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.

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.

This is a 1 bedroom 1 bath apartment with a private entrance, full bath, full kitchen with full-size appliances. Located in downtown Clermont, Florida. Convenient to all central Florida Theme Parks (40 min. drive), shopping including groceries, clothing, electronics, gas, jewelry, pharmacies, theater, and many more. The new Carrier AC system has an internal UV light, BiPolar Ionization system and 1900 Filtrete filter that all kill and remove bacteria, viruses, and mold in the air .

Jun 7 – 14

€ 107 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.

May 1 – 8

€ 126 per night
Guest favorite

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.

Aug 20 – 27

€ 202 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, 296 reviews

A SUITE RETREAT with a Garden View in the City

Mar 13 – 20

€ 87 per night
Guest favorite

Guest suite in Orlando

4.97 out of 5 average rating, 211 reviews

2/2 Spacious Modern House

Jul 17 – 24

€ 157 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

€ 133 per night
Guest favorite

Townhouse in Winter Park

4.98 out of 5 average rating, 195 reviews

Beautiful Downtown Winter Park

Jun 15 – 22

€ 145 per night
Guest favorite

Guest suite in Orlando

4.88 out of 5 average rating, 525 reviews

The Groves (2)

Sep 7 – 14

€ 56 per night
Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 127 reviews

Jefferson St. Cottage

Jan 25 – Feb 1

€ 107 per night
Guest favorite

Guest suite in Orlando

4.99 out of 5 average rating, 238 reviews

Location, Location, Location near all attractions

Oct 24 – 31

€ 163 per night
Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 207 reviews

Modern Guest Studio (Private) Pool / Spa available

Dec 31 – Jan 7

€ 130 per night
Guest favorite

Guest suite in Orlando

4.94 out of 5 average rating, 188 reviews

Luxury Suite Near Disney & Downtown Orlando

Apr 6 – 13

€ 117 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

Sep 22 – 29

€ 91 per night
Guest favorite

Guesthouse in Winter Garden

4.94 out of 5 average rating, 47 reviews

Blue Heron Bungalow

Nov 10 – 17

€ 113 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

€ 144 per night

Other great vacation rentals in Winter Garden

Guest favorite

Apartment in Ocoee

4.96 out of 5 average rating, 47 reviews

Completely Private and Cozy Studio

Aug 8 – 15

€ 85 per night
Guest favorite

Home in Winter Garden

4.9 out of 5 average rating, 42 reviews

Winter Garden Experience

Oct 16 – 23

€ 229 per night
Guest favorite

Apartment in Windermere

5.0 out of 5 average rating, 17 reviews

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

Aug 16 – 23

€ 157 per night
Guest favorite

Guest suite in Oakland

4.83 out of 5 average rating, 41 reviews

Historic, Private Quarters with Kitchenette

Jul 23 – 30

€ 158 per night
Guest favorite

Guest suite in Apopka

4.97 out of 5 average rating, 30 reviews

Private Deluxe Apartment, 1000 sqft with pool

May 19 – 26

€ 126 per night
Guest favorite

Cottage in Clermont

4.96 out of 5 average rating, 54 reviews

A-Frame Cottage near Disney, Universal, & Lakes

Aug 21 – 28

€ 161 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

€ 133 per night
Guest favorite

Guesthouse in Clermont

4.94 out of 5 average rating, 49 reviews

Coastal Cottage in Clermont

Apr 24 – May 1

€ 122 per night
Guest favorite

Guesthouse in Ocoee

4.93 out of 5 average rating, 28 reviews

25-30 min. Disney, Universal.

Apr 7 – 14

€ 95 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

€ 226 per night
Guest favorite

Apartment in Clermont

4.94 out of 5 average rating, 47 reviews

Relaxing 1-Bedroom Farm Retreat. Pets welcome!

Oct 15 – 22

€ 108 per night
Guest favorite

Apartment in Windermere

5.0 out of 5 average rating, 17 reviews

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

May 25 – Jun 1

€ 190 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