Vacation rentals with a hot tub in Windsor Hills

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Top-rated hot tub rentals in Windsor Hills

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Top guest favorite
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, 142 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.

Top guest favorite
The kitchen showcases modern grey cabinetry and sleek stainless steel appliances. A bright white countertop offers seating for four on padded bar stools. Coffee and tea-making supplies are visible on the counter, with accent decor displayed on the shelves. A pantry door stands closed nearby.
Townhouse in Kissimmee
4.94 out of 5 average rating, 125 reviews

Private Gated Community 8 mins away from Disney!

Gorgeous brand NEW luxury condo gated w 24 hr security guard. 8 mins from Disney & all parks!! 2 bedrooms, 2 bathrooms (rain shower & tub) Therapeutic beds in every room, including full size pull out. Smart TVs in every room w/cable, Netflix, Wifi. Extra steps to clean & sanitize. 2 min walk to Super Walmart. Walking distance to food, shopping, gas, Starbucks & more. washer dryer, coffee, tea, toiletries Clubhouse Resort with pool, jacuzzi, playground, gym, tennis & volley ball court, lake.

Top guest favorite
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, 174 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 favorite
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, 144 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!

Guest favorite
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, 147 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 favorite
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.
Condo in Kissimmee
4.98 out of 5 average rating, 182 reviews

Poolside 3Br Windsor Hills, Disney and Universal

Your Windsor Hills Getaway starts here! This 5-star 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 favorite
Condo in Kissimmee
4.98 out of 5 average rating, 114 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.

Top guest favorite
An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.
Condo in Kissimmee
4.94 out of 5 average rating, 170 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

Guest favorite
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, 108 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 favorite
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, 241 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.

Top guest favorite
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
4.98 out of 5 average rating, 104 reviews

Luxury Villa in Windsor Hills Resort, 2 miles / 5

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

Top guest favorite
The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.
Home in Four Corners
5 out of 5 average rating, 102 reviews

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Stylish Design, Luxurious Comfort & Endless Entertainment, with a sprawling 2200 ft2 southwest facing pool deck & outdoor kitchen, no rear neighbors on a beautiful forest in the stunning 3.5 square mile Reunion Resort. You will have your own private pool with overflow spa, movie room, billiards - game room, 4 theme rooms: OUTER SPACE, MARVEL SUPERHEROES with a TUBE SLIDE, FROZEN II, HARRY POTTER CUPBOARD, PS5, within minutes to Disney.

Popular amenities for Windsor Hills hot tub rentals

When is the best time to visit Windsor Hills?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$48,783 GYDG$48,993 GYDG$53,180 GYDG$55,483 GYDG$47,318 GYDG$49,621 GYDG$53,808 GYDG$48,365 GYDG$43,340 GYDG$47,527 GYDG$49,830 GYDG$53,808 GYD
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Quick stats about vacation rentals with a hot tub in Windsor Hills

  • Total vacation rentals

    Explore 450 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at G$10,469 GYD per night before taxes and fees

  • Verified guest reviews

    Over 9,100 verified reviews to help you choose

  • Family-friendly vacation rentals

    410 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    450 properties feature pools

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wi-Fi availability

    440 of Windsor Hills vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor Hills rentals

  • 4.7 Average rating

    Windsor Hills stays receive an average rating of 4.7 out of 5 from guests