
Fitness-friendly holiday rentals in Windsor Hills
Find and book unique fitness-friendly rentals on Airbnb
Quick stats about holiday rentals that are fitness-friendly in Windsor Hills

Total holiday rentals
Explore 410 holiday rentals in Windsor Hills

Nightly prices starting at
Windsor Hills holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 9,160 verified reviews to help you choose

Family-friendly holiday rentals
360 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
400 properties feature pools

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wifi availability
410 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!
Top-rated fitness-friendly rentals in Windsor Hills
Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness and more.

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.

Magical Adv 5 Star Villa Movie Room Arcade Pool an
Experience enchantment at Magical Adventure Villa, a top-rated 6-bedroom and 4-bath home for 12 guests. Conveniently located in Windsor Hills Resort, just 2 miles from Disney World®. Experience the highly acclaimed getaway that has garnered rave reviews. Enjoy a private pool, home theater, and a thrilling arcade. Unleash your inner Jedi at the state-of-the-art Star Wars gaming center with a movie theater, Xbox One, Nintendo Switch, and immersive 3D designs. *Work vehicles are not permitted to b

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.

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!!

Disney Retreat | Huge Pool with Spa | 2 King beds
Don’t leave that Disney Magic at the parks - experience it by coming home to your spacious 5 BR with 2 King suites, 3.5 baths, and newly renovated design. The high ceilings and open floor plan make it perfect for family time, while the private backyard oasis, complete with a pool and spa (heating optional) and Tiki Bar, offers a great space for relaxation. The themed bedrooms, including Star Wars, Frozen, and Mickey & Minnie, add a fun and whimsical touch that’s perfect for guests of all ages.

*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!

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!

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

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.

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!

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!

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.
Popular amenities for fitness-friendly rentals in Windsor Hills
Fitness-friendly apartment rentals

°o° Modern 3B/2B Condo in Windsor Hills by Disney

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

2-Bedroom Renovated Lakeside Condo Near Disney

Superb Townhouse Newly Renovated 1 mile to Disney

Themed Condo · Ground Floor · Walk to Waterpark

My Disney Grandview

Family Disney Retreat | Windsor Hills + Water Park

2 BD/ 2 BA Near Disney! Storey Lake (3150-103)
Fitness-friendly apartment rentals

Minutes to Disney best of Home, with a Resort feel

Magical Stay Near Disney & ESPN

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

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

The Tree House, only 1.5 Miles From Disney!

Andy's Toy Chest at Resort Minutes from Disney!

Poolside 3 Bed Vacation Retreat in Windsor Hills

Disney Oasis
Fitness-friendly house rentals

Pool/Spa,Arcade, 5 min to Disney, Resort amenities

Popular 6BR Resort Home 4 mi Disney/Pool/Game Room

2026 Themed 10 Bedrooms At Windsor Cay

Callaghan Cantina

Magical Vacation Home | Pool + Spa | Game Room

Once upon a galaxy: Star Wars/fairytale retreat

Themed Windsor Hills 6BR Private Pool Gameroom

Villa 2655, Heated Pool/Grill, Game Rm, & PS5
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $321 SGD | $331 SGD | $358 SGD | $338 SGD | $301 SGD | $307 SGD | $321 SGD | $294 SGD | $271 SGD | $291 SGD | $320 SGD | $365 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Destinations to explore
- Rentals with a washing machine and dryer Windsor Hills
- Rentals with an EV charger Windsor Hills
- Flat rentals Windsor Hills
- Apartment rentals Windsor Hills
- Villa rentals Windsor Hills
- Rentals with a hot tub Windsor Hills
- Rentals with pools Windsor Hills
- Rentals with a cinema Windsor Hills
- Pet-friendly rentals Windsor Hills
- House rentals Windsor Hills
- Rentals with a patio Windsor Hills
- Rentals with outdoor seating Windsor Hills
- Family-friendly rentals Windsor Hills
- Serviced apartment rentals Windsor Hills
- Fitness-friendly rentals Four Corners
- Fitness-friendly rentals Osceola County
- Fitness-friendly rentals Florida
- Fitness-friendly rentals United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- University of Central Florida
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club





