Family-friendly vacation rentals in Leesburg

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Leesburg family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
Home in Auburndale
4.94 out of 5 average rating, 158 reviews

Lake Whistler Beach House with lakefront pool

AndrewRating, 5 stars1 month ago
Very rarely do you find an Airbnb that super-exceeds your expectations. This home absolutely did that. Everything was nicely appointed, yet warm and homey feeling. We stayed as 2 adult couples and had a great time. That said, if you're a family of 8, you'll likely have a great time as well. The game room was a lot of fun, the kitchen had everything you'd want to cook inside or out. The pool was perfect sized, clean, and we'll kept. The grounds were beautiful. The lakeside area was awesome. literally zero complaints other than hating to leave.
Top guest favorite
Home in Kissimmee
4.8 out of 5 average rating, 125 reviews

Mickeys Movie House ,Cinema, Pinball, pool & spa

DeirdreRating, 5 stars1 week 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
Home in Kissimmee
4.9 out of 5 average rating, 163 reviews

Luxury Disney Vacation Home on Reunion Golf Resort

KennethRating, 5 stars1 week ago
We really enjoyed our stay! Lots to do in the area of course, but we had a few pool days and it was perfect! Plenty of space for everyone. The home is beautifully decorated and we found the beds comfortable. We had our dog with us and there were several beds available for him too! Very thoughtful. We recommend staying at Jason’s for an Orlando vacation.
Superhost
Apartment in Davenport
4.86 out of 5 average rating, 275 reviews

Recently Award Winning Renovated 2+2 Near Disney

SadieRating, 5 stars1 month ago
Cai Ling and John’s place was great. It was just as described. It was clean and had what we needed for our short stay. As they stated they only provide limited supplies so if you need additional supplies please bring them. I would definitely stay there again.
Guest favorite
Home in Kissimmee
4.98 out of 5 average rating, 155 reviews

5 acres of Nature - Private Retreat/Well Water

CharlotteRating, 5 stars4 months ago
We enjoyed our stay here as a bigger group with a little baby. Spacious, clean and private. Kitchen fully stocked, two bathrooms and 4 beds was great for our group. The location is a little out there, and with traffic, getting to Orlando can be a bit crazy. It does take a good 30 minutes to Disney and 1 hour to OCC convention center, depending on time of day. But we can’t control traffic, otherwise the place was great!
Top guest favorite
Condo in Davenport
4.93 out of 5 average rating, 107 reviews

Fabulous condo-Bahama Bay Resort, Close to Disney

AndrewRating, 5 stars5 days ago
This was one of my best Airbnb stays in a while. The resort location, amenities, and clubhouse staff were very convenient. The host had very clear instructions and was very communicative. The apartment itself was very spacious. Much larger than I expected. Thanks!
Superhost
Townhouse in Kissimmee
4.88 out of 5 average rating, 181 reviews

Elegant 4bdrs lakefront w/private pool

DestinyRating, 5 stars2 weeks ago
This space felt like home away from home. My family and I loved it! The location area is also nice and we felt safe and secure. Simone checked in on us after check-in which I appreciated very much.
Top guest favorite
Home in Kissimmee
4.87 out of 5 average rating, 220 reviews

RU Incredible Parents? Themed-7bed, 4mi. to Disney

ShyRating, 5 stars2 weeks ago
Loved our stay!! It's an adventure around every corner. Great themes!!

Family- and pet-friendly home rentals

Superhost
Townhouse in Kissimmee
4.71 out of 5 average rating, 167 reviews

Cozy Townhouse in Kissimmee, near Orlando!

LynnRating, 5 stars2 months ago
Maria's place was super cozy. It had everything we needed and then some. the property is beautiful. Pools were nice. and the staff at the gates were very welcoming. No problems. very relaxing.
Superhost
Condo in Kissimmee
4.76 out of 5 average rating, 256 reviews

King Bed Small Studio Disney World Universal

EvanRating, 5 stars5 days ago
Laura’s place was very accommodating to our week trip to Disney World! Close to all of the parks as well as all sorts of restaurants and convenience stores surrounding! Cool AC, a hot shower and a cozy bed—hard to beat after a HOT day at any of the parks! Very responsive to messages and suggested lots of great recommendations! Definitely a “bang for your buck” at Laura’s place! Looking forward to referring all of our friends and planning our next trip soon! Thanks again, Laura and staff! 🙂
Top guest favorite
Villa in Kissimmee
4.86 out of 5 average rating, 412 reviews

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

RosanneRating, 5 stars1 day ago
We had a great stay at this Airbnb in Orlando! The house was very clean, and the check-in process was smooth with clear, easy-to-follow instructions. The pool was a definite highlight, perfect for relaxing after a day out, though it’s worth noting it’s not super private as it’s close to neighboring homes. The space had all the basics, but be sure to bring your own essentials, as it’s lightly stocked with just the minimum. Overall, a comfortable and convenient place to stay.
Guest favorite
Condo in Orlando
4.99 out of 5 average rating, 140 reviews

Serene Lakeview By Disney -Universal Epic8.2 mi

ZacharyRating, 5 stars1 week ago
Adir’s space was in excellent condition and provided excellent communication throughout our stay! Beautiful view
Guest favorite
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.
Top guest favorite
Guesthouse in College Park
4.97 out of 5 average rating, 439 reviews

The Coach House- 2 bedroom/3 bath Orlando Getaway!

AyeshaRating, 5 stars3 weeks ago
We had such a lovely stay! Space was super clean, spacious, and full of natural light with beautiful high ceilings. The walk up to the guest house was charming and peaceful too. Really enjoyed our time here! 🏡
Superhost
Home in Kissimmee
4.8 out of 5 average rating, 105 reviews

View the Disney fireworks from your pool!

AmyRating, 5 stars3 days 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 favorite
Home in Orlando
5 out of 5 average rating, 120 reviews

Stay in the best neighborhood in downtown Orlando!

ChrisRating, 5 stars6 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

Guest favorite
Cottage in Kissimmee
4.95 out of 5 average rating, 483 reviews

Bright & Cozy Cottage Near Disney

MarissaRating, 5 stars5 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!
Superhost
Home in Kissimmee
4.9 out of 5 average rating, 126 reviews

5BD Windsor Westside Private Pool (WW 9025)

DennisRating, 5 stars1 week ago
My family enjoyed the stay on this property. Jose and Luis were always very fast in replying to my text messages. Never missed. The house is big and clean. Everything is so close and convenient to this property that we were able to avoid a lot of traffic. This property is also very close to the theme parks. I would recommend this property to anyone with no second thought. Will certainly make this my top priority on my next vacation to Orlando.
Top guest favorite
Condo in Davenport
4.98 out of 5 average rating, 207 reviews

Disney Orlando Bahama Bay Resort Theme Parks &More

CarmenRating, 5 stars6 days ago
Everything was perfect !
Superhost
Home in Clermont
4.88 out of 5 average rating, 155 reviews

Disney Pool Villa, Cranberry South,

JohnathanRating, 5 stars6 days ago
We enjoyed our time here! Marty was a kind and gracious host. Responsive on all our questions! The pictures of this place do not do it justice. It’s a lot bigger than it looks. We would definitely stay here again! The family loved the pool! Great times-Great memories!
Guest favorite
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 favorite
Villa in Kissimmee
4.8 out of 5 average rating, 486 reviews

7BD with Movie Theater Pool & Jacuzzi near Disney!

AngelaRating, 5 stars4 days ago
This home was in a great location. Within 30 minutes, we could get pretty much everywhere. Lots of grocery stores, restaurants, etc in under 15 minutes. The pool area was great! The view was unbeatable. It was nice to sit in the morning or at dusk and watch the birds. The hot tub heated itself up very fast. The whole house was super clean and beautiful. Comfortable beds, plenty of towels and pillows. The cooking utensils weren’t the best, but we only really ate in for lunch most days. Sam was very responsive. Any questions were responded to within 10-15 minutes. He was very helpful, as well. It’s perfect for multiple families, as there were two master bedrooms and multiple king sized beds and bathrooms. It gives a sense of privacy for everyone. Would definitely stay here again!
Top guest favorite
Townhouse in Kissimmee
4.89 out of 5 average rating, 293 reviews

Disney fireworks new house - 5 minutes to Disney

TiffanyRating, 5 stars3 weeks ago
Jader is a awesome host, communication 10/10. House was clean and spacious, neighborhood was very quiet and peacful, I would definitely recommend
Superhost
Condo in Kissimmee
4.77 out of 5 average rating, 126 reviews

1-101 Legacy Dunes, Gym, Tennis, Close To Disney!

ValentinaRating, 5 stars1 month 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!

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

  • Total rentals

    140 properties

  • Nightly prices starting at

    R708 ZAR before taxes and fees

  • Total number of reviews

    2.9K reviews

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    40 properties have a pool

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

Destinations to explore