Vacation rentals in Ocoee

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Top-rated vacation rentals in Ocoee

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Top guest favorite
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 favorite
A serene lakeside view is presented, featuring calm waters reflecting a gradient of soft colors during sunset. A wooden dock extends into the water, framed by lush greenery and grasses. The landscape conveys a tranquil setting, inviting moments of reflection in nature.
Home in Winter Garden
4.98 out of 5 average rating, 120 reviews

Waterfront EPIC views, Dock, wildlife Near Disney

Experience the stunning sunrise views over Lake Apopka from our newly refurbished, elegantly appointed 4-bedroom, 2.5-bath vacation home in Winter Garden, FL. This haven is close to Orlando's Universal Studios 20 min, Disney World 25 min) & shopping (Mall of Millenia, premium outlets 17 min) Modern amenities, spacious layout that promises relaxation and convenience making the perfect home for exploring all local attractions and enjoying Florida's natural beauty. Minutes from City Swimming Pool

Top guest favorite
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, 109 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 favorite
Guest suite in Orlando
4.98 out of 5 average rating, 243 reviews

Be Our Guest! 1 BR/1 Bath Guest Room

Be Our Guest! Close to all Major Attractions, Disney, Universal Studios, Orlando Airport, main shopping areas like the famous Premium Outlets, Florida Mall, Millenia Mall and more making it easy to plan your visit here in the Heart of Orlando! Read House Rules before booking! No Pets/Animals Allowed! πŸ™‚ Orlando MCO 6.7 Miles Premium Outlets I-Drive 3.7 Miles Premium Outlets Vineland 7.7 Miles Disney Springs 10 Miles Universal Orlando Parks 4.7 Miles The FL Mall 1 Mile Icon Park 4.9 Miles

Top guest favorite
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, 259 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 favorite
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, 211 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.

Top guest favorite
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, 178 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 favorite
A vibrant sunset reflects off the surface of a lake, with hues of orange, pink, and purple blending into the sky. Silhouetted trees frame the scene, adding depth to the tranquil waterscape, which sparkles gently as daylight fades.
Guest suite in Ocoee
4.83 out of 5 average rating, 172 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 favorite
A cozy bedroom is showcased with warm wood paneling and soft lighting. A spacious bed is adorned with neutral tones and decorative pillows. A flat-screen TV is mounted on the wall, and large windows, covered by modern shades, allow filtered light to enter the room.
Guest suite in Orlando
4.79 out of 5 average rating, 565 reviews

Private Studio Near Universal, Disney & Shopping!

Discover this cozy studio, completely private with its own entrance. It features a comfortable queen bed, a private bathroom, and a kitchen. It also includes a Luxurious Sofa and free parking. Just 15 minutes from Florida Mall, 15 minutes from the airport, 20 minutes from Disney, and 12 minutes from Universal Studios, as well as 8 minutes from I-Drive Orlando, Millenia Mall, and many more attractions. Perfect for a comfortable and private stay near Orlando’s top attractions!

Top guest favorite
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, 143 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 β€œno 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 favorite
A serene pool area features a vibrant red pool float resting in the clear water, surrounded by lush greenery. Comfortable outdoor seating is arranged near the pool, with large umbrellas providing shade. The backdrop showcases a charming pool house with multiple glass doors, inviting natural light.
Guesthouse in Lake Eola Heights
5 out of 5 average rating, 268 reviews

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

Guest favorite
An outdoor deck features a round table with two chairs beneath a vibrant orange umbrella. The entrance to the container studio is framed by glass doors, surrounded by plants. String lights are visible overhead, providing a cozy ambiance.
Shipping container in College Park
4.92 out of 5 average rating, 183 reviews

Cozy container in College Park and near Downtown

This is a unique stay in a container that has been transformed into a studio. Similar to a tiny home but without climbing into a loft. The Container is outfitted with a Kitchen, Bath and sleeping area. Cozy and quaint is the best way to describe it. The location is in my backyard in College park, near major roadways for easy travel to the theme parks, Winter Park restaurants and Downtown entertainment.

Popular amenities for Ocoee places to stay

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 οΊ©.οΊ‡73 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 & 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

  • Wi-Fi availability

    180 of Ocoee vacation rentals include wi-fi 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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