Apartment holiday rentals in Windsor Hills

A living room is presented with light wood flooring, featuring a comfortable sofa and loveseat adorned with tropical-themed cushions. A glass coffee table sits centrally, complemented by two lamps on side tables. Natural light filters through the large window, enhancing the inviting ambiance.

5 out of 5 average rating, 27 reviews

Everlasting Memories: 10 Min. From Disney!

Everlasting Memories is a peaceful 2 bedroom, 2 bathroom condominium located in the highly sought after Windsor Palms Resort! Located just 10 minutes from Walt Disney World, this third-floor unit has a kitchen, living room, laundry area, and a balcony that features breath-taking views of the resort! Guests have free access to Windsor Palms many amenities, such as the community pool, tennis court, arcade, clubhouse, movie theatre and more! Come and relax with your family at Everlasting Memories!

A vibrant water park area features colorful slides and splash pads. Water sprays from various playful fixtures, and guests can be seen enjoying the amenities. The backdrop includes a multi-story building with palm trees surrounding the area, providing a fun and engaging environment.

4.94 out of 5 average rating, 96 reviews

Newly Renovated Condo! 1.5 miles from Disney World

Make your next trip to Florida one to remember when you stay at our NEWLY RENOVATED 3 bedroom, 2 bath condo located at the Gated Resort Community of Windsor Hills, Four Corners. Just miles from Walt Disney World, Universal studios, Downtown districts, Shopping, golfing and many Restaurants, Windsor Hills has many resort's amenities that are perfect for the family vacation. Our condo grants access to an array of amazing amenities – water park, large pool, arcade room, movie theater and more!!

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, 67 reviews

Modern Luxury Kissimmee Retreat

Welcome to our stunning Kissimmee apartment, where modern luxury meets ultimate comfort! This renovated 2-bedroom, 2-bathroom retreat offers high-end finishes, a fully equipped kitchen, large screen TVs, PlayStation 5, and high-speed Wi-Fi. Enjoy blackout curtains and white noise machines for restful nights. Complex amenities include a pool, gym, sauna, and tennis court. Located near Walt Disney World, Universal Studios, and top shopping, our apartment is the perfect base for your adventures.

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.

4.86 out of 5 average rating, 111 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.

4.87 out of 5 average rating, 394 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.

4.93 out of 5 average rating, 153 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.

4.99 out of 5 average rating, 130 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 bright and airy living space features a cozy sofa and a circular coffee table surrounded by wooden chairs. Natural light fills the area through a large window adorned with light curtains, while greenery adds a touch of nature to the decor.

4.97 out of 5 average rating, 115 reviews

Sunny Oasis *FreeParkShuttle*Boho-inspired retreat

Welcome to Sunny Oasis, your perfect escape in the heart of Orlando. Immerse yourself in a beautifully curated Boho ambiance, filled with natural textures, earthy tones, and sunlit spaces. Whether you’re relaxing after a day at the parks or enjoying a peaceful getaway, Sunny Oasis offers the comfort and serenity you deserve. Book your stay with us and experience the allure of Orlando’s attractions in a clean, serene, and superbly located getaway.

4.89 out of 5 average rating, 107 reviews

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.

Flat in Bay Lake

Lush Green Retreat 10 Min to Parks Pets Allowed

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

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.

4.9 out of 5 average rating, 49 reviews

Walt’s Vision – Disney-Inspired 3BR Condo

Top 10% of homes on Airbnb ⭐️ Highly rated for reviews, reliability & guest satisfaction. Walt’s Vision is a ground-floor 3BR condo in Windsor Hills Resort, just 2 miles from Walt Disney World. Skip stairs and long walks—this walk-out unit is steps from the pool, clubhouse & water park. Perfect for families, grandparents & multi-gen Disney trips who want comfort, location, and zero hassle. Homes this close book fast—don’t miss it.

A spacious bedroom features a comfortable bed with decorative pillows and a modern ceiling fan. An open kitchen area showcases stylish cabinetry and stainless steel appliances. A living area is equipped with ample seating and large windows allowing natural light. Another bedroom is similar in style with neutral tones.

4.85 out of 5 average rating, 104 reviews

Luxury Resort Style Condo Near Disney-103

A 5-star stay 3bed/ 2.5bath resort-style condos where you’ll enjoy unprecedented access to amenities that are fun for the entire family. Lounge by multiple community pools and have fun. This relaxing family-friendly home is fully equipped with all modern conveniences and has everything you will need to make your dream Orlando vacation a reality! We have multiple units therefore all photos are not exact to this unit.

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, 51 reviews

Modern Condo: 10 Min to Disney + Fireworks Views!

✨ 7 Minutes to Disney • Sleeps 4 • Pool, Gym, Balcony Modern 1BR resort condo 7 mins from Disney. Sleeps 4 with king bed + sofa sleeper. Walkable to shops & short drive to all major parks. Enjoy a full kitchen, WiFi, Smart TVs, private balcony with nightly fireworks, resort pool, 24/7 gym, and in-unit laundry. Perfect for families, couples, or remote work stays.

Popular amenities for Windsor Hills apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.91 out of 5 average rating, 11 reviews

3141-208 - 3BD -Sunset View – Minutes from Disney

4.77 out of 5 average rating, 48 reviews

Orlando Oasis 15 min from Disney

4.88 out of 5 average rating, 32 reviews

A bright living area showcases a comfortable gray sofa with decorative pillows. Light streaming through sheer curtains enhances the space. A flat-screen television is mounted on the wall, while a small round table and two chairs provide additional seating. A patio door reveals outdoor views.

Flat in Davenport

Stylish 2BR/2BA Condo in Orlando

The spacious bedroom features a king-size bed adorned with premium bedding. Natural light filters in through the window, highlighting the elegant decor and serene atmosphere. An inviting living area showcases a modern sofa and stylish coffee table, providing a comfortable space to relax.

4.96 out of 5 average rating, 27 reviews

Golf View - Reunion Escape for 4

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.

4.95 out of 5 average rating, 41 reviews

2BR Family Retreat Minutes from Disney & Parks!

5 out of 5 average rating, 16 reviews

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.

Flat in Davenport

Stunning Resort 2BR Condo w/ Themed Room!

4.94 out of 5 average rating, 32 reviews

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.

Flat

Spacious Modern Penthouse

4.94 out of 5 average rating, 18 reviews

Villa of the Green Margaritavill

Private apartment rentals

5 out of 5 average rating, 6 reviews

Modern Vacation Home Just Minutes from Disney 8

A spacious bedroom features a wooden bed frame with white bedding and decorative pillows. Nightstands with lamps are positioned on either side. Soft grey curtains frame a window, while a large artwork hangs above the bed. A plush rug is placed on the floor.

4.91 out of 5 average rating, 85 reviews

Hidden gem 5 min from Disney’s

An aerial view of a spacious resort-style community pool area is displayed, featuring a large heated pool surrounded by lounge chairs and palm trees. The clubhouse is visible, along with a tiki bar and landscaped grounds providing an inviting atmosphere for relaxation.

4.88 out of 5 average rating, 72 reviews

King Bed• 14 min to Disney • $0 Parking • No Fees

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.

4.87 out of 5 average rating, 79 reviews

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

5 out of 5 average rating, 53 reviews

A spacious living area is highlighted by a large sectional sofa and a central dining table with upholstered chairs. A wall-mounted television presents entertainment options. Large windows offer views of the outdoor patio, allowing natural light to fill the room.

Flat in Four Corners

Reunion Resort Condo

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.

4.99 out of 5 average rating, 77 reviews

Apartment in Orlando

4.96 out of 5 average rating, 90 reviews

Disney Vacation – Pool + Waterpark + Family Fun!

4.58 out of 5 average rating, 19 reviews

2 Bd/2 Ba Sleeps 4! Storey Lake (3120-403 PCs)

Apartment rentals with a hot tub

A spacious living area showcases a gray sofa adorned with decorative pillows. A dark rug sits beneath the seating arrangement, while a dining set with light wooden chairs and a round table is visible in the adjacent open-concept kitchen. A ceiling fan and floor lamp provide ambient lighting.

4.87 out of 5 average rating, 91 reviews

Relax in Cozy Apt 1/1 near to Disney

An aerial view captures the amenity center surrounded by lush landscaping and palm trees. The heated pool, jacuzzi, and children's splash pad can be seen alongside tennis courts. The well-maintained resort grounds feature pathways and parking areas, set within a scenic residential environment.

4.88 out of 5 average rating, 49 reviews

Disney Close. Resort Savings. Family Paradise. YES

4.88 out of 5 average rating, 52 reviews

A dining area features a rectangular table surrounded by six black iron chairs. In the background, a cozy seating area includes a sofa, a wicker chair, and a lamp. Natural light fills the room through large windows near a glass door leading to the balcony.

Flat in Davenport

Disney's ideal family loan

4.91 out of 5 average rating, 116 reviews

Condo in Kissimmee

4.8 out of 5 average rating, 5 reviews

Nice 3B2B Windsor Hills Resort Condo 14 min Disney

A modern kitchenette is equipped with a black refrigerator, a microwave, and a dishwasher. A granite countertop provides workspace, with a coffee maker and sink present. Below, drawers and cabinets offer storage, while a decorative mat adds a subtle touch of home.

4.76 out of 5 average rating, 101 reviews

Modern Hotel Villa near Disney #07727

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, 52 reviews

Tuscana Gem 2 bed 2 bath condo nr Disney and Golf

A collage showcasing various aspects of the property. A cozy bedroom features a large bed with decorative pillows. A bright dining area opens onto a spacious living room. A stunning view of the lake and surrounding area is displayed, highlighting a night scene with fireworks.