Holiday rentals in Winter Garden

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Top-rated holiday rentals in Winter Garden

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

Guest favourite

Home in Winter Garden

4.92 out of 5 average rating, 164 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.

27 Aug – 3 Sep

₹9,172 per night
Guest favourite

Cottage in Winter Garden

4.99 out of 5 average rating, 102 reviews

Come Stay In The Heart Of Winter Garden

Stay in a completely renovated 1937 cottage that's located in the heart of historic downtown Winter Garden. It's walking distance from all of the shops, restaurants, and events (including the #1 rated farmers market in the nation every Saturday) that make Winter Garden one of the most desirable cities in Florida. Sit on the front porch and watch as people bike and jog on the famous West Orange Trail, or rent a bike from the corner and join them. The home is close to all major highways.

27 Aug – 3 Sep

₹14,625 per night
Guest favourite

Home in Clermont

4.99 out of 5 average rating, 153 reviews

Clermont Cottage Near the Lake

Enjoy your stay in beautiful sunny FL in our fully renovated 2 bed/2 bath home. We've added ENHANCED CLEANING AND DISINFECTING after every guest's stay. This home is located in a quiet neighborhood less than a mile from Clermont's WATERFRONT PARK and the WEST ORANGE TRAIL. It's a great location for Triathlons and activities at Victory Point. If you are visiting to enjoy Universal Studios and Disney, they are only 28 miles away! Come stay at our home with everything you'll need!

17–24 Sep

₹10,273 per night

Popular amenities for Winter Garden holiday rentals

Stay near Winter Garden's top sights

Winter Garden Downtown Pavilion and Farmers Market43 locals recommend
Miller's Ale House - Winter Garden3 locals recommend
The Whole Enchilada Fresh Mexican Grill & Bar9 locals recommend
Plant St. Market25 locals recommend
Crooked Can Brewing Company40 locals recommend
4 Rivers Smokehouse - Winter Garden BBQ7 locals recommend

Other great holiday rentals in Winter Garden

Guest favourite

Home in Winter Garden

4.94 out of 5 average rating, 17 reviews

Cozy home in Winter Garden

4–11 Jul

₹11,119 per night
Guest favourite

Farm stay in Winter Garden

4.95 out of 5 average rating, 44 reviews

Carriage House Studio Apt Peaceful & Private Ranch

1–8 Jul

₹12,359 per night
Guest favourite

Tiny home in Winter Garden

4.92 out of 5 average rating, 38 reviews

Enchanted TINY HOME SUITE - Downtown Winter Garden

30 Jul – 6 Aug

₹8,215 per night
Guest favourite

Cottage in Winter Garden

4.89 out of 5 average rating, 84 reviews

3 br/2 ba Downtown Winter Garden Cottage w\fence

21–28 Mar

₹13,014 per night
Guest favourite

Guest suite in Oakland

4.83 out of 5 average rating, 41 reviews

Historic, Private Quarters with Kitchenette

28 Jun – 5 Jul

₹10,430 per night
Guest favourite

Guest house in Winter Garden

4.96 out of 5 average rating, 25 reviews

Guest house in Winter Garden

22–29 May

₹13,273 per night
Guest favourite

Flat in Ocoee

4.96 out of 5 average rating, 47 reviews

Completely Private and Cozy Studio

27 Aug – 3 Sep

₹6,934 per night
Guest favourite

Flat in Windermere

5.0 out of 5 average rating, 17 reviews

1BR Cozy Oasis+King Bed+Fast WiFi+Pool+Gym

16–23 Aug

₹11,335 per night
Guest favourite

Guest suite in Apopka

4.97 out of 5 average rating, 30 reviews

Private Deluxe Apartment, 1000 sqft with pool

4–11 Aug

₹9,182 per night
Guest favourite

Home in Winter Garden

4.9 out of 5 average rating, 42 reviews

Winter Garden Experience

16–23 Oct

₹16,906 per night
Superhost

Flat in Windermere

4.83 out of 5 average rating, 52 reviews

Private Garage Apt., 5 Miles from Disney World

7–14 Oct

₹9,588 per night
Guest favourite

Cottage in Clermont

4.96 out of 5 average rating, 54 reviews

A-Frame Cottage near Disney, Universal, & Lakes

3–10 Dec

₹11,771 per night

Quick stats about holiday rentals in Winter Garden

Total rentals

110 properties

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

40 properties are a good fit for families

Total number of reviews

3.5T reviews

Destinations to explore

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