Holiday rentals with outdoor seating in Windsor Hills

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.

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

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, 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.

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, 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!

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.

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!

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.

4.86 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!

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!

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

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.

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.

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!!

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.

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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 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, 125 reviews

Disney Retreat | Huge Pool with Spa | 2 King beds

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, 161 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

5 out of 5 average rating, 51 reviews

Once upon a galaxy: Star Wars/fairytale retreat

The image showcases a colorful game room featuring themed decor, cozy lounging spots, and engaging game tables. A separate view displays a vibrant community water park with palm trees and pool areas. The combined images highlight the fun and relaxation available in the villa's surroundings.

4.9 out of 5 average rating, 72 reviews

ReDesigned | Windsor Hills | Location | Water Park

5 out of 5 average rating, 12 reviews

Themed Villa:10 min to Disney: Pool, Gameroom, 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, 105 reviews

NEW Stunning Villa located 5-10 Min from Disney

4.86 out of 5 average rating, 7 reviews

Newly Updated Windsor Hills 5 bed/5 bath Pool Home

Apartment rentals with outdoor seating

A welcoming living area features a dark brown sofa adorned with decorative pillows in warm tones. Greenery decorates the wall behind the sofa, complemented by a modern lamp. A nearby circular table and chair set add to the inviting space, with natural light filtering through a window.

4.9 out of 5 average rating, 136 reviews

Lush Green Retreat 10 Min to Parks Pets Allowed

4.86 out of 5 average rating, 113 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

4.97 out of 5 average rating, 38 reviews

Everlasting Memories: 10 Min. From Disney!

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, 83 reviews

Modern Disney Condo

4.97 out of 5 average rating, 107 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.

Flat in Orlando

2-Bedroom Renovated Lakeside Condo Near Disney

The landscaped pathway leading to Sunshine Bliss Villa showcases vibrant tropical plants and well-maintained hedges. Two people are seen walking together, framed by lush greenery and flowering shrubs, creating a welcoming entrance to the villa.

4.98 out of 5 average rating, 87 reviews

Cozy 3bdrm/2bath unit Just Minutes to Disney World

4.94 out of 5 average rating, 17 reviews

My Disney Grandview

Apartment 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

4.88 out of 5 average rating, 108 reviews

Apartment in Davenport

A luxurious living just 15 min/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, 106 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, 162 reviews

Disney Oasis

A vibrant pool area is depicted, featuring colorful water slides and various water play structures. Nearby, a spacious balcony can be seen with outdoor furniture, offering views of the resort. Inside, a cozy living area includes a children's play table, while a bright theme room showcases colorful wall art inspired by Disney.

4.8 out of 5 average rating, 146 reviews

Charming Windsor Hills Condo Near Disney Parks

A spacious pool area is featured, surrounded by palm trees and lounge chairs. The expansive waterpark includes vibrant waterslides, providing a lively atmosphere. A relaxing hot tub is also visible nearby, complemented by a well-maintained landscaping that enhances the resort's inviting ambiance.