Pet-friendly holiday rentals in Windsor Hills

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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
Townhouse in Kissimmee
4.93 out of 5 average rating, 109 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
The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.
Condo in Kissimmee
4.91 out of 5 average rating, 141 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Welcome to the Adventureland bungalow! This 2 bd/ 2 ba stay features a Tiki room living room with a sofa bed. The upgraded kitchen and bamboo bar are perfect to kick back and relax, or enjoy the screened in patio with tiki torches and seating area. The Jungle Cruise master bedroom features a king size bed and lovely waterfront views with lush greenery. The Pirate bedroom is fit for a captain (or two!) and has two twin xl beds. Air conditioning throughout. Located on the third floor/stair access.

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, 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 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, 170 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, 144 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 favourite
An outdoor dining area features a large, custom-built farmhouse table surrounded by benches. Refreshments and fruit are displayed on the table, with a private pool visible in the background, enclosed by a screened lanai. Lush green grass complements the serene atmosphere.
Home in Kissimmee
4.95 out of 5 average rating, 216 reviews

★Completely Renovated★ 3 mi to Disney+Free Resort!

Closest FREE resort to Disney Parks! Sandpiper Shores is a 6 bedroom 4 bathroom luxury villa that sleeps 14. BEST STAR RATING - OVER 200 REVIEWS! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting, & ROCK CLIMBING WALL! * Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW grill, & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

Top Guest favourite
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, 420 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 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.
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)

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.
Apartment 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 private pool area is enclosed by a protective screen, showcasing clear turquoise water. Lush palm trees are visible in the background, providing a tropical ambiance, while the surrounding patio features lounge chairs for relaxation. A spacious outdoor environment invites leisure and enjoyment.
Villa in Kissimmee
4.78 out of 5 average rating, 239 reviews

Feel the Magic: 9 min Disney • Pool • Pet • Relax

✨ Looking for comfort, privacy, and fun near Disney? Our pet-friendly home is ready to welcome your family — including your furry friend — for amazing days under the Florida sun. Magic Kings House invites you to create magical moments with your loved ones, offering comfort and exclusivity at Windsor Palms, the resort most loved by guests. Every detail has been carefully prepared to make your vacation easy, relaxing, and filled with wonderful memories. 🌴🐶☀️

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!

Guest favourite
A welcoming living area features a dark brown sofa adorned with decorative pillows in warm tones. Greenery decorates the wall behind the sofa, complemented by a modern lamp. A nearby circular table and chair set add to the inviting space, with natural light filtering through a window.
Apartment in Bay Lake
4.89 out of 5 average rating, 107 reviews

Lush Green Retreat 10 Min to Parks Pets Allowed

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Popular amenities for Windsor Hills pet-friendly home rentals

When is the best time to visit Windsor Hills?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$411 NZD$389 NZD$451 NZD$441 NZD$401 NZD$409 NZD$469 NZD$431 NZD$333 NZD$378 NZD$419 NZD$497 NZD
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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 $216 NZD 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 and kid-friendly amenities

  • Holiday 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 holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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