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.

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Top guest favorite
Home in Orlando
5 out of 5 average rating, 177 reviews

Orlando Cactus House! 5min from Universal Studios

Get ready to enjoy and relax in our beautiful cozyhouse, completely renovated just 5 min from UNIVERSAL STUDIOS,This gem is part of a DUPLEX with independent entrances. it is perfect for a quiet and comfortable stay close to all the tourist attractions. Volcano Bay(7mint)Convention Center International Drive(15min) Epic Universe(15min) Sea World(17mint)/Aquatica(15mint) Kia Center (20mins) Orlando International Airport(21 min) Magic Kingdom(23 min) Our cozy house is in the center of EVERYTHING

Top guest favorite
Home in Minneola
4.98 out of 5 average rating, 153 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.

Guest favorite
A spacious game room features a blue pool table at its center, surrounded by light wooden flooring. To one side, seating options include modern chairs and a couch, with natural light filtering through large windows. The kitchen and dining area are visible in the background.
Home in Orlando
4.94 out of 5 average rating, 140 reviews

Lake House Retreat w/ Firepit - Centrally Located

Our cozy lakefront retreat in the heart of Orlando boasts a fenced-in backyard with stunning lake views. Relax around the fire pit/wood-burning grill or enjoy a game of corn hole or ping pong on the porch. With a pool table in our game room and comfortable sleeping arrangements for up to 8 guests, this is the perfect place to relax and unwind. Located just minutes from downtown, Disney World, Universal Studios, and the airport, this is an ideal spot to experience all the area has to offer.

Top guest favorite
A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.
Guest suite in College Park
4.97 out of 5 average rating, 271 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

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
A vibrant living area is portrayed with bold turquoise walls. A light-colored sofa with decorative cushions is centered in the foreground, leading to a well-lit dining area in the background. Shelves adorned with books and decor can be seen alongside a workspace illuminated by soft lighting.
Townhouse in Clermont
4.92 out of 5 average rating, 263 reviews

Paradise Escape

Your paradise escape is finally here! In the Sunshine State, paradise is just one perfect cocktail away. Leave your worries away and relax - you are in a sunshine state of mind! My "paradise island" is conveniently located in the heart of Clermont. You will certainly enjoy the welcoming and colorful ambiance! Combination lock instructions will be sent after arrival time confirmation. I look forward to hosting all my guests and making sure that they have an unforgettable experience!

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, 173 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, 121 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 modern pool house is featured, with large glass doors opening to a swimming pool. The exterior includes a tree emblem and a small seating area with a chair. Sun loungers are positioned near the pool, surrounded by lush grass and a wooden fence.
Guesthouse in College Park
4.98 out of 5 average rating, 100 reviews

Amazing New Pool House!

A great choice for both tourists and business travelers looking for great value. A swimming pool and backyard oasis just outside your door! Awesome location close to the best neighborhoods in Orlando. We just built this pool house with a fully private entrance (side gate around main house). Totally comfy 1-bedroom house sleeps up to 3 people. Full kitchen and luxurious bathroom. Friendly hosts look forward to sharing their backyard paradise with you.

Top guest favorite
A modern living area features a vibrant red sofa and two gray armchairs, offering ample seating. A stylish coffee table sits centrally, complemented by a small plant centerpiece. A large television is positioned opposite the seating, with soft lighting from table lamps creating a welcoming ambiance.
Apartment in Clermont
4.98 out of 5 average rating, 128 reviews

Modern Suite in the Heart of Downtown Clermont 101

Experience luxury and excitement in our chic modern suite nestled in the vibrant heart of downtown Clermont. Perfectly poised for Triathletes, this suite is a beacon of comfort and convenience, mere steps away from charming downtown boutiques, delightful restaurants and local breweries. The location is unparalleled with close proximity to the celebrated Clermont/Minneola Trail, esteemed host of prestigious Triathlons and the serene Waterfront Park.

Superhost
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, 284 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.

Top guest favorite
A serene lakeside view is presented, featuring calm waters reflecting a gradient of soft colors during sunset. A wooden dock extends into the water, framed by lush greenery and grasses. The landscape conveys a tranquil setting, inviting moments of reflection in nature.
Home in Winter Garden
4.98 out of 5 average rating, 123 reviews

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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

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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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 1,280 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!