Family-friendly vacation rentals in Oakland

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!

The Legacy House - your home away from home.

Just a block away from the South Lake Bike Trail System, 18 minutes from beautiful Lake Minneola, and a mere 20 miles from the Disney Parks, and 5 minutes from the Bella Collina wedding venue, this peaceful neighborhood home will be a perfect spot to rest after a full day of fun. This is an ideal spot if you're coming for cycling events, fishing competitions, a wedding or simply to enjoy the most beautiful part of Florida! We hope you chose to book with us; it would be our pleasure to host you!

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.

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

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.

Mario-Themed Home! | Disney 30 Min | Pool + Lake

🍄 Mario's Mini Mansion is a boutique Mario-themed getaway for small families (1-3 kids) and local staycations. > Custom Yoshi’s Fort (queen + twin XL bunk + LIFE-SIZE Yoshi!) > King loft bedroom upstairs > 75" Smart TV + Nintendo Switch (Mario Wonder + games) > 4 streaming TVs > Heated neighborhood pool + large screened patio > Efficient kitchen with Breville Oven/Air Fryer > Sleeps 5 Glow-in-the-dark details, Mario games & more! Something magical for the whole family 🎮

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.

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.

Private Country House | 16 Guests | Gatherings

Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.

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!

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Enjoy the breathtaking sunrise views of Lake Apopka from this newly refurbished and well appointed 4 bed, 2.5 bath vacation home in Winter Garden, Fl. While the house offers total tranquility and relaxation, it is only a short drive from Orlando’s numerous theme parks (Universal Studios 20 min, Disney World 30 min) and all other local attractions (Mall of Millenia and premium outlet malls 20 min drive)