Some info has been automatically translated. Show original language

House holiday 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 favourite
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 favourite
Home in Orlando
5 out of 5 average rating, 175 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 favourite
A compact kitchen features white cabinetry and modern stainless steel appliances. An electric stovetop is positioned beside a microwave, with a coffee maker and various kitchen utensils visible. A small refrigerator stands nearby, complemented by decorative items on the open shelves.
Home in Kissimmee
4.99 out of 5 average rating, 159 reviews

Private Suite with Independent Entrance

Private Suite with Independent Entrance Kissimmee, Fl Enjoy a modern and fully equipped private suite, perfect for couples or travelers looking for comfort, privacy, and a relaxing stay just minutes away from Orlando’s top attractions. 📍Perfect Location Conveniently located in Kissimmee, just minutes from: 🎢 Disney World 🎬 Universal Studios 🌊 SeaWorld and Aquatica You’ll also find restaurants, supermarkets, outlets, and gas stations nearby an excellent location for your Orlando vacation!

Top guest favourite
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 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, 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.

Guest favourite
The kitchen features modern appliances, including a full-size stainless steel refrigerator and a microwave. A granite countertop offers workspace, complemented by light wood cabinetry. A small dining nook is positioned against the wall, with two stools and a potted plant adding a touch of decor.
Home in Metro West
4.94 out of 5 average rating, 113 reviews

Private Studio (Near Universal-Premiun Outlets)

Our cozy private studio to fill all your needs for short or long staying, just like home! Great for 2people looking to enjoy all that Orlando has to offer! Studio is attached to our home but has private entrance. Perfect for those guests who want to save money but like privacy and comfort. Near to ; Valencia College, Universal Studios and CityWalk, Downtown Orlando, International drive, Premium Outlet, Florida Mall,Disney Studios, SeaWorld ,Disney Springs, Orlando International Airport

Top guest favourite
A modern living space showcases a cozy sectional sofa adorned with patterned pillows, alongside a decorative rug. The open floor plan leads to a bright kitchen area with bar seating. Natural light fills the room through large windows, enhancing the warm wood flooring.
Home in Minneola
4.95 out of 5 average rating, 197 reviews

Modern Villa in Minneola near Disney, Orlando

Newly renovated modern villa 3 bed/2 bath cozy home nestled amongst beautiful oak trees and close to Downtown Clermont, National training center, and 35 minutes to Disney World and other major attractions. Home features soft comfy beds including one king, one queen, and two twin beds all with 3" memory foam mattress toppers. The kitchen is fully stocked with spices, coffee/tea station, blender and slow cooker. Game room located in the garage is equipped with foosball and air hockey.

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 favourite
A modern living area features an L-shaped sofa in a neutral tone, accompanied by a geometric area rug. A dining set with two blue chairs surrounds a small table by the window, separated from the entryway by decorative elements. A large wall-mounted TV is positioned across from the seating.
Home in Windhover
4.96 out of 5 average rating, 138 reviews

New & Modern 1 Bedroom - Walk to Universal Studios

Welcome to your vacation home, walking distance to Universal! This unit is part of a duplex and includes a full kitchen, with shared laundry on site. Located walking distance to Universal Studios, & within a short drive to Epic Universe, Volcano Bay Water Park, Wizarding World of Harry Potter, Disney World, Disney Springs, Sea World, Malls/Outlets, Downtown Orlando, Amway Center, Dr Phillips Performing Arts Center, International Drive, Convention Center.

Top guest favourite
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, 150 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 favourite
A bright bedroom features a spacious bed with a plush headboard and soft linens. Natural light enters through two windows, illuminating the room. A round mirror is mounted on the wall above a minimalistic desk with a chair, adding functionality to the cozy space.
Home in College Park
4.95 out of 5 average rating, 148 reviews

Priv. Modern Cozy CP 1B/1Ba Suite near DT Orl & WP

Private & Comfortable 1 bd/ba suite in a 2021 townhome with front view windows, queen size bed, walk-in shower& private entrance. Equipped w/ ceiling and portable fans, Roku smart TV, mini fridge/freezer, microwave, and Keurig. Located in a safe, quiet, walkable neighborhood. 5 minutes of College Park shops, 10 minutes from downtown Orlando, 25 minutes to Universal Studios, 30 minutes to Orlando International Airport, & 40 minutes to Disney.

Guest favourite
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.

Popular amenities for house rentals in Winter Garden

When is the best time to visit Winter Garden?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$142 SGD$124 SGD$126 SGD$126 SGD$125 SGD$135 SGD$126 SGD$126 SGD$113 SGD$142 SGD$155 SGD$166 SGD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about house rentals in Winter Garden

  • Total holiday rentals

    Explore 60 holiday rentals in Winter Garden

  • Nightly prices starting at

    Winter Garden holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 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!

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