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Family-friendly vacation rentals in Windsor Hills

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Windsor Hills

  • Total vacation rentals

    Explore 600 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at G$14,642 GYD per night before taxes and fees

  • Verified guest reviews

    Over 14,120 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    580 properties feature pools

  • Rentals with dedicated workspaces

    340 properties have a dedicated workspace

  • Wi-Fi availability

    600 of Windsor Hills vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor Hills rentals

  • 4.8 Average rating

    Windsor Hills stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Windsor Hills

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A colorful children's bedroom features vibrant wall murals of Mickey Mouse and playful numbers. A bunk bed is positioned against one wall, complemented by a gaming area with a foosball table. Bright decor and natural light create an engaging space for kids.
Condo in Kissimmee

2 miles to Disney-Free pool/waterpark-WindsorHills

♥ 2/2 top floor condo (sleeps 6) in Windsor Hills Resort,2 miles from Disney World entrance ♥ Free access to resort pool & waterpark ♥ All amenities open 365 days ♥ Free parking ♥ Free wifi, Smart TVs in all 3 rooms ♥ Master bedroom w/ queen bed & 12" memory foam mattress ♥ Mickey kids bedroom w/ bunk bed, XBox One, air hockey & toys ♥ Strollers, mini crib, pack n play, high chair, step stool in unit ♥ Fully equipped kitchen ♥ Washer & dryer in unit ♥ 2 elevators in building ♥ Valet trash pickup

4.83 out of 5 average rating, 151 reviews
Top guest favorite
Home in Kissimmee

Game & Theater Room, Castle Bunks, Pool & Spa

Vacation at Windsor’s Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.

4.99 out of 5 average rating, 161 reviews
Top guest favorite
A spacious living area is seen, featuring a large sectional sofa adorned with decorative pillows. Natural light enters through expansive glass doors, providing a view of the backyard and pool area. Elegant light fixtures hang from the ceiling, complementing the neutral color palette.
Home in Kissimmee

Cinderella's HolidayVilla-Minutes from Disney-NEW!

• Newest house in the #1 resort community in the Disney Area, Windsor Hills • ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. • 2 FUN children themed rooms (Star Wars & Frozen) • Onsite, driveway parking for 3 vehicles • FREE pool heat+BBQ with ALL rentals • Fully equipped+stocked kitchen; including Keurig machine • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1,000 Mbps! • Property is managed directly by owner FULLY REMODELED in Sept 2022!

5.0 out of 5 average rating, 120 reviews
Top guest favorite
Townhouse in Kissimmee

Themed room Walk to amenities 5 miles to Disney

Just 4 miles from Disney, our luxury townhome is your family’s perfect escape! With a private splash pool, brand-new 65” Smart TV, and family-friendly gear (stroller, pack n’ play, high chair), you’ll have everything needed for a carefree stay. Located across from Windsor Hills Resort’s clubhouse, enjoy resort perks like a pool, splash pad, fitness center, and theater! Sleeps 8 comfortably with 3 en-suite bedrooms, including a themed Disney beach kids’ room. Fun, comfort, and convenience await!

4.94 out of 5 average rating, 215 reviews
Top guest favorite
An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.
Villa in Kissimmee

*Hibiscus Hideaway* Minutes to Disney+Free Resort!

Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

4.97 out of 5 average rating, 175 reviews
Guest favorite
A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.
Home in Kissimmee

Resort Home 3.5 miles to Disney with home theater

We welcome you to stay in our home located in the Windsor Hills community with a water park, slides, theatre and so much more! The house is just 3.5 miles from Disney’s Animal Kingdom. Our home has 6 large bedrooms including laundry in the home, an 8 seat home theatre, TVs in every room, a large swimming pool & spa with a large patio cover, plus a large kitchen fully equipped with everything you need for your stay. Please message us if you have any questions, we look forward to hosting you!

4.85 out of 5 average rating, 158 reviews
Guest favorite
Villa in Kissimmee

The Manatee Manor | 5 BR•Windsor Hills•Game Room

Welcome To The Manatee Manor - A 5 bedroom, 5 bath home located in Windsor Hills, right in the heart of Kissimmee's tourist area, and mere minutes to the gates of Disney! With a feel of 'Better than home', you'll never want to leave. Outfitted with all the standards that you come to expect (Pool, Hot Tub, plenty of space, and serene décor), in addition to themed rooms, big screen smart TVs, and complimentary pool/hot tub heat - life doesn't get any better than when you stay at "The Manor"!

4.94 out of 5 average rating, 110 reviews
Top guest favorite
Home in Kissimmee

Disney Pool Villa | Windsor Hills | Sleeps 8

BOOK EARLY! ⭐ One of Windsor Hills “Rated Most Popular Top 1% Homes” & “Rated Guest Favorite!” Popular home books up 3-4 months in advance.⭐ Enjoy your own private pool just 3 miles from Disney! Newly renovated 3BR/3BA villa designed for families. Equipped with: 1 stroller, 2 high chairs, Pack ‘n Play, baby gate, and white-noise machines in every room. Full access to water park, splash pad, playground, and resort amenities, perfect for magical, stress-free family vacations. 😊

4.97 out of 5 average rating, 123 reviews
Superhost
A movie room designed for family entertainment features comfortable seating arranged in rows facing a large screen displaying animated characters. The walls are dark, enhancing the cinematic experience, while a framed movie poster adds a touch of décor to the space.
Home in Kissimmee

*Windsor Hills Ohana Oasis* 4/4 Disney Pool Home

A house perfect for families, located just minutes from Disney and other attractions in the Orlando area. This beautiful Windsor Hills pool home follows all federal, state, county, & CDC guidelines. All of our properties are properly cleaned for your safety. Maximum of 9 guests. This nearly 2,000 sq ft air-conditioned home has 4 bedrooms 4 bathrooms and a private pool. The house sleeps up to 9 people. Price includes taxes. House rules prohibit parties, pets, and smoking indoors. 

4.8 out of 5 average rating, 119 reviews
Guest favorite
An aerial view showcases a resort-style pool surrounded by lounge chairs. A colorful water park with slides is located nearby, complemented by lush greenery and palm trees. Multiple buildings are visible in the background, offering a welcoming atmosphere for families.
Condo in Kissimmee

WH Condo. Pool/Waterpark and close to Disney!

Take an elevator to unit 302 and witness beautifully decorated Disney themed rooms. Directly outside is a lovely pool and kid-friendly waterpark. All amenities included in cost: game room, theater, exercise room, tennis courts, play grounds, sand volleyball, putting green, basketball court and a marketplace and grill. Located 15 minutes to all 4 Disney parks and Sea World! Looking for more space? Check out our townhome also located in Windsor Hills at 7668 Fitzclarence

4.85 out of 5 average rating, 189 reviews
Top guest favorite
A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.
Home in Kissimmee

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

4.99 out of 5 average rating, 256 reviews
Top guest favorite
An overview of luxury amenities includes a vibrant water park with slides, a spacious pool surrounded by palm trees, and a modern game room featuring foosball and striking wall art. Nearby, a tranquil bedroom setup and an inviting private pool are also highlighted.
Villa in Kissimmee

Luxury Villa Windsor Hills Resort 2 miles / Disney

4 bed and 4 bath LUXURY VILLA located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Villa is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The Villa offers the ultimate game room, outdoor dinning, and a screened private pool & spa. All guests also have access to resort amenities. Lots of entertainment for all. * Security Deposit Required with reservation

4.98 out of 5 average rating, 129 reviews

Popular amenities for Windsor Hills family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
A townhouse exterior is shown beneath a gentle rainbow. Flanking palm trees provide a tropical setting, while the structure features multiple windows with white frames and dark shutters. A parked vehicle can be seen in front, enhancing the suburban feel.
Home in Kissimmee

Disney Escape at Windsor Hills

4.86 out of 5 average rating, 146 reviews
Guest favorite
A spacious pool area is surrounded by palm trees and tropical landscaping. Sun loungers line the pool deck, and a water park with slides is visible nearby. The multi-level condo buildings create a vibrant backdrop, ensuring a family-friendly environment.
Condo in Kissimmee

Lovely vacation condo close to Disney & Universal!

4.81 out of 5 average rating, 163 reviews
Guest favorite
Home in Kissimmee

WH7754 - 6BR house with private pool in Kissimmee

4.88 out of 5 average rating, 160 reviews
Top guest favorite
A serene backyard pool area is enclosed by a screened lanai, featuring two lounge chairs adorned with vibrant blue and green cushions. Lush greenery and trees are visible beyond the pool, enhancing the peaceful view. The clear water reflects the cloud-dotted sky.
Home in Kissimmee

4 bedroom, south facing pool 3 miles to Disney

4.95 out of 5 average rating, 193 reviews
Superhost
Townhouse in Kissimmee

Kids Mickey Room • Waterpark • 5 min to Disney

4.91 out of 5 average rating, 186 reviews
Top guest favorite
An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.
Condo in Kissimmee

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

4.94 out of 5 average rating, 214 reviews
Guest favorite
Condo in Kissimmee

New Luxury Condo near Disney

4.93 out of 5 average rating, 178 reviews
Top guest favorite
The living room features a playful Disney-themed design with a comfortable sectional sofa and an entertainment unit. A light-filled bedroom showcases a large bed with subtle Disney accents. The kitchen is equipped with modern appliances, and a dining area presents seating for multiple guests. A bird's-eye view reveals a sparkling pool area surrounded by lounge chairs.
Home in Kissimmee

Stunning Villa located 5-10 Min from Disney

4.97 out of 5 average rating, 110 reviews

Family- and pet-friendly home rentals

Guest favorite
A screened-in private splash pool is surrounded by comfortable seating, featuring playful Minion characters on the walls of the adjoining rooms. The layout includes vibrant décor and modern furnishings, creating a family-friendly space with direct access to outdoor relaxation.
Townhouse in Kissimmee

Themed Pool Home 2 Miles to Disney

4.82 out of 5 average rating, 181 reviews
Top guest favorite
A landscaped resort area is showcased, featuring a large swimming pool that reflects the evening sky. Surrounding palm trees and well-maintained greenery create a serene environment. The elegant clubhouse is visible in the background, inviting guests to explore the amenities.
Villa in Kissimmee

Relaxing Vacation Resort Villa

4.89 out of 5 average rating, 104 reviews
Top guest favorite
Home in Kissimmee

Disney 4M Pool, Spa, Cinema & Pinball

4.84 out of 5 average rating, 158 reviews
Top guest favorite
Townhouse in Kissimmee

Baby-friendly! End unit pool! Closest to Disney!

4.91 out of 5 average rating, 105 reviews
Superhost
A spacious living area features a large sectional sofa with an oversized ottoman, inviting comfort. Colorful wall decals of Mickey and Minnie Mouse add a fun theme, while framed pictures decorate the walls. Natural light enters through the vertical blinds of the sliding glass door.
Townhouse in Kissimmee

Disney R US! Universal Escape! 3BDR 3Bath

4.89 out of 5 average rating, 296 reviews
Superhost
An outdoor seating area features comfortable blue cushioned sofas arranged around a modern table. The pool is visible in the background, with a screened enclosure allowing natural light to brighten the space. Lush greenery is seen beyond the enclosure, enhancing the outdoor experience.
Home in Kissimmee

Special 30% 1 month stay 6br pool home

4.84 out of 5 average rating, 109 reviews
Top guest favorite
Home in Kissimmee

Disney, Toy Story, Minions, Pool+Gameroom and more

4.95 out of 5 average rating, 116 reviews
Guest favorite
A spacious outdoor seating area features a modern grey sofa set surrounded by lush green walls, with a ceiling fan above. The large pool area showcases palm trees and lounge chairs under a clear blue sky. The entertainment room includes vibrant murals and a slide, while the game area contains stylish bunk beds and a movie theater setup with colorful lighting.
Townhouse in Kissimmee

1.4 miles to Disney Luxury resort home by Walmart

4.92 out of 5 average rating, 135 reviews

Family-friendly home rentals with a pool

Guest favorite
Villa in Kissimmee

Arcade + Pool Villa • 2.5 Miles to Disney

4.9 out of 5 average rating, 29 reviews
Top guest favorite
Townhouse in Kissimmee

Disney Inspired 3 Bedroom Townhome w/Private Pool!

5.0 out of 5 average rating, 7 reviews
Top guest favorite
Condo in Kissimmee

Disney 10 Min · FREE Water Park · 2BR/2BA Condo

4.96 out of 5 average rating, 26 reviews
Top guest favorite
Home in Kissimmee

Coastal Magic Retreat at Windsor Hills

5.0 out of 5 average rating, 12 reviews
Guest favorite
Condo in Kissimmee

WH2778-201AL - Toy Story meets Star Wars

4.88 out of 5 average rating, 64 reviews
Guest favorite
Home in Kissimmee

Private Pool~BabyReady~Princess Playroom~Waterpark

4.92 out of 5 average rating, 48 reviews
Top guest favorite
A private pool area is enclosed with a screen, revealing a sparkling pool surrounded by lounge chairs. The living room features comfortable seating arranged around a coffee table, complemented by large windows. An entertainment area showcases arcade games and a race car setup, while a hot tub offers a spot for relaxation.
Villa in Kissimmee

Windsor Hills 5BR • Free Heat • Private Arcade

4.93 out of 5 average rating, 81 reviews
Top guest favorite
An engaging game room showcases colorful murals and a variety of arcade games, including basketball and foosball. A vibrant Toy Story-themed bedroom features bunk beds and playful decor, while a view of the private heated pool is presented from the charming living area, surrounded by large windows.
Home in Kissimmee

Themed villa: Pvt Pool: Near Disney: Gameroom, BBQ

4.94 out of 5 average rating, 51 reviews

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