Search Hotels in Oakland, Winter Garden

Top reasons to visit Oakland

• Family-Friendly Activities: Oakland offers a variety of outdoor adventures and entertainment options suitable for families, ensuring fun for all ages.
• Charming Atmosphere: The welcoming neighbourhood boasts friendly locals and a delightful ambiance, perfect for a relaxing getaway.
• Nearby Attractions: Explore popular theme parks, golf courses, and vibrant downtown areas in the surrounding Orange County.
• Diverse Accommodation: A range of lodging options, from family-friendly resorts to pet-friendly hotels, cater to every traveller's needs.
• Scenic Parks: Enjoy the tranquillity of picturesque parks, ideal for leisurely strolls and outdoor picnics.

Find great hotels near Oakland

Explore an array of delightful hotel options in Oakland, Winter Garden, Florida, perfect for every type of traveller. Whether you seek family-friendly resorts, pet-friendly accommodations, or business-themed hotels, Oakland offers a variety of choices to ensure a comfortable stay. With its proximity to Orlando, you'll find the best hotels that cater to your needs and preferences, making your vacation truly memorable.

• Universal's Cabana Bay Beach Resort: This vibrant 3.5-star hotel exudes a retro, family-friendly theme reminiscent of the 1950s and 60s. Located 7.5km from Oakland, it offers a delightful vacation experience for families, featuring spacious rooms and a nostalgic atmosphere. The resort boasts a variety of amenities for children, including a free crib service and an exciting arcade game room, ensuring that younger guests are entertained throughout their stay. With its lively pool area and themed dining options, families can unwind and enjoy quality time together in a whimsical setting.
• The Grove Resort & Water Park Orlando: A splendid 4-star resort situated 8.1km from Oakland, The Grove Resort & Water Park is a fantastic choice for families and LGBTQIA travellers alike. This modern resort promotes inclusivity and offers a wealth of amenities, including a children’s pool, onsite mini-golf, and games specifically for younger guests. The resort’s children’s club, available for a fee, ensures that kids can engage in fun activities while parents relax. The impressive water park and serene surroundings make it an ideal destination for a memorable family vacation.
• DoubleTree by Hilton at the Entrance to Universal Orlando: This elegant 4-star hotel, located 7.5km from Oakland, is perfect for families and pet owners seeking a welcoming atmosphere. The DoubleTree is LGBTQIA-friendly and offers a range of amenities suitable for children, including a pool and an arcade game room. For pet lovers, the hotel permits dogs and cats, with specific policies to ensure a comfortable stay for all. Guests appreciate the warm hospitality and signature chocolate chip cookies upon arrival, making it an inviting option for your Orlando adventure.

Where to stay near Oakland

Oakland, Florida, is a charming neighbourhood perfect for family-friendly adventures and outdoor activities. Nestled in Central Florida, it offers a welcoming atmosphere with friendly locals and a variety of excursions. Explore nearby attractions in Orange County, relax in the scenic parks, or visit the vibrant downtown of Lauderdale. Whether you're seeking entertainment or a tranquil escape, Oakland provides a delightful backdrop for an unforgettable holiday experience.

• Winter Garden: Located a mere 1.9km from Oakland, Winter Garden is a bustling city known for its delightful blend of family-friendly attractions and entertainment options. Visitors flock here year-round, particularly during the peak months of January to February and September. The city boasts a vibrant shopping area and a charming shopping mall, making it ideal for retail therapy. Furthermore, locals and tourists alike can enjoy nearby landmarks such as theme parks and beaches, ensuring a memorable experience filled with fun and relaxation.
• Reavills Corner: This quaint village, also situated 1.9km from Oakland, offers a unique outdoor experience for families and adventure-seekers alike. With visitor numbers peaking in March, July, and December, Reavills Corner provides a refreshing getaway at various times of the year. Its attractions include a delightful resort and shopping area, alongside educational venues. Nature enthusiasts will appreciate the proximity to beautiful lakes and beaches, which serve as perfect spots for picnics or leisurely strolls, adding to the village's charm.
• Montverde: Just 2.5km from Oakland, Montverde is a picturesque city that appeals to outdoor enthusiasts and families. Known for its sports facilities, particularly golf courses, this city attracts visitors mainly from January to March. With a rich array of activities, including access to resorts and scenic lakes, Montverde offers a relaxed yet engaging atmosphere. Close to film studios and theme parks, it provides ample opportunities for entertainment, ensuring that visitors leave with lasting memories of their stay.

Things to do near Oakland

Oakland, Florida, is an ideal destination for families seeking outdoor entertainment and relaxation. Visitors can enjoy a variety of activities, including exploring nearby resorts, shopping areas, and shopping mall centres. With its charming atmosphere and numerous attractions, Oakland promises a delightful vacation experience filled with fun and leisure for all ages.

Shopping

In Oakland, visit Clermont Regal Shopping Center, just 3.7km away, offering a vibrant selection of shops and eateries. If you're up for a drive, discover Oak Hill Village Shopping Center, located 6.2km away, or Flamingo Crossings Town Center, situated 7.5km away, both featuring family-friendly vibes.

Recreation

At Camping World Stadium, immerse yourself in the thrill of live sports events, just 8.7km from Oakland. Enjoy the serene greens at Disney's Magnolia Golf Course, situated 6.8km away, or embark on a fun-filled day at Congo River Golf, 7.5km from Oakland, perfect for families and adventurers alike.

Adventure

Universal’s Volcano Bay, a thrilling waterpark 7.5km from Oakland, offers exhilarating slides and relaxing lagoons for all ages. For hiking enthusiasts, the West Orange Trail, located 1.9km away, provides picturesque scenery and outdoor adventure. Alternatively, enjoy water sports at Watertoyz of Clermont, 5.0km from Oakland.

Nightlife

In Oakland, The Orlando Eye at ICON Park offers breathtaking views and family-friendly fun on its iconic Ferris wheel. For a unique experience, Sleuth's Mystery Dinner Show combines entertainment and romance, while Carter Family Bowl provides an exciting arcade atmosphere perfect for families seeking adventure.

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, avoiding the pricier March to April and December. Book your hotel about a month in advance, or check for last-minute deals on Expedia. Tuesdays are the most economical days to stay, while Saturdays are the priciest. Utilise Expedia’s search tools to filter for budget-friendly options, and consider package deals that combine flights and accommodation for additional savings. Exploring on foot can also help cut costs on transportation.

• 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: Take advantage of Expedia's search tool to refine your preferences, such as your budget, desired location, and the type of hotel you wish to stay in. To find the best prices and deals, simply adjust the price filter to sort from lowest to highest.
• Consider bundling your trip: You could potentially save money by combining your hotel accommodation in Oakland with your flights and activities through an Expedia package deal.

Find the best attractions near Oakland

Oakland, Florida, is perfect for families seeking entertainment and outdoor adventures. Popular attractions include theme parks, golf courses, and arts centres, offering a delightful mix of fun and cultural experiences. Whether you're looking to enjoy thrilling activities or immerse yourself in the local culture, Oakland has something for everyone, making it an ideal destination for a memorable holiday.

• Walt Disney World® Resort: Experience the magic of this iconic theme park, located 6.2km from Oakland. Enjoy thrilling rides, enchanting attractions, and family-friendly entertainment that will delight visitors of all ages.
• Orange County Convention Center: Situated 8.1km away, this arts centre boasts a vibrant cultural scene. Explore exhibitions and events that showcase the rich artistic heritage of the region, making it a great stop for art enthusiasts.
• Universal CityWalk: Just 7.5km from Oakland, this lively tourist precinct offers a fantastic outdoor atmosphere. Enjoy dining, shopping, and entertainment in a family-friendly setting, perfect for making lasting memories.

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 visiting Oakland, Winter Garden, Florida, the main airports to consider are Orlando International Airport (MCO) and Kissimmee Gateway (ISM). Orlando International Airport is situated 13.7km from Oakland, with nearby accommodation options like The Ritz-Carlton Orlando, Grande Lakes and Rosen Shingle Creek, both 5.0km away, offering various transportation services. Kissimmee Gateway is also 13.7km from Oakland, featuring hotels such as Waldorf Astoria Orlando, located 4.3km from the airport. Both airports provide convenient access to the area, making your travel experience seamless.