
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.

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*

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

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!

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.

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).

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!

Disney R US! Universal Escape! 3BDR 3Bath
Our Magic is your Magic, only 3 Miles from the park and in a gated community with all the amenities needed to stay and rest a day if you want to. Take a journey on the back of a banshee on your right of passage at Animal Kingdom. Try some grey stuff at Be Our Guest restaurant in Magic Kingdom. Travel only 15 minutes to wave a wand like Harry Potter in Universal Studios. Then come back and relax in the gated community pool/spa area for an night of rest. We want your trip to be Magical and Epic

★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!

Stunning 8BR @Encore next to Disney - 237
Modern luxury home built in 2020, located at world renowned Encore at Reunion. Almost 4,000sf of a/c area, featuring 8 bedrooms, 6 full baths, game room, private pool and spa. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

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!

Vibrant Haven 10 Min to Parks Pet-Friendly
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

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 :)
Popular amenities for Windsor Hills pet-friendly home rentals
Pet-friendly house rentals

Livin' the Dream, 3Kings, Closest FREE Resort WDW

Remy's Refuge: Stylish 4BR - 10 min to Disney!

4 bed/ 4 bath Windsor Hills

4m Disney, Sun All Day, Golf, Pool• Spa• Games

*Orlando Dream Retreat*by Disney/pool/dog friendly

Peaceful and Cozy 4bd pool home 12 mins to Disney

New 2025! 2 miles to Disney 3 Ensuites 3.5 Baths

Pet-Friendly Heated Pool with Mini Golf Disney
Pet-friendly home rentals with a pool

Comfy Villa | 5 Min to Dinsey! Hot Tub & BBQ*

Disney Area - Heated Pool - 3 Bedroom Townhome

Bluey Summer| Free Water Park | 8 min to Disney

Luxury 4 Bedrooms, 3.5 Bathrooms with pool.

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

Themed Family Pool Home 10 Min to Disney Game Room

8005 Elegant Villa Near to Disney Magic

Modern Condo: 10 Min to Disney + Fireworks Views!
Private, pet-friendly home rentals

Windsor Hills 5BR • Free Heat • Private Arcade

4 Season Vacay, Near Disney, King Bed ste

Golfers! Updated! 4/3, grill, GR, pool&spa 136

5BR Golf View Penthouse • Near Disney • Luxe Stay!

Luxury Townhouse Near Disney | 3BR

Luxury 5BR Villa Near Disney

Townhouse na Disney

4BD Near Disney | Pool, BBQ & Ping Pong Fun
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $317 SGD | $301 SGD | $348 SGD | $340 SGD | $310 SGD | $316 SGD | $362 SGD | $333 SGD | $257 SGD | $292 SGD | $324 SGD | $384 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
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 $167 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
Destinations to explore
- Rentals with a washing machine and dryer Windsor Hills
- Family-friendly rentals Windsor Hills
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- Serviced apartment rentals Windsor Hills
- Rentals with pools Windsor Hills
- Rentals with a hot tub Windsor Hills
- Rentals with an EV charger Windsor Hills
- Apartment rentals Windsor Hills
- Rentals with a cinema Windsor Hills
- Rentals with a patio Windsor Hills
- Fitness-friendly rentals Windsor Hills
- House rentals Windsor Hills
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- Pet-friendly rentals United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Give Kids the World Village
- Southern Dunes Golf and Country Club




