Holiday houses in Winter Garden

Find and book unique accommodation on Airbnb

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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

Guest suite in Orlando

4.98 out of 5 average rating, 302 reviews

A SUITE RETREAT with a Garden View in the City

27 May – 3 Jun

$150 NZD per night
Guest favourite

Guesthouse in Orlando

4.94 out of 5 average rating, 212 reviews

Modern Guest Studio (Private) Pool / Spa available

29 Jan – 5 Feb

$239 NZD per night
Guest favourite

Guest suite in Orlando

4.81 out of 5 average rating, 503 reviews

The Groves (1)

17–24 Sep

$121 NZD per night
Guest favourite

Home in Clermont

4.93 out of 5 average rating, 187 reviews

Lake Front Home with private Dock on Lake Louisa

16–23 Apr

$338 NZD per night
Guest favourite

Apartment in Winter Park

4.95 out of 5 average rating, 283 reviews

Get a Little Glam in a Retro Palm Beach-Style Boudoir

8–15 Dec

$239 NZD per night
Superhost

Home in Winter Garden

4.9 out of 5 average rating, 20 reviews

Pet Friendly Winter Garden Get-Away near Orlando

13–20 May

$150 NZD per night
Guest favourite

Tiny home in Winter Garden

4.93 out of 5 average rating, 40 reviews

Enchanted TINY HOME SUITE - Downtown Winter Garden

2–9 Nov

$210 NZD per night
Guest favourite

Guesthouse in Winter Garden

4.94 out of 5 average rating, 49 reviews

Blue Heron Bungalow

27 Dec – 3 Jan

$205 NZD per night

Quick stats about holiday rentals in Winter Garden

  • Total rentals

    100 properties

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Rentals with a pool

    20 properties have a pool

  • Pet-friendly rentals

    20 properties allow pets

  • Family-friendly rentals

    30 properties are a good fit for families

  • Total number of reviews

    3.6K reviews

Destinations to explore

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