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Vacation rentals in Ocoee

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Top-rated vacation rentals in Ocoee

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
A bright living area features a light gray sofa adorned with yellow and blue cushions, accompanied by a comfortable recliner. A decorative round ottoman sits in the center on a floral area rug. Natural light enters through two large windows, complemented by light-filtering curtains.
Home in Winter Garden
4.97 out of 5 average rating, 129 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!

Top guest favourite
An exterior view of the guesthouse displays a quaint two-story structure with a black garage and a welcoming front porch. Surrounding greenery provides a natural setting, enhancing the privacy of the location. The two upper windows are adorned with large curtains.
Guesthouse in Ocoee
5 out of 5 average rating, 116 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
A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.
Guest suite in College Park
4.97 out of 5 average rating, 268 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.

Guest favourite
A small, white house is framed by vibrant greenery and colorful plants. The front door, painted blue, adds a pop of color, while large windows allow light to fill the space. A wooden deck leads up to the entrance, enhancing the welcoming appeal.
Home in Winter Garden
4.91 out of 5 average rating, 214 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
The kitchen features modern appliances, including a full-size stainless steel refrigerator and a microwave. A granite countertop offers workspace, complemented by light wood cabinetry. A small dining nook is positioned against the wall, with two stools and a potted plant adding a touch of decor.
Home in Metro West
4.94 out of 5 average rating, 113 reviews

Private Studio (Near Universal-Premiun Outlets)

Our cozy private studio to fill all your needs for short or long staying, just like home! Great for 2people looking to enjoy all that Orlando has to offer! Studio is attached to our home but has private entrance. Perfect for those guests who want to save money but like privacy and comfort. Near to ; Valencia College, Universal Studios and CityWalk, Downtown Orlando, International drive, Premium Outlet, Florida Mall,Disney Studios, SeaWorld ,Disney Springs, Orlando International Airport

Top guest favourite
The exterior of a renovated cottage is showcased, featuring a welcoming front porch with two wooden chairs. Potted plants are placed on the porch and along the walkway, while a wooden fence stands in the background, enhancing privacy.
Cottage in Winter Garden
4.99 out of 5 average rating, 180 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
A pathway leads towards a white exterior home, framed by lush greenery and colorful flowers. Natural light reflects off the water view in the distance, enhancing the serene ambiance. The driveway is bordered by a smooth surface, providing easy access to the entrance.
Guest suite in Ocoee
4.83 out of 5 average rating, 173 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.

Superhost
A modern living space is presented, featuring an open layout that includes a kitchen with dark cabinetry and a dining area with a circular table. Stylish bar stools line the kitchen counter, and a television is positioned in the lounge area, which is complemented by a cozy blue sofa.
Home in Ocoee
4.82 out of 5 average rating, 134 reviews

★★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

Guest favourite
The bedroom features a spacious bed covered with crisp white linens, accented by decorative pillows. A wooden dresser stands against the wall, alongside a chair and circular shelf with decorative items. Natural light enters through a window, contributing to a bright ambiance.
Guest suite in Winter Garden
4.83 out of 5 average rating, 393 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

Top guest favourite
A living area features a plush sofa and two armchairs arranged around a circular coffee table. Natural light filters through the window, illuminating the space. A vibrant area rug anchors the seating area, while a bouquet of flowers adds a touch of color on the table.
Home in Winter Garden
4.99 out of 5 average rating, 151 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 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.

Top guest favourite
A welcoming outdoor space is presented with two patterned armchairs and a wicker chair arranged around a glass-topped table. A decorative wall feature adds texture, while potted plants and a decorative heron enhance the tranquil atmosphere. Warm light filters through the area.
Guesthouse in Winter Garden
4.94 out of 5 average rating, 109 reviews

Blue Heron Bungalow

The Blue Heron Bungalow is located within walking distance of downtown Winter Garden, where you can find great dining, shops, and entertainment. You can also connect with the West Orange Trail and enjoy 22 miles of walking, running, or biking. If you get adventurous Walt Disney World is less than 30 minutes away, as well as many other attractions. Located in the golf cart district.

Superhost
A spacious sleeping area features a large bed centered on a neutral carpet. A light area rug is placed beneath the bed. Simple furniture includes a white table and two chairs, along with a TV stand. Natural light filters through sheer curtains.
Apartment in Ocoee
4.93 out of 5 average rating, 136 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!

Popular amenities for Ocoee vacation rentals

When is the best time to visit Ocoee?

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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Ocoee?

    Yes! Work meets play with ease at over 80 vacation rentals in Ocoee featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Ocoee?

    Experience the best of Ocoee with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Ocoee?

    Four-legged friends are welcome in Ocoee. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there Ocoee vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 70 vacation homes with pools in Ocoee, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Ocoee have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Ocoee. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Ocoee have a gym?

    Absolutely! We offer over 10 apartment rentals with a gym in Ocoee. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ocoee have air conditioning?

    Absolutely! We offer over 120 house rentals with air conditioning in Ocoee. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Ocoee?

    Ocoee has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Ocoee have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Ocoee. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Ocoee?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a gym, over 20 homes with a bbq area, over 120 homes with wifi, over 120 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Ocoee

  • Total vacation rentals

    Explore 190 vacation rentals in Ocoee

  • Nightly prices starting at

    Ocoee vacation rentals start at $27 CAD per night before taxes and fees

  • Verified guest reviews

    Over 7,690 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    180 of Ocoee vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Ocoee rentals

  • 4.7 Average rating

    Ocoee stays receive an average rating of 4.7 out of 5 from guests

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