Vacation rentals with a pool in Windsor Hills

A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.

4.98 out of 5 average rating, 106 reviews

Mickey's Lakefront Villa at Sunset Lakes

Updated Pics Dec 2024. We have no gas burning appliances. We abide by the AirBnB enhanced cleaning protocol. We want our guests to be happy, healthy and safe in their home away from home. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

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, 140 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.

A townhouse exterior is shown beneath a gentle rainbow. Flanking palm trees provide a tropical setting, while the structure features multiple windows with white frames and dark shutters. A parked vehicle can be seen in front, enhancing the suburban feel.

4.87 out of 5 average rating, 119 reviews

Disney Escape at Windsor Hills

This is a fantastic family vacation townhouse located just four miles from Walt Disney World! Inside, you'll find a full kitchen with a breakfast bar, a dining table for six, and a living area with a TV for streaming all your favorite channels! Right outside, take a refreshing swim in your private pool. Guests will be able to enjoy a wide variety of resort-style amenities close by including a community clubhouse with a game room, Olympic-size pool, children's waterpark, putting green, and more!

4.95 out of 5 average rating, 119 reviews

The kitchen showcases modern grey cabinetry and sleek stainless steel appliances. A bright white countertop offers seating for four on padded bar stools. Coffee and tea-making supplies are visible on the counter, with accent decor displayed on the shelves. A pantry door stands closed nearby.

Townhouse in Kissimmee

Private Gated Community 8 mins away from Disney!

Gorgeous brand NEW luxury condo gated w 24 hr security guard. 8 mins from Disney & all parks!! 2 bedrooms, 2 bathrooms (rain shower & tub) Therapeutic beds in every room, including full size pull out. Smart TVs in every room w/cable, Netflix, Wifi. Extra steps to clean & sanitize. 2 min walk to Super Walmart. Walking distance to food, shopping, gas, Starbucks & more. washer dryer, coffee, tea, toiletries Clubhouse Resort with pool, jacuzzi, playground, gym, tennis & volley ball court, lake.

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, 176 reviews

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

Your Windsor Hills Getaway starts here! This top-rated 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!

4.97 out of 5 average rating, 137 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!

An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.

4.95 out of 5 average rating, 160 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

4.99 out of 5 average rating, 114 reviews

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

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!

4.96 out of 5 average rating, 147 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

4.96 out of 5 average rating, 167 reviews

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

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 vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.

5 out of 5 average rating, 237 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

A two-story vacation home is showcased with a tiled roof and a well-maintained front yard. Flanking the house are two neighboring properties, while a paved driveway leads to a garage. Green grass surrounds the structure, and the sky features a mix of clouds and blue.

4.88 out of 5 average rating, 125 reviews

2584 - 6 Bedroom w/ Pool and Water Park Included

Welcome to Your Ultimate Vacation Escape at Windsor Hills Resort! This charming vacation home in Windsor Hills Resort offers six spacious bedrooms and is perfect for the entire family. Located in one of the finest gated communities in the area, Windsor Hills Resort features 24-hour security, ensuring only permitted guests have access to the neighborhood. We’re just a short distance from Disney parks, shopping, dining, and many of Orlando’s top attractions.

Popular amenities for Windsor Hills rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.75 out of 5 average rating, 116 reviews

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291

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, 151 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

4.82 out of 5 average rating, 17 reviews

10 min to Disney| Themed | Sauna | Pool | Golf Sim

A cheerful bedroom features two twin beds adorned with Mickey Mouse-themed bedding. The walls are decorated with playful polka dots and images of Mickey and Minnie. A flat-screen TV is mounted on one wall, while bright red curtains frame the window, allowing natural light to enter.

4.97 out of 5 average rating, 145 reviews

Winter Specials - 6 Mi to Disney - 4 Master Suites

A private swimming pool is surrounded by a screened enclosure, featuring a poolside theatre with a large projector screen. Lush greenery is visible beyond the pool area, creating a serene environment. Lounge chairs are positioned nearby for relaxation.

4.9 out of 5 average rating, 112 reviews

8 mins. to Disney W/Poolside Theater & Game Room

5 out of 5 average rating, 13 reviews

4 minutes to Disney - Sleeps 14, Arcade, Pool

The exterior of a two-story yellow cottage is shown, featuring large windows and a fenced private pool. Sunlight reflects off the water, and lush greenery surrounds the pool area, enhancing the inviting atmosphere. Balconies are visible on the upper level, overlooking the pool.

4.96 out of 5 average rating, 227 reviews

"Vista Lago"Hotel Amenities/lake view,private pool

A spacious living area features a modern white sectional sofa arranged around a circular coffee table. A large flat-screen TV is mounted on the wall, and natural light enters through multiple windows. A textured accent wall adds depth, complementing the neutral color scheme.

4.95 out of 5 average rating, 123 reviews

5BD Windsor Westside Private Pool (WW 8920)

Condo rentals with a pool

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, 213 reviews

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

Superhost

A light-filled living area is furnished with a sectional sofa and a wooden coffee table. Two framed artworks are mounted on the wall beside a lamp. Tall windows with dark curtains offer views of the outdoor landscape, while a small chair and television provide additional seating and entertainment options.

4.77 out of 5 average rating, 245 reviews

Dumbo House

A vibrant outdoor water park is depicted, featuring two large water slides and a colorful kids' splash area. Surrounding palm trees provide shade, and a spacious pool area is visible in the background, inviting relaxation and fun.

4.9 out of 5 average rating, 214 reviews

Disney's Doorstep, 3 Bed 2 Bath, Waterslides!

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 large stone sign displays the name 'Windsor Palms' surrounded by lush greenery and colorful flowerbeds. Palm trees are seen flanking the sign, under a clear blue sky, indicating an inviting entrance to the gated resort community.

4.93 out of 5 average rating, 137 reviews

Resort condo minutes from Disney!!!

A modern living room features a light-toned sofa facing a wall-mounted television displaying tranquil landscape imagery. Soft blue LED lighting enhances the space, while a stylish area rug with geometric patterns adds texture. A glimpse of the kitchen can be seen in the background.

4.91 out of 5 average rating, 150 reviews

Chic Disney Resort Condo • Pool Access Near Parks

An aerial view captures a resort-style pool surrounded by lounge chairs and umbrellas, centered within the community. Nearby, tennis courts and a basketball court are visible, bordered by lush greenery. Ample parking spaces are noted in the surrounding area.

4.97 out of 5 average rating, 130 reviews

Sol y Mar Resort Style Condo - NO RESORT FEES

4.83 out of 5 average rating, 300 reviews

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!

Home rentals with a private pool

An open living space features a comfortable beige sectional sofa with colorful accent pillows. A dining table is visible beside a modern kitchen with stainless steel appliances. Large sliding glass doors provide a view of the pool area, enhancing the connection to the outdoors.

Villa in Championsgate Village

Wr001or (1stfororlando)

A spacious living area is highlighted by a large wall-mounted TV above a modern electric fireplace. The white sectional sofa, accented with colorful pillows, faces a sleek coffee table on a patterned rug. Natural light floods in through large windows draped with light curtains.

4.14 out of 5 average rating, 7 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

A private outdoor area showcases a pool surrounded by a sleek, turquoise enclosure. Comfortable lounge seating is present, alongside sun loungers. The spillover spa is integrated into the pool area, providing a welcoming space for relaxation. Natural light illuminates the entire setting.

7547oml-Solterra Resort

4.95 out of 5 average rating, 116 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Villa in Kissimmee

4.78 out of 5 average rating, 256 reviews

Visit Disney World from a Sunny Home with a Pool

Villa in Championsgate Village

Champions Gate 6bed 5bath Vacation Home

The image displays four distinct areas of the villa. A games room features a foosball table and a billiard table with a laundry area in the background. A cozy bedroom showcases a queen bed with nightstands. A private screened pool invites relaxation. A kitchen area includes modern appliances and seating at the bar.