Vacation rentals in Oakland

4.97 out of 5 average rating, 121 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!

4.97 out of 5 average rating, 32 reviews

Guest suite in Clermont

Cozy Studio with Kitchen & Bathroom

Enjoy easy access to Central Florida from this perfectly located home base. Garage converted into a studio apartment: -Private entrance -Full Kitchen -Private Bathroom -Driveway parking -community pool -20 miles from Disney -Less than 15 minutes to downtown Clermont/Waterfront Park -Easy Access to the South Lake/West Orange Trail (walking, biking, running) There is no thermostat in the studio. The temperature may vary slightly but will stay close to 75 (when outdoor temperature is above 75).

Farm stay in Winter Garden

4.95 out of 5 average rating, 57 reviews

Carriage House Studio Apt Peaceful & Private Ranch

Carriage House Studio Apartment & Ranch is a non smoking, peaceful and quiet horse ranch located one block from the West Orange Trail and one mile to historic downtown Winter Garden featuring Saturday morning Farmer’s Market, casual and fine dining, unique shops, brewery and local theater. Best small town in Central Florida Experience peace & tranquility surrounded by large oak, horses (big & mini), mini pigs and two friendly dogs Perfect for couples, solo/business travelers & traveling nurses

5 out of 5 average rating, 14 reviews

Entire clean comfortable house

This house is perfect for guest, seeking high-end experience and for professionals needing a place to work and rest. Located in a family friendly quiet neighborhood. The house is built in 2019 with high ceilings. Eight guests can comfortably enjoy the three bedrooms and a comfortable queen sleeper sectional. Enjoy attractions, bike rides at the trailer visit downtown Wintergarden for shopping and Saturday farmers market. You’re welcome to use the community pool for a nice and relaxing time.

Apartment in Winter Garden

5 out of 5 average rating, 6 reviews

Winter Garden Charm, Near Disney

2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Garden, this beautifully designed 2-bedroom, 2-bath apartment offers the perfect blend of modern luxury and small-town charm — just 20 minutes from Walt Disney World and Orlando’s top attractions. Located on the iconic Plant Street, you’ll be steps away from historic downtown Winter Garden, home to popular restaurants, boutiques, coffee shops, and the famous West Orange Trail.

4.91 out of 5 average rating, 53 reviews

Villa in Oakland

Historic Oakland Manor House

Originally built in the early 1900’s, this gracious manor was carefully renovated, preserving its historic craftsman-style. As you pass through the gates & moss-draped oaks, you will feel like you have stepped back in time. This magical, lakeside manor has been the site of many social gatherings, retreats and weddings. Enjoy biking/walking the trails, Speer park, fish from the pier of lake Apopka, or shop and dine just outside our doorstep. Orlando's theme parks are a within a 30 min drive.

4.91 out of 5 average rating, 203 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.

4.99 out of 5 average rating, 154 reviews

Cottage in Winter Garden

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.

4.91 out of 5 average rating, 235 reviews

Townhouse in Clermont

Paradise Escape

Your paradise escape is finally here! In the Sunshine State, paradise is just one perfect cocktail away. Leave your worries away and relax - you are in a sunshine state of mind! My "paradise island" is conveniently located in the heart of Clermont. You will certainly enjoy the welcoming and colorful ambiance! Combination lock instructions will be sent after arrival time confirmation. I look forward to hosting all my guests and making sure that they have an unforgettable experience!

4.95 out of 5 average rating, 154 reviews

Home in Minneola

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.

4.96 out of 5 average rating, 980 reviews

Treehouse in St. Cloud

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.

4.96 out of 5 average rating, 113 reviews

Apartment in Minneola

Spacious Apartment In Minneola

This spacious 1 bedroom / 1 bathroom apartment is located West of Orlando in the beautiful town of Minneola right next to Clermont in the heart of Central Florida and is perfect for a short or long term stay. Features a large bedroom & bathroom, comfortable couch w/ dual recliners, plenty of closet space & storage, and a Smart TV. Kitchen is stocked with all the essentials and has a dishwasher, gas stove, refrigerator w/ ice maker, coffee maker, microwave and crockpot.

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Other great vacation rentals in Oakland

Home in Oakland

4.93 out of 5 average rating, 29 reviews

Modern Florida Bungalow: 3 Miles to Winter Garden!

CherylRating, 5 stars1 month ago

Enjoyed our stay at your location. House was very clean and had a well stocked kitchen. The bathrooms were clean and bedrooms were clean and beds were well made with clean bedding. House smelled clean with no odors. Neighborhood was quiet and the neighbors were respectful and friendly. I would definitely stay there again.

5 out of 5 average rating, 22 reviews

Apartment in Ocoee

The Cozy Escape Close to Windermere & WinterGarden

BrittanyRating, 5 stars2 months ago

Love this spot! Will most definitely be staying here again! There is a lot around plus a lot that the apartment offers too.

Private room in Winter Garden

4.9 out of 5 average rating, 239 reviews

20-30 min. Disney, Universal & Downtown Orlando

RichardRating, 5 stars4 days ago

An absolutely amazing place to stay. If you need a room for a couple nights or just one, it is private, easy to access, and in an a beautiful neighborhood.

4.93 out of 5 average rating, 72 reviews

Home in Minneola

Downtown Minneola Luxury Home (211)

DerrickRating, 5 stars3 days ago

great place, excellent host,clean quiet, highly recommend,will stay again

4.89 out of 5 average rating, 19 reviews

Cottage in Winter Garden

The Swift House

PaigeRating, 5 stars2 weeks ago

What a great stay! Sweta was beyond helpful, meeting us at the unit, showing us through, making local recommendations for us. We had a little difficulty with the remotes (okay, we're old) and she was there in 2 minutes to walk us through the operation. Not only did she have our choice of wine chilled and waiting, but she delivered dog treats for our pooch, which were much appreciated. The area is incredible: a quiet street of mostly vintage houses, but within only a few blocks of wonderful restaurants, pubs, music, & activity... none of which you hear from this cottage. Honestly, there is no better location for a stay in Winter Garden, and if you're considering Orlando, it's a welcome reprieve from the shockingly busy city and still only 15 minutes to all the vacation attractions.