Winter Garden vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Winter Garden

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

Superhost

Guest suite in Winter Garden

4.81 out of 5 average rating, 256 reviews

Designer Guest Suite Near Disney/Universal/DT

This newly renovated, modern, and clean apartment has been freshly designed with wonderful & bright colors and all new furnishings. Everything is thoughtfully selected to create the perfect Airbnb stay. You'll have coffee, decaf, tea, 200mbps Wi-Fi, and high-end mattresses with thick memory foam toppers for the perfect night's sleep. You'll stay in the Orlando area, 20min from Disney/Universal/DT Orlando, and minutes from DT Winter Garden, shopping center, & famous 22mile West Orange Bike trail

Oct 23 – 30

G$30,395 GYD per night
Guest favorite

Home in Orlando

4.94 out of 5 average rating, 121 reviews

10 Minutes to Universal - Charming Private Home

Beautiful newly remodeled home centrally located. 3 bedrooms (2 King 1 Queen) and 2 full baths (1 walk in shower w/ grab bars). Carport. Huge and private yard to enjoy! Comfortable living room with big screen TV, couches and lazyboy recliners. Kitchen is fully stocked for cooking. Office desk and chair. Washer and Dryer. 10 Minutes to Universal Studios and just minutes more to International Drive, Mall of Millenia, Florida Mall, or Disney. Grocery, liquor, pizza, chinese within a 5 minute walk.

May 8 – 15

G$25,395 GYD per night
Guest favorite

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.

Aug 27 – Sep 3

G$22,971 GYD per night

Popular amenities for Winter Garden vacation 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 vacation rentals in Winter Garden

Guest favorite

Guest suite in Orlando

4.98 out of 5 average rating, 297 reviews

A SUITE RETREAT with a Garden View in the City

Oct 23 – 30

G$16,719 GYD per night
Guest favorite

Apartment in Clermont

4.93 out of 5 average rating, 246 reviews

1 bed/1 bath cozy apt. full kit. pvt. ent. New AC.

Jun 10 – 17

G$22,919 GYD per night
Guest favorite

Apartment in Winter Park

4.95 out of 5 average rating, 280 reviews

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

Nov 1 – 8

G$24,186 GYD per night
Guest favorite

Townhouse in Winter Park

4.98 out of 5 average rating, 195 reviews

Beautiful Downtown Winter Park

Nov 19 – 26

G$26,527 GYD per night
Guest favorite

Cottage in Tavares

4.97 out of 5 average rating, 204 reviews

Lakeside Cottage on Lake Dora

Nov 15 – 22

G$29,608 GYD per night
Guest favorite

Guest suite in Orlando

4.88 out of 5 average rating, 525 reviews

The Groves (2)

Sep 3 – 10

G$10,837 GYD per night
Guest favorite

Home in Winter Garden

4.88 out of 5 average rating, 16 reviews

Pet Friendly Winter Garden Get-Away near Orlando

Dec 7 – 14

G$16,760 GYD per night
Guest favorite

Guesthouse in Winter Garden

4.94 out of 5 average rating, 47 reviews

Blue Heron Bungalow

Jul 11 – 18

G$21,501 GYD per night
Guest favorite

Home in Winter Garden

4.94 out of 5 average rating, 17 reviews

Cozy home in Winter Garden

Jul 4 – 11

G$27,922 GYD per night
Guest favorite

Tiny home in Winter Garden

4.92 out of 5 average rating, 38 reviews

Enchanted TINY HOME SUITE - Downtown Winter Garden

Jul 30 – Aug 6

G$20,630 GYD per night
Guest favorite

Farm stay in Winter Garden

4.95 out of 5 average rating, 44 reviews

Carriage House Studio Apt Peaceful & Private Ranch

Jul 1 – 8

G$31,172 GYD per night
Guest favorite

Cottage in Winter Garden

4.89 out of 5 average rating, 84 reviews

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

Mar 21 – 28

G$32,680 GYD per night

Other great vacation rentals in Winter Garden

Guest favorite

Guest suite in Apopka

4.97 out of 5 average rating, 30 reviews

Private Deluxe Apartment, 1000 sqft with pool

Aug 4 – 11

G$23,059 GYD per night
Guest favorite

Home in Winter Garden

4.9 out of 5 average rating, 42 reviews

Winter Garden Experience

Oct 16 – 23

G$42,455 GYD per night
Guest favorite

Cottage in Clermont

4.96 out of 5 average rating, 54 reviews

A-Frame Cottage near Disney, Universal, & Lakes

Dec 3 – 10

G$29,560 GYD per night
Superhost

Apartment in Windermere

4.83 out of 5 average rating, 52 reviews

Private Garage Apt., 5 Miles from Disney World

Oct 7 – 14

G$24,078 GYD per night
Guest favorite

Apartment in Windermere

5.0 out of 5 average rating, 18 reviews

2BD Apt+LakeView+Balcony, Resort Style Pool, Wi-Fi

Sep 6 – 13

G$34,026 GYD per night
Guest favorite

Guesthouse in Ocoee

4.93 out of 5 average rating, 28 reviews

25-30 min. Disney, Universal.

Apr 7 – 14

G$16,194 GYD per night
Guest favorite

Home in Winter Garden

4.93 out of 5 average rating, 86 reviews

Luxury Home Winter Garden Near Disney & Universals

Jan 4 – 11

G$41,493 GYD per night
Guest favorite

Apartment in Clermont

4.94 out of 5 average rating, 47 reviews

Relaxing 1-Bedroom Farm Retreat. Pets welcome!

Jun 30 – Jul 7

G$19,156 GYD per night
Guest favorite

Condo in Winter Garden

4.92 out of 5 average rating, 73 reviews

Spacious Condo 10min to Disney with private patio!

Sep 25 – Oct 2

G$23,376 GYD per night
Guest favorite

Home in Winter Garden

4.89 out of 5 average rating, 56 reviews

WATERFRONTWinterGdnHSE+VIEWS+Dock+Wildlife+Firepit

Oct 18 – 25

G$107,661 GYD per night
Guest favorite

Home in Clermont

4.96 out of 5 average rating, 28 reviews

Updated Centrally Located Suite 839

Jun 26 – Jul 3

G$29,644 GYD per night
Guest favorite

Guesthouse in Clermont

4.94 out of 5 average rating, 49 reviews

Coastal Cottage in Clermont

Jun 16 – 23

G$27,984 GYD per night

Quick stats about vacation 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

3.5K reviews

Frequently Asked Questions

  • Where should I stay in Winter Garden?

    Make yourself at home in Winter Garden by choosing from our most frequently booked neighborhoods. We have over 40 vacation rentals in Johns Lake Point, and over 210 vacation rentals in Tildenville.

  • Are there vacation rentals with a dedicated workspace in Winter Garden?

    Yes! Work meets play with ease at over 40 vacation rentals in Winter Garden featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winter Garden?

    Four-legged friends are welcome in Winter Garden. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there Winter Garden vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Winter Garden, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Winter Garden have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Winter Garden. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Garden have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Winter Garden. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Garden have wifi?

    Absolutely! We offer over 70 house rentals with wifi in Winter Garden. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Winter Garden?

    Winter Garden has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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