Holiday houses in Ocoee

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Top-rated holiday rentals in Ocoee

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Top Guest favourite

Home in Winter Garden

4.97 out of 5 average rating, 125 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

Guesthouse in Ocoee

4.92 out of 5 average rating, 50 reviews

In-Law Suite with lake view in the gated community

This gated residential neighborhood called Wesmere is very quiet & safe. The owner (retired nurse) lives next door- no children, no pets. Comfortably furnished. High speed Wifi, smart TV & outdoor security cameras. Kitchenette has fridge, microwave, electric stove, coffee maker, tea kettle, etc. Private entrance into a suite- a large study room with a day bed. Large bedroom has a beautiful lake view with excess to the back yard & pool. Bathroom has indoor & outdoor showers, large jacuzzi-tub.

Top Guest favourite

Home in Ocoee

4.95 out of 5 average rating, 37 reviews

Cozy home near Disney with a king size bed

Welcome to your next getaway! This roomy, sunlit 4-bedroom, 3-bath home offers comfort, privacy, and plenty of space for everyone — including your pets! With two luxurious master suites, a homey atmosphere, it’s ideal for families, friends, or multiple couples traveling together. Just minutes from downtown Winter Garden, West Orange A short drive to Orlando attractions like Universal Studios and Walt Disney World. Close to local parks, lakes, and pet-friendly spots for walks and adventures.

Top Guest favourite

Guesthouse in Ocoee

5 out of 5 average rating, 84 reviews

NEW 1BRM Guesthouse | King Bed | Central Florida

Nestled in a private and central location, this newly constructed space offers everything needed for a relaxing stay. The space is perfect for up to four guests, featuring a king size bed, full kitchen, and smart TVs in every room. Enjoy the convenience of high-speed Wi-Fi, a spacious shower, washer / dryer, and a private driveway. Located close to Downtown, Theme Parks, the Stadiums, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for your short term or long term stay.

Top Guest favourite

Guest suite in College Park

4.97 out of 5 average rating, 215 reviews

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.

Top Guest favourite

Cottage in Winter Garden

4.99 out of 5 average rating, 163 reviews

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.

Guest favourite

Guest suite in Ocoee

4.83 out of 5 average rating, 162 reviews

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.

Top Guest favourite

Home in Ocoee

4.98 out of 5 average rating, 63 reviews

Orlando/Downtown/GameRoom/Disney/Lake

Indulge in the comfort of this three-bedroom, two-bath single-family residence. Beautifully styled home for family fun trips, romantic getaway or business trips. BBQ grill in your own fenced back yard. Come sit by the fire pit and relax. We also have fruit trees and a garden! We are next to all major highways, theme parks, golfing, lake and shopping. Downtown Orlando is 15 minutes away. Come stay with us and we will make you feel right at home with our southern hospitality!

Top Guest favourite

Treehouse in St. Cloud

4.96 out of 5 average rating, 1,017 reviews

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.

Guest favourite

Home in Winter Garden

4.96 out of 5 average rating, 52 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.

Top Guest favourite

Guesthouse in Orlando

5 out of 5 average rating, 15 reviews

Sunny Side Stay

Escape to this stylish and comfortable 1-bedroom, 1-bathroom pool house—perfect for a relaxing getaway or a weekend staycation. Enjoy indoor entertainment with pool table, and unwind outdoors in the beautifully landscaped yard featuring multiple seating areas ideal for morning coffee or evening drinks. Whether you’re here to relax or explore, this cozy guest space offers privacy, comfort, and a touch of fun.

Guest favourite

Apartment in Ocoee

4.95 out of 5 average rating, 122 reviews

Completely Private and Cozy Studio

Private, Peaceful, and Centrally-located studio with 1 Bedroom, Kitchenette, Private Bath, and Private Entry. Located close to Downtown, Theme Parks, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for a short term or long term stay. Special accommodations available upon request. Come bask in the Florida Sun!