Oakland Hotels, Winter Garden

Top reasons to visit Oakland

• Outdoor Adventures: Oakland offers a range of activities for families and outdoor enthusiasts, including scenic parks and recreational areas.
• Cultural Experiences: Engage with local attractions like the Oakland Arena and the Fox Theater for vibrant performances and events.
• Beautiful Scenery: Enjoy stunning views along the Oakland Embarcadero and Oakland Estuary, perfect for relaxing walks.
• Family-Friendly Activities: Explore the Oakland Zoo and nearby theme parks, catering to all ages and interests.
• Diverse Accommodation: Choose from a variety of family-friendly resorts and hotels, ensuring a comfortable stay.

Find great hotels near Oakland

For a memorable getaway in Oakland, Florida, you'll discover a variety of accommodation options ranging from family-friendly resorts to comfortable hotels. Whether you're seeking pet-friendly amenities or a business-themed stay, the hotels in Oakland cater to all types of travellers. With an array of choices, including affordable options and spacious suites, you're sure to find the perfect base to explore the charming surroundings and enjoy your holiday.

• Universal's Cabana Bay Beach Resort: Embrace the nostalgic charm of the 1950s and 60s at Universal's Cabana Bay Beach Resort, a family-friendly 3.5-star hotel that offers a fun-filled vacation experience. Located 19.3km away from Oakland, this vibrant resort features spacious family suites, a lazy river, and an expansive pool area perfect for relaxing after a day at the theme parks. Kids will love the arcade game room, while parents can enjoy complimentary cribs for the little ones. With a focus on family bonding and playful atmosphere, this resort is an excellent choice for those seeking a memorable getaway.
• The Grove Resort & Water Park Orlando: The Grove Resort & Water Park Orlando is a 4-star paradise for adventure seekers, situated 20.9km from Oakland. With its nature-themed surroundings and a welcoming atmosphere for LGBTQIA travellers, this resort offers an array of exciting activities, including onsite fishing, surfing lessons, and thrilling water sports. The expansive water park is a highlight, featuring slides and a lazy river, ensuring endless fun for all ages. Whether you’re looking to relax in nature or embark on thrilling adventures, The Grove is the perfect destination for an exhilarating vacation.
• DoubleTree by Hilton at the Entrance to Universal Orlando: A sophisticated 4-star hotel, the DoubleTree by Hilton at the Entrance to Universal Orlando caters to business and leisure travellers alike. Located 19.3km from Oakland, this LGBTQIA-friendly hotel offers exceptional business amenities, including multiple meeting rooms and a fully equipped business centre. Guests can indulge in a warm chocolate chip cookie upon arrival and enjoy a pet-friendly policy, making it a great choice for those travelling with furry companions. With its convenient location and superior facilities, this hotel ensures a comfortable and productive stay.

Where to stay near Oakland

Oakland, located in Winter Garden, Florida, offers a delightful blend of family-friendly fun and outdoor adventures. Just a short drive away, you can explore stunning attractions that showcase breathtaking views and a welcoming atmosphere. Whether you're enjoying the vibrant local community or seeking excursions that cater to all ages, Oakland is the perfect base for your holiday, ensuring you stay close to the top attractions while soaking in the charm of the East Side.

• Killarney: Killarney is a charming neighbourhood located 1.3km from Oakland, perfect for those seeking an outdoor adventure. While visitor numbers remain steady throughout the year, March, July, and December are particularly popular times to visit. Families and sports enthusiasts flock to this area for its golf courses and resort amenities. Nearby, you can explore enchanting local landmarks such as a theme park, a film studio, and serene lakes, making it an ideal spot for relaxation and fun.
• Winter Garden: As the city that Oakland calls home, Winter Garden offers a delightful blend of family-friendly activities and entertainment options. With peak visitor numbers in January, February, and September, this vibrant city is known for its shopping areas and malls. Visitors can indulge in a variety of experiences, from theme parks to picturesque beaches. Whether you're in the mood for a leisurely stroll or a day of shopping, Winter Garden has something for everyone.
• Reavills Corner: Just 4.8km away from Oakland, Reavills Corner is a quaint village that draws families and outdoor enthusiasts alike. The area enjoys consistent visitor traffic, with peaks in March, July, and December. Here, you can partake in a range of activities, from visiting local resorts to exploring shopping areas and educational venues. The nearby attractions, including a theme park, beach, and lake, make Reavills Corner a delightful destination for both relaxation and adventure.

Things to do near Oakland

Oakland, Winter Garden, Florida, is perfect for families and those seeking outdoor adventures. You'll find a range of activities, including vibrant shopping malls and resort experiences. Don't miss the local sightseeing opportunities and lively nightclubs that reflect the area's charm and entertainment options. Enjoy a delightful mix of relaxation and excitement during your visit!

Shopping

In Oakland, you can visit the Clermont Regal Shopping Center, just 9.7km away, offering a fantastic mix of shops and entertainment. If you're up for a drive, check out Flamingo Crossings Town Center, located 19.3km away, for a vibrant shopping experience with family-friendly vibes.

Recreation

Experience the thrill at Camping World Stadium, only 22.5km away, where you can soak in the energetic sports atmosphere. Enjoy a day of golfing at Disney's Magnolia or Palm Golf Courses, both 17.7km from Oakland, offering beautiful outdoor settings for relaxation and recreation.

Adventure

Universal’s Volcano Bay, located 19.3km from Oakland, is a thrilling waterpark filled with exhilarating slides and wave pools, perfect for family fun. The West Orange Trail, 4.8km away, offers scenic hiking amidst nature, while Watertoyz of Clermont, 12.9km distant, provides exciting water sports for adventure seekers.

Nightlife

In Oakland, the Orlando Eye at ICON Park offers breathtaking views and adventure vibes, perfect for families. The Garden Theatre, just 4.8km away, provides a romantic cultural experience, while the Carter Family Bowl is a fun-filled arcade adventure zone, ideal for family outings.

Booking tips and Expedia advantages for Oakland

For a budget-friendly visit to Oakland, consider travelling in August to September or November when accommodation prices drop. Booking your hotel about a month in advance or checking last-minute deals on Expedia can lead to savings, especially on Tuesdays, the cheapest day to stay. Use Expedia’s search tools to filter by budget and eco-friendly options. Don’t forget to explore free local attractions and combine your hotel with flights for additional discounts. These tips will help you enjoy your trip 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. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
• 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 lets you set your budget, choose your ideal location, and much more. You can organise your results to display prices from lowest to highest, making it easy to find 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 environmentally-friendly accommodations that you can book.
• Consider bundling your trip: You can save some dollars by combining your Oakland hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Oakland

Oakland, Florida, is perfect for families and outdoor enthusiasts seeking entertainment and cultural experiences. Explore local attractions such as the Oakland Arena, the scenic Oakland Embarcadero, and the engaging Oakland Zoo. For those who appreciate the arts, the Fox Theater offers great performances, while the Oakland Estuary provides beautiful views and recreational opportunities. Whether you're playing golf at a country club or enjoying a theme park, there's something for everyone in this charming town.

• Walt Disney World® Resort: Located 16.1km from Oakland, this iconic theme park offers a magical experience filled with entertainment for the whole family. Immerse yourself in enchanting attractions, meet beloved characters, and enjoy spectacular shows that create unforgettable memories.
• Orange County Convention Center: Situated 20.9km away, this arts centre is a hub of culture and creativity. Explore diverse exhibitions and events that showcase local and international art, making it a perfect spot for art enthusiasts and culture seekers.
• Universal CityWalk: Just 19.3km from Oakland, this vibrant tourist precinct features outdoor dining, shopping, and entertainment. Enjoy a lively atmosphere with family-friendly activities, live music, and a variety of restaurants to satisfy every palate.

Best time to go to Oakland

The best time to visit Oakland is dependant 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 visiting Oakland, Winter Garden, Florida, you have several airport options. Orlando International Airport (MCO) is located 35.4km away and offers nearby hotels like The Ritz-Carlton Orlando, Grande Lakes, and Rosen Shingle Creek, both 12.9km from the airport, with various shuttle services available. Daytona Beach International Airport (DAB), situated 90.1km away, features hotels such as Daytona Grande Oceanfront Resort, just 8.0km from the airport. Leesburg International Airport (LEE) is 33.8km away, with options like Mission Inn Resort & Club, located 11.3km from the airport, providing shuttle services as well. Enjoy your trip!