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, 157 reviews

Margaritaville Cottage 10 Minutes to DisneyWorld!

✨ Location, Location, Location! We’re conveniently located in the beautiful Margaritaville Resort—just a short drive from all the Orlando fun: 🎢 Disney World 🎬 Universal Studios 🌊 SeaWorld 🌴 Sunset Walk 💦 H2O Water Park ⚠️ Please Note: This stay does not include access to resort amenities or the main pool. However, many guests choose to purchase access to H2O Water Park using the savings from resort fees! ⸻ 🎉 Nearby Highlights 🍽️ Sunset Walk A vibrant destination filled with restaurants, shopping, live entertainment, and a movie theater. 💦 H2O Water Park Located right on the resort property with fun for all ages. Additional fees apply. 🍷 Formosa Garden Winery Just a 5-minute walk! Enjoy wine, beer, and beautiful views. Open Thursday–Sunday — we highly recommend making a brunch reservation! ⸻ 🏡 Cottage Accommodations • 2 spacious bedrooms • 2 full bathrooms • Convertible couch (turns into a queen bed) • Free & easy parking • Free WiFi • TVs with cable in the living room + both bedrooms (Netflix & Disney+ included) • High ceilings • Back patio with lounge chairs • Second-floor balcony with two Adirondack chairs • Fully stocked kitchen • Gated security + 24-hour watch ⸻ 📋 House Rules 🚫 No parties under any circumstance (per Airbnb policy) 🚭 No smoking — $200 fine if violated 👥 No unregistered guests 🐾 Pets If you plan to bring a pet, please let us know before arrival. • $50 service fee • Max 2 pets

Top guest favorite
Townhouse in Kissimmee
4.92 out of 5 average rating, 131 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
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
4.86 out of 5 average rating, 132 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 favorite
The exterior of the home features a spacious driveway, paved in light-colored bricks, leading up to an attached garage with an ornate door. A well-maintained lawn with green grass and palm trees is visible, complemented by a clear blue sky filled with clouds.
Home in Kissimmee
4.8 out of 5 average rating, 112 reviews

View the Disney fireworks from your pool!

Our home is close to Walt Disney World - Shopping - Restaurants . You’ll love the fully stocked granite kitchen, ALL SMART TVs in EVERY room, the views (fireworks), the location, the high ceilings & ceiling fans. Our home is great for couples, families (with kids), and furry friends (pets). Laundry room is INSIDE. The garage is full of games (air hockey, pool & foosball) The pool has a covered lanai with table & chairs for outdoor eating while overlooking our lake with a lighted fountain.

Guest favorite
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, 224 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 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, 182 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!

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, 158 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!

Superhost
Villa in Kissimmee
4.77 out of 5 average rating, 253 reviews

Feel the Magic 9 min Disney, Pool & Pet friendly

✨ Looking for comfort, privacy, and fun near Disney? Our home features a private pool and spa, perfect for relaxing after the parks. Optional pool heating is available for $49 per night. Thoughtfully prepared for families, the house welcomes guests, including those traveling with pets, for easy Florida days. Magic Kings House invites you to create unforgettable moments at Windsor Palms, a favorite resort among guests. Every detail has been carefully arranged to provide a memorable stay.

Top guest favorite
Home in Kissimmee
4.87 out of 5 average rating, 104 reviews

4m Disney Sun, Free Snacks, Golf, Pool• Spa• Games

SUN SUN SUN. All day sun with our Private LARGE sun deck. Newly added golf putt putt. Also Cornhole 🎉 Complimentary welcome snack basket with sweet & salty treats included with every stay. Hot Tub, Private pool , fully fenced large yard . A game room with pool table, darts, arcade game and just added , an electronic pinball machine , there’s also a retro record player. 4 miles to Disney. Disney themed, king bed, queen bed and twins, large fenced yard for dogs

Guest favorite
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
4.81 out of 5 average rating, 170 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? $250 pet fee on 1st; $125 each additional pet - Check out our 5 Star Reviews!

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, 130 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 :)

Guest favorite
A vibrant living area is showcased with modern teal chairs, artistic wall decor, and large windows allowing natural light. The room features a spacious layout, accompanied by colorful drapes and a stylish coffee table. A view of the private pool area can be glimpsed through the glass doors.
Townhouse in Kissimmee
4.85 out of 5 average rating, 140 reviews

Retro Retreat• Themed Stay• Near Disney• Waterpark

Guest favorite on Airbnb. Retro Retreat is a one-of-a-kind 3BR Disney-themed townhome just 2 miles from the parks. Step into a playful 1950s-inspired escape with immersive themed rooms, a private plunge pool, and easy access to resort amenities including a lagoon pool and waterslides. Pet-friendly, thoughtfully designed, and far from cookie-cutter—this is the stay families remember long after the trip ends.

Popular amenities for Windsor Hills pet-friendly home rentals

When is the best time to visit Windsor Hills?

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Avg. priceG$56,902 GYDG$56,902 GYDG$58,576 GYDG$55,438 GYDG$50,417 GYDG$51,463 GYDG$58,994 GYDG$54,183 GYDG$41,840 GYDG$47,488 GYDG$52,718 GYDG$62,551 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$29,288 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,430 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