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.

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Top guest favourite
Home in Mount Dora
4.97 out of 5 average rating, 106 reviews

Beautiful Mount Dora Charmer with Lake Ola Views

Step back in time in this beautifully updated Mount Dora home filled w/ original charm & character of the 1960’s! The entire 3bed/2bath home is private, fully fenced & yours to enjoy! Wake up to birds singing, a breathtaking view of Lake Ola & cozy up by the Tennessee stone fireplace. Inspired by Mid century design w/ several pieces remaining from the original owner of 60 years! The back yard is a relaxing dream filled w/ incredible landscape including oak, powder puff, magnolia & tabulia trees.

Top guest favourite
A spacious outdoor area features a large pool with crystal-clear water, accompanied by a hot tub and a soothing water fountain. Surrounding the pool, a stone patio hosts multiple seating areas beneath a pergola, providing a serene setting for relaxation.
Home in Orlando
4.97 out of 5 average rating, 104 reviews

Unique Spacious Home w/ Pool near Downtown Orlando

Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

Guest favourite
The exterior of the house showcases a striking blend of wood and stone finishes, featuring large windows that illuminate the interior. An expansive, clear blue pool reflects the sky, with a bridge extending over the water leading to the main entrance.
Villa in Orlando
4.95 out of 5 average rating, 124 reviews

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

Top guest favourite
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, 114 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 favourite
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, 226 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 favourite
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, 153 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 favourite
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, 222 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 favourite
Home in Davenport
4.99 out of 5 average rating, 101 reviews

Pool & Spa Oasis/Golf Retreat/Near Disney/3BR Home

Escape to paradise at our Davenport home, only 11 miles from Walt Disney World! Relax by the huge pool with spa, and savor BBQ delights. Rest in well-designed bedrooms: Master room with a king bed, second room with a queen bed, and third one with two twin beds. Experience ultimate fun in the game room, indulge your culinary skills in the fully equipped kitchen, and step out onto the greens from our backyard on a golf course. Don't miss out, book now and make the most of your vacation

Top guest favourite
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, 191 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 favourite
Guest house in Clermont
4.98 out of 5 average rating, 133 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 favourite
The living area features a modern design with sleek white tiles and a stylish light fixture. A glass coffee table sits in front of a comfortable sofa, while the fully equipped kitchen with bar seating is visible in the background, complemented by a contemporary color palette.
Townhouse in Clermont
4.96 out of 5 average rating, 99 reviews

The silver cottage

This unique place has a style all its own. Dogs Welcome! ( Pet fee applies). Newly renovated featuring white tiles throughout, granite countertops, fully equipped kitchen, smart tv in all bedrooms and living space. Modern stylish garden bath with floating cabinetry. This unit also features work space with desk and chair. One car garage and extra parking space included at no extra charge. At this time we are only accepting one pet per reservation, max 30lbs.

Guest favourite
A spacious living area features a sectional sofa and a round coffee table, complemented by soft lighting. A television is placed on a low cabinet, while decorative plants and a wall art piece add visual interest. Natural light enters through a window, enhancing the inviting atmosphere.
Flat in Winter Garden
4.89 out of 5 average rating, 169 reviews

Stay A While

Welcome to Your Secluded Getaway Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m | Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont: 14m Outlets: 28m | Florida Mall: 35m | I-Drive: 40m Travel MCO Airport: 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks. storage only

Popular amenities for Winter Garden pet-friendly home rentals

When is the best time to visit Winter Garden?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price€122€111€121€97€95€92€96€95€90€95€98€115
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°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 €34 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!