Vacation rentals in Oakland

A place with a view

Welcome to Your Secluded Getaway Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Urgent care , Emergency room & Hospital are all nearby Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m | Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont14m Outlets 28m | Florida Mall 35m | I-Drive 40m Travel MCO Airport 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks. storage only

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.

Emerald Grove - Close to 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.

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. Built in 2019 with high ceilings. 8 guests can comfortably enjoy the 3 BR (2 king & 1 queen beds) 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.

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.

Adorable Downtown Lakeview Home 1105

Experience unparalleled comfort and charm in our distinctive Lakeview home, ideally located in downtown Clermont's vibrant heart. This bright and captivating property exudes an inviting aura with its scenic lake views and exceptional decor. Start your day with a refreshing cup of coffee on the serene back porch, take a stroll to the nearby park, or enjoy the array of amenities in the vicinity. Families and athletes alike will enjoy the convenient proximity to key attractions.

Winter Garden Butterfly Retreat

Enjoy this quiet retreat in Winter Garden. One block from the 22-mile West Orange Trail. Walk into town under a canopy of oak trees and Spanish moss. Enjoy the historic downtown with coffee shops, restaurants, ice cream and a weekly farmer's market. This is a private 2-room suite with bathroom, kitchenette and independent driveway, patio and entrance. Unit is part of a larger home where owner lives, but private with no shared spaces. Note: Air Conditioner is a window unit.

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.

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 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.

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!

Cozy cottage in Winter Garden

This newly renovated, cute and cozy home is just what you're looking for your vacation in Orlando/Winter Garden area! It is in close proximity to Winter Garden Downtown with great restaurants, cafes and farmers market. Also the famous West Orange bike trail is just 4 minutes away. If you plan to visit Disney or Universal they're less than 30 minutes away. You'll have a great time at this comfortable place to stay.

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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)