Holiday rentals with a pool in Windsor Hills

A cozy living area features a light-colored sofa adorned with textured cushions, alongside a warm-toned armchair. Wall art in neutral hues adds character, and a wooden coffee table is centrally positioned. The kitchen area boasts wooden cabinetry and modern pendant lighting above the breakfast bar.

4.93 out of 5 average rating, 107 reviews

Boho Bliss Escape• Poolside•Minutes from Adventure

🌿✨ Welcome to Boho Bliss Townhouse! ✨🌿 Your boho-chic retreat near Kissimmee ’s top attractions! 🏰 8 min Walt Disney World w/o traffic!!!! 🎢 25 min Universal ✈️ 25 min Orlando Airport 🐊 Gatorland 🛍️ Old Town Kissimmee 🎡 ICON Park features The Wheel, dining, and SEA LIFE Aquarium 🌊 Lake Tohopekaliga 🍖 Medieval Times offers dinner and a show. 🎢 Fun Spot America provides amusement park fun 🌿 Kissimmee Lakefront Park offers a relaxing lakeside experience 🌳 Shingle Creek Park is perfect for nature

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.

4.88 out of 5 average rating, 123 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!

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.

4.94 out of 5 average rating, 127 reviews

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 living area is showcased, featuring a large sectional sofa with decorative pillows. A flat-screen TV is mounted on a media console, while a coffee table sits in the center. Light from nearby windows enhances the open atmosphere leading into the dining area.

4.93 out of 5 average rating, 242 reviews

Tito's Beachy Townhouse, 1.5 miles from Disney

One of the closest and newest communities to Walt Disney World! Located just 5 minutes from Disney, our freshly updated townhouse is the perfect location for your next Florida adventure. A fully equipped kitchen, super-fast Wifi, heated pool, and a brand new Walmart just down the street are only a few of the many amenities you will find with this incredible rental. Our 1600 sq. ft. home is bright, fresh, and waiting to welcome our next guests. Absolutely the best unit in the entire community!

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.

4.94 out of 5 average rating, 171 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, 129 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, 149 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 screened-in private splash pool is surrounded by comfortable seating, featuring playful Minion characters on the walls of the adjoining rooms. The layout includes vibrant décor and modern furnishings, creating a family-friendly space with direct access to outdoor relaxation.

4.83 out of 5 average rating, 156 reviews

Themed Pool Home 2 Miles to Disney

Welcome to your dream vacation home! - Newly remodeled 3 bedroom, 3 bathroom townhome with themed rooms - Private splash pool, fully screened-in - Prestigious Windsor Hills Resort with no resort fee - Access to a new kids water park, clubhouse, gym, and more - Free Wifi and fast internet for your Zoom meetings - 24 hour security and gated access - Have a pet? $150 pet fee on 1st; $75 each additional pet - Check out our 5 Star Reviews!

The open living and dining area features a large L-shaped sofa and a glass table, with natural light flowing through French doors. A wall mural showcases a Star Wars theme, while the private balcony offers expansive views of the Arnold Palmer PGA golf course and sunset skies.

4.91 out of 5 average rating, 109 reviews

Gorgeous Views: Golf Front, StarWars, XBox, 2Pools

This modern 3-bedroom luxury condo has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

4.88 out of 5 average rating, 169 reviews

The open living area features a round dining table with four chairs, a wall-mounted TV, and a comfortable sofa. Natural light enters through sliding glass doors leading to a scenic outdoor view. A rustic wood accent wall adds texture to the space.

Condo in Four Corners

"Ocean's Gate" - 2BD/2BA condo near Disney

Welcome to our beautiful ground-level condo! With the prime location at ChampionsGate Resort near Disney World and major parks, this 2BD/2BA condo unit is designed for your best accommodation. Spread out in 1,558 Sq. Ft., the unit offers a fully equipped kitchen, a cozy living room, a working station, and comfortable bedrooms. With access to the Clubhouse and resort amenities, you’ll spend amazing days in our home!

A Star Wars themed bedroom features two twin beds with themed bedding. A decorative quilt with a pattern of star fighters is placed over one bed, while the other is dressed in a space-themed cover. A bedside table holds a lamp shaped like a lightsaber, with blue walls adorned with framed artwork.

4.91 out of 5 average rating, 187 reviews

Themed Resort Condo | Pool | Spa | Mins to Disney

The Magic Galaxy – an affordable 3 bedroom, 2 bath condo in the gated Windsor Palms resort, known for its cleanliness and thematic charm. The retreat features themes from Star Wars, Mickey Mouse, Jurassic World, and Harry Potter. Enjoy resort amenities like a pool, spa, splash pad, courts for basketball, tennis, and volleyball, a movie theater, game room, gym, Tiki bar and grill, and a sundry shop.

4.88 out of 5 average rating, 140 reviews

7754 Windsor Hills 6B Luxury Pool Home Near Disney

Welcome to Your Ultimate Windsor Hills Vacation Escape! This newly renovated 6-bedroom beauty is the perfect blend of luxury and fun, designed for families looking to unwind and create unforgettable memories. Just a stone’s throw from Disney World and surrounded by world-class dining, top-notch shopping, and Orlando’s hottest attractions, you’ll have everything you need for an amazing getaway.

Popular amenities for Windsor Hills rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An outdoor space features a spacious pool surrounded by a sunbathing area. A covered seating area offers shade under a large umbrella, while palm trees add a touch of greenery. The screen enclosure provides protection while allowing for natural light and fresh air.

4.9 out of 5 average rating, 21 reviews

Dream vacation, near Disney

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.

4.95 out of 5 average rating, 20 reviews

Hibiscus Villa w/ themed rooms, game room and pool

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, 153 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

A spacious living area features two gray sofas facing a television mounted on the wall. A circular ottoman and a round coffee table are placed on a patterned area rug. Natural light enters through vertical blinds, and a potted plant adds a touch of greenery.

4.92 out of 5 average rating, 73 reviews

3 Bedroom / 2.5 Bath Townhome (Mins to Disney)

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, 60 reviews

ReDesigned | Windsor Hills | Location | Water Park

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.

4.84 out of 5 average rating, 38 reviews

Family Disney Home | Pool | Game Room | Hot Tub

A spacious living area features a large sectional sofa, paired with a round coffee table. Natural light floods in through sliding glass doors that open to the pool area. Decorative accents include coastal-themed artwork and soft lighting fixtures, enhancing the inviting ambiance.

4.83 out of 5 average rating, 139 reviews

Park Place! 7 Min from Disney, Pool, Theater

4.85 out of 5 average rating, 140 reviews

4BD 2BA Pool House Near Disney

Condo rentals with a pool

Superhost

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.

4.73 out of 5 average rating, 124 reviews

Minutes to Disney best of Home, with a Resort feel

Superhost

A comfortable living room features a spacious sectional sofa adorned with decorative cushions. A large TV is mounted on the wall, displaying a serene landscape. Light enters through sliding glass doors, leading to a balcony, enhancing the room's bright ambiance.

4.78 out of 5 average rating, 207 reviews

Magic Stay at Windsor Hills! 2 bedroom apartment!

An overhead view reveals the expansive pool area of the resort, featuring a large heated pool surrounded by lounge chairs. A vibrant water park with slides and play areas is visible, set among lush greenery and palm trees, providing ample recreation options.

4.87 out of 5 average rating, 217 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, 247 reviews

Dumbo House

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, 129 reviews

Oakwater Resort, Kissimmee , 1.5 Miles to Disney

A spacious living area is designed with light grey sofas and a glass coffee table, surrounded by greenery. Large windows with wooden blinds allow natural light to fill the room, while a ceiling fan enhances airflow. Soft, neutral tones create a relaxing atmosphere.

4.88 out of 5 average rating, 156 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

A comfortable living area features a cozy gray sofa and loveseat arranged around a wooden coffee table, with decorative pillows adding a touch of style. Natural light fills the space through sliding glass doors that lead to a screened balcony with outdoor seating.

4.93 out of 5 average rating, 132 reviews

Disney Dream Condo & Pool

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, 153 reviews

Disney Oasis

Other holiday rentals with a pool

The exterior of a two-story townhome is shown, featuring a light blue façade with dark shutters. A well-maintained front garden with various shrubs and foliage is visible, along with a paved walkway leading to the front door. The atmosphere is calm with a clear sky above.

5 out of 5 average rating, 21 reviews

Disney Area - Heated Pool - 3 Bedroom Townhome

5 out of 5 average rating, 14 reviews

Apartment in Kissimmee

Joyful Disney Getaway with Kids Room & Heated Pool

5 out of 5 average rating, 71 reviews

3 Miles 2 Disney | DisneyThemed | Fully Renovated

A private screened patio features a dining set with a glass table and wicker chairs, overlooking a serene lake. The clear blue sky is reflected in the water, while a pool glistens nearby, creating a peaceful outdoor space.

4.96 out of 5 average rating, 49 reviews

Serene 6BR Retreat | Pool, Lake View, Near Disney

5 out of 5 average rating, 42 reviews

The image features a collage of six photos showcasing various aspects of the condo. Highlights include a vibrant water park with dueling slides, a Star Wars themed bedroom with two beds and neon lights, a master bedroom with decorative bedding, a cozy living room with ample seating, and a modern kitchen equipped with stainless steel appliances and granite countertops.

Condo in Four Corners

Windsor Hill Fun Condo Starwars, Moana, Pool, Spa

5 out of 5 average rating, 39 reviews

Harry Potter 3BR• Windsor Hills+Pool• Near Disney

4.9 out of 5 average rating, 49 reviews

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.

Apartment in Kissimmee

Walt’s Vision – Disney-Inspired 3BR Condo