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 suite in Winter Garden
4.81 out of 5 average rating, 256 reviewsDesigner 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
Home in Orlando
4.94 out of 5 average rating, 121 reviews10 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
Home in Winter Garden
4.92 out of 5 average rating, 164 reviewsCozy 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
Vacation rentals for every style
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Popular amenities for Winter Garden vacation rentals
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Other great vacation rentals in Winter Garden
Guest suite in Orlando
4.98 out of 5 average rating, 297 reviewsA SUITE RETREAT with a Garden View in the City
Oct 23 – 30
Apartment in Clermont
4.93 out of 5 average rating, 246 reviews1 bed/1 bath cozy apt. full kit. pvt. ent. New AC.
Jun 10 – 17
Apartment in Winter Park
4.95 out of 5 average rating, 280 reviewsGet a Little Glam in a Retro Palm Beach-Style Boudoir
Nov 1 – 8
Townhouse in Winter Park
4.98 out of 5 average rating, 195 reviewsBeautiful Downtown Winter Park
Nov 19 – 26
Cottage in Tavares
4.97 out of 5 average rating, 204 reviewsLakeside Cottage on Lake Dora
Nov 15 – 22
Guest suite in Orlando
4.88 out of 5 average rating, 525 reviewsThe Groves (2)
Sep 3 – 10
Home in Winter Garden
4.88 out of 5 average rating, 16 reviewsPet Friendly Winter Garden Get-Away near Orlando
Dec 7 – 14
Guesthouse in Winter Garden
4.94 out of 5 average rating, 47 reviewsBlue Heron Bungalow
Jul 11 – 18
Home in Winter Garden
4.94 out of 5 average rating, 17 reviewsCozy home in Winter Garden
Jul 4 – 11
Tiny home in Winter Garden
4.92 out of 5 average rating, 38 reviewsEnchanted TINY HOME SUITE - Downtown Winter Garden
Jul 30 – Aug 6
Farm stay in Winter Garden
4.95 out of 5 average rating, 44 reviewsCarriage House Studio Apt Peaceful & Private Ranch
Jul 1 – 8
Cottage in Winter Garden
4.89 out of 5 average rating, 84 reviews3 br/2 ba Downtown Winter Garden Cottage w\fence
Mar 21 – 28
Other great vacation rentals in Winter Garden
Guest suite in Apopka
4.97 out of 5 average rating, 30 reviewsPrivate Deluxe Apartment, 1000 sqft with pool
Aug 4 – 11
Home in Winter Garden
4.9 out of 5 average rating, 42 reviewsWinter Garden Experience
Oct 16 – 23
Cottage in Clermont
4.96 out of 5 average rating, 54 reviewsA-Frame Cottage near Disney, Universal, & Lakes
Dec 3 – 10
Apartment in Windermere
4.83 out of 5 average rating, 52 reviewsPrivate Garage Apt., 5 Miles from Disney World
Oct 7 – 14
Apartment in Windermere
5.0 out of 5 average rating, 18 reviews2BD Apt+LakeView+Balcony, Resort Style Pool, Wi-Fi
Sep 6 – 13
Guesthouse in Ocoee
4.93 out of 5 average rating, 28 reviews25-30 min. Disney, Universal.
Apr 7 – 14
Home in Winter Garden
4.93 out of 5 average rating, 86 reviewsLuxury Home Winter Garden Near Disney & Universals
Jan 4 – 11
Apartment in Clermont
4.94 out of 5 average rating, 47 reviewsRelaxing 1-Bedroom Farm Retreat. Pets welcome!
Jun 30 – Jul 7
Condo in Winter Garden
4.92 out of 5 average rating, 73 reviewsSpacious Condo 10min to Disney with private patio!
Sep 25 – Oct 2
Home in Winter Garden
4.89 out of 5 average rating, 56 reviewsWATERFRONTWinterGdnHSE+VIEWS+Dock+Wildlife+Firepit
Oct 18 – 25
Home in Clermont
4.96 out of 5 average rating, 28 reviewsUpdated Centrally Located Suite 839
Jun 26 – Jul 3
Guesthouse in Clermont
4.94 out of 5 average rating, 49 reviewsCoastal Cottage in Clermont
Jun 16 – 23
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.
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