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Holiday rentals with outdoor seating in Windsor Hills

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Windsor Hills

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Superhost
An expansive game room features themed decor, including a vibrant mural of a surfboarder. The private pool area, enclosed with a screen, showcases a clear blue water surface surrounded by spacious lounge chairs. Aerial views of the community pool and water park amenities are also visible.
Home in Kissimmee
4.83 out of 5 average rating, 144 reviews

Magical Adv 5 Star Villa Movie Room Arcade Pool an

Experience enchantment at Magical Adventure Villa, a top-rated 6-bedroom and 4-bath home for 12 guests. Conveniently located in Windsor Hills Resort, just 2 miles from Disney World®. Experience the highly acclaimed getaway that has garnered rave reviews. Enjoy a private pool, home theater, and a thrilling arcade. Unleash your inner Jedi at the state-of-the-art Star Wars gaming center with a movie theater, Xbox One, Nintendo Switch, and immersive 3D designs. *Work vehicles are not permitted to b

Top Guest favourite
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.
Home in Kissimmee
4.99 out of 5 average rating, 152 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.

Top Guest favourite
Condo in Kissimmee
4.92 out of 5 average rating, 166 reviews

New Luxury Condo near Disney

A passos da piscina e parque aquático. Covid-19 safe. Wi-fi de 500 megabytes! O apartamento possui localização privilegiada: está no condomínio fechado Windsor Hills, o mais próximo dos parques. A 10 minutos do Animal Kingdom, Epcot, Hollywood Studios e Magic Kingdom e a 25 minutos dos parques da Universal. Além disso, possui fácil acesso ao aeroporto (US 192, FL 417 e I-4), Downtown Orlando, Miami e a todos os atrativos da região da Central Flórida (Daytona Beach, Clearwater, St. Petersburg).

Top Guest favourite
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
4.97 out of 5 average rating, 159 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!

Top Guest favourite
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
4.97 out of 5 average rating, 101 reviews

NEW Stunning Villa located 5-10 Min from Disney

Welcome to this BRAND-NEW dreamscape Vacation Villa with private views. Located at the desirable Summerville Resort offering a PRIME location, only 10 minutes from Disney World and 20 minutes from Universal Orlando, Sea World and Aquatica. Amazing entertainment and dining within minutes from your Villa, Disney Springs, Sunset Walk, City Walk, Disney’s Boardwalk, Walmart, Starbucks and more. This Villa is hypoallergenic and carefully cleaned and sanitized. The perfect getaway for your family!

Guest favourite
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
4.86 out of 5 average rating, 145 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!

Guest favourite
The exterior of the house is showcased, featuring a two-story design with light-colored walls and a prominent entrance. A spacious driveway accommodates up to four vehicles, bordered by well-maintained green lawns and trees. The property is set within a landscaped community.
Home in Kissimmee
4.96 out of 5 average rating, 160 reviews

Highest Rated Minutes to Disney! -Newly Renovated

• Newest house in the #1 community in the Disney Area, Windsor Hills • Only home with 7 bedrooms in the community (3 KING beds) • Extra privacy: only one side & no rear neighbors • 4 children themed bedrooms (Mickey, Star Wars, Toy Story, & Frozen) • Onsite, driveway parking for 4 vehicles • FREE pool heat + BBQ with all rentals • Fully equipped + stocked kitchen • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1000 Mbps • Property is managed directly by owner

Top Guest favourite
A charming two-story cottage is set within a vibrant neighborhood, featuring a pastel green exterior and a welcoming balcony. Lush palm trees line the front, while well-maintained landscape provides an inviting approach to the entrance. Additional colorful homes can be seen in the background.
Cottage in Kissimmee
4.98 out of 5 average rating, 175 reviews

Margaritaville cottage minutes from Disney

Gorgeous 2 bedroom/2bath cottage located in gated Margaritaville Resort just 6 miles from the Magic Kingdom. This immaculate cottage sleeps six people and has everything you will need to enjoy your vacation. Sunset Walk is an easy 10 minute stroll with plenty of shopping and unique restaurants to choose from. Orlando's newest waterpark, Island H2O Live, is right next to Sunset Walk to enjoy on a hot day. It's time to waste away in Margaritaville, and come enjoy a little "Peace of Paradise".

Top Guest favourite
Condo in Kissimmee
4.98 out of 5 average rating, 122 reviews

11 am checkout, Windsor Hills, Family, Disney.

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.

Top Guest favourite
Villa in Kissimmee
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!

Guest favourite
A colorful logo for Floridian Riviera is positioned at the top, accompanied by a private pool illuminated by underwater lights. Below, a large outdoor screen displays a movie, enhancing an inviting space. The themed game room features vibrant superhero graphics and game tables, while a themed children's bedroom is decorated with Mickey Mouse motifs.
Home in Kissimmee
4.95 out of 5 average rating, 21 reviews

Luxury 6BR | Game Room, Outdoor Theater & Pool/Spa

Discover fun and relaxation at Floridian Riviera in Windsor Hills! Themed game room and bedrooms and private pool and spa featuring an outdoor theater. Plus, free access to the resort’s clubhouse and water park. All just 5 minutes from Disney! 🎮Avengers Game Room. Pool, Air Hockey, Arcades, PS4, and Oculus 3D. 🏊Private South-Facing Heated Pool/Spa ($30/day for heat). Lots of Seating w/TV, Bar, and Poolside Theater. 🛏️6 BR & 4 BA. 2 Themed Bedrooms (Mickey and Harry Potter).

Guest favourite
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
4.97 out of 5 average rating, 117 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.

Popular amenities for Windsor Hills outdoor seating rentals

When is the best time to visit Windsor Hills?

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Avg. price$427 NZD$434 NZD$480 NZD$442 NZD$386 NZD$396 NZD$425 NZD$377 NZD$343 NZD$379 NZD$418 NZD$482 NZD
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Quick stats about holiday rentals with outdoor seating in Windsor Hills

  • Total holiday rentals

    Explore 330 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at $120 NZD per night before taxes and fees

  • Verified guest reviews

    Over 9,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    320 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    330 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wi-Fi availability

    330 of Windsor Hills holiday 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!