Hotels in Oakland, Winter Garden

Top reasons to visit Oakland

• Outdoor Adventures: Oakland offers a variety of outdoor activities, perfect for family-friendly fun, including golfing and tennis.
• Cultural Attractions: Explore local culture through historic sites like the Paramount Theatre and Fox Theatre.
• Vibrant Downtown: Discover the charm of Oakland's downtown area, filled with shops and eateries.
• Family-Friendly Excursions: Enjoy visits to the Oakland Zoo and nearby theme parks for all ages.
• Comfortable Accommodations: Choose from a range of hotels and resorts catering to both leisure and business travellers.

Find great hotels near Oakland

Discover a range of delightful accommodations in Oakland, Florida, perfect for every type of traveller. From family-friendly resorts to convenient hotels, you’ll find options that cater to both business and leisure needs. Whether you're seeking pet-friendly facilities or a relaxing vacation experience, Oakland's hotels offer the ideal blend of comfort and convenience to ensure an unforgettable stay.

• Universal's Cabana Bay Beach Resort: Embrace the vibrant spirit of the 1950s and 1960s at Universal's Cabana Bay Beach Resort, a 3.5-star hotel that celebrates retro charm. Located 19km from Oakland, this family-friendly resort is designed for those seeking a nostalgic getaway. Guests can enjoy amenities tailored for children, including a fun-filled arcade game room and complimentary cribs. Start your day with breakfast options for the little ones and unwind in stylish, comfortable rooms that reflect a classic Americana vibe.
• The Grove Resort & Water Park Orlando: Discover a world of adventure at The Grove Resort & Water Park Orlando, a 4-star resort situated 21km from Oakland. Perfect for families looking for excitement, this property features a variety of recreational activities such as onsite fishing, surfing lessons, and nearby swimming opportunities. Children can splash about in the resort's free water park or engage in mini-golf and arcade games. The combination of adventure and relaxation makes this resort a splendid choice for family vacations.
• DoubleTree by Hilton at the Entrance to Universal Orlando: Just 19km from Oakland, the DoubleTree by Hilton at the Entrance to Universal Orlando offers a blend of comfort and convenience for families, business travellers, and pet owners alike. This 4-star hotel is known for its warm hospitality, ensuring a welcoming atmosphere. With amenities for children, including a dedicated pool and arcade room, families will find plenty to enjoy. The hotel also accommodates pets, making it a versatile option for those travelling with furry companions.

Where to stay near Oakland

Oakland, located in Winter Garden, Florida, offers a delightful blend of outdoor activities and family-friendly entertainment. Visitors can explore the vibrant downtown area, uncover the charm of the surrounding neighbourhoods, and enjoy excursions that showcase the welcoming atmosphere. Just a short distance from the Oakland Arena, this thriving locale is perfect for those seeking relaxation and memorable experiences. Discover all that Oakland has to offer for a truly enjoyable vacation.

• Winter Garden: Nestled in the heart of Florida, Winter Garden is a vibrant city where Oakland is situated. This delightful area attracts visitors year-round, particularly peaking in January, February, and September. Known for its family-friendly atmosphere and entertainment options, Winter Garden offers a plethora of activities including resorts, shopping areas, and shopping mall centres. Local attractions such as theme parks, film studios, and waterparks make it a fantastic destination for family adventures and leisure seekers alike.
• Lake Buena Vista: Located approximately 21km from Oakland, Lake Buena Vista is a lively city renowned for its entertainment and business opportunities. Visitors typically flock to this area from January to March, with quieter months from October to December. The city boasts a variety of resorts and shopping venues, catering to both families and professionals. Major landmarks nearby include famous theme parks, film studios, and sports facilities, ensuring a wealth of exciting experiences for all types of travellers.
• Ocoee: Just 8km from Oakland, Ocoee is a charming city that offers a delightful mix of family and outdoor experiences. Its visitor numbers peak in March, July, and September, making it a popular spot for both leisure and entertainment. Ocoee features various resorts and shopping centres, ideal for those looking to unwind and explore. Its proximity to thrilling theme parks, film studios, and sports facilities ensures an engaging and diverse experience for all who visit.

Things to do in Oakland

Shopping

Located in the heart of Oakland, the nearby Winter Garden Village offers a delightful shopping experience with a mix of retail shops and boutiques. You can explore local markets for unique souvenirs and gifts, ensuring a memorable selection from your visit to Florida.

Recreation

In Oakland, indulge in rejuvenating treatments at the serene Zen Wellness Spa, where holistic therapies and calming environments promote relaxation. For outdoor enthusiasts, explore the scenic trails at the nearby Lake Apopka, ideal for leisurely walks and birdwatching amidst nature’s beauty.

Adventure

Explore the scenic Lake Apopka Wildlife Drive, where you can observe diverse wildlife and enjoy the natural beauty of the wetlands. For a thrilling experience, visit the nearby Orlando Tree Trek Adventure Park, featuring zip lines and challenging obstacle courses amidst the lush forest.

Nightlife

Explore the vibrant nightlife in Oakland with a visit to The 101, where you can enjoy crafted cocktails and a lively atmosphere. For a more relaxed vibe, check out the nearby Oakland Village Tavern, known for its cosy setting and friendly locals, perfect for unwinding after a day of exploration.

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 perfect for family-friendly outdoor adventures and entertainment. Visitors can explore a variety of attractions, including theme parks, golf courses, and amusement parks. Notable points of interest include the Oakland Estuary, the historic Paramount Theatre and Fox Theatre, and the Oakland Zoo, offering a blend of culture and recreation for all ages. This charming area promises a memorable experience for every traveller.

• Walt Disney World® Resort: Located 16km from Oakland, this iconic theme park offers a magical experience with its enchanting attractions, parades, and character meet-and-greets, making it a delightful destination for families seeking joy and wonder.
• Universal Orlando Resort: Situated 19km from Oakland, this thrilling theme park immerses visitors in the worlds of blockbuster films, featuring exhilarating rides and shows that captivate audiences of all ages while providing a vibrant atmosphere.
• Magic Kingdom® Park: Just 16km from Oakland, this beloved park invites guests to explore its whimsical lands, enjoy classic attractions, and witness spectacular fireworks, creating cherished memories in a charming setting.

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

Flying into Oakland, Winter Garden, Florida, is convenient with several major airports nearby. Orlando International Airport (MCO) is located 35km away, with excellent hotel options like The Ritz-Carlton Orlando, Grande Lakes and Rosen Shingle Creek, both 13km from the airport. Tampa International Airport (TPA) is 109km away, offering luxurious stays at The Tampa EDITION and JW Marriott Tampa Water Street, both just 10km from the airport. Daytona Beach International Airport (DAB) is 90km from Oakland, with comfortable accommodations like Daytona Grande Oceanfront Resort and Hilton Daytona Beach Oceanfront Resort, both 6km from the airport. All hotels provide various transport services for airport access.