Condo holiday rentals in Windsor Hills

A modern living area features a cozy sofa facing a mounted TV, displaying a serene landscape. Behind the sofa, an electric fireplace adds ambiance. The open layout connects to a well-equipped kitchen, enhancing a sense of space within the inviting atmosphere. Accessibility to dining areas is evident.

4.91 out of 5 average rating, 159 reviews

Chic Disney Resort Condo • Pool Access Near Parks

Magical Disney getaway that sleeps up to 6 guests just 7 miles from Disney. Enjoy full resort perks & amenities, fast free Wi-Fi, and year-round pool & hot-tub access. • Enjoy a heated pool, hot tub, game room, and fitness center, and Smart TVs • Full kitchen and cookware • Free parking steps from elevator • Located in a secure, gated community Perfect for families, couples, or business travelers. Near Universal, SeaWorld & top dining! Relax on a balcony & reach every park in under 15min!🏰✨

4.92 out of 5 average rating, 153 reviews

New Luxury Condo near Disney

A passos da piscina e parque aquático. Covid-19 safe. Wi-fi de 500 megabytes! O apartamento possui localização privilegiada: está no condomínio fechado Windsor Hills, o mais próximo dos parques. A 10 minutos do Animal Kingdom, Epcot, Hollywood Studios e Magic Kingdom e a 25 minutos dos parques da Universal. Além disso, possui fácil acesso ao aeroporto (US 192, FL 417 e I-4), Downtown Orlando, Miami e a todos os atrativos da região da Central Flórida (Daytona Beach, Clearwater, St. Petersburg).

A spacious bedroom is highlighted by a large mural depicting autumn trees. A white bed frame is complemented by a dark blanket and patterned pillows. Two bedside tables with lamps are positioned on either side, providing balanced lighting.

4.95 out of 5 average rating, 212 reviews

New Lovely 3-bedroom Condo 5 minutes from Disney’s

This is a totally remodel Beautiful Condo! Nice small community with heated pool, fitness center, barbecue area, tennis courts in a quiet private park like setting! Enjoy breakfast on a comfortable screened balcony overlooking a serene conservation area. This 3/2 First floor condo is in a perfect location, just 5 miles from Disney World with lots of shopping & restaurants close by...for golfers, the property is surrounded by lots of beautiful courses, don't delay schedule your Vacations today!

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.

4.86 out of 5 average rating, 160 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

Welcome to our Star Wars themed rental in Kissimmee, FL, just 3 miles from Disney World! Experience the ultimate vacation in a galaxy far, far away. Located in Windsor Hills Resort with a heated community pool and two water slides. The kids bedroom has Star Wars decor, twin bunk beds, and an electronic pinball machine. The condo is decorated with Star Wars artwork and a half-sized Darth Vader figure. The kitchen is fully equipped. Don't miss this chance to live out your Star Wars fantasies.

4.82 out of 5 average rating, 308 reviews

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

Brand new flooring, mattresses, AC, water heater and more! Disney SO close! Our Property Manager will see to any needs during your stay, a rental registration is required. Beautiful, clean and comfy condo in Windsor Hills Resort with a new WATER PARK and tons of amenities. Stainless appliances and granite, free wifi/cable, desk/charging station and PS 3 with games, Pack N play, stroller, high chair, wash/dryer, a starter kit of supplies. No hidden fees, free parking. Perfect for families!

The community pool area features a winding pool surrounded by palm trees and lounge chairs. A colorful water slide is visible, along with shaded cabanas. The well-maintained grounds include lush greenery and pathways leading to residential buildings in the background.

4.98 out of 5 average rating, 114 reviews

Family, Windsor Hills, Sleep In with 11AM Checkout

Walk into your home away from home. Enjoy a relaxing stay. Located on 4th floor. Enjoy morning coffee on a screened-in balcony or a late snack. Pet-free home. Please NO Smoking. Children are always welcome. Come enjoy all of the accommodating facilities at Windsor Hills with a top-notched 24/7 gated security. FREE parking & leisure activities! Maximum of 3 cars allowed per reservation. This includes all guest that are visiting. All unregistered drivers will be denied access by HOA.

Superhost

Aerial view captures the expansive Windsor Hills water park, with colorful slides and pools. The lower images showcase a family-friendly living room, brightened by wall murals featuring iconic Disney characters and cozy furnishings, including a spacious bed with vibrant bedding.

4.73 out of 5 average rating, 147 reviews

Toy Story Retreat Near Disney

Immerse yourself in the magic of Disney and create lifelong memories at your very own Toy Story Retreat. - Newly remodeled 3-bedroom, 2-bathroom condo - Family-friendly atmosphere with Disney-inspired design - Access to Windsor Hills Clubhouse with pools and gym - Ground-floor unit with greenspace views - Fully equipped kitchen and in-unit washer/dryer - Free WiFi and parking - Kid-friendly amenities like high chair and stroller - No extra fees, including resort fees

A spacious lagoon-style pool is surrounded by palm trees, with lounge chairs arranged around its perimeter. A welcoming clubhouse is visible in the background, featuring large windows and a tiled roof.

4.98 out of 5 average rating, 164 reviews

Heavenly Bliss - 3 bed 2 bath condo near Disney!

We invite you to come stay in our beautifully decorated condo. A fully air conditioned 3 bedroom condo, with 2 bathrooms, Heavenly Bliss is extremely well furnished with your comfort in mind. Heavenly Bliss is at a convenient location that will save you Money and Time. It is easy to get around the Parks, Stores and Restaurants of your choice, and less than 1.5 miles from the gates of Disney. Our Florida Getaway vacation condo provides all the benefits you need while on vacation.

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, 218 reviews

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

1ST FLOOR! 3 Bedroom/2 Bathroom Condo with 2 Master Suites! Main Master Suite has a King bed, TV and DVD player, walk in closet and a walk in shower. Second Master Suite has a King bed, TV and DVD player, and a door with direct access to the second bathroom. Guest Bedroom 3 has two Twin beds and a TV and DVD player. The living room features a TV over a beautiful electric fireplace and leather sofas - one is a sofa sleeper!

4.88 out of 5 average rating, 171 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!

4.97 out of 5 average rating, 192 reviews

Condo in Four Corners

Orlando Fun: Minutes to Disney and Margaritaville

A cozy, comfortable, and convenient 2-bedroom condominium with 2 full bathrooms, a fully-equipped kitchen (coffee and tea provided), a beautifully decorated living/ dining room, 2 walk-in closets (with plenty of shelves, drawers, and hangers), a washer, a dryer (with laundry detergent provided), an iron, AC (or heating in winter), cable TV, WiFi, and a screened-in balcony.

The exterior of the Westgate Vacation Villas showcases an elegantly designed building with multiple levels. Soft lighting from street lamps illuminates the entrance. Rows of golf carts are parked in front, surrounded by manicured landscaping and palm trees under a clear blue sky.

4.85 out of 5 average rating, 149 reviews

Westgate Vacation Villas - 1 Bedroom

Offering a 1 Bedroom apartment at Westgate Vacation Villas with King Bed, Sofa Bed and full Kitchen Westgate Vacation Villas comforts of a furnished only home 1 mile from Disney and close to the other Orlando attractions, restaurants and shopping. with studios - 2 bedr'm suites+variety of amenities 14 heated pools + award-winning Drafts Sports Bar & Grill

Popular amenities for Windsor Hills condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

4.85 out of 5 average rating, 131 reviews

Stylish Condo 20 mins to Disney/King Bed

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, 208 reviews

Magic Stay at Windsor Hills! 2 bedroom apartment!

4.89 out of 5 average rating, 94 reviews

Luxurious Living 15 minutes from Disney

An open dining area features a modern table set for six, surrounded by stylish white chairs. Framed art pieces adorned with nature motifs are mounted on the warm-toned walls, providing a tranquil ambiance. A chandelier provides soft lighting over the table.

4.78 out of 5 average rating, 199 reviews

Beautiful Roomy Condo near Disney & Universal

A children's bedroom is decorated with a vibrant Lion King theme. Two twin beds are covered with colorful bedding featuring characters from the movie. A bedside table with a lamp sits between the beds, and a large, eye-catching curtain depicting a jungle scene enhances the playful atmosphere.

4.95 out of 5 average rating, 215 reviews

Close To Disney! 3 Bedroom Condo in Windsor Palms

A patio area is presented under a covered porch, featuring a round table set for two with a white tablecloth and colorful cups. Two comfortable chairs with blue cushions are positioned around the table. A scenic view of a lake with greenery can be seen in the background.

4.84 out of 5 average rating, 147 reviews

Stunning view, near Disney.

The image captures a vibrant outdoor resort area featuring a lagoon-style pool and waterslides in shades of blue and green. Sun loungers are arranged around the pool, surrounded by palm trees and open green spaces. A two-story condo building stands in the background.

4.95 out of 5 average rating, 38 reviews

Sunny Condo Retreat ~ Clean. Cozy. Convenient.

A spacious pool area is surrounded by palm trees and tropical landscaping. The clear blue water reflects the sunlight, while shaded cabanas with white roofs provide relaxing spots for guests. The rock formations enhance the natural ambiance around the inviting pool.

4.91 out of 5 average rating, 117 reviews

A 3BR Resort Style Divine Getaway Near Theme Parks

Pet-friendly condo rentals

4.94 out of 5 average rating, 143 reviews

9 miles from Disney - Bella Piazza spacious condo

4.86 out of 5 average rating, 291 reviews

An aerial view of a resort pool area showcases a winding pool surrounded by lush palm trees and tropical landscaping. Lounge chairs are arranged along the poolside, with shaded cabanas nearby. The resort features a terracotta roof and is set against a backdrop of greenery.

Condo in Champions Gate

Magical Champions Gate 3/2 Tuscan Penthouse

The image captures a vibrant pool area surrounded by lush palm trees and comfortable lounge chairs. An inviting infinity pool is centrally located, accompanied by cabanas and umbrellas. Multiple water slides are visible in one corner, enhancing the family-friendly atmosphere of the space.

4.92 out of 5 average rating, 125 reviews

Pet friendly Orlando area near ESPN Center

4.96 out of 5 average rating, 106 reviews

The living room features large sliding glass doors that open to the balcony, providing a view of the lake. A contemporary electric fireplace sits beneath a 65-inch smart TV. Comfortable seating includes a sofa, an armchair, and a coffee table, with warm curtains adding a touch of color.

Condo in Orlando

Penthouse Lakeview Minutes to Disney/ Universal

The living room features a spacious sectional sofa and a flat-screen TV mounted on a wooden console. Large glass doors provide a view of the patio and golf course, while natural light fills the room through the sheer curtains. A potted plant adds a touch of greenery.

4.94 out of 5 average rating, 139 reviews

3 Bedroom w/large patio on Resort Golf Course

A spacious bedroom features a plush, tufted headboard and a large window allowing natural light to fill the room. Two bedside lamps provide additional illumination, while modern furnishings add contemporary flair. A round mirror is mounted above the bed, reflecting the inviting ambiance.

4.78 out of 5 average rating, 255 reviews

Brand New AwardWinning Renovated Condo Near Disney

A spacious living area features large windows allowing natural light and views of green trees outside. A sectional sofa in a neutral tone is complemented by decorative blue cushions. A glass coffee table rests on a textured area rug, and a television is positioned on a low media console.

4.9 out of 5 average rating, 125 reviews

Home away from home for the Parks!

Superhost

A clear view of a pool surrounded by lounge chairs and palm trees, reflecting the sunlight. Umbrellas provide shade, and green lawns are visible in the background. The calm water enhances the serene environment, creating a relaxing outdoor space.

4.82 out of 5 average rating, 238 reviews

Family Friendly I Mins from Disney I Resort Pool

Condo rentals with a pool

The vibrant resort area features a lagoon-style pool with colorful water slides, offering a fun place for guests to enjoy. Lounge chairs are arranged around the pool, and lush palm trees provide shade in the background.

4.94 out of 5 average rating, 72 reviews

Windsor Hills Fun Lake View Mickey Disney Condo

A view of a spacious resort-style pool area featuring various sections including a water park with slides and a splash pad. Surrounding palm trees offer shade, while lounge chairs are positioned around the pool's edge, creating an inviting atmosphere for relaxation.

4.93 out of 5 average rating, 92 reviews

Poolside 3 Bed Vacation Retreat in Windsor Hills

The inviting living area features a blue sofa adorned with patterned cushions, providing ample seating. A glass coffee table sits atop a soft rug, and a flat-screen TV is positioned on a dark wood entertainment unit. Large windows offer natural light, showcasing a view of greenery.

4.82 out of 5 average rating, 38 reviews

Beautiful Vacation Condo at Windsor Palms Resort

The living area features sleek white tile flooring and a modern aesthetic. A large flat-screen TV is mounted on the wall, while a stylish coffee table sits at the center. Sunlight filters through the window, illuminating a lush green plant beside the entrance.

4.78 out of 5 average rating, 91 reviews

BEAUTIFUL NEW APARTMENT A FEW MINUTES FROM DISNEY

5 out of 5 average rating, 12 reviews

*Pixie Dust Penthouse* Totally Remodeled, Luxury

4.93 out of 5 average rating, 40 reviews

A large resort-style pool is viewed in the foreground, surrounded by a spacious deck featuring lounge chairs. A clubhouse sits in the background, with palm trees lining the perimeter under a clear blue sky scattered with clouds.

Condo in Four Corners

2BD Champions Gate Magical Near Disney (CG 1177)

4.92 out of 5 average rating, 13 reviews

Cozy condo in waterpark resorts and golf course