Find hotels in Oakland, Winter Garden

Top reasons to visit Oakland

• Family-Friendly Atmosphere: Oakland is a charming destination perfect for family vacations, offering a welcoming community and low crowds.
• Outdoor Adventures: Explore the Oakland Nature Preserve for enriching outdoor experiences and beautiful scenery.
• Proximity to Attractions: Enjoy easy access to nearby theme parks, water parks, and the vibrant Downtown Orlando.
• Diverse Accommodation Options: Choose from a variety of lodging, including family-friendly resorts and pet-friendly hotels.
• Recreational Activities: Engage in golf, shopping, and recreational activities that cater to all interests.

Find great hotels near Oakland

Oakland, Florida, offers a variety of lodging options to suit every traveler's needs. Whether you're seeking a family-friendly resort, a pet-friendly hotel, or accommodations ideal for business travelers, you'll find a range of hotels in Oakland and nearby areas. Enjoy the comfort and convenience of well-equipped hotels that cater to vacationers looking for an unforgettable experience in this charming region.

• Universal's Cabana Bay Beach Resort: Embrace a vibrant, retro-inspired atmosphere at Universal's Cabana Bay Beach Resort, where family fun takes center stage. Located 19.3km from Oakland, this 3.5-star hotel offers a nostalgic 1950s and 1960s theme, perfect for families looking to create lasting memories. With amenities tailored for children, including a free crib service and an engaging arcade game room, your little ones will be entertained. The resort also features two refreshing pools and a lazy river, making it an ideal spot for relaxation and play.
• The Grove Resort & Water Park Orlando: Nestled 20.9km away from Oakland, The Grove Resort & Water Park Orlando presents a nature-themed retreat that seamlessly blends relaxation and adventure. This 4-star resort is LGBTQIA-friendly and offers a plethora of family-friendly amenities, including a fantastic water park, children’s pool, and a dedicated children’s club (available for a fee). With its lush surroundings, guests can enjoy tranquil walks while having access to exciting activities like arcade games. The Grove is an inviting destination for families and nature lovers alike.
• DoubleTree by Hilton at the Entrance to Universal Orlando: Located 19.3km from Oakland, DoubleTree by Hilton provides a warm welcome with its delicious signature cookie and family-friendly atmosphere. This 4-star hotel is both LGBTQIA-welcoming and pet-friendly, ensuring everyone feels at home. Children will enjoy the arcade game room and the dedicated children’s pool. Additionally, the property allows pets, so you can bring your furry companions along for the adventure. With a prime location near Universal Studios, this hotel is perfect for families seeking comfort and excitement.

Where to stay near Oakland

Oakland, Florida, is a charming neighborhood perfect for family-friendly vacations and business trips. Nearby attractions include the vibrant Downtown Orlando and the serene Oakland Park, offering low crowds and a welcoming atmosphere. Explore the local excursions, enjoy the friendly community, and find great vacation rentals to make your stay comfortable. Whether you're seeking relaxation or adventure, Oakland and its surroundings promise memorable experiences for every traveler.

• Killarney: Nestled a mere 1.3km from Oakland, Killarney is a charming neighborhood that attracts visitors year-round, particularly peaking in March, July, and December. Known for its family-friendly atmosphere, outdoor activities, and cultural experiences, Killarney offers an array of engaging options. Golf enthusiasts will appreciate the nearby golf courses and resorts, while families can explore local attractions such as science museums and theme parks. Whether you're looking to relax or engage in recreational activities, Killarney provides a delightful mix of experiences for all ages.
• Winter Garden: As the city encompassing Oakland, Winter Garden is a vibrant destination for families and business travelers alike. Visitor numbers rise during January to February and September, making it an ideal time to explore the city's dynamic shopping areas and malls. With a plethora of entertainment options, including theme parks and water parks, Winter Garden promises a lively vacation experience. The blend of family-friendly activities and business amenities ensures that whether you're seeking relaxation or productivity, Winter Garden has something for everyone.
• Reavills Corner: Located approximately 4.8km from Oakland, Reavills Corner is a quaint village that draws visitors for its cultural, family-oriented, and entertainment-themed experiences. With peak travel times in March, July, and December, this charming locale offers accessible theaters and educational venues, making it perfect for families and culture enthusiasts alike. Nearby attractions include an institute, theme parks, and a marina, providing endless opportunities for exploration and adventure. Reavills Corner strikes a wonderful balance between leisure and cultural immersion, making it a must-visit during your stay.

Things to do near Oakland

Oakland, Winter Garden, Florida, is perfect for family vacations and offers an array of entertainment options. Visitors can enjoy ocean views, recreational activities, and outdoor experiences. Nearby, you'll find a resort, shopping mall center, and shopping centers, as well as exciting water parks. Whether you're looking to relax or have fun, Oakland has something for everyone to enjoy.

Shopping

For shopping in Oakland, visit Clermont Regal Shopping Center, 9.7km away, offering a lively atmosphere. Westgate Square Shopping Center, 17.7km away, and Hiawassee Wood Shopping Center, 16.1km away, both provide a mix of entertainment, dining, and retail options perfect for gifts and souvenirs.

Recreation

Camping World Stadium, 22.5km from Oakland, offers an energetic atmosphere perfect for sports enthusiasts. Enjoy a round of golf surrounded by nature at Forest Lake Golf Club, just 11.3km away. For family fun, visit Pirate's Cove Adventure Golf, located 20.9km from Oakland, featuring exciting mini-golf challenges.

Adventure

At Universal’s Volcano Bay, experience thrilling water rides and relaxing lagoons, perfect for families and adventure seekers alike, located 19.3km from Oakland. Explore the scenic West Orange Trail, a 4.8km hiking path offering breathtaking views. For water sports enthusiasts, Watertoyz of Clermont, 12.9km away, provides exciting outdoor activities.

Nightlife

Experience the excitement at The Orlando Eye at ICON Park, a stunning ferris wheel offering adventure and family vibes. For a romantic evening, catch a show at the Garden Theatre, rich in entertainment and culture. Don’t miss the fun at Carter Family Bowl, an arcade adventure zone perfect for all ages.

Booking tips and Expedia advantages for Oakland

To save on your trip to Oakland, plan your visit during the cheaper months of August to September or November, and aim to book your hotel about a month in advance for better rates. Tuesdays are typically the least expensive days to stay, while Saturdays are the most costly. Utilize Expedia to find deals by sorting prices from lowest to highest, and consider package deals that combine flights, hotels, and activities for additional savings. Don't forget to check for last-minute deals for further discounts.

• 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, such as budget, desired location, and the type of hotel you want. For instance, selecting the Eco-certified option 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 through an Expedia package deal.

Find the best attractions near Oakland

Oakland, Florida, is an ideal destination for family vacations, offering a mix of entertainment and business-themed activities. Visitors can enjoy local attractions such as theme parks, arts centers, and golf courses. For those seeking outdoor and cultural experiences, the Oakland Nature Preserve is a must-visit. Whether you're traveling with family or looking for recreational activities, Oakland provides a variety of options to make your trip memorable.

• Walt Disney World® Resort: Experience the magic at Walt Disney World®, a premier theme park that offers enchanting attractions, thrilling rides, and beloved characters. Families will create unforgettable memories while exploring its diverse lands and enjoying captivating entertainment.
• Orange County Convention Center: Immerse yourself in the vibrant culture at the Orange County Convention Center, a hub for various events and exhibitions. Discover unique art displays, local crafts, and engaging programs that showcase the rich artistic heritage of the region.
• Universal CityWalk: Enjoy a lively atmosphere at Universal CityWalk, an outdoor entertainment district filled with shops, restaurants, and exciting nightlife. Perfect for families, it offers a variety of dining options and entertainment that cater to all ages.

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

When traveling to Oakland, Winter Garden, Florida, you have a few major airport options. Orlando International Airport (MCO) is located 35.4km away, with nearby hotel choices like The Ritz-Carlton Orlando, Grande Lakes, and Rosen Shingle Creek, both offering shuttle services. Leesburg International Airport (LEE) is 33.8km away, with accommodations such as Mission Resort and Club, providing airport transport options. Kissimmee Gateway Airport (ISM) is also 35.4km from Oakland, featuring luxury stays like Waldorf Astoria Orlando. Each airport has hotels that provide convenient transportation services, making your journey seamless.