KING SUITES

ArlindaRating, 5 stars2 weeks ago
Good location with lots of restaurants in the area. The building feels dated but the apartment is clean and good value. We cooked a couple meals and the kitchen was adequate. The host communicated throughout our stay and friendly. There was adequate parking. We did not check out the amenities.
Superhost
Flat in Orlando
4.89 out of 5 average rating, 248 reviews

Vista Cay Orlando Convention Luxury 3 bed condo

RobertRating, 5 stars1 month ago
Great place no issues at all Jetty allowed us to extend our stay 2 days no problems definitely will return.
Guest favourite
Apartment in Orlando
4.89 out of 5 average rating, 209 reviews

VISTA CAY RESORT, 3 BEDROOM STANDARD APARTMENT

FatemehRating, 5 stars1 month ago
We felt right at home while in Orlando because of this Air BnB. I was worried we would struggle because it is a large complex, but the GPS was spot on at the correct building and the unit was very easy to find. The complex is in amazing condition, amenities were great, and the unit was so relaxing. Everyone in my group kept raving about how comfortable the mattresses and pillows were. There was an abundance of towels and they hostess will quickly respond if you need additional towels. We LOVED this Air BnB and will definitely be renting it again. Right outside the gates of the complex there are stores, liquor stores, Chipotle and other food/store options (you can walk there it is so close). Thank you for a great experience & amazing stay!
Guest favourite
Townhouse in Kissimmee
4.88 out of 5 average rating, 321 reviews

Roomy 2br w/ jacuzzi close to Disney

JonishaRating, 5 stars2 weeks ago
Great location place was very nice and kept well enjoyed the hot tub and the resort this place was well equipped with all necessities for your stay it was very welcoming! Great place to stay would Love to visit again!
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 stars3 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
Apartment in Orlando
4.92 out of 5 average rating, 490 reviews

Cozy Cay 2BR 4beds *low cleaning fee for May

RicardoRating, 5 stars2 weeks ago
We stayed only one night and it was very pleasant! The location is perfect! We intend go back for few more days.
Guest favourite
Townhouse in Kissimmee
4.83 out of 5 average rating, 190 reviews

Orlando Disney ºoº 3BD in Resort | Kissimmee

MelissaRating, 5 stars3 weeks ago
The home is very comfy. Super clean and easy to get to. The size was perfect for my family of five. Will definitely stay again?

Family- and pet-friendly home rentals

Top guest favourite
Home in Kissimmee
4.8 out of 5 average rating, 124 reviews

Mickeys Movie House ,Cinema, Pinball, pool & spa

DeirdreRating, 5 stars5 days ago
The Mickey house is fabulous… you feel right at home… John and Yvonne were quick to respond and it was a minor issue about a missing remote… John came quickly and fixed in a matter of minutes… the pool was awesome… the decor was so cute and the theater room was awesome… You felt at home and able to relax after a fun day at Disney!!!! Highly Recommend !! 100/100 We were a family of 8 and had lots of room and when we needed space to ourselves, each group had a spot!! Thank you Yvonne and John for a great place and experience… Dee, Kelly, Jaela, Marcel and Family Washington/Watson Disney trip 2025
Superhost
Townhouse in Kissimmee
4.7 out of 5 average rating, 166 reviews

Cozy Townhouse in Kissimmee, near Orlando!

LakmalRating, 5 stars2 months ago
We stayed for 7 days at this lovely townhouse and had a fantastic time. The location was ideal—just a short drive from Disney and other major attractions. The neighborhood felt safe and quiet, which was great for relaxing after busy days out. The townhouse was clean, spacious, and well-equipped. The kitchen had everything we needed to cook meals, and having a washer and dryer was super convenient. The Wi-Fi worked well, and the air conditioning kept the whole place cool and comfortable. The kids especially loved the community pool.
Guest favourite
Home in Oviedo
4.9 out of 5 average rating, 311 reviews

🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s

Paramount Property GroupRating, 5 stars3 days ago
Jeremy was a great host! The home came with everything we needed. The pool was a little dirty when we arrived, but I contacted Jeremy and he came right out to clean it so we could swim the next day.
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 stars1 week ago
We had a wonderful stay !! It was very roomy and exactly like the pictures! Definitely would recommend and stay again !
Top guest favourite
Townhouse in Kissimmee
4.99 out of 5 average rating, 104 reviews

Family friendly/Pet friendly Orlando paradise

CatherineRating, 5 stars5 days ago
We spent two weeks at Disney parks and this place was an excellent choice for our family of 3. We were close enough to take breaks during the hottest parts of the day. Andrea's place was very clean and comfortable. We appreciated all the amenities provided and clear instructions for check in/out. We would not hesitate to stay here again. Excellent host!!
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!
Guest favourite
Home in Davenport
4.83 out of 5 average rating, 103 reviews

Highgate Palace-near Disney World. 20min Drive

AleishaRating, 5 stars1 month ago
Aaron is an amazing host that truly cares about what is happening with his guests. We had a little trouble with our travel and Aaron went above and beyond to accommodate us when things went out of our control. The home is very nice and exactly as described. It was clean and looked well kept. The beds are extremely comfortable and the home is spacious. I will definitely book with Aaron again if I am back in Orlando!
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

Guest favourite
Flat in Sorrento
4.93 out of 5 average rating, 342 reviews

Quiet Neighborhood in the Country

YarleneRating, 5 stars1 week ago
The person in charge very attentive and willing to help in whatever is necessary flexible and very accessible entrance. Very clean place, super clean pool and very cosy place. Very quiet neighborhood.
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
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.
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 stars6 days 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 Clarcona
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.
Superhost
Home in Davenport
4.81 out of 5 average rating, 126 reviews

Mintra’s Villa Pool & Spa

DemetriusRating, 5 stars1 month ago
My girl had a wonderful time her first time in Florida and the place was amazing and felt like home….this a great place and would rent it again…top tier
Superhost
Apartment in Kissimmee
4.77 out of 5 average rating, 126 reviews

1-101 Heated Pool, gym, tennis, Close To Disney!

ValentinaRating, 5 stars3 weeks ago
I had a great stay! The place was clean, comfortable, and just as described. The host was very friendly and responsive, which made everything super easy. I’d definitely stay here again!
Guest favourite
Villa in Kissimmee
4.77 out of 5 average rating, 140 reviews

Villa pool (Disney) beautiful lakeview

BelindaRating, 5 stars1 month ago
Gérard’s home was beautiful. It was in a such a convenient location to everything we needed- especially the Disney parks, and Walmart and Aldi for our weekly groceries. My family and I enjoyed the pool each day and even got to see gators come out of the canal. The only minor thing I wish would be if we had control of the temperature in the home. It was 95-98 degrees everyday we visited, and the home got quite warm even with the blinds closed and fans on. Otherwise, it was a great home and we surely enjoyed our stayed. Thank you!

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

  • Total rentals

    50 properties

  • Nightly prices starting at

    $26 SGD before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore