
Pet-friendly holiday rentals in Winter Garden
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Winter Garden
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

Pool + Heated spa Family friendly King suite Oasis
Welcome to your perfect Florida getaway! This beautifully updated 3-bedroom, 2-bath home in Minneola offers everything you need for a relaxing and fun-filled stay. Whether you're traveling with family, friends, or pets, this home is designed to make you feel right at home. Step outside to your private backyard oasis featuring a sparkling pool, hot tub, and serene views overlooking a peaceful pond. Fire up the grill, unwind under the market lights, or soak up the sun with your favorite drink.

Lake Front Home with private Dock on Lake Louisa
Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow cleaning and disinfecting of the house

Huge pool & Lakeview home | 5 Min Universal
Welcome to your ideal vacation retreat! This spacious and cozy lakefront pool house offers everything you need for a memorable family getaway. Perfectly designed for unforgettable trips with 4 BD and 2 BTH, there's plenty of room for everyone to relax. Located just minutes from Universal, Disney and SeaWorld, this house offers the perfect blend of convenience and tranquility. After a day of adventures, return to your serene lakeside retreat and create lasting memories with your loved ones.

Hook's Cabin- Lake & Pool near Disney A-frame
Hook’s Cabin is nestled within the peaceful gated community of Vacation Village it is a beautifully renovated A-Frame home and your perfect place to stay & play! You will enjoy private Lake Louisa access, Heated Olympic-sized community Pool, Pickleball / Basketball courts, play grounds, & FREE parking, Fast WiFi, flat screen smart Tv's w/ cable, full kitchen, & in home laundry. All less than 25 mins from Disney & other Orlando theme parks, and 5 miles from the National Training Center.

Cozy Winter Garden Home 20 MINUTES FROM DISNEY
Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

Spacious Getaway ~ Heated LED Pool & Ping Pong
Welcome to your Spacious Getaway! Exterior Features: ★ LED Lights in Pool and on Pool Cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ Ping Pong Table ★Large Shower in Master Bathroom ★ROKU on each TV Extras: ★ Heated Pool up to 95 Degrees - $40 per day (Pool Water is normally at 75 degrees without the Pool Heater) ⚠️ Pet-Friendly, but the pet must be added to the reservation ($75 Pet fee)⚠️ {Willing to Negotiate Monthly Prices}

Charming Downtown Apartment - Walk to Everything
Stay in the heart of historic downtown Clermont- steps from the lakefront, breweries, shops, & dining. This light-filled, stylish apartment above our garage offers cozy aesthetics, comfy beds, a double shower, two spacious bedrooms, and a smart TV. Thoughtfully stocked for a stress-free stay, with garage storage for your bikes or paddle gear upon request. More than a stay—we proudly offer a distinct Clermont experience. We hope you love our charming town just as much as we do!

Premier Clermont Suite /Prime Downtown 103
Immerse yourself in the sophisticated serenity of our strategically located prime suite, nestled in the vivacious heart of downtown Clermont. elegantly appointed with meticulous attention to detail our suite offers a harmonious blend of opulence and home-like comfort-whichever way you look, every corner is designed to offer an unrivalled stay experience. This property is a dream come true for Triathletes! Standing right at the epicenter of Clermont.

Tranquil Azure Haven 10 Min to Parks Pets 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

3.5 Acre Modern Country Farmhouse |23 mi to Disney
Enjoy your stay at the perfect modern country hideaway located on over 3.5 acres. Spacious open concept living area spanning over 2000 sq ft. Completely refreshed new floor and furniture. All you will hear will be the cows that come wandering up to the property while you swing on the porch! If you want to experience peace and serenity but also some of that Disney magic this is the place for you because it is also within 30 minutes of Disney!

Paradise nook near Orlando's theme parks
A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Enjoy the breathtaking sunrise views of Lake Apopka from this newly refurbished and well appointed 4 bed, 2.5 bath vacation home in Winter Garden, Fl. While the house offers total tranquility and relaxation, it is only a short drive from Orlando’s numerous theme parks (Universal Studios 20 min, Disney World 30 min) and all other local attractions (Mall of Millenia and premium outlet malls 20 min drive)
Popular amenities for Winter Garden pet-friendly home rentals
Pet-friendly house rentals

Beautiful House Completely Remodeled

Villa Resort Club

Amazing Pool • Huge Yard • 5 Min Universal

Orlando Cactus House! 5min from Universal Studios

Our Poolhome by the Mouse house with Game Room.

There is no other place you want to be than here.

Magnificent Lakefront Home•Swim&Relax•Long Stay OK

Spacious Home with Pool & Hot Tub near Downtown
Pet-friendly home rentals with a pool

Comfy 4BR near Disney/pool and Hottub

Cute N Cozy Villa near Disney, pool, Wi-Fi

Near Disney 5bed home with pool and game room

Swim & Chill Hideaway | Heated Pool + Fire Pit

Modern Condo: 10 Min to Disney + Fireworks Views!

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

Comfy Family Villa|5min->Disney!

Eden Escape Suite, Lake Harris, Florida
Private, pet-friendly home rentals

The silver cottage

Comfy Farm Studio Stay

Cozy guesthouse in Clermont

PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

Spaciious Countryside Home In Sanford | 3BR, 2.5BA

Bright 3BR Downtown Clermont | Parking + Deck

Cozy home near Disney with a king size bed

3BR DT ORL | Fenced Yard + On-Site Car Rental
When is the best time to visit Winter Garden?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £83 | £85 | £83 | £83 | £81 | £79 | £82 | £81 | £77 | £81 | £84 | £98 |
| 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 Winter Garden

Total holiday rentals
Explore 30 holiday rentals in Winter Garden

Nightly prices starting at
Winter Garden holiday rentals start at £29 per night before taxes and fees

Verified guest reviews
Over 1,270 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Winter Garden holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Garden rentals

4.8 Average rating
Winter Garden stays are highly rated by guests – averaging 4.8 out of 5!
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- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Orange County Convention Center
- Walt Disney World Resort Golf
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
- 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!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club




