
Holiday rentals with outdoor seating in Windsor Hills
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
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!
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.

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.

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

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.

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).

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!

Disney Retreat | Huge Pool with Spa | 2 King beds
Don’t leave that Disney Magic at the parks - experience it by coming home to your spacious 5 BR with 2 King suites, 3.5 baths, and newly renovated design. The high ceilings and open floor plan make it perfect for family time, while the private backyard oasis, complete with a pool and spa (heating optional) and Tiki Bar, offers a great space for relaxation. The themed bedrooms, including Star Wars, Frozen, and Mickey & Minnie, add a fun and whimsical touch that’s perfect for guests of all ages.

*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!

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!

Themed Windsor Hills 6BR Private Pool Gameroom
Welcome to Happy Thoughts Villa Enjoy this luxurious 6-bedroom, 4-bathroom home in Windsor Hills Resort, just 3 miles from Disney! Features include a private heated pool/spa, game room, updated kitchen, 2 king suites, a queen room on the main level, and 3 themed kids’ rooms (Frozen, Minions, Mandalorian). Resort amenities include a water park, arcade, gym, playgrounds, and more—all within an 8-minute walk. Located in a 24-hour gated community, it’s the perfect spot for your dream vacation!

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.

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!

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
Holiday House Rentals with Outdoor Seating

Popular 6BR Resort Home 4 mi Disney/Pool/Game Room

Luxury and Perfect Family Vacay 3 min from Disney!

Lakeside Paradise, 15 min Disney + Saltwater Pool

Themed Rooms • Private Pool • Family Dream Stay

6BR Disney Villa | Pool, Spa & Theater | Sleeps 14

Elevated Disney Themes| Pool + Hot Tub | Game Room

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

Luxury 2 Master Suite Pool Hot Tub Pool Table BBQ
Apartment rentals with outdoor seating

3BD Family Resort near Disney & Parks!

Luxury 2BR-2BA Windsor Hills Condo - Direct Entry

Modern Disney Condo

2-Bedroom Renovated Lakeside Condo Near Disney

My Disney Grandview

Family Disney Retreat | Windsor Hills + Water Park

Your Gateway to Adventure and Relaxation

2 BD/ 2 BA Near Disney! Storey Lake (3150-103)
Condo rentals with outdoor seating

Minutes to Disney best of Home, with a Resort feel

Magical Stay Near Disney & ESPN

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

The Tree House, only 1.5 Miles From Disney!

Andy's Toy Chest at Resort Minutes from Disney!

Poolside 3 Bed Vacation Retreat in Windsor Hills

Disney Oasis

Waterfront Condo minutes to Disney & Universal
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $426 NZD | $433 NZD | $479 NZD | $441 NZD | $385 NZD | $395 NZD | $424 NZD | $376 NZD | $342 NZD | $378 NZD | $417 NZD | $480 NZD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Destinations to explore
- Fitness-friendly rentals Windsor Hills
- Rentals with a washing machine and dryer Windsor Hills
- Rentals with an EV charger Windsor Hills
- Apartment rentals Windsor Hills
- Condo rentals Windsor Hills
- Villa rentals Windsor Hills
- Rentals with a hot tub Windsor Hills
- Rentals with pools Windsor Hills
- Rentals with a home theatre Windsor Hills
- Pet-friendly rentals Windsor Hills
- House rentals Windsor Hills
- Rentals with a patio Windsor Hills
- Family-friendly rentals Windsor Hills
- Serviced apartment rentals Windsor Hills
- Rentals with outdoor seating Four Corners
- Rentals with outdoor seating Osceola County
- Rentals with outdoor seating Florida
- Rentals with outdoor seating United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- University of Central Florida
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club





