Holiday houses in Winter Garden

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Top-rated holiday rentals in Winter Garden

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Guest favourite

Guesthouse in Orlando

5.0 out of 5 average rating, 162 reviews

Treehouse Inn Downtown Orlando, 2 bedrooms 2 bath

Treehouse in Downtown Orlando is surrounded by majestic heritage Oaks. Two Bed Two Bath with a Mini-Master & full Kitchen. Very private deck near Bamboo Hedge. Two blocks from a small neighborhood Deli serving breakfast, lunch and dinner with Great coffee & Craft beers. We are walking distance from popular Thornton Park pubs and restaurants. Lake Greenwood and Lake Davis are close by for a leisurely walk or brisk jog. Enhanced cleaning in use. Jakob and Marty are happy to help with your stay.

3 – 10 July

$1,534 AUD total

Guest favourite

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.

11 – 18 May

$1,752 AUD total

Guest favourite

Home in Winter Garden

4.92 out of 5 average rating, 166 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.

12 – 19 Aug

$1,463 AUD total

Guest favourite

Cottage in Winter Garden

4.99 out of 5 average rating, 106 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.

22 – 29 Aug

$2,376 AUD total

Guest favourite

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!

22 – 29 Mar

$1,354 AUD total

Guest favourite

Tiny home in Orlando

4.98 out of 5 average rating, 636 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.

6 – 13 Aug

$1,616 AUD total

Superhost

Home in Winter Garden

4.9 out of 5 average rating, 20 reviews

Pet Friendly Winter Garden Get-Away near Orlando

Enjoy easy access to everything around Orlando from this perfectly located home base. Disney, Universal, SeaWorld, and more are only a short drive away, and downtown Winter Garden is a gem!✨ This pet-friendly and comfortable studio will be an easy place to rest from all the magic and fun!🪄 Quaint and cozy, we have what matters! A very comfortable new king bed, a great TV and wifi, coffee (or tea - if that's your preference), and endless hot water in the shower!🤗

13 – 20 May

$970 AUD total

Guest favourite

Tiny home in Winter Garden

4.93 out of 5 average rating, 40 reviews

Enchanted TINY HOME SUITE - Downtown Winter Garden

Your unique Winter Garden experience begins at this enchanted tiny home. 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 much more. From live music and 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.

11 – 18 Nov

$1,359 AUD total

Guest favourite

Guesthouse in Winter Park

4.98 out of 5 average rating, 249 reviews

Private and Peaceful with Full Kitchen

Welcome to our spacious, secure getaway tucked in a quiet Winter Park neighborhood. Enjoy full kitchen, hardwood floors, high ceilings, superfast WiFi and lots of TV steaming options, walk-in closets and walk-in shower. The hosts live in a separate space attached to the house. Your suite and patio are completely private. Please register all guests when making your reservation. For everyone’s safety, we ask that there be no visitors besides registered guests.

19 – 26 May

$1,316 AUD total

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

10 – 17 Aug

$949 AUD total

Guest favourite

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.

20 – 27 Jan

$2,086 AUD total

Guest favourite

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.

27 Dec – 3 Jan

$1,783 AUD total