House holiday rentals in Winter Garden

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Top-rated house rentals in Winter Garden

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Guest favourite

Home in Winter Garden

4.96 out of 5 average rating, 113 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!

Guest favourite

Home in Orlando

4.95 out of 5 average rating, 183 reviews

10 Minutes to Universal - Charming Private Home

Beautiful newly remodeled home centrally located. 3 bedrooms (2 King 1 Queen) and 2 full baths (1 walk in shower w/ grab bars). Carport. Huge and private yard to enjoy! Comfortable living room with big screen TV, couches and lazyboy recliners. Kitchen is fully stocked for cooking. Office desk and chair. Washer and Dryer. 10 Minutes to Universal Studios and just minutes more to International Drive, Mall of Millenia, Florida Mall, or Disney. Grocery, liquor, pizza, chinese within a 5 minute walk.

Guest favourite

Home in Apopka

4.88 out of 5 average rating, 119 reviews

Country Pool home on 2 acres-30 minutes to Disney

Relax with friends and family at this country pool home just northwest of Orlando and all of the attractions! 30 minutes to Disney and Universal Studios. 10 minutes to Historic Mount Dora. 8 minutes to Kelly Park/Rock Springs Run. One hour to Daytona Beach. What a great location and place to stay to explore Central Florida! Pets are welcome! 3 queen beds & couch **The hot tub you might see in a photo is not advertised because it is not operational. The pool is very refreshing but not heated.

Guest favourite

Home in Winter Garden

4.91 out of 5 average rating, 116 reviews

Luxury Home Winter Garden Near Disney & Universals

Looking for luxury and convenience? Stay in our newly renovated home, just minutes from Disney and Universal. With a one-minute walk to local shops, bars, restaurants, and farmers market, you'll experience the best Winter Garden has to offer. Book now for a memorable stay! Golf Cart and Bike Rentals Available! Send DM NO PETS Strict No Parties or Gatherings Allowed Quiet Hours from 9pm-8am as this is a family friendly neighborhood No more than 8 guests Only 2 Cars allowed on the property.

Guest favourite

Home in Sanford

4.97 out of 5 average rating, 173 reviews

Famous Tiny Houseboat Historic Downtown Sanford FL

The Famous Tiny Houseboat named ‘Downtown Dharma’ is a gorgeous floating houseboat parked at the Monroe Harbour Marina in beautiful Historic Downtown Sanford, Florida just 20 minutes North of Orlando FL. It was made famous after being built on HGTV’s Tiny House Hunters TV show in Season 4, Episode 12. Over 500 sq ft, entire house on the water, full bath, kitchen, living room, bedroom, chill space (extra couch for tiny person) and porch. Super unique and cool space you're sure to love!

Guest favourite

Home in Winter Garden

4.91 out of 5 average rating, 186 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.

Guest favourite

Home in Winter Park

4.94 out of 5 average rating, 138 reviews

Modern, Quiet & Cozy - Entire house 2/2

Embrace Tranquil Living in Winter Park, Florida. Located in a quiet neighborhood NE of downtown this recently renovated house is modern, clean, and cozy. Short drive to other great attractions in Orlando. Its central location is minutes away from Park Ave, the University of Central Florida, Rollins College, Full Sail University, Downtown Orlando, MCO Airport, Amway Center, Dr. Phillips, Science Center, Orlando City Stadium, and much more! You need to be at least 18 years old to book.

Guest favourite

Home in Minneola

4.96 out of 5 average rating, 109 reviews

Modern Villa in Minneola near Disney, Orlando

Newly renovated modern villa 3 bed/2 bath cozy home nestled amongst beautiful oak trees and close to Downtown Clermont, National training center, and 35 minutes to Disney World and other major attractions. Home features soft comfy beds including one king, one queen, and two twin beds all with 3" memory foam mattress toppers. The kitchen is fully stocked with spices, coffee/tea station, blender and slow cooker. Game room located in the garage is equipped with foosball and air hockey.

Guest favourite

Home in Winter Garden

4.99 out of 5 average rating, 125 reviews

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.

Guest favourite

Home in Orlando

4.91 out of 5 average rating, 164 reviews

Hidden Gem in SODO! - MCO ~16min

Enjoy your stay in this cozy & comfy 1 bedroom and bath house located in the desirable South Downtown Orlando. Rest well in the large queen size bed, with a 65 inch smart TV, equipped with Netflix. Restaurants and stores in walking distance. Wifi & parking are included MCO Airport: ~16 Min Drive Disney: ~20 Min Drive Universal Studios: ~15 Min Drive Hollywood Studios: ~20 Min Drive Sea World: ~15 Min Drive Downtown Orlando: ~5 Min Drive

Guest favourite

Home in Ocoee

4.89 out of 5 average rating, 136 reviews

Lakeview Sunsets with Loft Escape West of Orlando

We are proud to announce No Smoking on premises property. This Duplex A Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.

Guest favourite

Home in Clermont

5 out of 5 average rating, 100 reviews

Cozy Home near Waterfront Park

This newly constructed unique and cozy home sits in the heart of lakes near downtown, shops, restaurants, and breweries. It is surrounded by tropical greenery that lets you relax and wind down in a private backyard. It is within walking distance to the lake beach, biking trail, splash pad, and playground. There are plenty of activities for you to enjoy!