Pet-friendly vacation 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 favorite
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, 145 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*

Guest favorite
A cozy living area features a light-colored sofa adorned with textured cushions, alongside a warm-toned armchair. Wall art in neutral hues adds character, and a wooden coffee table is centrally positioned. The kitchen area boasts wooden cabinetry and modern pendant lighting above the breakfast bar.
Townhouse in Kissimmee
4.93 out of 5 average rating, 107 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

Superhost
The living room features a comfortable sofa and two accent chairs, complemented by a wooden coffee table. A flat-screen TV is mounted on the wall, and natural light fills the space from sliding glass doors that lead to a private outdoor area.
Condo in Davenport
4.9 out of 5 average rating, 329 reviews

Amazing 2 Bed, 2 Bath condo only 10 min to Disney

Tuscana Resort Orlando is a Mediterranean-style villa resort minutes from DisneyWorld. Universal, Sea World ,LEGOLAND are close as well. A family friendly villa resort the amenities are top notch with a beautiful swimming complex that includes pool, hot tub, cabanas, kiddie pool, fitness centre. The very spacious 2-bed/2-bath condo is 1200sqft! Recently painted with fully equipped kitchen and washer and dryer! The unit has 1 King size bed in Master room and two twin beds in the spare bedroom.

Guest favorite
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, 123 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 favorite
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, 169 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 favorite
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, 143 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.

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, 146 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 favorite
A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.
Condo in Orlando
4.97 out of 5 average rating, 419 reviews

Waterfront Condo minutes to Disney & Universal

Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlando’s top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.

Top guest favorite
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.
Condo 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)

Guest favorite
A private screened patio features a heated swimming pool and a Jacuzzi surrounded by a spacious deck. Outdoor seating is provided, with a dining table and lounge chairs positioned for relaxation. Sunlight glimmers on the water, creating a serene atmosphere.
Villa in Davenport
4.92 out of 5 average rating, 123 reviews

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi

Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

Top guest favorite
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 favorite
A modern kitchen is equipped with stainless steel appliances, including a refrigerator, oven, and microwave. Wooden cabinets provide ample storage, and a sleek countertop enhances the workspace. Contemporary light fixtures hang above, while a dining table with transparent chairs is positioned nearby.
Townhouse in Kissimmee
4.9 out of 5 average rating, 261 reviews

Charming and Classic Decor House Decor near 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?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$51,279 GYDG$48,580 GYDG$56,262 GYDG$55,016 GYDG$50,034 GYDG$51,072 GYDG$58,546 GYDG$53,771 GYDG$41,522 GYDG$47,750 GYDG$53,563 GYDG$58,753 GYD
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Quick stats about vacation rentals that are pet-friendly in Windsor Hills

  • Total vacation rentals

    Explore 40 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at G$26,989 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,190 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 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