Hotels in Oakland, Winter Garden

Top reasons to visit Oakland

• Family-Friendly Adventures: Oakland offers a variety of engaging activities suitable for families, ensuring a memorable holiday for all ages.
• Outdoor Exploration: Enjoy picturesque gardens and thrilling outdoor pursuits, perfect for nature enthusiasts and adventure seekers alike.
• Cultural Experiences: Immerse yourself in local culture through arts centres and nearby attractions, enhancing your holiday experience.
• Diverse Accommodation: Choose from a range of lodging options, including family-friendly resorts and pet-friendly hotels, to suit your needs.
• Welcoming Atmosphere: Experience the warm hospitality of locals, making your visit to Oakland truly inviting.

Find great hotels near Oakland

Discover an array of accommodation options in Oakland, Winter Garden, Florida, catering to various needs. Whether you seek a family-friendly resort, a pet-friendly hotel, or a business travel experience, you'll find suitable choices. Popular selections include the AC Hotel and other establishments that offer comfortable stays and excellent amenities. Enjoy your vacation in this charming area with lodging that meets all your requirements.

• Universal's Cabana Bay Beach Resort: Embrace the nostalgic charm of Universal's Cabana Bay Beach Resort, a family-friendly haven that immerses guests in a vibrant retro theme reminiscent of the 1950s and 60s. Located 19.3km from Oakland, this 3.5-star hotel is perfect for families seeking an unforgettable vacation experience. With amenities tailored for children, including an Arcade Game Room and complimentary cribs, families can relax and play together. The resort features a sprawling pool area, outdoor fire pits, and a lazy river, ensuring both kids and adults have endless fun during their stay.
• The Grove Resort & Water Park Orlando: Set amidst nature and adventure, The Grove Resort & Water Park Orlando is a 4-star retreat located 20.9km from Oakland. This resort offers a thrilling experience for families and adventure seekers alike, with a plethora of onsite activities such as boat tours, surfing lessons, and a complimentary water park for guests. Children can enjoy mini-golf, an arcade game room, and a dedicated children's club, ensuring they remain entertained while parents unwind. The lush surroundings and recreational activities create a perfect backdrop for a family getaway where adventure meets relaxation.
• DoubleTree by Hilton at the Entrance to Universal Orlando: The DoubleTree by Hilton at the Entrance to Universal Orlando is a welcoming 4-star hotel located 19.3km from Oakland, catering to families and business travellers alike. Known for its warm hospitality, guests are greeted with a signature warm cookie upon arrival. This hotel is LGBTQIA-friendly and provides an array of amenities for children, including an arcade game room and a dedicated children's pool. With convenient access to Universal Orlando and a range of business facilities, it offers a balanced blend of leisure and productivity for all types of travellers.

Where to stay near Oakland

Discover the charm of Oakland, Winter Garden, where family-friendly adventures await. Enjoy abundant outdoor options, from picturesque gardens to beachside allure. Explore nearby destinations like Bal Harbour for a delightful mix of relaxation and entertainment. Experience the warm atmosphere and friendly locals who make this area so inviting. Whether it’s a leisurely stroll or a thrilling excursion, Oakland offers a perfect blend of nature and community for an unforgettable vacation.

• Winter Garden: Nestled in the heart of central Florida, Winter Garden boasts a charming downtown area with historic architecture and vibrant local shops. The city offers a delightful blend of family-friendly attractions and entertainment-themed venues, making it a perfect destination for visitors of all ages. With popular shopping areas and resorts, Winter Garden serves as a gateway to nearby theme parks and water parks, ensuring an exciting experience. The peak travel months, particularly from January to February and September, attract visitors eager to enjoy its welcoming atmosphere and fun-filled activities.
• Ocoee: Located a mere 8.0km from Oakland, Ocoee is a lively city renowned for its outdoor recreational activities and family-oriented attractions. Its proximity to various shopping centres and resorts adds to its appeal, making it a convenient stop for visitors. Ocoee welcomes travellers throughout the year, with peak seasons in March, July, and September. The city is also close to notable landmarks such as theme parks and film studios, ensuring an entertaining getaway for those seeking adventure and excitement.
• Lake Buena Vista: Situated 20.9km from Oakland, Lake Buena Vista is synonymous with family fun and entertainment. This vibrant city is home to world-class resorts and shopping areas, catering to both leisure and business travellers. With peak visitor numbers from January to March, Lake Buena Vista offers easy access to renowned theme parks and sports facilities, making it an ideal destination for thrill-seekers and sports enthusiasts alike. The combination of family-friendly experiences and business-themed venues makes Lake Buena Vista a versatile choice for all types of visitors.

Things to do near Oakland

Oakland, Florida, offers a delightful mix of family-friendly activities and outdoor adventures. Visitors can explore local resorts, indulge in shopping at nearby malls, and engage in thrilling pursuits like bird watching and art gallery visits. For those seeking an adrenaline rush, the area caters to adventure seekers with various active adventures, making it an ideal destination for an entertaining and engaging holiday.

Shopping

The nearby Plant Street Market, located 4.8km from Oakland, offers a vibrant atmosphere with local produce and artisan goods. For a broader selection, head to Clermont Regal Shopping Center, 9.7km away, featuring various shops and entertainment options, or visit Westgate Square Shopping Center, 17.7km from Oakland, for a family-friendly experience.

Recreation

Experience the vibrant atmosphere at Camping World Stadium, just 22.5km from Oakland, where you can enjoy live sports events. For a serene day outdoors, visit Clermont National, 6.4km away, or the Forest Lake Golf Club, 11.3km away, both offering beautiful landscapes for a round of golf.

Adventure

Experience the thrills at Universal’s Volcano Bay, a fantastic waterpark 19.3km from Oakland, offering exhilarating rides and family fun. For a scenic adventure, hike the West Orange Trail, located 4.8km away, surrounded by stunning landscapes, or dive into water sports at Watertoyz of Clermont, 12.9km from Oakland.

Nightlife

Experience the enchanting Orlando Eye, a stunning ferris wheel with family-friendly vibes, located 20.9km from Oakland. For a touch of romance and culture, visit the Garden Theatre, just 4.8km away. Alternatively, unleash your adventurous spirit at the Carter Family Bowl arcade, also 4.8km from Oakland.

Booking tips and Expedia advantages for Oakland

To save money on your visit to Oakland, plan your trip during the off-peak months of August to September and November for lower accommodation prices. Book your hotel about a month in advance or explore last-minute deals on Expedia, especially on Tuesdays for the best rates. Utilise Expedia's filters to find eco-friendly options and sort by price for the best deals. Combining your hotel, flights, and activities in a package deal can also yield significant savings. Additionally, take advantage of free local attractions and consider using public transport to keep costs down.

• 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: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To discover the most affordable prices and offers, 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, Winter Garden, Florida, is an ideal destination for families seeking outdoor entertainment and cultural experiences. Visitors can explore a variety of attractions, including theme parks, arts centres, and golf courses. These points of interest provide enjoyable activities for those looking to immerse themselves in the local culture while engaging in fun family-friendly adventures.

• Walt Disney World® Resort: Located 16.1km from Oakland, this iconic theme park offers a magical experience with enchanting attractions, beloved characters, and spectacular shows, making it a perfect family destination filled with joy and wonder.
• Orange County Convention Center: Situated 20.9km away, this arts centre showcases a vibrant cultural scene featuring exhibitions, trade shows, and events that celebrate creativity and artistic expression, providing a unique glimpse into the local culture.
• Universal Orlando Resort: Just 19.3km from Oakland, this thrilling theme park is renowned for its exciting rides and immersive experiences based on popular films, ensuring a fun-filled day for families and adventure seekers alike.

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

To reach Oakland, Winter Garden, Florida, you have several airport options. Orlando International Airport (MCO) is located 35.4km away, offering hotels like the 4.5-star Rosen Shingle Creek, 12.9km from MCO, and the 4-star Marriott's Grande Vista, 14.5km from the airport. Nearby, Daytona Beach International Airport (DAB) is 90.1km away, with accommodation options such as the 4-star Hilton Daytona Beach Oceanfront Resort, just 6.4km from DAB. Lastly, Leesburg International Airport (LEE) is 33.8km away, featuring the 3.5-star Mission Resort and Club, located 11.3km from LEE. Each hotel provides various transportation services to their respective airports.