Oakland Hotels near Winter Garden

Top reasons to visit Oakland

• Family-Friendly Activities: Oakland offers a variety of attractions suitable for all ages, ensuring a fun-filled holiday for families.
• Outdoor Adventures: Engage in recreational pursuits at local parks and water parks, perfect for enjoying Florida's sunny weather.
• Cultural Experiences: Explore nearby arts centres and theme parks that showcase the region's vibrant culture.
• Nature Enthusiasts: Visit the Oakland Nature Preserve for a serene escape into Florida's natural beauty.
• Charming Accommodations: Discover a range of comfortable lodging options, from family-friendly resorts to pet-friendly hotels.

Find great hotels near Oakland

Discover a variety of accommodation options in Oakland, Winter Garden, Florida, tailored to suit every traveller. Whether you seek family-friendly resorts, pet-friendly hotels, or convenient options for business travel, Oakland offers a selection of lodgings designed for comfort and convenience. With its inviting atmosphere and proximity to local attractions, you'll find the perfect home away from home in this charming area.

• Universal's Cabana Bay Beach Resort: Embracing a vibrant retro theme, Universal's Cabana Bay Beach Resort is perfect for families seeking a fun-filled vacation experience. Located 19.3km from Oakland, this 3.5-star hotel offers a variety of family-friendly amenities, including a complimentary crib service and an engaging arcade game room. The colourful décor and lively atmosphere make it an inviting retreat for guests of all ages, ensuring that the little ones are entertained while adults unwind by the pool.
• The Grove Resort & Water Park Orlando: With an adventurous spirit, The Grove Resort & Water Park Orlando is an exhilarating 4-star resort situated 20.9km from Oakland. Ideal for families and thrill-seekers alike, it boasts an array of onsite activities including fishing, boat tours, and water sports equipment. The resort also features a mini-golf course and a children's club, ensuring a memorable holiday for younger guests. The water park, complete with slides and pools, is a highlight, providing endless fun for the entire family.
• DoubleTree by Hilton at the Entrance to Universal Orlando: Combining comfort with a welcoming environment, the DoubleTree by Hilton is a sophisticated choice for business travellers and holidaymakers alike. Located 19.3km from Oakland, this 4-star hotel is pet-friendly and LGBTQIA welcoming, catering to a diverse range of guests. With its modern amenities and attentive service, including a waived fee for service animals, guests can expect a pleasant stay. The hotel's convenient location makes it an excellent base for exploring the attractions of Orlando.

Where to stay near Oakland

Oakland, nestled in Winter Garden, Florida, offers a delightful blend of family-friendly activities and relaxing excursions. Visitors can explore nearby destinations such as Fort Lauderdale for resort experiences or the vibrant atmosphere of downtown Orlando. With low crowds and a welcoming community, Oakland is ideal for both leisure and business-themed vacations. Don't miss the opportunity to discover charming vacation rentals that enhance your stay in this picturesque neighbourhood.

• Killarney: Nestled just 1.3km from Oakland, Killarney is an inviting neighbourhood perfect for families and outdoor enthusiasts alike. Its charm lies in its tranquil atmosphere, offering a delightful blend of cultural experiences. Visitors can enjoy a round of golf at the local golf course or unwind at nearby resorts. Killarney's proximity to attractions such as a science museum and a theme park adds to its appeal, making it an ideal spot for a leisurely day out.
• Winter Garden: As the city that encompasses Oakland, Winter Garden is a vibrant hub for family fun and entertainment. The city is known for its engaging shopping areas and bustling mall centres, ensuring visitors have plenty of retail therapy options. With peak travel periods in January to February and September, Winter Garden offers a wealth of attractions, including a renowned theme park and a thrilling waterpark. It's a place where business and leisure seamlessly intertwine, making it a must-visit on your itinerary.
• Downtown Winter Garden: Located 4.8km from Oakland, Downtown Winter Garden is a picturesque neighbourhood that captures the essence of urban charm. It is ideal for families seeking outdoor adventures and city experiences. With a variety of resorts, a water park, and educational venues, there is something for everyone. The area's local landmarks, such as an urban park and a vibrant tourist precinct, provide a delightful backdrop for exploration and relaxation. Visit Downtown Winter Garden to immerse yourself in its lively atmosphere and rich offerings.

Things to do near Oakland

Oakland, Florida, offers a delightful blend of family-friendly activities and entertainment options. Visitors can enjoy stunning ocean views and engage in various recreational pursuits. Outdoor experiences abound, with water parks providing fun for all ages. Additionally, the area boasts shopping malls and centres, ensuring a fantastic holiday filled with leisure and excitement.

Shopping

The nearest shopping destination is Plant Street Market, a vibrant market just 4.8km away, perfect for local gifts and souvenirs. For more variety, head to Clermont Regal Shopping Center, 9.7km away, offering entertainment and family-friendly shopping experiences.

Recreation

At Camping World Stadium, immerse yourself in the vibrant atmosphere of local sports events, just 22.5km from Oakland. West Orange Country Club and Clermont National, both 6.4km away, offer serene golfing experiences amid lush landscapes, perfect for relaxation and outdoor enjoyment.

Adventure

At Universal’s Volcano Bay, about 19.3km from Oakland, immerse yourself in a thrilling waterpark experience filled with slides and lazy rivers. The West Orange Trail, merely 4.8km away, offers scenic hiking amidst nature, while Watertoyz of Clermont, located 12.9km away, provides exhilarating water sports adventures.

Nightlife

In Oakland, the Orlando Eye at ICON Park offers a thrilling ride on a Ferris wheel, perfect for families and adventurers alike. Just a short distance away, the Garden Theatre presents a romantic atmosphere filled with culture, while the Carter Family Bowl provides exciting arcade adventures for all ages.

Booking tips and Expedia advantages for Oakland

For a budget-friendly trip to Oakland, visit between August to September or November when prices are lower. Book your hotel about a month in advance, or check Expedia for last-minute deals. Tuesday is the cheapest day to stay, while Saturday tends to be pricier. Use Expedia's search tool to filter hotels by budget and eco-friendly options. Consider booking a package that combines flights, accommodation, and activities for additional savings. Don’t miss out on free local attractions to enhance your experience without straining your wallet.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Oakland are August to September and November, where the prices are slightly lower. This is in comparison to March to April and December, where prices are slightly higher.
• The best time to book a hotel: The cheapest time to book a hotel around Oakland is usually 1 month out from when you are planning to stay, though if you're late to the party, have a look at Expedia's last minute deals - the green banner below the hotel's price indicates a discounted rate.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Oakland is Tuesday. The most expensive day to stay around Oakland is Saturday.
• Find cheap hotels on Expedia: Expedia's search tool enables you to set your budget, choose your desired location, and much more. You can arrange your search results to display prices from lowest to highest, ensuring that you see the most affordable hotels first. Additionally, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and eco-friendly accommodations available for booking.
• Consider bundling your trip: You can potentially save money by combining your hotel accommodation in Oakland with your flights and activities by opting for an Expedia package.

Find the best attractions near Oakland

Oakland, Florida, offers a delightful mix of attractions suitable for family, entertainment, and business-themed vacations. Visitors can explore a variety of points of interest, including theme parks, arts centres, and golf courses. The local attractions provide excellent opportunities for outdoor activities and cultural experiences, with the Oakland Nature Preserve being a notable highlight for nature enthusiasts. Whether you're seeking fun or relaxation, Oakland has something to cater to every traveler's needs.

• Walt Disney World® Resort: Experience the magic of Walt Disney World® Resort, a spectacular theme park that offers thrilling rides, enchanting shows, and beloved characters. Perfect for families, it promises a day filled with joy and unforgettable memories, just 16.1km from Oakland.
• Orange County Convention Center: Immerse yourself in the vibrant culture at the Orange County Convention Center. Known for its diverse arts events and exhibitions, this venue showcases local and international talent, located 20.9km away from Oakland.
• Universal CityWalk: Enjoy the lively atmosphere of Universal CityWalk, a dynamic tourist precinct featuring shops, dining, and entertainment. With its outdoor spaces and family-friendly vibes, it's an ideal spot for relaxation and fun, situated 19.3km from Oakland.

Best time to go to Oakland

The best time to visit Oakland is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with moderate rain. January is its coolest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	59.9°F (15.5°C)	Light Rain	Mostly Sunny	Slightly High	Average
February	63.9°F (17.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
March	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
April	72.5°F (22.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
May	77.2°F (25.1°C)	Light Rain	Mostly Sunny	Average	Average
June	81.0°F (27.2°C)	Moderate Rain	Mostly Sunny	Average	Average
July	82.4°F (28.0°C)	Moderate Rain	Mostly Sunny	Average	Average
August	82.6°F (28.1°C)	Moderate Rain	Mostly Sunny	Slightly Low	Slightly Low
September	80.2°F (26.8°C)	Moderate Rain	Mostly Sunny	Average	Slightly Low
October	74.8°F (23.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	67.8°F (19.9°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Average	Slightly High

The nearest major airports for your trip to Oakland

To reach Oakland, Florida, you have several airport options. Orlando International Airport (MCO) is approximately 35.4km away, with nearby hotels such as The Ritz-Carlton Orlando, Grande Lakes and Rosen Shingle Creek, both about 12.9km from the airport, offering shuttle services. Leesburg International Airport (LEE) is located 33.8km from Oakland, with options like Mission Resort and Club, which is 11.3km away. For those considering Daytona Beach International Airport (DAB), it is 90.1km away, with hotels like Hilton Daytona Beach Oceanfront Resort just 6.4km from the airport. Each of these hotels provides various transportation services to facilitate your travels.