Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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Top Guest favourite
A tiny home is showcased with a grey exterior and a metal roof. Two wooden chairs are positioned on a grassy area in front, and flower pots add color near the entrance. Steps lead up to the front porch, providing access to the inviting interior.
Tiny home in Howey-in-the-Hills
4.96 out of 5 average rating, 158 reviews

Horse Farm- (2) Tiny Homes 33mi from Orlando

Rest & Relaxation at its finest! This Tiny Home is set to impress! Add on the natural beauty of the rolling hills of Howey, with some of Thee most impressive sunsets over the water & this becomes an Incredible Unique Stay! After sunset, enjoy a nice campfire in your firepit, as you STARGAZE into the night! This Tiny Home is fully equipped with ALL of your needs. Located on the back 3 acres of property, from which you will have your own Golf Cart to travel to/from our Designate Parking Area.

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, 206 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 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, 168 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
The exterior of a single-story house is depicted, showcasing a brown facade with a pitched roof. A covered porch features two orange chairs. A driveway leads to an attached garage, surrounded by a landscaped yard with mature trees and blue skies above.
Guest suite in Clermont
4.89 out of 5 average rating, 148 reviews

Private In-Law Suite. House in Hills. BIKE Trail

Completely PRIVATE In-law Suite in front section of house. Consists of: 2 bedrooms Bedroom 1: King size bed Bedroom 2: 2 Full size beds Full bathroom Washer/Dryer Kitchen (no oven, no dishwasher) Full living room with Smart TV Coffee station Located in a residential neighborhood Close to Route 50 and close to Route 27 1.5 miles from NTC 2.9 miles from Waterfront Park/Victory Point 27 miles from Disney West Orange 🍊Trail passes about 100 yards behind house n runs 33 miles

Guest favourite
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
4.82 out of 5 average rating, 165 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 favourite
An open studio layout is showcased, featuring a comfortable queen bed with decorative pillows and a soft throw blanket. A multi-functional sofa and coffee table are positioned in front of a flat-screen TV. A dining table for four is also visible, enhancing the inviting atmosphere.
Home in Minneola
4.97 out of 5 average rating, 153 reviews

Cozy Studio Near Disney/Universal/Training center

This cozy stylish studio, detached guest house is perfect for short-term or extended stay in the beautiful city of Minneola. Sleeps 2, can accommodate up to 4. Features a large backyard and a fire pit.  Close to Downtown Clermont, National Training Center, and 35 minutes to Disney World and other major attractions. This tranquil space features a queen bed with 3" memory foam mattress topper and a spacious living space that has a Multi-Functional Sofa that converts into a Bed.

Top Guest favourite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 113 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Superhost
A small bedroom features a spacious bed with a patterned white and navy coverlet. A window with light curtains allows natural light to enter. A wooden shelf with various items is visible next to a desk with a lamp. A closet door reflects the room's layout.
Guest suite in Orlando
4.73 out of 5 average rating, 845 reviews

Cozy & Private Studio close to the Attractions

Is a small space completely private attached to the side of the house with a separated entrance from the main area. Clean, quite and safe. The studio has a bedroom, a bathroom and there is also an area with microwave, mini fridge, toaster and coffee maker. Wi-fi is available. You’ll be located 17 minutes from Universal Studios and 25 minutes from Disney World driving. Feels free to contact us at any time, we would be happy to help you in any way possible. HABLAMOS ESPAÑOL

Top Guest favourite
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
4.96 out of 5 average rating, 1,049 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 favourite
A comfortable living area features a spacious couch with reclining sections and soft cushions. A Smart TV is placed on a black media console next to a stylish clock, while light filters through striped curtains. A small table holds a notepad, providing additional convenience.
Apartment in Minneola
4.96 out of 5 average rating, 131 reviews

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.

Guest favourite
A modern bedroom features a spacious bed layered with crisp white linens against a neutral wall. A tall dresser with a natural wood finish stands beside a chair. Natural light enters through two windows, and decorative elements like wall art and plants add a touch of style.
Guest suite in Winter Garden
4.83 out of 5 average rating, 374 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, 135 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.

Popular amenities for Oakland holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Oakland