Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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

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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, 130 reviews

Downtown Bungalow with fire pit and putting green

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 favorite
Guest suite in Winter Garden
4.84 out of 5 average rating, 402 reviews

Designer Guest Suite Near Disney/Universal/DT

This newly renovated, modern, and clean apartment has been freshly designed with wonderful & 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 with thick memory foam toppers 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 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, 132 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
Home in Clermont
4.94 out of 5 average rating, 226 reviews

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow cleaning and disinfecting of the house

Top guest favorite
Apartment in Minneola
4.94 out of 5 average rating, 113 reviews

Private Cedar Hideaway

You won’t regret choosing this peaceful, secluded hidden gem. 40 min. to Disney, 10 min. to downtown Clermont, Waterfront Park, the Howie Mansion and Mission Inn's world class golf courses. 15 min. to National Training Center. Home to some of Florida's only hills, this is a popular cyclist destination! *kitchenette. Not a full kitchen. *this is a private apartment attached to a home occupied by the hosts. All spaces are private. They're are NO shared SPACES, other than the driveway! :)

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, 221 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, 192 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.

Superhost
Guest suite in Montverde
4.93 out of 5 average rating, 101 reviews

Cottage in the Hills

Relax with the whole family at this peaceful place to stay. Wedding venues: 5 minutes to Bella Collina, 10 to The Springs by Sterling, & 15 to Howie Mansion. Sport venues: 15 minutes to the National Training Center & Clermont Sportsplex, 5 to Montverde Academy. Fl attractions: 90-120 minutes to many beaches. Pick your beach, I'll help with supplies! 45 minutes from most theme parks. Our little town has a walking trail that leads to a lake where one can usually spot an alligator.

Guest favorite
A covered porch is showcased, adorned with climbing plants and vibrant foliage. Two sets of double doors lead into the cottage. A mix of potted plants and outdoor seating arrangements provides a welcoming atmosphere, inviting guests to enjoy the surrounding natural beauty.
Guesthouse in Mount Dora
4.87 out of 5 average rating, 348 reviews

A Lakeshore Cottage vintage 1926

What's new for 2019 a brand new dock and fishing pier. Additional boat docking available. Brand new Central Cold & Dependable Air Condition- Brand new 8 foot tall privacy fence & gate, parking pad beside cottage. -Eco Smart: lock, cork floors, instant hot H2O, solar lighting, copper sink, antiques, refurbished architecture ,charming! 2 nights/festivals ABSOLUTE RESTRICTION to ANIMALS! NO EXCEPTIONS. DO NOT Instant book if you are with any animals. Sorry allergies don’t allow.

Top guest favorite
A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.
Treehouse in St. Cloud
4.97 out of 5 average rating, 1,129 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.

Top guest favorite
Apartment in Clermont
4.98 out of 5 average rating, 107 reviews

Premier Clermont Suite /Prime Downtown 103

Immerse yourself in the sophisticated serenity of our strategically located prime suite, nestled in the vivacious heart of downtown Clermont. elegantly appointed with meticulous attention to detail our suite offers a harmonious blend of opulence and home-like comfort-whichever way you look, every corner is designed to offer an unrivalled stay experience. This property is a dream come true for Triathletes! Standing right at the epicenter of Clermont.

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, 158 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.

Popular amenities for Oakland vacation rentals

Quick stats about vacation rentals in Oakland

  • Nightly prices starting at

    Oakland vacation rentals start at R 817 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 90 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oakland rentals

  • 5 Average rating

    Oakland stays are highly rated by guests—averaging 5 out of 5!

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