Family-friendly holiday rentals in Windsor Hills

The spacious living area features comfortable seating arrangements, large windows, and a decorative area rug. The view leads to the private screened-in pool, providing a seamless indoor-outdoor experience. The room is illuminated by natural light and complemented by a modern ceiling fan.

4.99 out of 5 average rating, 138 reviews

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.

A spacious pool area is featured, surrounded by palm trees and lounge chairs. The expansive waterpark includes vibrant waterslides, providing a lively atmosphere. A relaxing hot tub is also visible nearby, complemented by a well-maintained landscaping that enhances the resort's inviting ambiance.

4.98 out of 5 average rating, 173 reviews

Poolside 3Br~Windsor Hills~Waterpark~2mi to Disney

Your Windsor Hills Getaway starts here! This top-rated condo overlooks the resort pool & waterpark and is just minutes from Disney World! New appliances and updated furnishings, this 3rd floor condo sleeps 8, with plenty of parking. The screened-in balcony can’t be beat, overlooking the pool, hot tub, and waterpark with waterslides! The clubhouse is just steps away, with a store, food, drinks, game room, and fitness center. No resort, parking, or hidden fees. Full access to all amenities!

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.

4.97 out of 5 average rating, 136 reviews

*Brand New!* 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!

A vibrant children's bedroom is adorned with a whimsical mural depicting fairytale scenes. Two beds with elegant metal canopies frame the room, each dressed in colorful bedding featuring princess themes. Natural light filters in through a window, complementing the playful decor.

4.95 out of 5 average rating, 168 reviews

🏰 Disney Princess Crownhouse! Closest to Disney!

PRINCESS CROWNHOUSE!! *100% 5-star reviews in 2025* Message for discounts Baby friendly end unit! South facing pool Magical 3 bed, 3 bath luxury crownhouse in 5 star gated Windsor Hills Resort. *2 miles from the gate of Disney World! Our magical Mickey and Princess Rooms designed with adults, kids in mind. Your little princess will love our Princess room with Disney collection furniture. *Resort pool, fully equipped kitchen, your family will have a truly magical vacation! Princess-tastic

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.

4.96 out of 5 average rating, 157 reviews

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

Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

A light-filled living area features a gray sectional sofa with accent pillows, arranged around a low coffee table. A patterned rug sits beneath, while a tall floor lamp adds warmth. Large sliding glass doors provide views of the outdoor patio, framed by sheer curtains.

4.96 out of 5 average rating, 105 reviews

Star Wars Bungalow | 4 Mi to Disney | Waterpark

Enjoy your stay at this gorgeous, freshly renovated home! MINUTES to Walt Disney World. • 🎢 WATER SLIDES • 🌟THEMED Star Wars Retreat •🍴 Entertainer's Kitchen • 🤱 BOB Jogger Stroller available • 🏖️ Private patio with HEATED POOL • ☕️ **Latte and Coffee Bar** • 📶 Fiber High Speed Wi-Fi Thoughtfully curated for your ultimate ENJOYMENT. Beautiful modern interior, ceramic tile floors, and high quality decor throughout. This impeccable 3 bedroom, 3 bath home sleeps up to 8.

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.

4.85 out of 5 average rating, 184 reviews

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

A recreational game room is presented, featuring an air hockey table and a pool table centered in the space. Two gaming chairs are positioned near flat-screen monitors on the wall. Colorful LED lighting creates an engaging atmosphere in the room.

4.96 out of 5 average rating, 145 reviews

Mr. Clean's Cozy Disney Home w/ Luxury Finishes

• 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

A queen bed with white linens is centered in this room, complemented by matching nightstands and lamps. Behind the bed, a large mural depicts a castle under a starry sky. A mirror reflects the room's decor, adding to the bright and open atmosphere.

4.96 out of 5 average rating, 167 reviews

Heated Mickey Pool, Frozen, Slides, Next 2 Disney

✨ Experience the magic as you step into our 3 bedroom townhome in the closest resort to the Disney Parks, Windsor Hills. Relax in your private, heated Mickey pool. Be transported to a land of ice and snow in a Frozen-themed bedroom. Watch your favorite movie on one of 4 smart TVs. Take a break from the parks by enjoying the resort pool, hot tubs, water park, movie theater, playgrounds, and more. Experience all the magic together with family and friends. Book today! ✨

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.

5 out of 5 average rating, 237 reviews

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.

A private pool area is enclosed by a protective screen, providing a serene oasis. The pool is surrounded by tiled flooring, with a table and chairs nearby for relaxation. Bright curtains frame the entrance to the living space, enhancing the overall inviting atmosphere.

4.91 out of 5 average rating, 242 reviews

DISNEY, WATER park, Private POOL, Comfort by A3G

Your dream getaway, starts In this 3beds 3 baths vacation home away from home! With private pool, Located in the amazing 5 stars resort at WINDSOR HILLS, only 3 miles away from all the wonders and magic of Disney. For Endless entertainment just walk to the Clubhouse and encounter the beautiful typhoon style pool, jacuzzi, brand new water park, arcade, fitness center, volleyball and basquetbol courts, kids playground and much more

The aerial view showcases a spacious pool area surrounded by lush palm trees and lounge chairs. A bright water slide is visible in the background, leading to the pool. A serene lake serves as a picturesque backdrop, enhancing the resort's atmosphere.

4.86 out of 5 average rating, 193 reviews

One in a Minion condo your kids will love +450Mbps

Enjoy of sophisticated and modern accommodations on your next visit to Orlando. This One in a Minion themed two bedroom condo boasts 1082 SQ FT of living space and it's fully equipped for 6 guests. Conveniently located on the ground floor and a short stroll to the clubhouse, pool and dueling water slides. It features a smart lock, High-speed WIFI Internet +450Mbps, cable TV, telephone line, linens & towels and washer/dryer.

Popular amenities for Windsor Hills family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An entertaining game room features a pool table, arcade machines, and a bowling simulator. Colorful wall art and vibrant lighting create an engaging environment for guests. The space is designed for enjoyment and includes various gaming options suitable for all ages.

4.88 out of 5 average rating, 51 reviews

Free Arcade! All Rooms Themed! South Facing Pool!

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.

4.96 out of 5 average rating, 170 reviews

4 bedroom, south facing pool 3 miles to Disney

4.97 out of 5 average rating, 145 reviews

NEW Amazing Decorated house just 5 min to Disney

4.97 out of 5 average rating, 31 reviews

free waterpark-2 king suites-minutes to parks

4.9 out of 5 average rating, 30 reviews

Themed home 10 mins from Disney|Pool, Free BBQ

A private screened-in pool area features a clear blue pool surrounded by a spacious deck. Two lounge chairs are set alongside the pool, providing a space for relaxation. The backdrop includes a green lawn and trees, creating a serene outdoor environment.

5 out of 5 average rating, 26 reviews

Luxury 6 Bedroom Pool Home in Windsor Hills

A private heated pool area is surrounded by a screened enclosure, featuring lounge chairs and outdoor dining options. The pool is complemented by multi-colored lights, creating an inviting space. The image also includes three themed kids' bedrooms, showcasing vibrant decor and comfortable sleeping arrangements.

4.9 out of 5 average rating, 67 reviews

Themed Windsor Hills 6BR Private Pool Gameroom

An outdoor dining area is displayed, featuring a white table surrounded by six grey chairs. A large TV is mounted on the wall, showcasing a performance. A stainless steel grill is positioned nearby, complemented by drinks and a platter of fresh strawberries on the table.

5 out of 5 average rating, 38 reviews

Poolside TV, 3 Kings, FREE Waterpark, AC Game Rm

Family- and pet-friendly home rentals

A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.

4.86 out of 5 average rating, 424 reviews

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

4.95 out of 5 average rating, 105 reviews

A colorful bunk bed structure is featured, decorated in vibrant shades of yellow, blue, and orange. The mural backdrop depicts a jungle scene with a leopard and tropical plants, enhancing the playful atmosphere of the room. Spiral staircases offer access to the upper sleeping area.

Townhouse in Davenport

Themed Home + Near Disney + Arcade + King Bed + Water Park + Spa

An engaging Star Wars-themed game room features a foosball table, arcade machines, and a spacious seating area. Murals depict scenes from the franchise, with screens displaying games. The room is designed for fun and entertainment, offering a vibrant environment for guests.

4.82 out of 5 average rating, 151 reviews

Orlando Home with Private Pool & Game Room !

An equipped kitchen features wooden cabinets and sleek appliances, including a stainless steel refrigerator and stove. A spacious island with high stools provides a gathering spot. Natural light enters through large windows, complementing the adjacent dining area with a simple table and chairs.

4.85 out of 5 average rating, 298 reviews

Prime Location near Disney - Modern Decor

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.

4.93 out of 5 average rating, 238 reviews

Disney R US! Universal Escape! 3BDR 3Bath

Superhost

A playful bedroom features a bunk bed framed by vibrant dinosaur murals and soft green lighting. The room combines adventure and comfort with a cozy seating area and themed decor, creating an engaging space for families.

4.72 out of 5 average rating, 107 reviews

Fantasy World Jurassic Park Villa, Free Water Park

4.99 out of 5 average rating, 110 reviews

Bongo’s Pad~ Gated Resort~ 3 Miles to Disney!

Superhost

The exterior of the Westgate Vacation Villas showcases an elegantly designed building with multiple levels. Soft lighting from street lamps illuminates the entrance. Rows of golf carts are parked in front, surrounded by manicured landscaping and palm trees under a clear blue sky.

4.86 out of 5 average rating, 118 reviews

Westgate Vacation Villas - 1 Bedroom

Family-friendly home rentals with a pool

5 out of 5 average rating, 8 reviews

Windsor Hills, Disney/Universal, Pool/SPA, 5BR5BA

A large swimming pool is surrounded by palm trees and lounge chairs, creating an inviting atmosphere. Guests can be seen enjoying the water, while an expansive clubhouse is visible in the background, featuring a warm color palette and shaded areas.

4.92 out of 5 average rating, 51 reviews

Windsor Hills|8 min to Disney|Free Water Park

5 out of 5 average rating, 5 reviews

NEW!-Fun-Relaxing-Private-Beautiful Vacation Home

An outdoor living space features comfortable seating arranged around a fire pit, facing a large screen displaying animated characters. The screened-in area includes a private pool, while lush greenery surrounds the space, offering a serene atmosphere for relaxation and entertainment.

4.82 out of 5 average rating, 17 reviews

10 min to Disney| Themed | Sauna | Pool | Golf Sim

5 out of 5 average rating, 28 reviews

Once upon a galaxy: Star Wars/fairytale retreat

The image showcases a colorful game room featuring themed decor, cozy lounging spots, and engaging game tables. A separate view displays a vibrant community water park with palm trees and pool areas. The combined images highlight the fun and relaxation available in the villa's surroundings.

4.9 out of 5 average rating, 50 reviews

ReDesigned | Windsor Hills | Location | Water Park

A whimsical children's bedroom features a train-themed bunk bed with a vibrant yellow slide. The walls are decorated with a mural depicting a lush landscape, complemented by cartoon elements. A 50” Roku TV is mounted on the wall, while colorful bedding enhances the playful atmosphere.

4.91 out of 5 average rating, 55 reviews

Mickey Train Bed, Free Waterpark, 10 min to Disney

An outdoor lanai is shown, featuring a rectangular dining table set for six with colorful plates and blue glasses. A lounge area with a sectional sofa is present, accented by patterned cushions. The pool area is enclosed by a mesh screen, providing a clear view of the lush green surroundings.