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.

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Guest favorite

Guesthouse in Clermont

4.98 out of 5 average rating, 101 reviews

Downtown Apartment - Walk to Lake, Shops & Dining

This stylish apartment, in Downtown Clermont is @ the center of the coast-to-coast bike trail. Enjoy the quaint lake town experience to the fullest without having to drive anywhere. Lakefront, breweries, retail, dining- all within a 3 min walk! Best features indoors include comfy beds, a double shower, smart TV, & cozy aesthetics. The space is well stocked w/ all the essentials. Small appliances for cooking include an air fryer, crockpot & skillet. Garage storage available 4 recreational gear.

May 1 – 8

€ 148 per night

Guest favorite

Guesthouse in Orlando

4.94 out of 5 average rating, 212 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

Dec 6 – 13

€ 134 per night

Guest favorite

Home in Winter Garden

4.92 out of 5 average rating, 165 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.

Dec 12 – 19

€ 133 per night

Guest favorite

Cottage in Winter Garden

4.99 out of 5 average rating, 105 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.

Dec 27 – Jan 3

€ 204 per night

Guest favorite

Townhouse in Clermont

4.93 out of 5 average rating, 191 reviews

Paradise Escape

Your paradise escape is finally here! In the Sunshine State, paradise is just one perfect cocktail away. Leave your worries away and relax - you are in a sunshine state of mind! My "paradise island" is conveniently located in the heart of Clermont. You will certainly enjoy the welcoming and colorful ambiance! Combination lock instructions will be sent after arrival time confirmation. I look forward to hosting all my guests and making sure that they have an unforgettable experience!

Aug 30 – Sep 6

€ 132 per night

Guest favorite

Home in Clermont

4.99 out of 5 average rating, 156 reviews

Clermont Cottage Near the Lake

Enjoy your stay in beautiful sunny FL in our fully renovated 2 bed/2 bath home. We've added ENHANCED CLEANING AND DISINFECTING after every guest's stay. This home is located in a quiet neighborhood less than a mile from Clermont's WATERFRONT PARK and the WEST ORANGE TRAIL. It's a great location for Triathlons and activities at Victory Point. If you are visiting to enjoy Universal Studios and Disney, they are only 28 miles away! Come stay at our home with everything you'll need!

Sep 25 – Oct 2

€ 140 per night

Guest favorite

Home in Clermont

4.93 out of 5 average rating, 187 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow full disinfecting of the house.

Jul 31 – Aug 7

€ 191 per night

Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 634 reviews

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.

Dec 28 – Jan 4

€ 141 per night

Guest favorite

Guest suite in Orlando

4.99 out of 5 average rating, 241 reviews

Location, Location, Location near all attractions

This is a poolside in-law apartment with a full kitchen, bedroom, full bath and a living room located in a quiet, residential neighborhood in an upper scale part of town. It has a king size bed & will accommodate 2 adults comfortably. This in-law apartment is an addition that was built onto the back of our home. It is completely closed off from the our main house and has it's own main entrance so it is private. So, you will have the apartment all to yourselves.

Jan 4 – 11

€ 166 per night

Superhost

Guest suite in Winter Garden

4.82 out of 5 average rating, 286 reviews

Private In-Law Suite Near Disney/Universal/DT

This newly renovated, modern, and clean Mother-in-Law Suite is freshly designed with 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 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 28 – Nov 4

€ 99 per night

Guest favorite

Treehouse in Saint Cloud

4.97 out of 5 average rating, 788 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. For a video tour type the following link into your browser: https://tinyurl.com/a72vevp5 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; meemaws-country -cottage which sleeps six.

Feb 27 – Mar 6

€ 182 per night

Guest favorite

Guesthouse in Windermere

4.94 out of 5 average rating, 239 reviews

Small Guesthouse 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.

Aug 7 – 14

€ 136 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winter Garden vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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

4.81 out of 5 average rating, 501 reviews

The Groves (1)

Sep 27 – Oct 4

€ 69 per night

Guest favorite

Guesthouse in Winter Garden

4.94 out of 5 average rating, 48 reviews

Blue Heron Bungalow

Nov 28 – Dec 5

€ 116 per night

Superhost