Holiday rentals with outdoor seating in Windsor Hills

4.97 out of 5 average rating, 102 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.

A playful bedroom features twin beds with a colorful 'Aloha' theme. The living area showcases a dining table for six and a comfortable seating arrangement. A screened patio displays a private pool. An entertainment room is equipped with game tables and superhero-themed decor.

5 out of 5 average rating, 23 reviews

Disney Family Fun Villa

Windsor Hills - NEW Fully Renovated 6Bed&4Bath Villa with FREE pool heat - Private South Facing Pool and Spa - Smart TVs in every room - Free WIFI - Fully renovated & equipped kitchen with granite countertops & new appliances - 1.5 Miles to Disney - Close to Universal Studios, Shopping,Restaurants,Waterparks - Gated Community - Free Clubhouse Access with New Waterpark, Basketball, Tennis & Volleyball Courts & Putting Green - Newly renovated Marketplace Bar & Grill, Games Room & Convenience Store

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.

4.83 out of 5 average rating, 143 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

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.

4.97 out of 5 average rating, 156 reviews

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

*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 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.

4.96 out of 5 average rating, 182 reviews

4 bedroom, south facing pool 3 miles to Disney

Create unforgettable family memories in our beautiful pool home with Star Wars, Minnie and Mickey themed twin rooms. Relax in the elegant king master suite with a private bath and soaking tub. Charming queen bedroom also includes its own private bathroom with shower. Enjoy a heated south-facing pool (heating extra charge) with no rear neighbors. Located in a guard-gated community offering a large resort-style pool, clubhouse with fitness center, arcade, movie room, and multiple sports courts.

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, 144 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

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.

4.99 out of 5 average rating, 104 reviews

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.

Villa in Kissimmee

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!

4.88 out of 5 average rating, 102 reviews

Themed 3bd/2ba Condo_Water Park_ 2 miles to Disney

¡Welcome to Mickey’s Casa! Located just 2 miles away from Disney World, Windsor Hills is an upscale gated community resort offering: Resort with 24hr Security Giant Resort Pool + Sun Deck 2 Story Water Slide & Children Splash Area Gaming and Arcade Center Family Activities at Clubhouse Movie Theatre Professional Fitness Center Basketball, Tennis, Pickle Ball, and Sand Volleyball Putting Green Grills and picnic pavilion Multiple playgrounds Newly renovated Market Grill and Cafe

4.96 out of 5 average rating, 158 reviews

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.

Villa in Kissimmee

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 spacious living area features a contemporary design with a large flat-screen TV mounted on the wall, surrounded by comfortable seating. A stylish coffee table is centered on a soft area rug, and decorative plants add a touch of greenery. The bright space is complemented by warm lighting.

4.96 out of 5 average rating, 24 reviews

Hibiscus Villa w/ themed rooms, game room and pool

Welcome to your luxurious single story 4-bedroom getaway in the heart of a gated resort just 2.6 miles from the magic of Disney World! This meticulously designed vacation home offers not only comfort and convenience but also an array of resort amenities that promise an unforgettable stay. Your dream vacation home is not just a place to stay; it's a gateway to a world of enchantment and relaxation. Book your stay now and let the magic begin!

Popular amenities for Windsor Hills outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A home theater room features plush reclining sofas arranged for optimal viewing. Colorful murals of trees and a moon adorn the walls, complemented by vibrant blue ambient lighting. A large screen is mounted on the front wall, enhancing the immersive experience.

5 out of 5 average rating, 6 reviews

Hilltop 6BR Disney Villa: Theater, Pool/Spa, View

A clear view of a spacious outdoor pool area is presented, surrounded by a landscaped garden. Comfortable white lounge chairs are positioned around the pool, which features a water feature. Colorful umbrellas provide shade, enhancing the inviting atmosphere of the community.

4.93 out of 5 average rating, 158 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

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

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.

4.97 out of 5 average rating, 100 reviews

NEW Stunning Villa located 5-10 Min from Disney

An outdoor seating area features vibrant blue chairs and a shaded patio overlooking a private pool. Surrounded by a screened enclosure, the view includes manicured grass and trees, creating a serene setting for relaxation and enjoyment.

4.89 out of 5 average rating, 18 reviews

Themed Luxury 6BR Getaway with Resort Amenities Pr

4.91 out of 5 average rating, 32 reviews

Free Heated Pool · 2mi Disney · 5BR Villa

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.

4.86 out of 5 average rating, 42 reviews

Family Disney Home | Pool | Game Room | Hot Tub

4.83 out of 5 average rating, 6 reviews

Newly Updated Windsor Hills 5 bed/5 bath Pool Home

Apartment rentals with outdoor seating

4.89 out of 5 average rating, 110 reviews

Cozy Apartment Close to Disney

A whimsical room features two full-sized beds adorned with colorful bedding inspired by a popular animated theme. The walls are decorated with snowflake motifs and soft, twinkling lights, creating a playful atmosphere. A connecting ensuite bathroom is visible in the background.

4.75 out of 5 average rating, 130 reviews

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

4.92 out of 5 average rating, 131 reviews

Condo in Kissimmee

A well-lit bedroom features two spacious beds positioned side by side, each adorned with neutral-toned bedding. Decorative wall art with abstract designs enhances the ambiance. Natural light filters through the window, illuminating the minimalist decor and adding to the room's inviting atmosphere.

4.7 out of 5 average rating, 77 reviews

Modern Disney Condo

4.97 out of 5 average rating, 104 reviews

A private balcony is showcased with a round table and two woven chairs, providing a serene view of the lake and surrounding landscape. Soft morning light reflects on the water, while a small potted plant adds a touch of greenery to the setting.

Apartment in Orlando

2-Bedroom Renovated Lakeside Condo Near Disney

An aerial view reveals a sprawling lagoon-style pool surrounded by lush green landscapes, highlighted by winding water features. A well-appointed bedroom presents a spacious bed framed by modern decor and natural light filtering through a window. The living area showcases an elegant dining setup alongside a stylish sofa, while a vibrant children's room features a bunk bed and playful accents.

4.82 out of 5 average rating, 220 reviews

2Bedrooms/2 Bathrooms Storey Lake Resort 3150-404

A spacious dining area features a large wooden table set for multiple guests with white dinnerware. Soft lighting hangs above, and a modern artwork piece adorns the wall. In the background, a well-lit living area with a large screen TV and a balcony can be seen.

4.87 out of 5 average rating, 119 reviews

3175-205 Resort 3BR Apt by Disney World Orlando

4.93 out of 5 average rating, 124 reviews

The open-plan living area features large windows offering expansive views of the water and surrounding landscape. A dining table accommodates six, while a comfortable seating area is arranged for relaxation. Natural light fills the space, enhancing the modern decor.

Apartment in Orlando

Spectacular 2B Condo Disney/Lake views 2 Balconies

Condo rentals with outdoor seating

A large condominium structure stands under a clear blue sky. Several palm trees frame the entrance, and well-maintained landscaping lies around the building. Vehicles are parked in designated spaces in front, with a visible path leading to the entrance.

4.72 out of 5 average rating, 127 reviews

Minutes to Disney best of Home, with a Resort feel

The living area features a comfortable sofa facing a large smart TV mounted on the wall. Natural light enters through windows, enhancing the space. A round coffee table sits in the center, surrounded by potted plants, with a dining area and a modern kitchen visible in the background.

4.93 out of 5 average rating, 215 reviews

Magical Stay Near Disney & ESPN

4.87 out of 5 average rating, 102 reviews

Condo in Davenport

The thrill of luxurious living just 15 min/Disney!

A bright living area features a comfortable brown sofa and loveseat, accented with decorative pillows. A modern coffee table is centered on tiles that enhance the spaciousness. Natural light filters through large windows, while a flat-screen TV is mounted on the wall, framed by stylish light curtains.

4.86 out of 5 average rating, 161 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

4.94 out of 5 average rating, 235 reviews

Andy's Toy Chest at Resort Minutes from Disney!

A spacious living area features a large leather sofa and wall art, creating an inviting space. The open-concept layout connects to the kitchen and dining area, while large windows allow natural light to fill the room. A vibrant resort-style pool area and water slides are visible outside.

4.96 out of 5 average rating, 160 reviews

Disney Oasis

4.97 out of 5 average rating, 433 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Condo in Orlando

Waterfront Condo minutes to Disney & Universal