Find hotels in Oakland, Winter Garden from $72

Top reasons to visit Oakland

• Family-Friendly Activities: Oakland offers numerous attractions perfect for families, including theme parks and recreational areas.
• Outdoor Adventures: Enjoy outdoor experiences at the Oakland Nature Preserve and water parks, perfect for nature lovers and adventure seekers.
• Vibrant Community Atmosphere: Experience the friendly spirit of the community while exploring local shops and dining options.
• Proximity to Orlando: Oakland's location allows easy access to the vibrant attractions of downtown Orlando.
• Diverse Accommodation Options: Find a variety of hotels, from family-friendly resorts to business-themed stays, catering to all travelers.

Find great hotels near Oakland

Discover a variety of hotel accommodations in Oakland, Winter Garden, Florida, perfect for every type of traveler. Whether you're seeking a family-friendly resort, a pet-friendly getaway, or a business-themed stay, Oakland offers a range of options to suit your needs. With convenient access to local attractions and amenities, finding the ideal hotel in Oakland is a breeze. Experience comfort and hospitality in this charming area of Florida.

• Universal's Cabana Bay Beach Resort: Embrace the nostalgia of the 1950s and 60s at Universal's Cabana Bay Beach Resort, a vibrant family-friendly destination located 12 miles from Oakland. This 3.5-star hotel showcases a playful retro theme, complete with a lazy river pool and a dedicated children's arcade game room. Families will appreciate the complimentary cribs and family-centric amenities, making it an ideal choice for those traveling with young ones. Enjoy a relaxed atmosphere while being close to the thrills of Universal Orlando, ensuring a memorable vacation experience for all ages.
• The Grove Resort & Water Park Orlando: Discover a world of fun and relaxation at The Grove Resort & Water Park Orlando, located 13 miles from Oakland. This 4-star resort caters to families and welcomes LGBTQIA travelers, offering a unique blend of amenities designed for both adventure and leisure. Kids can enjoy a water park, mini-golf, and an arcade game room, while parents can unwind in spacious accommodations. With a children's club available for a fee, this resort ensures that everyone finds something enjoyable during their stay, making it perfect for those seeking a welcoming and inclusive environment.
• DoubleTree by Hilton at the Entrance to Universal Orlando: Experience a blend of business and leisure at the DoubleTree by Hilton at the Entrance to Universal Orlando, situated 12 miles from Oakland. This 4-star hotel is perfect for business travelers with accessible business centers and multiple meeting rooms, while also catering to families and LGBTQIA guests. Children will love the pool designed just for them and the arcade game room. The welcoming atmosphere and attentive service ensure a comfortable stay, making it an excellent choice for those looking to balance work and play during their visit.

Where to stay near Oakland

Oakland, Florida, offers a delightful mix of family-friendly activities and outdoor adventures. Explore the nearby charm of downtown Orlando, with its vibrant attractions, or enjoy the serene ambiance of Oakland Park, perfect for relaxation. With low crowds and a welcoming atmosphere, you’ll find plenty of resort destinations and excursions that cater to all ages. Discover the friendly community spirit while making unforgettable memories in this picturesque neighborhood.

• Killarney: Nestled only 0.8 miles from Oakland, Killarney is a charming neighborhood known for its outdoor activities and family-friendly atmosphere. Visitors flock to Killarney for its excellent sports facilities, including golf courses and resorts. The area is perfect for families looking to enjoy some quality time together. Key attractions nearby include a popular theme park and a scenic lake, providing ample opportunities for adventure and relaxation. With travel peaks in March, July, and December, this neighborhood offers a welcoming retreat throughout the year.
• Winter Garden: As the city that encompasses Oakland, Winter Garden offers a vibrant blend of family entertainment and business opportunities. The city experiences its highest visitor numbers from January to February and in September. Notable for its shopping areas and malls, Winter Garden is a haven for those who love to shop and dine. The proximity to theme parks and beaches makes it an ideal destination for families and visitors seeking fun experiences. The city's lively atmosphere and diverse entertainment options ensure that there’s always something happening.
• Reavills Corner: Located 3 miles from Oakland, Reavills Corner is a quaint village that draws visitors with its outdoor and family-oriented experiences. It enjoys consistent traveler arrivals throughout the year, with peak times in March, July, and December. Visitors can enjoy local resorts, shopping areas, and educational opportunities, making it a great spot for families. The village’s closeness to theme parks and beautiful beaches adds to its allure, offering the perfect blend of relaxation and excitement for vacationers.

Things to do near Oakland

Oakland, Winter Garden is perfect for family vacations and outdoor adventures. Enjoy a variety of activities including visits to nearby resorts, shopping areas, and malls. Delight in outdoor experiences at water parks, soak in ocean views, and partake in various recreational activities. This vibrant destination offers something for everyone, making it an ideal spot for entertainment and relaxation.

Shopping

Flamingo Crossings Town Center, 12 miles from Oakland, offers a vibrant mix of entertainment, dining, and shopping. Clermont Regal Shopping Center, located 6 miles away, features a family-friendly atmosphere with various shops. Westgate Square Shopping Center, 11 miles from Oakland, combines business and leisure for a delightful shopping experience.

Recreation

Camping World Stadium offers an energetic atmosphere, perfect for sports enthusiasts seeking excitement. For a relaxing day, Disney's Palm Golf Course provides a scenic outdoor experience with lush landscapes. Windermere Country Club brings luxury vibes, ideal for unwinding and enjoying top-notch amenities amidst beautiful surroundings.

Adventure

Experience the thrills at Universal’s Volcano Bay, a vibrant waterpark featuring exhilarating rides and family-friendly attractions, located 12 miles from Oakland. For outdoor enthusiasts, hike the scenic West Orange Trail, only 3 miles away, or engage in exciting water sports at Watertoyz of Clermont, situated 8 miles from Oakland.

Nightlife

Experience the thrill of The Orlando Eye at ICON Park, just 13 miles away, offering stunning views and adventure vibes. For family-friendly fun, visit Carter Family Bowl, 3 miles away, featuring arcade games and excitement. Don't miss the Garden Theatre, also 3 miles away, for a taste of culture and romance.

Booking tips and Expedia advantages for Oakland

To save money on your trip to Oakland, plan your visit during the off-peak months of August to September or November for lower hotel rates. Booking about a month in advance and choosing Tuesday for your stay can further reduce costs. Consider using Expedia's last-minute deals and packages to combine hotel, flight, and activities for extra savings. Utilize filters for eco-friendly accommodations and sort by price to find the best deals. Joining Expedia's One Key membership can also provide exclusive discounts and earn you future savings.

• 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: Booking a hotel around Oakland about 1 month out from when you are planning to stay is usually when prices are lowest. If you're a little more spontaneous, you could also peruse Expedia's last minute deals for hotels, look out for the green banner below the price, as this indicates a cheaper deal.
• 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: Utilize Expedia’s search tool to tailor your travel options according to your budget, preferred location, and desired hotel type. For instance, selecting the Eco-certified filter will show you a list of sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your Oakland hotel reservation with your flights and activities through an Expedia package.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Oakland

Oakland, Florida, is perfect for family-oriented and outdoor vacations, boasting attractions like theme parks, golf courses, and arts centers. Visitors can explore the Oakland Nature Preserve for a taste of local ecology, while the area's diverse offerings cater to those seeking family fun, cultural experiences, and outdoor adventures. Enjoy the vibrant community atmosphere as you create lasting memories in this charming destination.

• Walt Disney World® Resort: Experience the magic of Walt Disney World® Resort, a family-friendly theme park located 10 miles from Oakland. With thrilling rides, enchanting attractions, and beloved characters, it’s a place where dreams come true for visitors of all ages.
• Orange County Convention Center: Situated 13 miles from Oakland, the Orange County Convention Center is a hub of culture and creativity. Explore its art exhibits, attend engaging events, and immerse yourself in the vibrant atmosphere that showcases Florida's artistic flair.
• Universal CityWalk: Just 12 miles away, Universal CityWalk offers a lively outdoor experience with entertainment, dining, and shopping. Perfect for families, this bustling tourist precinct is a great spot to unwind and enjoy the vibrant atmosphere after a day at the parks.

Best time to go to Oakland

The best time to visit Oakland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Oakland falls in August, when visitor numbers are slightly low and weather is mostly sunny with moderate rain. The coolest average temperature around Oakland falls in January, 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

When planning your trip to Oakland, Winter Garden, Florida, you have several airport options. Orlando International Airport (MCO) is 22 miles away, with nearby hotels like The Ritz-Carlton Orlando, Grande Lakes and Hyatt Regency Orlando offering shuttle services. Daytona Beach International Airport (DAB) is 56 miles from Oakland, with the Hilton Daytona Beach Oceanfront Resort conveniently located just 4 miles away. Leesburg International Airport (LEE) is 21 miles away, featuring hotels like Mission Resort and Club, which provide transportation services to the airport. Each airport offers various accommodations and transportation options, ensuring a smooth arrival for your vacation.