Holiday rentals with a hot tub in Windsor Hills

4.97 out of 5 average rating, 100 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

BOOK EARLY! Rated top 1% & Guest Favorite. Our popular home fills up 3-4 months in advance. 3BR/3BA Private Pool Villa in Windsor Hills Resort, Kissimmee! Newly renovated, gated resort, 3 miles to Disney World. Modern beach-coastal design, updated kitchen, family-friendly layout. Free parking, Wi-Fi, full resort access (pool, splash park, gym, playground). Near Universal (20 min), SeaWorld (18 min), Legoland (40 min). Perfect location for vacations Disney trips, sports events, and conventions.

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, 149 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.

Superhost

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.

4.87 out of 5 average rating, 130 reviews

Disney Escape at Windsor Hills

This is a fantastic family vacation townhouse located just four miles from Walt Disney World! Inside, you'll find a full kitchen with a breakfast bar, a dining table for six, and a living area with a TV for streaming all your favorite channels! Right outside, take a refreshing swim in your private pool. Guests will be able to enjoy a wide variety of resort-style amenities close by including a community clubhouse with a game room, Olympic-size pool, children's waterpark, putting green, and more!

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, 154 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 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.

4.87 out of 5 average rating, 142 reviews

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!

4.98 out of 5 average rating, 121 reviews

Apartment in Kissimmee

Disney, Windsor Hills, 11 am checkout, Family,

Walk into your home away from home. Enjoy a relaxing stay. Located on 4th floor. Enjoy morning coffee on a screened-in balcony or a late snack. Pet-free home. Please NO Smoking. Children are always welcome. Come enjoy all of the accommodating facilities at Windsor Hills with a top-notched 24/7 gated security. FREE parking & leisure activities! Maximum of 3 cars allowed per reservation. This includes all guest that are visiting. All unregistered drivers will be denied access by HOA.

An open-plan living area features a comfortable sofa beside a wooden coffee table, set against a backdrop of a vibrant landscape artwork. A well-equipped kitchen with modern cabinetry and bar seating is visible, illuminated by natural light flowing through large windows.

4.97 out of 5 average rating, 176 reviews

Luxury 2 Master Suite Pool Hot Tub Pool Table BBQ

Welcome to Mickey's Landing. A beautifully renovated home featuring four bedrooms, three bathrooms, two luxurious master suites, a fully equipped chef’s kitchen, a game room, and a private screened-in pool with an above-ground hot tub. It is just two miles from Disney World and combines whimsical Disney charm with modern comforts like high-speed WiFi and Smart TVs. Perfect for families or groups, it’s the ultimate destination for relaxation, adventure, and creating unforgettable memories.

A collage of vibrant images showcases the luxurious amenities available, featuring a spacious pool area, themed bedrooms, an arcade room, and outdoor seating. The photos capture a welcoming environment ideal for family gatherings and entertainment, beautifully arranged in a Mickey Mouse shape.

4.99 out of 5 average rating, 104 reviews

Cozy Themed Villa 6 BR | Close to Disney

🏖️☀️🏄‍♀️Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort — one of the closest communities to Disney World — you’ll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool — great for relaxing after a fun day at Disney.🌴👙🩳🥽🩴 ❤️❤️We'd love to welcome you here!

4.96 out of 5 average rating, 114 reviews

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.

Townhouse in Kissimmee

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.

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, 158 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 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.

4.99 out of 5 average rating, 247 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.

4.94 out of 5 average rating, 155 reviews

Townhouse in Kissimmee

Mickey’s Dream House | Private Pool + Free Waterpa

10 minutes to Disney! Stay in our Mickey-themed retreat inside Windsor Hills Resort — a gated community just 10 min to Walt Disney World. Enjoy a private, screened splash pool plus FREE access to the resort waterpark, lagoon-style pool, hot tub, arcade, and sports courts. Features include a Mickey-themed kids’ room with arcade games, smart TVs throughout, fully equipped kitchen, and baby gear — perfect for longer family stays.

Popular amenities for rentals with a hot tub in Windsor Hills

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a hot tub

5 out of 5 average rating, 16 reviews

The Disney House • Immersive Rooms • Gaming Lounge

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.

4.88 out of 5 average rating, 26 reviews

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

The outdoor area features a screened-in heated pool and hot tub, surrounded by a spacious deck. Lounge chairs are positioned nearby, while colorful inflatable floats are seen in the water. Natural light filters through the mesh cover, creating a bright atmosphere.

4.93 out of 5 average rating, 42 reviews

Resort Villa! Pool, Hot Tub & Game Room by Disney!

4.83 out of 5 average rating, 24 reviews

15 minutes to Disney - Sleeps 14, Arcade, Pool

5 out of 5 average rating, 46 reviews

Once upon a galaxy: Star Wars/fairytale retreat

5 out of 5 average rating, 17 reviews

Disney & ESPN Sports | Pool + Hot Tub | Game Room

The outdoor patio features a private heated swimming pool surrounded by lounge chairs and a dining area. A screened enclosure provides protection while allowing plenty of natural light. The spacious deck offers a relaxing space for families to enjoy the warm weather and nearby views.

4.92 out of 5 average rating, 13 reviews

Disney Vacation Home w/ Pool, Hot Tub + GameRoom

A spacious poolside dining area is featured, with a large table set for meals. Elegant place settings include green plates and silverware. A large screen is visible, showcasing outdoor entertainment, with colorful sunset hues reflecting through the screened enclosure.

4.94 out of 5 average rating, 82 reviews

8 Mins To Disney W/Poolside Theater & Games Room

Villa rentals with a hot tub

A spacious themed room is depicted, featuring an imaginative design with a dark, cosmic ceiling. The room includes a large blue slide and a staircase, adjacent to cozy bean bag chairs for seating. Colorful space-themed murals enhance the playful atmosphere.

4.98 out of 5 average rating, 125 reviews

4mi to Disney | Games | Private Pool

A private pool area is enclosed with a screened patio. The pool features a built-in spa and a spacious deck, providing ample space for relaxation. Comfortable seating options are arranged nearby, overlooking the water. The area is designed for leisure and comfort.

4.89 out of 5 average rating, 114 reviews

Luxurious Pool Villa, Minutes From Disney World

A themed bedroom features dark walls adorned with a space mural, creating an immersive atmosphere. A large bed is dressed in colorful bedding featuring popular characters. A wall-mounted television is positioned above a dresser, complementing the room's playful design.

4.97 out of 5 average rating, 270 reviews

Disney-Themed Home w/ Game Room & Private Hot Tub!

4.86 out of 5 average rating, 133 reviews

Cheerful Villa (7br / 6.5ba) Minutes to Disney

A spacious living area features light-colored sofas arranged around a glass coffee table atop a patterned rug. Natural light floods the room through large windows, highlighting the high vaulted ceiling. An archway leads to another room, while greenery adds a touch of nature.

4.92 out of 5 average rating, 168 reviews

Relax & Play :Luxury Villa Near Disney w/ Pool&Spa

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

4.93 out of 5 average rating, 104 reviews

Luxury Villa! /Game Room/ Pool Heater

The exterior of a two-story home is showcased, featuring a well-manicured lawn and palm trees in the front yard. A spacious driveway leads to a garage with a white door, while the house displays a neutral color scheme and large windows allowing natural light.

4.92 out of 5 average rating, 114 reviews

Disney Dream Villa- 10 Minutes From Disney!

A clear glass rests on a table beside a cozy lounge chair, accompanied by a notepad featuring a puzzle. The background showcases a tranquil private pool enclosed by protective screening, with sunlight reflected on the water's surface.

4.96 out of 5 average rating, 150 reviews

⁕ Disney parks! Luxury resort villa • Private pool

Cabin rentals with a hot tub

A cozy cabin exterior is illuminated by soft lighting during twilight. The wooden logs are complemented by vibrant green doors and an American flag hanging from the porch. A welcoming ambiance is created by the warm glow of lights and the surrounded greenery.

5 out of 5 average rating, 13 reviews

Authentic Disney Fort Wilderness Cabin near WDW-1

A private pool area features a spacious hot tub adjacent to a rectangular pool, both surrounded by paved decking. Sun loungers are positioned nearby, with a backdrop of pastel-colored cottages and a clear blue sky.

Cabin in Four Corners

Sunny Margaritaville Cottage - Private Pool, Full

4.8 out of 5 average rating, 10 reviews

The porch

A cozy cabin exterior features natural wood siding, complemented by vibrant green doors. A spacious front deck with a railing offers seating, while a picnic table sits on the grassy area nearby, surrounded by lush trees and foliage.

4.98 out of 5 average rating, 44 reviews

Mouse House Cabin/ Legacy Disney Fort Wilderness

The exterior of a rustic cabin is adorned with warm string lights, creating a welcoming ambiance. A porch with steps leads up to the entrance, flanked by lush greenery. The wooden structure features a lighted wheel decoration and bright windows, giving it a charming appearance at dusk.

5 out of 5 average rating, 21 reviews

Authentic Disney Fort Wilderness Cabin near WDW-2

An outdoor seating area is displayed, featuring a square table surrounded by four light-colored chairs. The setting is complemented by a pathway of large stone pavers and nearby greenery, with a yellow exterior wall and glass doors providing a welcoming entrance.