Vacation rentals in Oakland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakland

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Leesburg

4.98 out of 5 average rating, 364 reviews

Silver Lake Guest Pool House

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

Guest favorite

Guesthouse in Deer Island

4.94 out of 5 average rating, 101 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

We are on 5 beautiful wooded acres with a boat dock on the canal. Relax by the pool, enjoy a BBQ by the firepit, fish from the boat dock, enjoy nature, or simply read a book in the gazebo. Sapphire Cottage has a Master with a queen size bed, a fully equipped kitchen, 2 full size sofa-beds, dinning area for 6, and a full size bathroom. Whether you are looking to relax or a bit of adventure we have the perfect remote location for you. 2 kayaks, 2 bikes, & pontoon tours available…ask 4 details.

Superhost

Cottage in Clermont

4.82 out of 5 average rating, 190 reviews

Charming Lakefront Cottage Near Disney

Newly renovated 800 sq ft Cottage located in South Clermont, less than 25 minutes to Downtown Orlando, Walt Disney World, and all Central Florida attractions. Lake Sawgrass is available for fishing, kayaking, boating, and other watersports activities. Our location is quiet and peaceful located in the countryside. We are located on the newly paved Schofield Road, with less than 1-mile of dirt road now on Cook Road. The unit is on well water, with water softening and filtration installed.

Guest favorite

Home in Winter Garden

4.91 out of 5 average rating, 116 reviews

Luxury Home Winter Garden Near Disney & Universals

Looking for luxury and convenience? Stay in our newly renovated home, just minutes from Disney and Universal. With a one-minute walk to local shops, bars, restaurants, and farmers market, you'll experience the best Winter Garden has to offer. Book now for a memorable stay! Golf Cart and Bike Rentals Available! Send DM NO PETS Strict No Parties or Gatherings Allowed Quiet Hours from 9pm-8am as this is a family friendly neighborhood No more than 8 guests Only 2 Cars allowed on the property.

Guest favorite

Home in Winter Garden

4.91 out of 5 average rating, 186 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 favorite

Cottage in Winter Garden

4.98 out of 5 average rating, 133 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

Townhouse in Clermont

4.91 out of 5 average rating, 211 reviews

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!

Guest favorite

Treehouse in Saint Cloud

4.96 out of 5 average rating, 887 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.

Superhost

Guest suite in Ocoee

4.82 out of 5 average rating, 144 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 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

Guest suite in Winter Garden

4.82 out of 5 average rating, 321 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

Guest favorite

Home in Winter Garden

4.99 out of 5 average rating, 125 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 fenced in 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.

Guest favorite

Tiny home in Apopka

4.99 out of 5 average rating, 136 reviews

Tiny Home Near the Springs

Fresh air and stars at night. Imagine a comfortable little hotel room in a back-to-nature setting. This 190 sq. ft. tiny house is pet friendly, although the yard is not fenced. It is a ten minute drive to either Rock Springs or Wekiva Springs, a four minute bike ride to the West Orange Trail which runs for 22 miles, and a 15 minute drive to the Lake Apopka Wildlife Drive. The major theme parks are a 30 to 45 minute drive, depending on traffic.