Pet-friendly vacation 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.

%{current} / %{total}1 / 1
Top guest favorite
Home in Minneola
4.98 out of 5 average rating, 156 reviews

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.

Top guest favorite
A collage of images depicting the Cute N Cozy villa in Clermont, FL. Highlights include a cozy living room with a couch, a spacious pool area, a well-equipped kitchen, and scenic lake access. The villa features modern decor and family-friendly spaces, inviting guests to enjoy a relaxing stay.
Villa in Clermont
4.94 out of 5 average rating, 108 reviews

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

Welcome to our Cute N Cozy villa, located in the beautiful Vacation Village community in Clermont, FL! This clean and beautifully updated 2 bed/2 bath, family friendly villa sleeps 6 and has all you need for an enjoyable getaway. Community amenities include an Olympic size heated pool, tennis/pickle ball courts, basketball, shuffle board, playgrounds, and lake access to Lake Louisa. Located approximately 25 minutes to Walt Disney World and conveniently located to other major theme parks.

Top guest favorite
Two wooden cabins are positioned under tall trees, reflecting on the calm water's surface. A small seating area with bright blue chairs and a fire pit is situated on the grassy shore, providing a relaxed outdoor space, while the surrounding nature complements the serene setting.
Home in Clermont
4.94 out of 5 average rating, 220 reviews

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

Guest favorite
The interior of Hook's Cabin features a spacious living area with natural light flooding through large windows, complemented by modern furniture. A heated pool and outdoor lounge area are visible through the glass doors, highlighting the community's inviting amenities.
Home in Clermont
4.88 out of 5 average rating, 152 reviews

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.

Guest favorite
A small, white house is framed by vibrant greenery and colorful plants. The front door, painted blue, adds a pop of color, while large windows allow light to fill the space. A wooden deck leads up to the entrance, enhancing the welcoming appeal.
Home in Winter Garden
4.91 out of 5 average rating, 214 reviews

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.

Top guest favorite
The exterior of the property features a fenced yard with shaded trees and a front lawn leading to a single-story house. A pool area with protective mesh surrounds the heated pool, illuminated with vibrant LED lights in evening settings. Indoor spaces exhibit an open layout with natural light and comfortable seating.
Home in Minneola
4.98 out of 5 average rating, 179 reviews

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}

Top guest favorite
A dining table is set with a tray of assorted cheeses, fruits, and spreads, while glasses sit ready for drinks. Large glass doors reveal views of Bear Lake and a deck with seating, enhancing the inviting ambiance.
Home in Apopka
5 out of 5 average rating, 105 reviews

Magnificent Lakefront Home•Swim&Relax•Long Stay OK

Water-ski, swim, boat, and fish in the pristine, spring-fed waters of the 310-acre Bear Lake beside this expansive home. Canoe and paddle boards provided! Enjoy the sunset from the swing on the boat dock, watch the sunrise from the screened deck while lounging in the hammock, or spend a lazy afternoon with the family playing board games. The rental is the private half of a duplex, completely separated from the owner's side, with no shared areas. (2 kings, 2 queens, 3.5 baths)

Top guest favorite
Guesthouse in Clermont
4.98 out of 5 average rating, 124 reviews

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!

Top guest favorite
A covered swing hangs from a sturdy wooden frame, positioned near a fire pit surrounded by a circular stone border. Red chairs are arranged nearby, with trees and a rustic fence in the background, creating a serene outdoor setting.
Home in Apopka
4.99 out of 5 average rating, 138 reviews

5 Springs Close Goats Chicken Free Eggs Memories

5 natural springs 4 to 10 minutes away Fur Babies WELCOME FREE Farm Fresh Eggs Pet the goats Feed the Chickens NO ROOSTERS! Fire pit (we set up the wood daily) Tree swing/bench swing Cornhole Grills Picnic pavilion 5 Acres 2 King 1 Twin pull-out 1 queen inflatable bed The kitchen is fully stocked. Disney 40 min Rock Springs 3 min Kings Landing, Kelly Park, Wekiwa Springs, Barrel Springs, and Wekiva Springs are all less than 5 MILES away. Wekiva Island is a Must VISIT!

Top guest favorite
A modern living area features a cozy gray sofa draped with a textured throw, complemented by a wooden coffee table. An open kitchen with bar seating is visible, along with neutral walls and tile flooring, providing a spacious and bright environment.
Apartment in Clermont
4.98 out of 5 average rating, 103 reviews

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.

Guest favorite
The exterior of the home is shown, featuring a wraparound porch with accessible steps leading up. The structure is surrounded by greenery, highlighting the peaceful countryside setting. Large windows contribute to a light and inviting atmosphere.
Home in Clermont
4.94 out of 5 average rating, 106 reviews

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!

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, 127 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 :)

Popular amenities for Winter Garden pet-friendly home rentals

When is the best time to visit Winter Garden?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ411ﺩ.ﺇ426ﺩ.ﺇ411ﺩ.ﺇ411ﺩ.ﺇ404ﺩ.ﺇ393ﺩ.ﺇ408ﺩ.ﺇ404ﺩ.ﺇ382ﺩ.ﺇ404ﺩ.ﺇ419ﺩ.ﺇ488
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about vacation rentals that are pet-friendly in Winter Garden

  • Total vacation rentals

    Explore 30 vacation rentals in Winter Garden

  • Nightly prices starting at

    Winter Garden vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 1,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Winter Garden vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Garden rentals

  • 4.9 Average rating

    Winter Garden stays are highly rated by guests—averaging 4.9 out of 5!