Hotels in Oakland, Winter Garden from CA $71

Top reasons to visit Oakland

• Family-Friendly Atmosphere: Oakland is perfect for families, offering a range of outdoor activities and attractions.
• Cultural Experiences: Explore local points of interest like the Oakland Museum and the Oakland Temple.
• Historic Charm: Stroll through downtown Oakland and the historic Old Oakland for a glimpse of its rich heritage.
• Diverse Accommodations: Enjoy a variety of lodging options, from affordable hotels to luxurious resorts.
• Vibrant Community: Experience the lively atmosphere of the Heart of Uptown with welcoming locals.

Find great hotels near Oakland

In Oakland, Winter Garden, Florida, you'll discover a diverse selection of accommodations to suit every traveller's needs, from affordable options to luxurious stays. With an array of hotels and resorts boasting family-friendly, pet-friendly, and business-focused amenities, there's something for everyone. Whether you're searching for the ideal hotel in Oakland or the renowned Oaklander Hotel, you're sure to find a perfect place to relax and enjoy your vacation.

• The Grove Resort & Water Park Orlando: This 4-star resort is an ideal getaway for families and adventure seekers, located 20.9km from Oakland. The Grove Resort & Water Park Orlando immerses guests in a fun-filled environment, featuring an array of adventure sports such as surfing, fishing, and swimming. Kids will love the on-site water park, arcade game room, and mini-golf, ensuring that every family member has a good time. With a strong focus on adventure and family bonding, this resort provides the perfect setting for creating lasting memories.
• Universal's Cabana Bay Beach Resort: A vibrant 3.5-star hotel only 19.3km from Oakland, Universal's Cabana Bay Beach Resort captures the essence of retro fun and family-friendly accommodation. The hotel boasts a nostalgic atmosphere reminiscent of the 1950s and 60s. Families will appreciate the complimentary cribs and the engaging arcade game room, making it a convenient choice for parents travelling with children. The property’s emphasis on family-oriented fun and relaxation makes it an excellent base for exploring nearby attractions.
• DoubleTree by Hilton at the Entrance to Universal Orlando: This 4-star hotel, located 19.3km from Oakland, caters to a diverse range of travellers, including families, business professionals, and pet owners. Offering multiple meeting rooms and a fully accessible business centre, it’s perfect for those needing to mix business with leisure. Families will enjoy the children’s pool and arcade game room, while pets are welcome with specific policies in place. The DoubleTree combines comfort with practicality, making it a fantastic choice for all types of visitors.

Where to stay near Oakland

Discover the charm of Oakland, Florida, where family-friendly outings meet vibrant entertainment. Explore downtown Oakland, stroll through the historic Old Oakland, and enjoy the lively atmosphere of the Heart of Uptown. With its welcoming locals and romantic spots, you're sure to create unforgettable memories. Whether you're seeking outdoor adventures or quaint excursions, Oakland offers a delightful blend of experiences for every traveller.

• Killarney: Nestled a mere 1.3km from Oakland, Killarney is a charming neighborhood that offers a delightful mix of outdoor activities and family-friendly experiences. Visitors flock here for its picturesque landscapes, including nearby lakes and parks, ideal for sports enthusiasts and nature lovers alike. The peak seasons in March, July, and December see an influx of travellers drawn to its golf courses and resorts. Killarney's proximity to a vibrant theme park and film studio adds an extra layer of excitement, making it a must-visit for families seeking adventure.
• Winter Garden: As the city that encompasses Oakland, Winter Garden is a bustling hub perfect for family outings and entertainment. With visitor numbers peaking in January, February, and September, there's always something happening in this lively locale. Winter Garden boasts a plethora of shopping areas and malls, great for those looking to indulge in retail therapy. In addition, its close proximity to renowned theme parks and beautiful beaches ensures that there’s no shortage of fun. This city is ideal for business travellers too, offering a variety of venues suitable for meetings and conferences.
• Reavills Corner: Located just 4.8km from Oakland, Reavills Corner is a quaint village that beckons families and outdoor enthusiasts. With similar travel patterns to Killarney, the village sees peaks in March, July, and December. Visitors can enjoy a blend of shopping experiences and educational venues, making it a great spot for those travelling with children. Surrounded by stunning lakes and beaches, it offers ample opportunities for relaxation and recreation. The nearby theme park adds an element of thrill, ensuring a memorable experience for all.

Things to do near Oakland

Oakland, Winter Garden, Florida, offers a delightful family-friendly atmosphere perfect for an outdoor vacation. Visitors can enjoy a variety of activities, including exploring nearby resorts, shopping areas, and a bustling shopping mall centre, making it an ideal destination for entertainment and leisure.

Shopping

In Oakland, you can visit Clermont Regal Shopping Center, only 9.7km away, offering a variety of family-friendly shops. If you're up for a drive, check out Flamingo Crossings Town Center and Shoppers World Shopping Center, both 19.3km away, featuring diverse entertainment and shopping options.

Recreation

Experience the lively atmosphere at Camping World Stadium, just 22.5km from Oakland, where you can immerse yourself in sports events. For golf enthusiasts, Disney's Palm Golf Course, located 17.7km away, offers a perfect blend of outdoor activity and relaxation amidst beautiful surroundings.

Adventure

At Universal’s Volcano Bay, located 19.3km from Oakland, experience thrilling water rides and a tropical paradise perfect for families. The West Orange Trail, 4.8km away, offers spectacular scenery for hiking enthusiasts. For water sports, Watertoyz of Clermont, 12.9km distant, provides exhilarating outdoor adventures.

Nightlife

Experience the vibrant nightlife in Oakland by visiting the Garden Theatre for a captivating show. For thrilling fun, head to The Wheel at ICON Park™ or Wonderworks, both offering adventure-filled activities perfect for families and friends alike, just a short drive away.

Booking tips and Expedia advantages for Oakland

When visiting Oakland, Florida, you can save money by taking advantage of free activities such as the Orlando International Premium Outlets, Universal CityWalk, and West Orange Trail. Travel during the cheaper months of August to September and November, and aim to book your hotel about a month in advance for the best rates. Tuesdays typically offer the lowest prices for stays, while Saturdays are the most expensive. Utilize Expedia to compare hotel deals, filter by budget, and consider package options to combine flights and accommodations for additional 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: Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your search results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to narrow down 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 money by combining your hotel stay in Oakland with your flights and activities by booking an Expedia package.

Find the best attractions near Oakland

Oakland, Winter Garden, Florida, is perfect for family-friendly and outdoor adventures, offering attractions like theme parks, golf courses, and arts centres. Visitors can explore local points of interest, including the Oakland Museum, City of Oakland, and the Oakland Temple. Whether seeking cultural experiences or leisure activities, Oakland caters to all travellers looking to enjoy a vibrant community atmosphere.

• Walt Disney World® Resort: Immerse yourself in the magic of this iconic theme park, just 16.1km from Oakland. With thrilling rides, enchanting entertainment, and beloved Disney characters, it's a family-friendly destination that promises unforgettable memories.
• Orange County Convention Center: Located 20.9km away, this arts centre is a cultural hub featuring exhibitions, trade shows, and events that celebrate creativity and innovation. Experience the vibrant atmosphere and engage with local art and culture.
• Arnold Palmer's Bay Hill Golf Club: Only 16.1km from Oakland, this golf course country club is perfect for families and adventure-seekers. Enjoy friendly competition on picturesque greens while soaking in the camaraderie among fellow golf enthusiasts.

Best time to go to Oakland

Visitor numbers around Oakland is generally unchanged in popularity throughout the year. 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

To visit Oakland, Winter Garden, Florida, you can fly into two major airports. Orlando International Airport (MCO) is situated 35.4km away, with nearby accommodations such as The Ritz-Carlton Orlando, Grande Lakes, and Rosen Shingle Creek, offering various transportation services. Alternatively, Daytona Beach International Airport (DAB) is 90.1km from Oakland, with options like Hilton Daytona Beach Oceanfront Resort and Daytona Grande Oceanfront Resort. Lastly, Orlando Sanford International Airport (SFB) is 45.1km away, featuring hotels like Hilton Orlando/Altamonte Springs and The Westin Lake Mary, both providing shuttle services. Each airport presents convenient access to Oakland for your vacation needs.