Family-friendly holiday rentals in Oakland

10 Minutes to Universal - Charming Private Home

Beautiful newly remodeled home centrally located. 3 bedrooms (2 King 1 Queen) and 2 full baths (1 walk in shower w/ grab bars). Carport. Huge and private yard to enjoy! Comfortable living room with big screen TV, couches and lazyboy recliners. Kitchen is fully stocked for cooking. Office desk and chair. Washer and Dryer. 10 Minutes to Universal Studios and just minutes more to International Drive, Mall of Millenia, Florida Mall, or Disney. Grocery, liquor, pizza, chinese within a 5 minute walk.

Tiny Home Near the Springs

Fresh air and back to nature. Imagine a tiny but comfortable hotel room in a rural setting. You'll hear roosters crow as the sun rises. Take a walk on a moonless cloudless night, and you may see stars. This 190 sq. ft. tiny house 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.

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.

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.

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

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.

Charming Downtown Apartment - Walk to Everything

Stay in the heart of historic downtown Clermont- steps from the lakefront, breweries, shops, & dining. This light-filled, stylish apartment above our garage offers cozy aesthetics, comfy beds, a double shower, two spacious bedrooms, and a smart TV. Thoughtfully stocked for a stress-free stay, with garage storage for your bikes or paddle gear upon request. More than a stay—we proudly offer a distinct Clermont experience. We hope you love our charming town just as much as we do!

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.

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.

Green Mountain Getaway (No indoor Smoking or Pets)

(Non Smoker & No Pets) A secluded lot surrounded by FL’s beautiful tropical landscape. Golfer? We are 3 min. from the beautiful Bella Collina's luxury 18 hole golf course, a Nick Faldo design. Also 8 min. from Sanctuary Ridge Golf Club, a more affordable option. Biker? “Killarney Station", is an affordable place to rent bikes or bring your own to ride the beautiful 26 mile trail. 28 minutes to all the attractions!

Blue Heron Bungalow

The Blue Heron Bungalow is located within walking distance of downtown Winter Garden, where you can find great dining, shops, and entertainment. You can also connect with the West Orange Trail and enjoy 22 miles of walking, running, or biking. If you get adventurous Walt Disney World is less than 30 minutes away, as well as many other attractions. Located in the golf cart district.

Cozy Home near Waterfront Park

This newly constructed unique and cozy home sits in the heart of lakes near downtown, shops, restaurants, and breweries. It is surrounded by greenery that lets you relax and wind down in a tropical backyard. It is within walking distance to the lake beach, biking trail, splash pad, and playground. There are plenty of activities for you to enjoy!