Fitness-friendly holiday rentals in Windsor Hills

4.97 out of 5 average rating, 106 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

BOOK EARLY! Rated top 1% & Guest Favorite. Our popular home fills up 3-4 months in advance. 3BR/3BA Private Pool Villa in Windsor Hills Resort, Kissimmee! Newly renovated, gated resort, 3 miles to Disney World. Modern beach-coastal design, updated kitchen, family-friendly layout. Free parking, Wi-Fi, full resort access (pool, splash park, gym, playground). Near Universal (20 min), SeaWorld (18 min), Legoland (40 min). Perfect location for vacations Disney trips, sports events, and conventions.

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, 153 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.

4.92 out of 5 average rating, 167 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).

4.98 out of 5 average rating, 161 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!

A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.

4.86 out of 5 average rating, 146 reviews

Resort Home 3.5 miles to Disney with home theater

We welcome you to stay in our home located in the Windsor Hills community with a water park, slides, theatre and so much more! The house is just 3.5 miles from Disney’s Animal Kingdom. Our home has 6 large bedrooms including laundry in the home, an 8 seat home theatre, TVs in every room, a large swimming pool & spa with a large patio cover, plus a large kitchen fully equipped with everything you need for your stay. Please message us if you have any questions, we look forward to hosting you!

The exterior of the house is showcased, featuring a two-story design with light-colored walls and a prominent entrance. A spacious driveway accommodates up to four vehicles, bordered by well-maintained green lawns and trees. The property is set within a landscaped community.

4.96 out of 5 average rating, 162 reviews

Highest Rated Minutes to Disney! -Newly Renovated

• Newest house in the #1 community in the Disney Area, Windsor Hills • Only home with 7 bedrooms in the community (3 KING beds) • Extra privacy: only one side & no rear neighbors • 4 children themed bedrooms (Mickey, Star Wars, Toy Story, & Frozen) • Onsite, driveway parking for 4 vehicles • FREE pool heat + BBQ with all rentals • Fully equipped + stocked kitchen • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1000 Mbps • Property is managed directly by owner

4.91 out of 5 average rating, 81 reviews

Themed Windsor Hills 6BR Private Pool Gameroom

Welcome to Happy Thoughts Villa Enjoy this luxurious 6-bedroom, 4-bathroom home in Windsor Hills Resort, just 3 miles from Disney! Features include a private heated pool/spa, game room, updated kitchen, 2 king suites, a queen room on the main level, and 3 themed kids’ rooms (Frozen, Minions, Mandalorian). Resort amenities include a water park, arcade, gym, playgrounds, and more—all within an 8-minute walk. Located in a 24-hour gated community, it’s the perfect spot for your dream vacation!

4.98 out of 5 average rating, 123 reviews

11 am checkout, Windsor Hills, Family, Disney.

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.

4.99 out of 5 average rating, 104 reviews

A collage of vibrant images showcases the luxurious amenities available, featuring a spacious pool area, themed bedrooms, an arcade room, and outdoor seating. The photos capture a welcoming environment ideal for family gatherings and entertainment, beautifully arranged in a Mickey Mouse shape.

Villa in Kissimmee

Cozy Themed Villa 6 BR | Close to Disney

🏖️☀️🏄‍♀️Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort — one of the closest communities to Disney World — you’ll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool — great for relaxing after a fun day at Disney.🌴👙🩳🥽🩴 ❤️❤️We'd love to welcome you here!

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.

4.99 out of 5 average rating, 249 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.

4.98 out of 5 average rating, 116 reviews

An overview of luxury amenities includes a vibrant water park with slides, a spacious pool surrounded by palm trees, and a modern game room featuring foosball and striking wall art. Nearby, a tranquil bedroom setup and an inviting private pool are also highlighted.

Villa in Kissimmee

Luxury Villa Windsor Hills Resort 2 miles / Disney

4 bed and 4 bath LUXURY VILLA located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Villa is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The Villa offers the ultimate game room, outdoor dinning, and a screened private pool & spa. All guests also have access to resort amenities. Lots of entertainment for all. * Security Deposit Required with reservation

4.91 out of 5 average rating, 253 reviews

A private pool area is enclosed by a protective screen, providing a serene oasis. The pool is surrounded by tiled flooring, with a table and chairs nearby for relaxation. Bright curtains frame the entrance to the living space, enhancing the overall inviting atmosphere.

Townhouse in Kissimmee

DISNEY, WATER park, Private POOL, Comfort by A3G

Your dream getaway, starts In this 3beds 3 baths vacation home away from home! With private pool, Located in the amazing 5 stars resort at WINDSOR HILLS, only 3 miles away from all the wonders and magic of Disney. For Endless entertainment just walk to the Clubhouse and encounter the beautiful typhoon style pool, jacuzzi, brand new water park, arcade, fitness center, volleyball and basquetbol courts, kids playground and much more

Popular amenities for Windsor Hills fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-Friendly apartment accommodation

4.89 out of 5 average rating, 112 reviews

Cozy Apartment Close to Disney

Superhost

A whimsical room features two full-sized beds adorned with colorful bedding inspired by a popular animated theme. The walls are decorated with snowflake motifs and soft, twinkling lights, creating a playful atmosphere. A connecting ensuite bathroom is visible in the background.

4.75 out of 5 average rating, 130 reviews

Luxury 2BR-2BA Windsor Hills Condo - Direct Entry

4.97 out of 5 average rating, 105 reviews

A private balcony is showcased with a round table and two woven chairs, providing a serene view of the lake and surrounding landscape. Soft morning light reflects on the water, while a small potted plant adds a touch of greenery to the setting.

Apartment in Orlando

2-Bedroom Renovated Lakeside Condo Near Disney

An aerial view reveals a sprawling lagoon-style pool surrounded by lush green landscapes, highlighted by winding water features. A well-appointed bedroom presents a spacious bed framed by modern decor and natural light filtering through a window. The living area showcases an elegant dining setup alongside a stylish sofa, while a vibrant children's room features a bunk bed and playful accents.

4.83 out of 5 average rating, 226 reviews

2Bedrooms/2 Bathrooms Storey Lake Resort 3150-404

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.

4.88 out of 5 average rating, 125 reviews

3175-205 Resort 3BR Apt by Disney World Orlando

4.95 out of 5 average rating, 107 reviews

Family Disney Retreat | Windsor Hills+ Water Park

4.91 out of 5 average rating, 129 reviews

2 BD/ 2 BA Near Disney! Storey Lake (3150-103)

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, 155 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Fitness-friendly condo rentals

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.

4.72 out of 5 average rating, 127 reviews

Minutes to Disney best of Home, with a Resort feel

The living area features a comfortable sofa facing a large smart TV mounted on the wall. Natural light enters through windows, enhancing the space. A round coffee table sits in the center, surrounded by potted plants, with a dining area and a modern kitchen visible in the background.

4.93 out of 5 average rating, 216 reviews

Magical Stay Near Disney & ESPN

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, 162 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

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.

4.91 out of 5 average rating, 233 reviews

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

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.

4.94 out of 5 average rating, 104 reviews

Poolside 3 Bed Vacation Retreat in Windsor Hills

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, 160 reviews

Disney Oasis

A spacious pool area is surrounded by palm trees and tropical landscaping. Sun loungers line the pool deck, and a water park with slides is visible nearby. The multi-level condo buildings create a vibrant backdrop, ensuring a family-friendly environment.

4.8 out of 5 average rating, 158 reviews

Lovely vacation condo close to Disney & Universal!

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, 199 reviews

Poolside, 3Br Windsor Hills, Waterpark, By Disney

Fitness-Friendly Holiday House

A screened-in pool area features a clear blue pool with floatation devices, surrounded by a sunlit deck. A Tiki bar with seating stands to one side, while lounge chairs are arranged along the edge. Lush greenery is visible beyond the enclosure.

4.95 out of 5 average rating, 124 reviews

Disney Retreat | Huge Pool with Spa | 2 King beds

5 out of 5 average rating, 32 reviews

Disney 7 Min • Luxury 5 Suites • Jacuzzi • Arcade

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, 160 reviews

Luxury and Perfect Family Vacay 3 min from Disney!

4.86 out of 5 average rating, 7 reviews

Themed Rooms • Private Pool • Family Dream Stay

4.92 out of 5 average rating, 12 reviews

Villa 2655, Heated Pool/Grill, Game Rm, & PS5

4.96 out of 5 average rating, 71 reviews

*NEW*Theater, FREE Resort, 3 King, WDW Close!

5 out of 5 average rating, 10 reviews

Themed Villa:10 min to Disney: Pool, Gameroom, BBQ

The outdoor patio features a private heated swimming pool surrounded by lounge chairs and a dining area. A screened enclosure provides protection while allowing plenty of natural light. The spacious deck offers a relaxing space for families to enjoy the warm weather and nearby views.