House vacation rentals in Winter Garden

Find and book unique houses on Airbnb

Top-rated house rentals in Winter Garden

Guests agree: these houses are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Top guest favorite
A bright living area features a light gray sofa adorned with yellow and blue cushions, accompanied by a comfortable recliner. A decorative round ottoman sits in the center on a floral area rug. Natural light enters through two large windows, complemented by light-filtering curtains.
Home in Winter Garden
4.97 out of 5 average rating, 129 reviews

Experience Downtown Winter Garden, One Block from It All

This 1920's home has been fully updated to include new kitchen, bath, fixtures, appliances, and more. The home has 2 bedrooms with one having a king bed and the other a queen bed. Beds feature super comfy Tuft & Needle mattresses ! Kitchen covers all of your basic cooking needs, has stainless appliances, refrigerator with ice maker, and Keurig coffee maker. The dining table comfortably seats 4 and is perfect for a meal or to use as a work space. New full size washer and dryer in carport laundry room. Grab a bottle of wine from Tony's less than 1 block away and relax in the screened-in front porch. Depending on the season grab a Valencia orange off the citrus tree in the back yard. You can use the entire home! There are 2 spacious bedrooms, 1 bath, dining room, kitchen, and a full washer and dryer in the laundry room (located in the carport). Owners live less than a mile away and are available as needed. We can meet you if you need anything! Just a few short steps from the famous Farmer's Market, Crooked Can Brewing, the Plant Street Market, the West Orange Bike Trail, Garden Theater, countless restaurants, and all that Downtown Winter Garden has to offer. This historic home is the perfect escape from the bustle of the tourist district, less than 30 minutes to Disney World, 25 minutes to Universal Studios, 30 minutes to Sea World. You can easily walk the 1 block to Plant St where most of the amenities of Downtown Winter Garden are located. You'll be just 25 minutes from Universal Studios and I-Drive via the Turnpike and 25 minutes from Disney via hwy 429. Also if you are into biking you can rent them at Wheel Works or the West Orange trail head and hit the famous West Orange Trail. There is a 2 car covered carport on site. Across the street from an elementary school so during the school year, there is some traffic in the morning and afternoon. Please be mindful and a good neighbor!

Top guest favorite
A single-story home is set within a spacious yard, surrounded by trees and lush greenery. A driveway leads up to the entrance, while Spanish moss dangles from the branches of nearby trees. The sky is partly cloudy, adding to the tranquil atmosphere.
Home in Montverde
4.97 out of 5 average rating, 154 reviews

The Legacy House - your home away from home.

Just a block away from the South Lake Bike Trail System, 18 minutes from beautiful Lake Minneola, and a mere 20 miles from the Disney Parks, and 5 minutes from the Bella Collina wedding venue, this peaceful neighborhood home will be a perfect spot to rest after a full day of fun. This is an ideal spot if you're coming for cycling events, fishing competitions, a wedding or simply to enjoy the most beautiful part of Florida! We hope you chose to book with us; it would be our pleasure to host you!

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
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, 176 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 living area features a cozy couch with a blue and white design, paired with a wooden coffee table at the center. Bright light filters through the window with white blinds. The kitchen is visible in the background, showcasing wooden cabinets and modern appliances.
Home in Clermont
4.97 out of 5 average rating, 106 reviews

Adorable Downtown Lakeview Home 1105

Experience unparalleled comfort and charm in our distinctive Lakeview home, ideally located in downtown Clermont's vibrant heart. This bright and captivating property exudes an inviting aura with its scenic lake views and exceptional decor. Start your day with a refreshing cup of coffee on the serene back porch, take a stroll to the nearby park, or enjoy the array of amenities in the vicinity. Families and athletes alike will enjoy the convenient proximity to key attractions.

Guest favorite
An open studio layout is showcased, featuring a comfortable queen bed with decorative pillows and a soft throw blanket. A multi-functional sofa and coffee table are positioned in front of a flat-screen TV. A dining table for four is also visible, enhancing the inviting atmosphere.
Home in Minneola
4.95 out of 5 average rating, 173 reviews

Cozy Studio Near Disney/Universal/Training center

This cozy stylish studio, detached guest house is perfect for short-term or extended stay in the beautiful city of Minneola. Sleeps 2, can accommodate up to 4. Features a large backyard and a fire pit.  Close to Downtown Clermont, National Training Center, and 35 minutes to Disney World and other major attractions. This tranquil space features a queen bed with 3" memory foam mattress topper and a spacious living space that has a Multi-Functional Sofa that converts into a Bed.

Top guest favorite
A living area features a plush sofa and two armchairs arranged around a circular coffee table. Natural light filters through the window, illuminating the space. A vibrant area rug anchors the seating area, while a bouquet of flowers adds a touch of color on the table.
Home in Winter Garden
4.99 out of 5 average rating, 152 reviews

Downtown Winter Garden, Florida

Charming two bedroom, one bathroom home just three blocks from downtown Winter Garden Florida. Across the street from the West Orange Bike Trail and walking distance to restaurants, Splash pond, shopping and Farmers Market. The back yard is shaded by a 100 year old live oak tree. There is a “no pet policy” at the house. We do not accept guests under the age of 12. There are NO cameras on or around the property. I respect the privacy of my guests.

Top guest favorite
A modern living area features two comfortable sofas, a wooden coffee table, and a vibrant green plant. A sleek television is mounted on the wall, while the open kitchen area showcases contemporary cabinetry and a light backsplash. Natural light flows in through large windows.
Home in Orlando
4.96 out of 5 average rating, 269 reviews

The Lake House - Next to Universal Studios - NEW ♥️

Luxurious, modern and completely remodeled single-family home with lake access in the prestigious Doctor Phillips neighborhood. Centrally located hops away from all Orlando has to offer, 1.1 miles (3 minutes) from Universal Studios Theme Parks, 9.5 miles to Disney World and 5 miles to Seaworld Orlando. No other Airbnb offers this upscale living space with stunning outdoor area to kick back and enjoy after a long day at the parks.

Guest favorite
A scenic view overlooking Starke Lake is presented, featuring a spacious deck with railing. A tranquil pool is visible in the foreground, while vibrant clouds reflect the colors of a sunset in the background, enhancing the natural beauty of the surroundings.
Home in Ocoee
4.89 out of 5 average rating, 166 reviews

Lakeview Sunsets with Loft Escape West of Orlando

We are proud to announce No Smoking on premises property. This Duplex A Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.

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
4.96 out of 5 average rating, 128 reviews

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)

Guest favorite
Home in Spring Lake
4.97 out of 5 average rating, 878 reviews

The Little Tree House at Country Club of Orlando

Urban cool meets childhood fancy in this upper separate downtown boutique bungalow in the Country Club of Orlando. The Little Treehouse is the perfect Central Florida romantic getaway for two in this 260 sq. ft. 2nd floor renovated 1926 carriage house. Conveniently located 5 minutes from Downtown, Amway Arena, Camping World Stadium and just 15 minutes to Universal Studio and 25 minutes from Disney!

Popular amenities for Winter Garden house rentals

When is the best time to visit Winter Garden?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ411ﺩ.ﺇ360ﺩ.ﺇ367ﺩ.ﺇ367ﺩ.ﺇ364ﺩ.ﺇ393ﺩ.ﺇ367ﺩ.ﺇ367ﺩ.ﺇ327ﺩ.ﺇ411ﺩ.ﺇ452ﺩ.ﺇ481
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about house rentals in Winter Garden

  • Total vacation rentals

    Explore 60 vacation rentals in Winter Garden

  • Nightly prices starting at

    Winter Garden vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 2,930 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 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!

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Winter Garden
  6. House rentals