Holiday rentals with outdoor seating in Windsor Hills

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, 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.

4.94 out of 5 average rating, 191 reviews

5 miles to Disney- Private Pool - Arcade Games

Just 4 miles from Disney, our luxury townhome is your family’s perfect escape! With a private splash pool, brand-new 65” Smart TV, and family-friendly gear (stroller, pack n’ play, high chair), you’ll have everything needed for a carefree stay. Located across from Windsor Hills Resort’s clubhouse, enjoy resort perks like a pool, splash pad, fitness center, and theater! Sleeps 8 comfortably with 3 en-suite bedrooms, including a themed Disney beach kids’ room. Fun, comfort, and convenience await!

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, 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.

A colorful kids' retreat features vibrant, themed wall art depicting racing characters against a bright, rainbow backdrop. A flat-screen TV is mounted on the wall, and a multi-drawer storage unit is positioned nearby. The room is designed to inspire imagination and enjoyment.

4.95 out of 5 average rating, 112 reviews

*NEW*FREEwtrprk/5mins2disney/3Bdm/freebreakfast

Before exploring your vacation home- please click the heart and save us as a favorite!! This truly does help us be seen and is greatly appreciated. Plus, you can always find us when you are ready to book :) check out our website theprimrosewh and find us on IG MINUTES to DISNEY WORLD & US 192 with lots of restaurants/shops/walmart 1min. NEWLY renovated BRIGHT & VIBRANT 3 bed, 3 bath END UNIT townhome with private pool in the popular WINDSOR HILLS Closest townhome to the CLUBHOUSE steps away

4.97 out of 5 average rating, 141 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!

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.

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

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.

4.98 out of 5 average rating, 179 reviews

Poolside Windsor Hills 3BR~Waterpark~2mi to Disney

Your Windsor Hills Getaway starts here! This 5-star condo overlooks the resort pool & waterpark and is just minutes from Disney World! New appliances and updated furnishings, this 3rd floor condo sleeps 8, with plenty of parking. The screened-in balcony can’t be beat, overlooking the pool, hot tub, and waterpark with waterslides! The clubhouse is just steps away, with a store, food, drinks, game room, and fitness center. No resort, parking, or hidden fees. Full access to all amenities!

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.

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.

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.

4.99 out of 5 average rating, 119 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!

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.

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! ✨

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.

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

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 outdoor seating rentals in Windsor Hills

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A collage of images showcases the villa's vibrant interiors and amenities. The staircase features colorful beach-themed decor. The open living area contains comfortable seating and artistic wall murals. Bedrooms are themed with playful elements, and the outdoor area features a private pool and spa surrounded by greenery.

4.95 out of 5 average rating, 20 reviews

Paradise Cove at Windsor Hills Resorts

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, 152 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

An expansive lagoon-style pool is surrounded by lush palm trees and comfortable seating areas, inviting relaxation. Below, a dining table is set with white plates, bowls, and cutlery, arranged on a decorative placemat, showcasing a cozy dining atmosphere.

4.96 out of 5 average rating, 81 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

A private heated pool area is surrounded by a screened enclosure, featuring lounge chairs and outdoor dining options. The pool is complemented by multi-colored lights, creating an inviting space. The image also includes three themed kids' bedrooms, showcasing vibrant decor and comfortable sleeping arrangements.

4.9 out of 5 average rating, 68 reviews

Themed Windsor Hills 6BR Private Pool Gameroom

5 out of 5 average rating, 29 reviews

Once upon a galaxy: Star Wars/fairytale retreat

A tranquil pool area features a clear blue pool and adjacent spa, both enclosed within a screened-in area. Lush greenery is visible beyond the pool deck, with a serene lake view in the background under a bright, blue sky.

4.92 out of 5 average rating, 84 reviews

Windsor Hills 5 bed/5 bath Pool Home, Games Room

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, 132 reviews

Resort Home 3.5 miles to Disney with home theater

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.

4.88 out of 5 average rating, 17 reviews

Themed Luxury 6BR Getaway with Resort Amenities Pr

Apartment rentals with outdoor seating

4.89 out of 5 average rating, 90 reviews

Cozy Apartment Close to Disney

4.93 out of 5 average rating, 105 reviews

Condo in Kissimmee

Superhost

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, 66 reviews

Modern Disney Condo

A modern living room is depicted with a full sofa, coffee table, and a smart TV. Natural light enters through the sliding glass door leading to the balcony. Three framed botanical prints decorate the wall, while a floor lamp adds soft illumination.

5 out of 5 average rating, 46 reviews

Modern Condo: 10 Min to Disney + Fireworks Views!

A bright and inviting living and dining area features a large table set for dinner, surrounded by colorful decorations. A blue mural and modern light fixtures enhance the atmosphere. Nearby, playful artifacts and themed elements add charm, contributing to a family-friendly environment.

4.93 out of 5 average rating, 45 reviews

3BR Themed Condo • Ground-Floor + Resort Pool

A cozy living area features dark leather sofas and a glass coffee table. A ceiling fan hangs above, while natural light filters in through sliding glass doors leading to an outdoor view. A television is mounted on the wall opposite the seating.

4.95 out of 5 average rating, 38 reviews

3/2 unit by Disney, Walmart

5 out of 5 average rating, 6 reviews

My Disney Grandview

4.95 out of 5 average rating, 86 reviews

Encanto 3BR | Windsor Hills near Disney + Pool

Apartment rentals with outdoor seating

A modern living area features a white sectional sofa and a stylish coffee table with gold accents. A flat-screen television is mounted on the wall, complemented by minimalist shelving. Large windows dressed with sheer curtains allow natural light to fill the space, creating a bright and welcoming environment.

4.94 out of 5 average rating, 99 reviews

Resort Style Sunshine Oasis near Theme Parks

The living room features a comfortable sofa with colorful accent pillows, a coffee table, and a flat-screen TV mounted on the wall. A round dining table with chairs is visible in the background, along with artwork and decor that add a touch of elegance.

4.86 out of 5 average rating, 214 reviews

@Look@ ~ 3bed/2bath/1st floor! ~ Sleeps 7!

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, 158 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

A spacious living area is designed with light-colored walls and a large sectional sofa adorned with decorative pillows. A round coffee table sits in the center on a patterned area rug. Large sliding doors provide access to a balcony, framed by greenery.

4.97 out of 5 average rating, 126 reviews

Oakwater Resort, Kissimmee , 1.5 Miles to Disney

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, 125 reviews

The Tree House, only 1.5 Miles From Disney!

A spacious living area features large windows framed by bright curtains, providing natural light. A cozy bed is adorned with themed decor, and a comfortable sofa complements the surrounding furnishings. An aerial view showcases the resort's heated pool, surrounded by lush landscaping.

4.9 out of 5 average rating, 248 reviews

Disney Oasis by the lake

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.

4.97 out of 5 average rating, 149 reviews

Disney Oasis