Fitness-friendly holiday rentals in Windsor Hills

Find and book unique fitness-friendly rentals on Airbnb

Top-rated fitness-friendly rentals in Windsor Hills

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness and more.

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Top guest favourite
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.
Home in Kissimmee
4.99 out of 5 average rating, 138 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.

Guest favourite
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.
Home in Kissimmee
4.87 out of 5 average rating, 117 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!

Top guest favourite
A serene backyard pool area is enclosed by a screened lanai, featuring two lounge chairs adorned with vibrant blue and green cushions. Lush greenery and trees are visible beyond the pool, enhancing the peaceful view. The clear water reflects the cloud-dotted sky.
Home in Kissimmee
4.96 out of 5 average rating, 170 reviews

4 bedroom, south facing pool 3 miles to Disney

Create family memories in our stunning pool home with Star Wars, Minnie and Mickie themed twin rooms. Elegant and comfortable king bed master bedroom with your own private bathroom and soaking tub! Delightful queen bedroom that also features its own private bathroom with shower. Enjoy a heated south facing pool (heating extra charge) with no rear neighbors. We are located in a guard gated community that features a large pool, clubhouse with a gym, arcade, movie room, and various sports courts.

Top guest favourite
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.
Apartment in Kissimmee
4.98 out of 5 average rating, 173 reviews

Poolside 3Br~Windsor Hills~Waterpark~2mi to Disney

Your Windsor Hills Getaway starts here! This top-rated condo overlooks the resort pool & waterpark and is just minutes from Disney World! New appliances and updated furnishings, this 3rd floor condo sleeps 8, with plenty of parking. The screened-in balcony can’t be beat, overlooking the pool, hot tub, and waterpark with waterslides! The clubhouse is just steps away, with a store, food, drinks, game room, and fitness center. No resort, parking, or hidden fees. Full access to all amenities!

Top guest favourite
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
4.97 out of 5 average rating, 136 reviews

*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!

Top guest favourite
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.
Home in Kissimmee
4.97 out of 5 average rating, 140 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

Top guest favourite
Apartment in Kissimmee
4.98 out of 5 average rating, 109 reviews

Family, Disney, Windsor Hills, 11 am 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.

Guest favourite
A light-filled living area features a gray sectional sofa with accent pillows, arranged around a low coffee table. A patterned rug sits beneath, while a tall floor lamp adds warmth. Large sliding glass doors provide views of the outdoor patio, framed by sheer curtains.
Townhouse in Kissimmee
4.96 out of 5 average rating, 106 reviews

Star Wars Bungalow | 4 Mi to Disney | Waterpark

Enjoy your stay at this gorgeous, freshly renovated home! MINUTES to Walt Disney World. • 🎢 WATER SLIDES • 🌟THEMED Star Wars Retreat •🍴 Entertainer's Kitchen • 🤱 BOB Jogger Stroller available • 🏖️ Private patio with HEATED POOL • ☕️ **Latte and Coffee Bar** • 📶 Fiber High Speed Wi-Fi Thoughtfully curated for your ultimate ENJOYMENT. Beautiful modern interior, ceramic tile floors, and high quality decor throughout. This impeccable 3 bedroom, 3 bath home sleeps up to 8.

Top guest favourite
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.
Home in Kissimmee
5 out of 5 average rating, 237 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.

Guest favourite
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
4.91 out of 5 average rating, 242 reviews

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

Top guest favourite
Home in Kissimmee
4.87 out of 5 average rating, 132 reviews

7754 Windsor Hills 6B Luxury Pool Home Near Disney

🌟 Welcome to Your Ultimate Windsor Hills Vacation Escape! 🌟 Discover the perfect blend of luxury, comfort, and fun in this newly renovated 6-bedroom, 4-bathroom villa at Windsor Hills Resort Orlando, located just 5 miles from Walt Disney World. With a private pool, game room, and access to world-class resort amenities, this home is designed for families and groups who want an unforgettable Orlando vacation.

Top guest favourite
The image features a collage of vibrant themed bedrooms and a modern kitchen area. One room showcases a playful bunk bed against a backdrop reminiscent of a train station, while another has colorful Disney-themed décor. A spacious living area boasts light-colored furniture and a contemporary kitchen with stainless steel appliances.
Home in Kissimmee
4.97 out of 5 average rating, 106 reviews

3BD/3BA Themed House Near Disney

Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Popular amenities for fitness-friendly rentals in Windsor Hills

When is the best time to visit Windsor Hills?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$304 SGD$308 SGD$324 SGD$344 SGD$306 SGD$312 SGD$327 SGD$299 SGD$276 SGD$303 SGD$316 SGD$334 SGD
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Quick stats about holiday rentals that are fitness-friendly in Windsor Hills

  • Total holiday rentals

    Explore 440 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 8,640 verified reviews to help you choose

  • Family-friendly holiday rentals

    380 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    430 properties feature pools

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wifi availability

    430 of Windsor Hills holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Windsor Hills rentals

  • 4.8 Average rating

    Windsor Hills stays are highly rated by guests – averaging 4.8 out of 5!