Vacation rentals in Winter Garden

4.97 out of 5 average rating, 121 reviews

Experience Downtown Winter Garden, One Block from It All

This 1920's home has been fully updated to include new kitchen, bath, fixtures, appliances, and more. The home has 2 bedrooms with one having a king bed and the other a queen bed. Beds feature super comfy Tuft & Needle mattresses ! Kitchen covers all of your basic cooking needs, has stainless appliances, refrigerator with ice maker, and Keurig coffee maker. The dining table comfortably seats 4 and is perfect for a meal or to use as a work space. New full size washer and dryer in carport laundry room. Grab a bottle of wine from Tony's less than 1 block away and relax in the screened-in front porch. Depending on the season grab a Valencia orange off the citrus tree in the back yard. You can use the entire home! There are 2 spacious bedrooms, 1 bath, dining room, kitchen, and a full washer and dryer in the laundry room (located in the carport). Owners live less than a mile away and are available as needed. We can meet you if you need anything! Just a few short steps from the famous Farmer's Market, Crooked Can Brewing, the Plant Street Market, the West Orange Bike Trail, Garden Theater, countless restaurants, and all that Downtown Winter Garden has to offer. This historic home is the perfect escape from the bustle of the tourist district, less than 30 minutes to Disney World, 25 minutes to Universal Studios, 30 minutes to Sea World. You can easily walk the 1 block to Plant St where most of the amenities of Downtown Winter Garden are located. You'll be just 25 minutes from Universal Studios and I-Drive via the Turnpike and 25 minutes from Disney via hwy 429. Also if you are into biking you can rent them at Wheel Works or the West Orange trail head and hit the famous West Orange Trail. There is a 2 car covered carport on site. Across the street from an elementary school so during the school year, there is some traffic in the morning and afternoon. Please be mindful and a good neighbor!

Tiny home in Winter Garden

4.95 out of 5 average rating, 75 reviews

Enchanted TINY HOME SUITE - Downtown Winter Garden

Your unique Winter Garden experience begins at this enchanted tiny home, 2 blocks away from the golf cart district. Either hideaway at this retreat with everything you need to relax, or take a walk or bike ride to the nearby shops, restaurants, history, art, nature trails, and more. From live music & farmers markets in town, to a car ride to wine tasting at the vineyards, or let your inner child run wild and take a drive to Disney, Universal, or SeaWorld! This convenient location offers plenty.

Apartment in Winter Garden

4.98 out of 5 average rating, 40 reviews

StylishAptWtrGrdnOppLake&Prk&Yrd

*Brand new one bedroom apartment near downtown Winter Garden, across from Lake Apopka and Newton Park *Private fenced yard with BBQ, picnic table, and hammock. *Short golf cart ride to shops and restaurants in downtown Winter Garden *Opposite Newton Park with its breathtaking sunset views and many amenities (playground, public pool, boat ramp) and wildlife *Nearby Tanner Hall is available for private events and functions *Less than 30 min to Orlando Airport, Universal, Disney, and major malls

Apartment in Winter Garden

5 out of 5 average rating, 5 reviews

Winter Garden Charm, Near Disney

2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Garden, this beautifully designed 2-bedroom, 2-bath apartment offers the perfect blend of modern luxury and small-town charm — just 20 minutes from Walt Disney World and Orlando’s top attractions. Located on the iconic Plant Street, you’ll be steps away from historic downtown Winter Garden, home to popular restaurants, boutiques, coffee shops, and the famous West Orange Trail.

4.91 out of 5 average rating, 202 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.

4.99 out of 5 average rating, 153 reviews

Cottage in Winter Garden

The Heart of Winter Garden: Walk to shops & dining

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.

4.82 out of 5 average rating, 158 reviews

Guest suite in Ocoee

Charming Studio with Garden (West of Orlando)

We are proud to present a No Smoking on Premises Airbnb. My studio apartment is just the perfect place to hangout. There is a nice fire pit on the back patio and logs to relax with friends and enjoy the warm weather. The black gravel parking space in front is for the use of the Studio guests. The main house guests park in the driveway. We have an onsight massage therapist that can come to your place as an upgrade. Text me for more details. Please NO SMOKING on premises.

4.98 out of 5 average rating, 123 reviews

Home in Minneola

Cozy Studio Near Disney/Universal/Training center

This cozy stylish studio, detached guest house is perfect for short-term or extended stay in the beautiful city of Minneola. Sleeps 2, can accommodate up to 4. Features a large backyard and a fire pit. Close to Downtown Clermont, National Training Center, and 35 minutes to Disney World and other major attractions. This tranquil space features a queen bed with 3" memory foam mattress topper and a spacious living space that has a Multi-Functional Sofa that converts into a Bed.

4.96 out of 5 average rating, 979 reviews

Treehouse in St. Cloud

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

4.94 out of 5 average rating, 269 reviews

Guesthouse in Windermere

Paradise nook near Orlando's theme parks

A quick escape to an amazing stay. Immersed in green tropical vegetation, our unique tiny Guesthouse is where we usually host our visiting family and friends from out of town. It is also open to Airbnb guests who are visiting Greater Orlando! Perfect location to escape from the hustle and bustle of a big city, yet close to everything. Take advantage of its availability and join the great experience our guests are always talking about.

4.98 out of 5 average rating, 200 reviews

Guest suite in Montverde

Green Mountain Getaway (No indoor Smoking or Pets)

(Non Smoker & No Pets) A secluded lot surrounded by FL’s beautiful tropical landscape. Golfer? We are 3 min. from the beautiful Bella Collina's luxury 18 hole golf course, a Nick Faldo design. Also 8 min. from Sanctuary Ridge Golf Club, a more affordable option. Biker? “Killarney Station", is an affordable place to rent bikes or bring your own to ride the beautiful 26 mile trail. 28 minutes to all the attractions!

4.98 out of 5 average rating, 43 reviews

Cozy cottage in Winter Garden

This newly renovated, cute and cozy home is just what you're looking for your vacation in Orlando/Winter Garden area! It is in close proximity to Winter Garden Downtown with great restaurants, cafes and farmers market. Also the famous West Orange bike trail is just 4 minutes away. If you plan to visit Disney or Universal they're less than 30 minutes away. You'll have a great time at this comfortable place to stay.

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Popular amenities for Winter Garden vacation rentals

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Other great vacation rentals in Winter Garden

4.92 out of 5 average rating, 62 reviews

Private room in Ocoee

Simple & Clean 2

CaitlinRating, 5 stars3 weeks ago

Have been to quite a few Airbnb’s in the area, this is definitely the best deal available. Safe neighborhood, clean house, and all the amenities you could need to be comfortable. Everything is labeled, easy to find, and host is very responsive as well. Highly recommend.

Hotel room in Kissimmee

4.78 out of 5 average rating, 923 reviews

Your Orlando Escape | Infinity Pool. Gym. 1BR

TanyaRating, 5 stars2 weeks ago

Loved it! Very peaceful, easy access to the room, pool area. Not far from Disney resort or restaurants.

Private room in Winter Garden

4.9 out of 5 average rating, 237 reviews

20-30 min. Disney, Universal & Downtown Orlando

BrysonRating, 5 stars1 week ago

Raana's home is really beautiful and very peaceful. Even though I didn't get the chance to talk with her in person due to our different schedules she was always responsive to my messages and I felt comfortable in her home. I stayed with her the night before I moved into my new apartment complex as I started my Disney College Program and after a couple of days of stress her home helped me to relax and get a good night of sleep before my big day.

4.89 out of 5 average rating, 47 reviews

Private room in Ocoee

Centrally located Private Studio

LatoyaRating, 5 stars2 weeks ago

Very quiet place, very neat and description matches pictures.

Private room in Winter Garden

4.96 out of 5 average rating, 28 reviews

Private Room close to Disney

GerardoRating, 5 stars2 months ago

Karen is a great host, quick to respond to any of my questions, flexible with the arrival time and accomodations for my dog. Highly recommended specially if you have a pet traveling with you

Tiny home in Winter Garden

4.82 out of 5 average rating, 45 reviews

FunTropicalTinyHomeGolfCartLake

StephenRating, 5 stars2 weeks ago

Great tiny home experience, fun private backyard area, gorgeous location right across from a park on Lake Apopka (beautiful sunsets over the water!), 1 mile away from downtown Winter Garden, golf cart available that's more affordable and convenient than going to one of the places in town. My family and I loved it! 😄

4.89 out of 5 average rating, 19 reviews

Cottage in Winter Garden

The Swift House

PaigeRating, 5 stars1 week ago

What a great stay! Sweta was beyond helpful, meeting us at the unit, showing us through, making local recommendations for us. We had a little difficulty with the remotes (okay, we're old) and she was there in 2 minutes to walk us through the operation. Not only did she have our choice of wine chilled and waiting, but she delivered dog treats for our pooch, which were much appreciated. The area is incredible: a quiet street of mostly vintage houses, but within only a few blocks of wonderful restaurants, pubs, music, & activity... none of which you hear from this cottage. Honestly, there is no better location for a stay in Winter Garden, and if you're considering Orlando, it's a welcome reprieve from the shockingly busy city and still only 15 minutes to all the vacation attractions.