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House vacation rentals in Winter Garden

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Top-rated house rentals in Winter Garden

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

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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 private, screened-in pool area features a sparkling blue pool with a built-in hot tub on one side. Sunlight reflects off the water, creating a serene environment, while surrounding greenery provides a sense of privacy.
Home in Clermont
4.93 out of 5 average rating, 161 reviews

Stylish Villa Private Pool-SPA Near Parks Disney!

Stylish villa 4 bed/3 bath family home with private facing pool & SPA, living room, family room, kitchen, breakfast bar, dining table, a game room, Wi-Fi, smart TVs, wheelchair accessible, close to the parks, shops, and restaurants, Pool & SPA heater at additional cost, located at Glenbrook community. We have it all and much more to enjoy. The pool & SPA heater fee is $25 (USD) per day. The BBQ grill is an additional $45 (USD) charge for the whole stay, including 1 propane gas and cleaning.

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, 174 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}

Guest favorite
An open-concept living area features a modern kitchen with a central island and stainless steel appliances. A comfortable sectional sofa is paired with wooden armchairs, and a round coffee table sits in the center. Large windows bring natural light into the space, enhancing the clean, neutral decor.
Home in Apopka
4.86 out of 5 average rating, 148 reviews

2-bedroom home with pool near Kings Landings!

Private 2-bedroom home with a queen size bed and a separate room with a twin daybed. There are many exciting things to do in the area! My home is about 30 minutes from theme parks such as Universal, SeaWorld, and Disney parks. Extra activities to do are Southern Hill Farms to pick fresh fruits and sunflowers. Want more fun in the sun? There is Wekiwa National park which is 7 miles away for kayaking and water springs. Additionally, Kings Landings is located 10 minutes away.

Superhost
A modern living space is presented, featuring an open layout that includes a kitchen with dark cabinetry and a dining area with a circular table. Stylish bar stools line the kitchen counter, and a television is positioned in the lounge area, which is complemented by a cozy blue sofa.
Home in Ocoee
4.82 out of 5 average rating, 134 reviews

★★House in Little Loma ★★ 4 beds ★ Jacuzzi

Enjoy this charming remodeled home with 3 bedrooms, 2 bathrooms, and a JACUZZI waiting for your and your family. Each room has a TV. The kitchen has all you need to make a home cook dinner after a really fun day!!! A minute walking distance to VANDERGRIFT CENTRAL PARK which features: Baseball Fields (Lighted), Basketball Court, Volleyball, Boardwalk, Concession Stand, Fishing Dock, Football Field, Non-Motorized Boat Launch, Parking, Picnic Tables, Playground, Restrooms

Top guest favorite
A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.
Home in Clermont
4.94 out of 5 average rating, 141 reviews

Spacious Bungalow with Pool and Courtyard

Whether you seek relaxation or adventure, this house offers the best of both worlds! Relax in this spacious bungalow with a courtyard, pool, hot tub, and fire pit! Take a short walk to downtown Clermont and discover the charming shops, restaurants, and breweries! Explore the sights and attractions that Central Florida has to offer! Whether you crave the vibrancy of downtown or the tranquility of your own oasis, this property offers the best of both worlds!

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.

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, 164 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
Home in Winter Garden
4.98 out of 5 average rating, 125 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)

Top guest favorite
Home in Spring Lake
4.97 out of 5 average rating, 873 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!

Superhost
An inviting A-Frame log home is displayed, featuring natural wood paneling and a spacious sleeping area with a neatly made bed. A cozy living space is visible, showcasing a smart TV and comfortable seating. A serene bathroom is equipped with modern fixtures and light blue walls.
Home in Clermont
4.82 out of 5 average rating, 104 reviews

Pumba's Place - FUN, Lake, Pool- NO Cleaning fees!

Pumba’s Place is a renovated A-Frame log cabin in the family-friendly gated community of Vacation Village. Perfect for families and adventurers, it features fast WiFi, smart TVs, a fully stocked kitchen & laundry. Enjoy private Lake Louisa access, a heated Olympic pool, tennis, basketball, biking trails & more. Just 25 mins to Disney and 5 mins to Downtown Clermont & the National Training Center

Popular amenities for Winter Garden house rentals

When is the best time to visit Winter Garden?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$23,310 GYDG$20,396 GYDG$20,813 GYDG$20,813 GYDG$20,605 GYDG$22,270 GYDG$20,813 GYDG$20,813 GYDG$18,523 GYDG$23,310 GYDG$25,600 GYDG$27,265 GYD
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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 G$6,244 GYD 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!

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