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Pet-friendly vacation rentals in Winter Garden

Find and book unique pet-friendly homes on Airbnb

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 G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,270 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

  • 4.8 Average rating

    Winter Garden stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated pet-friendly home rentals in Winter Garden

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Minneola
4.98 out of 5 average rating, 158 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
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, 222 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, 215 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, 182 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
Guesthouse in Clermont
4.98 out of 5 average rating, 126 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, 140 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
Cottage in Clermont
4.92 out of 5 average rating, 138 reviews

Beautiful country house

Take the whole family to this fantastic place with many areas to have fun. We have 5 acres of land just for you, beautiful country house in the only hills of the state of Florida, you will enjoy the tranquility, privacy, connection with nature and you will witness a beautiful sunset unparalleled, stay and watch the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and hiking. NOTE: if you want an event, check first for our rates

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, 104 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.

Superhost
A screened patio features a clear view of the serene lake, with sunlight reflecting off the water. Lounge chairs are positioned around the pool, designed for relaxation. Soft greenery and a wooden deck enhance the backdrop, creating an inviting outdoor space.
Home in Orlando
4.85 out of 5 average rating, 100 reviews

Lake House - Downtown Orlando

Welcome to lakefront paradise! This charming residence in Downtown Orlando, offers an oasis of tranquility and comfort for the whole family. Located in a picturesque lakefront setting, this home is the perfect place to enjoy the serenity of the water and create unforgettable memories. With spacious indoor and outdoor areas, there's plenty of room to relax and entertain. - Pool Heather Available upon request(extra charge due to electricity)

Top guest favorite
A single-story residence is shown with a light-colored exterior and a brown shingle roof. The garage door is centered, flanked by two sets of evenly spaced windows with white shutters. A neatly manicured lawn and mailbox complete the front view.
Home in Clermont
4.88 out of 5 average rating, 155 reviews

Our Poolhome by the Mouse house with Game Room.

Spacious four-bedroom, two-bathroom residence conveniently located near Disney and Universal Studios. Enjoy the expansive screened-in south-facing pool and fenced backyard for ultimate privacy. Entertain in the fantastic game room, perfect for family fun. Rest assured with 24/7 monitoring of security cameras installed outside the property. Additionally, the pool can be heated upon request for an additional fee—reach out for current rates.

Guest favorite
A charming guesthouse is nestled among lush tropical vegetation, surrounded by diverse greenery and tall trees. Sunlight filters through the leaves, casting dappled light on the exterior and patio area, creating a serene and inviting atmosphere.
Guesthouse in Windermere
4.93 out of 5 average rating, 286 reviews

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.

Popular amenities for Winter Garden pet-friendly home rentals

When is the best time to visit Winter Garden?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$23,431 GYDG$24,268 GYDG$23,431 GYDG$23,431 GYDG$23,013 GYDG$22,385 GYDG$23,222 GYDG$23,013 GYDG$21,757 GYDG$23,013 GYDG$23,850 GYDG$27,824 GYD
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