Holiday rentals with outdoor seating in Windsor Hills

4.97 out of 5 average rating, 104 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.

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, 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

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, 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.

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).

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.

5 out of 5 average rating, 112 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!

A screened-in pool area features a clear blue pool with floatation devices, surrounded by a sunlit deck. A Tiki bar with seating stands to one side, while lounge chairs are arranged along the edge. Lush greenery is visible beyond the enclosure.

4.95 out of 5 average rating, 124 reviews

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.

4.98 out of 5 average rating, 160 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 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.

4.84 out of 5 average rating, 147 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!

4.91 out of 5 average rating, 80 reviews

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!

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.

4.99 out of 5 average rating, 104 reviews

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!

4.97 out of 5 average rating, 117 reviews

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

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A vibrant water park features colorful slides and spray features set against a lush green backdrop. Children can be seen playing in the splash area, while various water attractions provide entertainment. The area is enclosed with safety fencing, ensuring a secure environment for families.

4.85 out of 5 average rating, 135 reviews

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

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, 160 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

4.93 out of 5 average rating, 107 reviews

Lakeside Paradise, 15 min Disney + Saltwater Pool

4.86 out of 5 average rating, 7 reviews

Themed Rooms • Private Pool • Family Dream Stay

5 out of 5 average rating, 25 reviews

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

5 out of 5 average rating, 19 reviews

Elevated Disney Themes| Pool + Hot Tub | Game Room

4.95 out of 5 average rating, 21 reviews

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

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, 177 reviews

Luxury 2 Master Suite Pool Hot Tub Pool Table BBQ

Apartment rentals with outdoor seating

4.77 out of 5 average rating, 136 reviews

3BD Family Resort near Disney & Parks!

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

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.

4.72 out of 5 average rating, 81 reviews

Modern Disney Condo

4.97 out of 5 average rating, 105 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

4.93 out of 5 average rating, 15 reviews

My Disney Grandview

4.95 out of 5 average rating, 106 reviews

Family Disney Retreat | Windsor Hills + Water Park

A cozy living space features a large blue sofa and a comfortable gray chaise lounge. A colorful rug lies under a round coffee table. A wall with palm tree wallpaper adds a playful touch, while a flat-screen TV is positioned near an open kitchen and dining area.

4.86 out of 5 average rating, 105 reviews

Your Gateway to Adventure and Relaxation

4.91 out of 5 average rating, 127 reviews

2 BD/ 2 BA Near Disney! Storey Lake (3150-103)

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, 216 reviews

Magical Stay Near Disney & ESPN

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.

4.85 out of 5 average rating, 162 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

A spacious bedroom features a tranquil tree mural on the dark wall, complemented by a large window allowing natural light. The inviting living area includes modern seating and a wall-mounted TV. A rooftop view shows the community, highlighting its green spaces and swimming pool.

4.93 out of 5 average rating, 141 reviews

The Tree House, only 1.5 Miles From Disney!

4.94 out of 5 average rating, 238 reviews

Andy's Toy Chest at Resort Minutes from Disney!

A view of a spacious resort-style pool area featuring various sections including a water park with slides and a splash pad. Surrounding palm trees offer shade, while lounge chairs are positioned around the pool's edge, creating an inviting atmosphere for relaxation.

4.94 out of 5 average rating, 102 reviews

Poolside 3 Bed Vacation Retreat in Windsor Hills

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