Find hotels in Oakland, Winter Garden

Top reasons to visit Oakland

• Family-Friendly Attractions: Oakland offers a variety of family-friendly activities, including nearby theme parks and water parks.
• Outdoor Adventures: Enjoy the natural beauty at the Oakland Nature Preserve, perfect for hiking and wildlife viewing.
• Charming Neighborhood: Experience the welcoming atmosphere of Oakland, ideal for relaxation and exploration.
• Variety of Accommodations: Choose from family-friendly resorts to pet-friendly hotels that cater to every traveler's needs.
• Entertainment Options: Engage in recreational activities and enjoy local shopping and dining experiences.

Find great hotels near Oakland

Discover the perfect getaway in Oakland, Florida, where a variety of hotels cater to every traveler's needs. From family-friendly resorts to pet-friendly accommodations, you'll find options that ensure a comfortable stay. Whether you're here for business or leisure, Oakland hotels offer essential amenities and a welcoming atmosphere, making it an ideal destination for your vacation. Explore the charm of Oakland and unwind in a hotel that suits your style.

• Universal's Cabana Bay Beach Resort: This vibrant, retro-themed hotel offers a unique family vacation experience reminiscent of the 1950s and 60s. Located 19.3km from Oakland, it features a lively atmosphere with spacious family suites and an array of kid-friendly amenities. Children can enjoy the Arcade Game Room, and complimentary cribs are available for the little ones. The resort also boasts a lazy river and multiple pools, making it a perfect spot for relaxation and fun. With its engaging decor and family-centric services, Universal’s Cabana Bay Beach Resort is a fantastic choice for travelers seeking a nostalgic getaway.
• The Grove Resort & Water Park Orlando: Nestled 20.9km from Oakland, this nature-themed resort offers a tranquil escape combined with family-friendly fun. The Grove Resort features a stunning water park, children's activities like a dedicated pool area and a games room, ensuring that younger guests are entertained. The resort also includes a children’s club (available for a fee), catering to families looking for a mix of relaxation and adventure. Surrounded by lush landscapes, this resort creates a perfect balance for guests wanting to immerse themselves in nature while enjoying quality family time.
• DoubleTree by Hilton at the Entrance to Universal Orlando: Located 19.3km from Oakland, this contemporary hotel is ideal for families, business travelers, and LGBTQIA guests. Known for its welcoming atmosphere, the DoubleTree features rooms equipped with amenities for children, including a children’s pool and an arcade game room. The hotel also offers a signature warm chocolate chip cookie upon arrival, adding a sweet touch to your stay. With its strategic location and inclusive services, this hotel ensures a comfortable and enjoyable experience for all guests.

Where to stay near Oakland

Experience the charm of Oakland, Florida, a family-friendly neighborhood perfect for a relaxing getaway. Enjoy the low crowds while exploring nearby attractions like Fort Lauderdale and the scenic Orange County. With its welcoming atmosphere, Oakland offers a blend of entertainment and business opportunities, making it ideal for all types of travelers. Don't miss the Oakland Park area for delightful excursions and friendly locals, ensuring a memorable vacation filled with adventure and relaxation.

• Killarney: Killarney is a charming neighborhood located 1.3km from Oakland. It attracts a steady flow of travelers year-round, with peak visits in March, July, and December. This area is perfect for families seeking outdoor adventures and cultural experiences. Popular activities include golfing at local courses and enjoying the nearby resort amenities. Visitors can also explore attractions such as a science museum, a theme park, and a film studio, all within easy reach, making Killarney a delightful spot for a fun-filled getaway.
• Winter Garden: Situated in the heart of Winter Garden, Oakland offers a vibrant city experience. The area sees an influx of travelers, especially from January to February and September. Families and business travelers alike are drawn to the city's entertainment options, including resorts and shopping centers. Local attractions feature a theme park, a film studio, and a waterpark, ensuring there’s something for everyone. With its welcoming atmosphere and diverse activities, Winter Garden is an excellent hub for your Florida vacation.
• Downtown Winter Garden: Just 4.8km from Oakland, Downtown Winter Garden is a lively neighborhood ideal for families seeking outdoor and urban experiences. The area maintains a consistent flow of visitors, peaking in March, July, and December. Highlights include a variety of resorts and a popular water park, alongside educational venues perfect for family outings. Local attractions such as an urban park and a vibrant tourist precinct enhance the appeal of Downtown Winter Garden, making it a must-visit on your journey.

Things to do near Oakland

Oakland, Florida, offers a great mix of family-friendly and entertainment options for your vacation. Enjoy nearby attractions like resorts and shopping centers, and explore exciting activities such as water parks and recreational adventures. With plenty of outdoor experiences and stunning ocean views, Oakland is perfect for those seeking both relaxation and fun in the sun.

Shopping

For shopping in Oakland, visit Clermont Regal Shopping Center, located 9.7km away, offering vibrant family and entertainment vibes. Westgate Square Shopping Center, 17.7km away, and Hiawassee Wood Shopping Center, 16.1km away, also provide diverse shopping experiences with a lively atmosphere.

Recreation

Experience the thrill of sports at Camping World Stadium, just 22.5km from Oakland. Enjoy a round of golf surrounded by nature at Forest Lake Golf Club, only 11.3km away. For family fun, visit Pirate's Cove Adventure Golf, located 20.9km from Oakland, offering a lively mini-golf experience.

Adventure

Universal’s Volcano Bay, located 19.3km from Oakland, offers thrilling water rides and relaxation in a tropical paradise. For hiking enthusiasts, the West Orange Trail, 4.8km away, features scenic views and outdoor adventures. Additionally, Watertoyz of Clermont, 12.9km from Oakland, provides exciting water sports experiences.

Nightlife

Experience the nightlife in Oakland by visiting The Orlando Eye at ICON Park for thrilling views and family fun. Enjoy a romantic evening at the Garden Theatre for captivating performances, or unleash your competitive spirit at the Carter Family Bowl arcade, perfect for family adventures and excitement.

Booking tips and Expedia advantages for Oakland

To save money on your trip to Oakland, plan your visit during the cheaper months of August to September or November, and aim for a Tuesday stay, as it's the least expensive day. Book your hotel about a month in advance, or check Expedia for last-minute deals. Consider combining your hotel, flights, and activities in a package to maximize savings. Utilize Expedia’s filters to find eco-friendly accommodations and sort by price for the best rates. Lastly, take advantage of free activities and public transport to explore the area without breaking the bank.

• 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: Utilize Expedia’s search tool to refine your preferences based on your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase 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 hotel stay in Oakland with your flights and activities when you book an Expedia package.

Find the best attractions near Oakland

Oakland, Winter Garden, Florida, is an ideal destination for family vacations, entertainment, and business retreats. Visitors can explore popular attractions such as theme parks, art centers, and golf courses, all catering to those seeking family fun, outdoor adventures, and cultural experiences. Don't miss the chance to visit the Oakland Nature Preserve for a taste of local wildlife and natural beauty.

• Walt Disney World® Resort: Located 16.1km from Oakland, this iconic theme park offers a magical experience filled with thrilling rides, beloved characters, and enchanting entertainment for families. Enjoy immersive themed lands and unforgettable attractions that cater to all ages.
• Orange County Convention Center: Situated 20.9km away, this vibrant arts center showcases a rich cultural scene. Attend diverse events, exhibitions, and conventions that celebrate local and international art, making it a hub for creativity and inspiration.
• Universal CityWalk: Just 19.3km from Oakland, this lively outdoor precinct features dining, shopping, and entertainment options. Enjoy a family-friendly atmosphere with vibrant nightlife and attractions that bring fun and excitement to your visit.

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

Traveling to Oakland, Winter Garden, Florida is convenient with several nearby airports. Orlando International Airport (MCO) is 35.4km away and offers luxurious accommodations like The Ritz-Carlton Orlando, Grande Lakes, and transportation options including airport shuttles. Daytona Beach International Airport (DAB), 90.1km from Oakland, features hotels like Hilton Daytona Beach Oceanfront Resort, also providing shuttle services. Lastly, Leesburg International Airport (LEE) is 33.8km away, with options such as Mission Resort and Club, which offers various transportation services to the airport. Each of these airports provides accessibility and comfort for travelers visiting the area.