Family-friendly holiday rentals in Longwood

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Longwood family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Apartment 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.
Guest favourite
Home in Kissimmee
4.89 out of 5 average rating, 172 reviews

VerandaPalms/HeatedPool/Carpet free/NearDisney

YessicaRating, 5 stars6 days ago
The house was incredibly clean and very spacious. I appreciated that someone came regularly to clean the pool—especially since I’m very clean and a bit of a germophobe! The host was also very responsive, which I truly appreciated. We had a small issue with the HOA, and I’m grateful the host was on top of it and supportive throughout. I felt safe at all times in the gated community, and my kids really enjoyed the pool.
Guest favourite
Home in Kissimmee
4.9 out of 5 average rating, 107 reviews

6 mins. to Disney W/Poolside Theater & Game Room

ClintonRating, 5 stars1 month ago
Andrea’s place was awesome! My family and I enjoyed the space outside and how open the house was gave everyone their own spot. The pool and back patio were so nice and relaxing. Would definitely stay here again in the future!
Top Guest favourite
Home in Kissimmee
4.92 out of 5 average rating, 144 reviews

Private Pool & Spa, Close Disney, Disney Playhouse

SarahRating, 5 stars2 weeks ago
Very clean and convenient transportation
Superhost
Condo in Orlando
4.83 out of 5 average rating, 134 reviews

Fantastic 3BR Condo close to OCCC & Epic Universe!

HelenaRating, 5 stars2 weeks ago
Very comfortable, in a great location - close to amenities and easy for Uber to find. Dennis was super helpful and responded in minutes.
Superhost
Condo 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
Condo 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!

Family- and pet-friendly home rentals

Top Guest favourite
Home in Kissimmee
4.84 out of 5 average rating, 110 reviews

5 Stars Vacation Home with Private Pool/Jacuzzi

TammiRating, 5 stars1 month ago
Kenia was very responsive if we needed anything! The home is exactly how it looks in the pics and all that’s listed was there. Kenia provides you with all you need for your stay, the kitchen is very well equipped to whip up a 5 course meal! Definitely will be booking this home again in the future
Guest favourite
Apartment in CHAMPIONS GT
4.88 out of 5 average rating, 203 reviews

Magical Newly Renovated 10 minutes to Disney 2+2

JazzRating, 5 stars1 month ago
Great check in process! Would boom again when in the area! Very clean, smelled good and great space!
Guest favourite
Home in Oviedo
4.9 out of 5 average rating, 312 reviews

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

Paramount Property GroupRating, 5 stars1 week 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 stars2 weeks 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, 105 reviews

Family friendly/Pet friendly Orlando paradise

CatherineRating, 5 stars1 week 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!
Superhost
Home in Kissimmee
4.8 out of 5 average rating, 105 reviews

View the Disney fireworks from your pool!

AmyRating, 5 stars1 day ago
We loved our stay here! We were greeted by the welcoming committee of ducks and White Ibises when we walked out to the patio - they are adorable. The house was very clean and nicely decorated. The pool was nice to cool down after a day at the parks and it is conveniently located near stores and restaurants and also very close to the parks - which was awesome!! I highly recommend staying here. Judy was a great host to work with and we look forward to our next visit! Oh! And I caught a bass in the pond…added bonus!
Top Guest favourite
Home in Orlando
5 out of 5 average rating, 120 reviews

Stay in the best neighborhood in downtown Orlando!

ChrisRating, 5 stars4 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.

Family-friendly home rentals with a pool

Superhost
Townhouse in Kissimmee
4.77 out of 5 average rating, 314 reviews

Free Waterpark! Fantasy World - Fun at BnB

LindsayRating, 5 stars1 week ago
Our family had a great experience. If we return we will look to see if this same condo is available. The hosts were very helpful and responsive. The pool was a bonus.
Guest favourite
Cottage in Kissimmee
4.95 out of 5 average rating, 483 reviews

Bright & Cozy Cottage Near Disney

MarissaRating, 5 stars3 days ago
Johann’s place was AMAZING! It was super nice and affordable and perfect for me and my husband’s trip to Disney. The private entrance made us feel safe and the place itself was clean and so cozy. We will definitely be trying to stay here again for future trips!
Guest favourite
Cottage in Kissimmee
4.94 out of 5 average rating, 472 reviews

Entire cottage for 5, close to Disney, Universal!

AdrianRating, 5 stars2 days ago
This place was exactly what we were looking for when staying for our Disney vacation and then heading out for our cruise. It's cute, has what you need, and they are fantastic communicators! The community pool was nice especially after a long hot day at the parks. Would definitely stay here 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
Townhouse in Kissimmee
4.94 out of 5 average rating, 210 reviews

Relaxing Resort Stay Hot Tub Lake View Near Disney

MariaRating, 5 stars1 month ago
This was our second time staying at Nathalie’s place! We are just as happy as before. Thank you again and we will be back soon!
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
Guest favourite
Home in Kissimmee
4.8 out of 5 average rating, 289 reviews

3 bedroom Orlando Florida pool home

EricRating, 5 stars1 week ago
This was a perfect family vacation spot we stayed 5 nights and enjoyed the pool.
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 Longwood

  • Total rentals

    40 properties

  • Nightly prices starting at

    $50 NZD before taxes and fees

  • Total number of reviews

    2K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore