Apartment holiday rentals in Windsor Hills

5 out of 5 average rating, 3 reviews

My Disney Grandview

One-of-a-Kind Corner Penthouse Overlooking the Pool The Crown Jewel of Windsor Hills -the only top-floor corner condo directly overlooking the resort . No long walks or loading the car - step outside and you’re there ★ Perfect for Disney Families Sleeps 8-3 Bed/2 Bath Free Resort Access, and parking Gated community 9 min to Disney World Pack n’ play, high chair, stroller, Add my listing to your wishlist by clicking the ❤ in the upper-right I want you! Tell me what I can do to be your host

A large lagoon-style pool is illuminated under a colorful sunset, surrounded by palm trees and lounge chairs. The well-lit area features gentle slopes leading into the water, enhancing the inviting appeal of the recreational space.

4.9 out of 5 average rating, 52 reviews

Whiskey Bent Disney Townhouse 3 bedroom 3 bath

Come relax at our townhouse with private pool in Windsor Hills Resort. A 24/7 gated resort offering a clubhouse, with a lagoon style Swimming Pool that is heated for use year round and has a Water Park,fitness center, Tennis court,Putting Green, Basketball court,Sand Volleyball, Ping Pong,playground, game room,DVD rental and ATM You will be located just a couple of miles from the Walt Disney World entrances and also close to Universal, golfing, shopping and many other attractions. No resort fee

The open living area features a large, light blue sofa with decorative cushions set before a wooden coffee table. A vibrant beach-themed wall mural showcases a serene seaside view. A spacious dining table with six chairs is positioned nearby, with a view extending into the kitchen.

4.76 out of 5 average rating, 328 reviews

2BR Nice/Convenient Resort Condo 3 Miles to Disney

On 2nd fl/No elevator. Regular Condo Not Childproofed. We had a new AC system with internal germicidal UVC light -kills 99.9 % bacteria and virus! Our 2 bedroom 2 bath 1022 sqft resort-style luxury condo at Windsor Palms Resort offers you a “Home Away From Home” experience. You can relax and unwind in an informal setting with all included amenities of an upscale resort. The new AC system ensure a cool stay, while the internal UV light sterilize the air! Unique guest code = higher security.

A modern kitchen features crisp white cabinetry and sleek stainless-steel appliances. A spacious island is complemented by contemporary stools, with an organized countertop housing kitchen essentials. Gray tile backsplash adds a subtle texture, while natural light brightens the open layout.

4.94 out of 5 average rating, 151 reviews

BRAND NEW 2BR Apt, 5mi to Disney - Storey Lake 401

BRAND NEW UNIT! This magnificently clean and luxurious 2 bedroom and 2 bathroom condo is located in the prestigious Story Lake Resort. The master BR has a king size bed and the second BR has a double/full and a twin bed with new comfy mattresses. Storey Lake Resort is the closest community from Disney, Disney Springs, Malls and Walmart. The clubhouse has great amenities including water slides, a lazy river, hot tubs, a tiki bar, putt putt, a beach volleyball court, gym, restaurants and more!

The image showcases a vibrant family-friendly condo, featuring colorful Disney-themed decor throughout the open living space. A spacious pool area is visible beyond the window, highlighting water features and play areas, while the cozy sleeping area is highlighted in the foreground.

4.85 out of 5 average rating, 150 reviews

Toy Story Retreat Near Disney in Windsor Hills

Experience the magic of Disney at your very own “Toy Story Retreat.” - 3 bedrooms and 2 bathrooms with Disney-inspired design - Family-friendly atmosphere in a newly remodeled condo - Full access to Windsor Hills Clubhouse amenities - Ground-floor unit with greenspace views - Free WiFi and basic cable included - Just minutes from Walt Disney World® Resort It's important that the title is as close to 50 characters. You should use some of the other characteristics of the listing.

A spacious dining area features a large wooden table set for multiple guests with white dinnerware. Soft lighting hangs above, and a modern artwork piece adorns the wall. In the background, a well-lit living area with a large screen TV and a balcony can be seen.

4.85 out of 5 average rating, 103 reviews

3175-205 Resort 3BR Apt by Disney World Orlando

Just minutes from DISNEY, Stylish BRAND NEW fully renovated 3bed/2bath fully equipped apartment for up to 8 guests, located in the family friendly Secret Lake Resort. Master suite has a KING bed & 55" TV. Second bedroom has 2 QUEEN beds & 65" TV. Third Bedroom has 2 FULL beds & 65" TV. The open floor plan blends Kitchen, Dining & Living room w/ a 65" TV. Close to Disney Parks, Margarita Ville Water Park, Outlet malls & Retail stores. Amenities: Wi-Fi, Pool, BBQ & Gym. NO RESORT FEES

A welcoming living area features orange accent chairs and plush beige sofas arranged around a glass coffee table. Decorative mirrors adorn the walls, while vibrant floral arrangements add a touch of color. Natural light filters through the window, draped with patterned curtains.

4.88 out of 5 average rating, 383 reviews

Superb Townhouse Newly Renovated 1 mile to Disney

This 2-bedroom rental in Kissimmee is just 1 mile from Walt Disney and only 14 miles from Universal. This home has been completely renovated as of May 2017 with all brand new furniture and linens. This gated community is ideal for families and features plenty of updated, modern conveniences. Take advantage of the many on-site resort amenities including a swimming pool, hot tub, fitness center, tennis and basketball courts, and a fully-equipped game room with a pool table and air hockey.

A spacious living area is furnished with a light-colored sectional sofa and brown leather chairs. A round coffee table sits at the center, complemented by a decorative bowl. The adjacent kitchen is equipped with modern appliances and a breakfast bar, creating an open and inviting layout.

4.92 out of 5 average rating, 145 reviews

Luxury condo near Walt Disney Parks - Kissimmee FL

Entire family will enjoy this luxury condominium located in Kissimmee Florida. Minutes away from all Walt Disney parks, quick drive to Disney Springs and close to major highways. Many attractions within walking distance such as water parks, Studio Grille movie theater, grocery stores, pharmacies, gift shops and plenty restaurants. The condominium includes two primary bedroom suites with en-suite fully remodeled bathrooms. Entire condo is beautifully remodeled to make you feel at home.

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.

5 out of 5 average rating, 111 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 modern living area features a cozy sofa and dining table, with a kitchenette visible in the background. A desk is positioned beside the doorway. A spacious sleeping area can be seen through an open entryway, showcasing a king-size bed and additional seating.

4.82 out of 5 average rating, 289 reviews

King Bed First Floor Disney Universal Family Condo

Welcome🌞This unit is on the first floor! Your much-deserved fun vacation away from home starts here 😎! Located in the heart 💗 of Walt Disney World and all Kissimmee and Orlando’s best fun spots! Includes 1 kingbed and 1 fullsize sofa bed. Just added BIG SMART TVs with Disney+, Netflix, Amazon Video, perfect for relaxing after a fun filled day.✨ 🚗NEED A CAR? Ask us about our 8-passenger minivan. You can plan your stay and car rental all in one go. Ask us for the link!

5 out of 5 average rating, 4 reviews

Nice 3B2B Windsor Hills Resort Condo 14 min Disney

Discover the perfect family getaway at our 3-bedroom, 2-bath condo in the gated Windsor Hills Resort, just 10 minutes from Disney! This first-floor, accessible-friendly unit features a fully equipped kitchen, spacious living areas, and resort-style amenities: lagoon pool, water park, gym, movie theater, and more. With grab bars, lowered outlets, and extra space, it’s ideal for all guests. Enjoy comfort, convenience, and magic—book your Orlando vacation today!

4.86 out of 5 average rating, 116 reviews

A cozy living room is shown with a brown sofa and bright orange throw pillows. A coffee table with yellow legs sits on a plush area rug. Large windows allow natural light, complemented by a ceiling fan and decorative wall art.

Flat in Bay Lake

Contemporary Stay 10 min to Parks Pets Friendly

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Popular amenities for Windsor Hills apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A spacious bedroom features a king-size bed adorned with soft linens and decorative pillows. A blue accent wall complements the room, while a lamp and side table provide additional functionality. A serene ocean-themed artwork hangs above the bed, contributing to the calming atmosphere.

4.92 out of 5 average rating, 86 reviews

Cozy Apartment Close to 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.

4.99 out of 5 average rating, 77 reviews

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

A game room is featured, highlighted by a polished pool table centered under a modern light fixture. Nearby, arcade games and a television are visible on a light gray wall, while a wall-mounted rack displays several billiard cues.

4.92 out of 5 average rating, 36 reviews

Luxury LakeFront Condo by Disney

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, 44 reviews

3BR Themed Condo • Ground-Floor + Resort Pool

The living area features a spacious gray sectional sofa arranged around a white coffee table, with decorative items adding style. A large window provides natural light, complemented by modern shelving and a lamp. The open kitchen is visible in the background, emphasizing a comfortable layout.

5 out of 5 average rating, 57 reviews

Modern Luxury Kissimmee Retreat

4.99 out of 5 average rating, 72 reviews

A private balcony features outdoor seating with a view of a tranquil lake. The railing provides an unobstructed sight of the serene water and surrounding greenery, illuminated by natural light on a clear day.

Flat in Orlando

Apartamento em Orlando

The image depicts a large communal pool area featuring a winding pool with a water slide and surrounded by lounge chairs. Lush palm trees provide shade, while colorful waterslides add a playful touch. The backdrop includes a well-maintained resort building.

4.73 out of 5 average rating, 26 reviews

3 BD/ 2 BA Single Level! Windsor Hills (7675-105)

The entrance to Bella Piazza features a stone façade complemented by lush greenery and palm trees. The sign is prominently displayed in the foreground, and the building showcases a blend of architectural styles with arched windows and a terracotta roof.

4.9 out of 5 average rating, 50 reviews

Apartamento 313 Club House -Davenport/Orlando- FL

Private apartment rentals

A modern living area is highlighted by a dark leather sofa adorned with light-colored pillows. A decorative mirror adds depth to the wall, while a table and chairs create a dining space. Colorful artwork enhances the atmosphere, and a corner plant adds a touch of greenery.

4.92 out of 5 average rating, 24 reviews

Chic & Stylish Apt | Near Disney & Universal

A spacious pool area is surrounded by lush tropical plants and palm trees. The clear blue water reflects the bright sky. Lounge chairs and umbrellas are positioned around the pool, creating inviting spots for relaxation. The vibrant pink flowers add color to the serene landscape.

4.98 out of 5 average rating, 47 reviews

Tuscana Gem 2 bed 2 bath condo nr Disney and Golf

A winding lazy river is surrounded by tropical palm trees, with lounge chairs positioned nearby. The pool area features a relaxed ambiance, complemented by a backdrop of a multi-story building, bright sunshine, and a clear blue sky enhancing the inviting atmosphere.

4.87 out of 5 average rating, 23 reviews

1BR w/ Lazy River in Kissimmee!

An inviting swimming pool is surrounded by lounge chairs and umbrellas. Palm trees and greenery create a relaxed atmosphere. A paved area provides access to the pool, which is complemented by shaded seating options, perfect for enjoying the sun or relaxing in the shade.

4.85 out of 5 average rating, 41 reviews

Cozy Disney apartment

A cozy living area features comfortable seating arrangements with two modern armchairs and a light-colored sofa. Natural light filters in through sliding glass doors that open to a balcony. A wall-mounted TV displays a serene beach scene, and a decorative rug adds warmth to the space.

5 out of 5 average rating, 10 reviews

Stunning Resort 2BR Condo w/ Themed Room!

A patio area features two wicker chairs and a glass-top table, overlooking a lush green golf course. The scene captures an expansive view of the manicured landscape, with well-maintained grass and trees in the distance under a cloudy sky.

4.86 out of 5 average rating, 72 reviews

Golf Course View/Free Parking/Pool /Gated/Disney

The exterior of the building features a light yellow façade with multiple balconies. Lush green palm trees line the walkway, and well-maintained grass areas are visible. Parking spaces are provided in front, including designated accessible parking.

4.91 out of 5 average rating, 34 reviews

Mins to Disney/Gated Resort/New Lv Rm Furniture

A bright living area features a comfortable couch, a coffee table, and a ceiling fan, with an open view into the kitchen area. The bedroom showcases a spacious bed with crisp linens, while a dining area includes a wooden table surrounded by black chairs, enhancing the functional layout.

4.86 out of 5 average rating, 57 reviews

2 Bedroom Condo 15 mins to Disney - No Extra Fees

Apartment rentals with a hot tub

5 out of 5 average rating, 21 reviews

A modern living area showcases a mix of comfortable seating, including a plush blue couch and a tan sofa, arranged around a stylish, round ottoman. A large television is mounted above a lighted console, and natural light filters through the nearby window, enhancing the warm decor.

Flat in Osceola County

Magic Moments | Walk to Fine Dining & Disney

A living area features a comfortable sofa adorned with colorful cushions, complemented by a blue armchair with a yellow accent pillow. A wooden coffee table sits centrally, while a flat-screen TV is positioned on a dark wood console. Natural light enters through sliding glass doors, leading to a private balcony.

4.9 out of 5 average rating, 49 reviews

Beautiful Condo near Disney

4.94 out of 5 average rating, 101 reviews

Condo in Kissimmee

5 out of 5 average rating, 17 reviews

A wooden pergola with two swings is positioned beside a lake, surrounded by lush greenery. Beyond the water, buildings are visible against a clear blue sky, offering a serene outdoor space for relaxation.

Flat in Orlando

Tropical resort many pools -2 bd top 10

A colorful two-story townhome is framed by palm trees and shrubs. The exterior features warm yellow and peach tones, complemented by a well-maintained pathway leading to the entrance. Blue skies with fluffy clouds create a sunny atmosphere.

4.78 out of 5 average rating, 23 reviews

Peaceful Disney Escape!

A spacious outdoor pool area features numerous lounge chairs and umbrellas for shade. Palm trees surround the pool, providing a tropical ambiance. A large building with a distinctive tower is visible in the background, emphasizing a relaxed community atmosphere.

4.97 out of 5 average rating, 32 reviews

2BR Family Retreat Minutes from Disney & Parks!

A bright living area features a light-colored couch with decorative cushions, a patterned armchair, and a wooden coffee table. Natural light enters through large windows adorned with blinds. A ceiling fan hovers above, and a potted plant adds a touch of greenery.

4.9 out of 5 average rating, 147 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

The penthouse offers a view of the expansive neighborhood, featuring several buildings and lush greenery. A large swimming pool is visible below, surrounded by lounge chairs. The balcony is furnished with seating, ideal for enjoying scenic landscapes and sunlight.