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.
Apartment in Clermont
4.93 out of 5 average rating, 246 reviews1 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
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.
May 1 – 8
Cottage in Winter Garden
4.99 out of 5 average rating, 102 reviewsCome 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Garden vacation rentals
Stay near Winter Garden's top sights
Other great vacation rentals in Winter Garden
Guest suite in Orlando
4.98 out of 5 average rating, 296 reviewsA SUITE RETREAT with a Garden View in the City
Mar 13 – 20
Guest suite in Orlando
4.97 out of 5 average rating, 211 reviews2/2 Spacious Modern House
Jul 17 – 24
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
Jun 15 – 22
Guest suite in Orlando
4.88 out of 5 average rating, 525 reviewsThe Groves (2)
Sep 7 – 14
Guesthouse in Orlando
4.94 out of 5 average rating, 127 reviewsJefferson St. Cottage
Jan 25 – Feb 1
Guest suite in Orlando
4.99 out of 5 average rating, 238 reviewsLocation, Location, Location near all attractions
Oct 24 – 31
Guesthouse in Orlando
4.94 out of 5 average rating, 207 reviewsModern Guest Studio (Private) Pool / Spa available
Dec 31 – Jan 7
Guest suite in Orlando
4.94 out of 5 average rating, 188 reviewsLuxury Suite Near Disney & Downtown Orlando
Apr 6 – 13
Home in Winter Garden
4.88 out of 5 average rating, 16 reviewsPet Friendly Winter Garden Get-Away near Orlando
Sep 22 – 29
Guesthouse in Winter Garden
4.94 out of 5 average rating, 47 reviewsBlue Heron Bungalow
Nov 10 – 17
Home in Winter Garden
4.94 out of 5 average rating, 17 reviewsCozy home in Winter Garden
Jul 4 – 11
Other great vacation rentals in Winter Garden
Apartment in Ocoee
4.96 out of 5 average rating, 47 reviewsCompletely Private and Cozy Studio
Aug 8 – 15
Home in Winter Garden
4.9 out of 5 average rating, 42 reviewsWinter Garden Experience
Oct 16 – 23
Apartment in Windermere
5.0 out of 5 average rating, 17 reviews1BR Cozy Oasis+King Bed+Fast WiFi+Pool+Gym
Aug 16 – 23
Guest suite in Oakland
4.83 out of 5 average rating, 41 reviewsHistoric, Private Quarters with Kitchenette
Jul 23 – 30
Guest suite in Apopka
4.97 out of 5 average rating, 30 reviewsPrivate Deluxe Apartment, 1000 sqft with pool
May 19 – 26
Cottage in Clermont
4.96 out of 5 average rating, 54 reviewsA-Frame Cottage near Disney, Universal, & Lakes
Aug 21 – 28
Apartment in Windermere
4.83 out of 5 average rating, 52 reviewsPrivate Garage Apt., 5 Miles from Disney World
Oct 7 – 14
Guesthouse in Clermont
4.94 out of 5 average rating, 49 reviewsCoastal Cottage in Clermont
Apr 24 – May 1
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!
Oct 15 – 22
Apartment in Windermere
5.0 out of 5 average rating, 17 reviews2BD Apt+LakeView+Balcony, Resort Style Pool, Wi-Fi
May 25 – Jun 1
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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