
Vacation rentals with outdoor seating in Winter Garden
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Winter Garden
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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!

Horse Farm & (2) Tiny Homes to choose from
Rest & Relaxation at its finest! This Tiny Home is set to impress! Add on the natural beauty of the rolling hills of Howey, with some of Thee most impressive sunsets over the water & this becomes an Incredible Unique Stay! After sunset, enjoy a nice campfire in your firepit (wood avail) as you STARGAZE into the night! This Tiny Home is fully equipped with ALL of your needs. On the back 3 acres of property, from which you will have your own Golf Cart to travel to/from our Designate Parking Area.

Waterfront EPIC views, Dock, wildlife Near Disney
Experience the stunning sunrise views over Lake Apopka from our newly refurbished, elegantly appointed 4-bedroom, 2.5-bath vacation home in Winter Garden, FL. This haven is close to Orlando's Universal Studios 20 min, Disney World 25 min) & shopping (Mall of Millenia, premium outlets 17 min) Modern amenities, spacious layout that promises relaxation and convenience making the perfect home for exploring all local attractions and enjoying Florida's natural beauty. Minutes from City Swimming Pool

New Mid Century-Modern Studio
Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

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.

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.

The Little Treehouse 2 at Country Club of Orlando
With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

Chic Vibes Comfy King Bed Next to Parks/Food/shops
Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

★★House in Little Loma ★★ 4 beds ★ Jacuzzi
Enjoy this charming remodeled home with 3 bedrooms, 2 bathrooms, and a JACUZZI waiting for your and your family. Each room has a TV. The kitchen has all you need to make a home cook dinner after a really fun day!!! A minute walking distance to VANDERGRIFT CENTRAL PARK which features: Baseball Fields (Lighted), Basketball Court, Volleyball, Boardwalk, Concession Stand, Fishing Dock, Football Field, Non-Motorized Boat Launch, Parking, Picnic Tables, Playground, Restrooms

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.

Modern Suite in the Heart of Downtown Clermont 101
Attention Triathletes! Newer, Modern Suite, "Heart" of Downtown Clermont. Steps to quaint downtown restaurants, shops, and local Breweries. Conveniently close to the Clermont/Minneola Trail, Host of the Prestigious Triathlons and the Waterfront Park. Unique location for athletes! See all Clermont has to offer including the National Training Center and enjoy close proximity to Walt Disney World, Sea World and International Drive. Only 30 Min. to Downtown Orlando.

Downtown Winter Garden, Florida
Charming two bedroom, one bathroom home just three blocks from downtown Winter Garden Florida. Across the street from the West Orange Bike Trail and walking distance to restaurants, Splash pond, shopping and Farmers Market. The fenced in back yard is shaded by a 100 year old live oak tree. There is a “no pet policy” at the house. We do not accept guests under the age of 12. There are NO cameras on or around the property. I respect the privacy of my guests.
Popular amenities for Winter Garden outdoor seating rentals
House rentals with outdoor seating

Private 3-bedroom pool & waterfront home

Private Suite with Independent Entrance

Beautiful House Completely Remodeled

Spacious Bungalow with Private Pool and Courtyard

Orlando Cactus House! 5min from Universal Studios

Pool + Heated spa Family friendly King suite Oasis

Lakefront in West Orlando Florida

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney
Apartment rentals with outdoor seating

King Bed Apartment, Close to Disney

Private Rooftop Suite! No resort fees! 5 star

Relaxing 1-Bedroom Farm Retreat. Pets welcome!

3121-402 Resort Lake View Disney Universal Orlando

Escape to Orlando near Universal Studios.

Apartamento 313 Club House -Davenport/Orlando- FL

Chic 1-Bedroom Apt in Lake Nona

One Bedroom close to Disney
Condo rentals with outdoor seating

Resort Style Sunshine Oasis near Theme Parks

303_To Infinity & the Ocean Breeze Apartment

tranquil resort, near Disney, no extra fee.208

ORLANDO SUITE@ UNIVERSAL/DISNEY/CONVENTION CENTER

Suites at Lake Buena Vista close Disney Spring A2

Waterfront Condo minutes to Disney & Universal

Chic Disney Resort Condo • Pool Access Near Parks

IS4-405 - Lakefront condo - Newly Renovated
When is the best time to visit Winter Garden?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $166 CAD | $158 CAD | $155 CAD | $155 CAD | $152 CAD | $141 CAD | $138 CAD | $173 CAD | $147 CAD | $144 CAD | $166 CAD | $166 CAD |
| Avg. temp | 16 °C | 18 °C | 20 °C | 22 °C | 25 °C | 27 °C | 28 °C | 28 °C | 27 °C | 24 °C | 20 °C | 17 °C |
Quick stats about vacation rentals with outdoor seating in Winter Garden

Total vacation rentals
Explore 30 vacation rentals in Winter Garden

Nightly prices starting at
Winter Garden vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 2,360 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Winter Garden vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winter Garden rentals

4.9 Average rating
Winter Garden stays are highly rated by guests—averaging 4.9 out of 5!
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Walt Disney World Resort Golf
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Old Town Kissimmee
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Universal's Islands of Adventure
- Ventura Country Club
- Shingle Creek Golf Club




