Pet-friendly holiday rentals in Windsor Hills

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Windsor Hills

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

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Top guest favourite
A charming two-story cottage is featured, exhibiting a cheerful yellow exterior. A small balcony is visible above the entrance, flanked by white railings. Lush palm trees and landscaped foliage surround the property, enhancing the inviting open space in a sunny environment.
Home in Kissimmee
5 out of 5 average rating, 146 reviews

Margaritaville Cottage 10 Minutes to DisneyWorld!

Location location location! We are conveniently located at the Margaritaville Resort. We are just minutes away from DisneyWorld, Universal, and Seaworld, Sunset walk, and H20 Water Park. * THIS DOES NOT INCLUDE ACCESS TO THE RESORT AMENITIES/POOL, however many of our guests chose to purchase a membership at H20 water park with the money they’re saving in resort fees* • Sunset Walk - A brand new experience that provides a plethora of restaurants, shopping, live entertainment, and movie theatre. (Resort shuttle is available, or a 15 min walk). •H20 - A new water park located on the resort property that includes offerings for all ages. ADDITIONAL fees apply. • Formosa Garden Winery - a five minute walk to an abundance of wine and beer with incredible views. The winery is open Thursday-Sunday. We recommend a brunch reservation! Cottage Accommodations - • 2 spacious bedrooms • 2 full bathrooms • Couch that can be converted into queen bed • Free and easy parking • Free WiFi • TV’s with cable in living room and both bedrooms (Netflix & Disney plus available) • High ceilings • Back patio with lounge chairs • Balcony on second floor with two adirondack chairs • All kitchen supplies included • Security for entrances and 24 hour watch House Rules • NO parties under any circumstance per airbnb policy. • No smoking, a $200 fine will be imposed for guests who break this rule • No unregistered guests *if you’ll be bringing a pet, please let us know before your arrival, there is a $50 service fee, max 2 pets*

Top guest favourite
A cozy living area features a light-colored sofa adorned with cushions, accompanied by a vibrant orange accent chair. A round wooden coffee table holds decorative items, and plants add natural greenery. The space is softly illuminated by a stylish pendant light above.
Townhouse in Kissimmee
4.93 out of 5 average rating, 110 reviews

Boho Bliss Escape• Poolside•Minutes from Adventure

🌿✨ Welcome to Boho Bliss Townhouse! ✨🌿 Your boho-chic retreat near Kissimmee ’s top attractions! 🏰 8 min Walt Disney World w/o traffic!!!! 🎢 25 min Universal ✈️ 25 min Orlando Airport 🐊 Gatorland 🛍️ Old Town Kissimmee 🎡 ICON Park features The Wheel, dining, and SEA LIFE Aquarium 🌊 Lake Tohopekaliga 🍖 Medieval Times offers dinner and a show. 🎢 Fun Spot America provides amusement park fun 🌿 Kissimmee Lakefront Park offers a relaxing lakeside experience 🌳 Shingle Creek Park is perfect for nature

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
4.88 out of 5 average rating, 124 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!

Guest favourite
The exterior of the house displays a light blue facade with white trim and multiple windows. A well-manicured garden with shrubs borders the entrance, while a concrete pathway leads to the front door. Tall trees provide shade in the front yard.
Home in Kissimmee
4.88 out of 5 average rating, 222 reviews

Disney Home Windsor Hills 3BED 3BATH Pool Parking

Recently renovated. Steps to Clubhouse + no rear neighbour. 500 mb wi-fi! The Disney Vacation Home is well located: the resort is one of the closest to the parks entrances. 10 minutes away from Animal Kingdom, Epcot, Hollywood Studios and 25 minutes away from Universal Studios, Island of Adventure and Volcano Bay. With an easy access to the airport (US 192, FL 417 and I-4 roads), Downtown Orlando, Miami and all the attractions in Central Florida (Daytona Beach, Clearwater and St. Petersburg).

Top guest favourite
A spacious living area features a comfortable dark gray sofa and a stylish coffee table, surrounded by neutral decor. A large flat-screen TV is positioned on a modern console against a bright wall, while natural light fills the space through multiple windows.
Home in Kissimmee
4.97 out of 5 average rating, 171 reviews

Cozy Disney Oasis Pool Home 10 Mins from Parks!

Our charming, pet-friendly home is located in the prime area of Kissimmee, Florida. Your family will be close to Disney parks, restaurants, Old Town, and Downtown Disney. Just bring your bag—we have everything you need! Settle into our fully equipped home, thoughtfully designed to create lasting memories with family and friends. Enjoy the Florida weather by cooling off in our open-air pool or grilling by the poolside lounges. Relax in our airy bedrooms, including Mickey and Minnie themed rooms!

Guest favourite
A spacious living area features a blend of modern and mid-century design elements. A large wooden dining table is accompanied by comfortable seating, while a green feature wall and decorative plants add a touch of nature. Light filters through the windows, illuminating the inviting space.
Townhouse in Kissimmee
4.91 out of 5 average rating, 145 reviews

Disney Themed Townhome- 5 miles to Disney Property

Give your family the Disney Resort experience in this magical townhome located only 10 mins (5 miles) from Disney property. Not only do you have access to your own personal hot tub, you will have access to the clubhouse which includes two pools, a fitness center, and a restaurant. This home will fit all your Disney needs with artwork from all your favorite movies, a castle themed primary bedroom, and a Mickey Mouse kids bedroom with twin beds. This home fits 6, including a pull out bed couch.

Guest favourite
An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.
Apartment in Osceola County
4.9 out of 5 average rating, 117 reviews

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

Top guest favourite
An outdoor dining area features a large blue farmhouse table surrounded by matching turquoise chairs. The setting includes tableware arranged neatly, with the private pool visible in the background. A grill and greenery are also present, providing a relaxed atmosphere for outdoor meals.
Villa in Kissimmee
4.94 out of 5 average rating, 142 reviews

*Brand New*! Minutes to Disney! + Free Resort!

Closest FREE resort to Disney Parks! We've named it "Coral Cove" - a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in Dec 22! * Kitchen is loaded, & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! *Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! *New Roku smart TVs & NEST tech! *Every detail has been thought of!

Superhost
A welcoming living area features orange accent chairs and plush beige sofas arranged around a glass coffee table. Decorative mirrors adorn the walls, while vibrant floral arrangements add a touch of color. Natural light filters through the window, draped with patterned curtains.
Flat in Kissimmee
4.87 out of 5 average rating, 395 reviews

Superb Townhouse Newly Renovated 1 mile to Disney

This 2-bedroom rental in Kissimmee is just 1 mile from Walt Disney and only 14 miles from Universal. This home has been completely renovated as of May 2017 with all brand new furniture and linens. This gated community is ideal for families and features plenty of updated, modern conveniences. Take advantage of the many on-site resort amenities including a swimming pool, hot tub, fitness center, tennis and basketball courts, and a fully-equipped game room with a pool table and air hockey.

Guest favourite
A screened-in private splash pool is surrounded by comfortable seating, featuring playful Minion characters on the walls of the adjoining rooms. The layout includes vibrant décor and modern furnishings, creating a family-friendly space with direct access to outdoor relaxation.
Townhouse in Kissimmee
4.83 out of 5 average rating, 158 reviews

Themed Pool Home 2 Miles to Disney

Welcome to your dream vacation home! - Newly remodeled 3 bedroom, 3 bathroom townhome with themed rooms - Private splash pool, fully screened-in - Prestigious Windsor Hills Resort with no resort fee - Access to a new kids water park, clubhouse, gym, and more - Free Wifi and fast internet for your Zoom meetings - 24 hour security and gated access - Have a pet? $150 pet fee on 1st; $75 each additional pet - Check out our 5 Star Reviews!

Top guest favourite
The cottage features a charming exterior with bright yellow siding and a classic gabled roof. Lush palm trees and manicured hedges frame the entrance, which includes a welcoming porch with yellow chairs. Large windows allow natural light to enhance the inviting facade.
Cottage in Kissimmee
4.98 out of 5 average rating, 124 reviews

1BD Cottage "Limoncello" in Margaritaville

Welcome to your own island-inspired oasis. Our charming cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. All Pets Must Be Preapproved :)

Top guest favourite
A bright living area features a light-colored sofa and a modern side table with a decorative lamp. Natural light floods through large windows, illuminating a dining space with a table and chairs, alongside a kitchen counter visible in the background.
Townhouse in Kissimmee
4.89 out of 5 average rating, 311 reviews

Disney fireworks new house - 5 minutes to Disney

Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

Popular amenities for Windsor Hills pet-friendly home rentals

When is the best time to visit Windsor Hills?

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Avg. price$312 SGD$295 SGD$342 SGD$335 SGD$304 SGD$311 SGD$356 SGD$327 SGD$253 SGD$287 SGD$318 SGD$378 SGD
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Quick stats about holiday rentals that are pet-friendly in Windsor Hills

  • Total holiday rentals

    Explore 40 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at $164 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Windsor Hills holiday rentals include wifi 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