Vacation rentals with outdoor seating in Windsor Hills

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Windsor Hills

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

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Top guest favorite
A cozy living area features a light-colored sofa adorned with textured cushions, alongside a warm-toned armchair. Wall art in neutral hues adds character, and a wooden coffee table is centrally positioned. The kitchen area boasts wooden cabinetry and modern pendant lighting above the breakfast bar.
Townhouse in Kissimmee
4.93 out of 5 average rating, 101 reviews

Boho Bliss Escape• Poolside•Minutes from Adventure

🌿✨ Welcome to Boho Bliss Townhouse! ✨🌿 Your boho-chic retreat near Kissimmee ’s top attractions! 🏰 8 min Walt Disney World w/o traffic!!!! 🎢 25 min Universal ✈️ 25 min Orlando Airport 🐊 Gatorland 🛍️ Old Town Kissimmee 🎡 ICON Park features The Wheel, dining, and SEA LIFE Aquarium 🌊 Lake Tohopekaliga 🍖 Medieval Times offers dinner and a show. 🎢 Fun Spot America provides amusement park fun 🌿 Kissimmee Lakefront Park offers a relaxing lakeside experience 🌳 Shingle Creek Park is perfect for nature

Top guest favorite
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, 142 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 favorite
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.
Home in Kissimmee
4.96 out of 5 average rating, 173 reviews

4 bedroom, south facing pool 3 miles to Disney

Create family memories in our stunning pool home with Star Wars, Minnie and Mickie themed twin rooms. Elegant and comfortable king bed master bedroom with your own private bathroom and soaking tub! Delightful queen bedroom that also features its own private bathroom with shower. Enjoy a heated south facing pool (heating extra charge) with no rear neighbors. We are located in a guard gated community that features a large pool, clubhouse with a gym, arcade, movie room, and various sports courts.

Top guest favorite
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, 141 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 favorite
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, 132 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 favorite
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
4.97 out of 5 average rating, 143 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

Guest favorite
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
4.96 out of 5 average rating, 107 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.

Top guest favorite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 118 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Guest favorite
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.
Townhouse in Kissimmee
4.96 out of 5 average rating, 172 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! ✨

Guest favorite
A screened-in private splash pool is surrounded by comfortable seating, featuring playful Minion characters on the walls of the adjoining rooms. The layout includes vibrant décor and modern furnishings, creating a family-friendly space with direct access to outdoor relaxation.
Townhouse in Kissimmee
4.82 out of 5 average rating, 152 reviews

Themed Pool Home 2 Miles to Disney

Welcome to your dream vacation home! - Newly remodeled 3 bedroom, 3 bathroom townhome with themed rooms - Private splash pool, fully screened-in - Prestigious Windsor Hills Resort with no resort fee - Access to a new kids water park, clubhouse, gym, and more - Free Wifi and fast internet for your Zoom meetings - 24 hour security and gated access - Have a pet? $150 pet fee on 1st; $75 each additional pet - Check out our 5 Star Reviews!

Guest favorite
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.
Townhouse in Kissimmee
4.91 out of 5 average rating, 243 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

Top guest favorite
Home in Kissimmee
4.97 out of 5 average rating, 115 reviews

3BD/3BA Themed House Near Disney

Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Popular amenities for Windsor Hills outdoor seating rentals

When is the best time to visit Windsor Hills?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$47,493 GYDG$48,957 GYDG$52,723 GYDG$53,978 GYDG$47,074 GYDG$48,329 GYDG$51,886 GYDG$46,028 GYDG$41,844 GYDG$47,911 GYDG$48,120 GYDG$54,397 GYD
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Quick stats about vacation rentals with outdoor seating in Windsor Hills

  • Total vacation rentals

    Explore 330 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at G$14,645 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,190 verified reviews to help you choose

  • Family-friendly vacation rentals

    310 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation 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 vacation 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!