Holiday rentals with outdoor seating in Windsor Hills

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Windsor Hills

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Kissimmee
4.96 out of 5 average rating, 107 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.

Guest favourite
Home in Kissimmee
4.83 out of 5 average rating, 145 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, 154 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
Apartment in Kissimmee
4.92 out of 5 average rating, 167 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
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
5 out of 5 average rating, 114 reviews

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!

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
4.98 out of 5 average rating, 162 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!

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, 148 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!

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 private backyard oasis features a heated pool and hot tub, framed by a screened enclosure. Large sun loungers are placed on the pool deck, offering a relaxing space. The scenic view includes lush greenery with no rear neighbors, ensuring privacy for guests.
Home in Kissimmee
4.86 out of 5 average rating, 42 reviews

Family Disney Home | Pool | Game Room | Hot Tub

This 4-bed home in Windsor Hills is the ultimate Disney retreat. Just 3 miles from the parks, it offers a private pool and total privacy with no rear neighbors. - Space: Sleeps 8 in 4 bedrooms, each with a private bathroom and TV. - Pool & Spa: Screened-in heated pool and hot tub with a fenced yard. - Family Fun: Game room with pool/air hockey plus resort water park access. - Convenience: Full kitchen, laundry, and parking. Minutes from Disney, dining, and shopping.

Superhost
Villa in Kissimmee
4.72 out of 5 average rating, 69 reviews

Villa | Game Room & Summer Kitchen | 8 min Disney

Welcome to your dream Orlando getaway! Perfectly located just minutes from Disney, this beautiful 6-bedroom home is designed for families and groups seeking both comfort and fun. Enjoy a private pool with spa and summer kitchen, spacious living areas, and a fully equipped kitchen for family meals. Everyone will love can gather in the game room for entertainment. The clubhouse with resort-style amenities is just a short walk away for even more vacation fun.

Guest favourite
Villa in Kissimmee
4.89 out of 5 average rating, 45 reviews

Luxury Disney Villa 5BR (4 Miles from Disney)

This family-friendly luxury 5-bedroom, 5-bath, with private pool and spa home has everything you need for a relaxing Disney vacation. Located in Windsor Hills, a beautiful, gated vacation resort community, the house is just 4 miles from the gates of Walt Disney World theme parks. This spacious, clean, well-maintained, and aesthetically decorated home comfortably hosts up to 12 guests. We invite you to relax and make vacation memories in sunny Florida!!

Guest favourite
The image showcases a private pool surrounded by a screened lanai with colorful floatation devices resting on the water's surface. In the background, the open green space and Windsor Hills Resort amenities, including water slides and playgrounds, extend beyond the pool area, offering recreational opportunities.
Home in Kissimmee
4.94 out of 5 average rating, 53 reviews

Single-Level Pool Home, Resort Amenities, Disney

Welcome to this single-level fun house by FunStay Homes featuring unique themed rooms and a private pool/spa. - 24/7 gated community - Amazing Windsor Hills Resort amenities - No rear neighbors with open green space - Themed rooms: Harry Potter, Star Wars, Spiderman, Minions - 2 King Beds and 4 twin beds - Free Wifi and TV in every room - Pool/Spa heat available for an additional fee - Complimentary offerings include no resort fees

Popular amenities for outdoor seating rentals in Windsor Hills

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 $90 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    330 of Windsor Hills holiday rentals include wifi 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!