Search Hotels in Oakland, Winter Garden

Top reasons to visit Oakland

• Outdoor Adventures: Oakland is perfect for outdoor activities like golf and tennis, ensuring fun for the whole family.
• Cultural Attractions: Explore local sites such as the Oakland Museum, historic buildings, and the vibrant downtown area.
• Family-Friendly Entertainment: Enjoy nearby theme parks and amusement parks, offering excitement for all ages.
• Scenic Beauty: Take in the stunning views from the Oakland Hills, perfect for relaxation and sightseeing.
• Diverse Accommodations: Choose from a variety of hotels and resorts catering to every traveller’s needs.

Find great hotels near Oakland

Discover a range of delightful accommodations in Oakland, Winter Garden, Florida, perfect for every type of traveller. From family-friendly resorts to pet-friendly hotels, you'll find the ideal base for your holiday. Whether you seek a relaxing vacation or a business-friendly stay, Oakland offers some of the best hotels to cater to your needs. Experience comfort and hospitality in this charming area, ensuring a memorable visit to the Sunshine State.

• Universal's Cabana Bay Beach Resort: A vibrant 3.5-star hotel with a guest rating of 9.0, Universal's Cabana Bay Beach Resort captures the spirit of retro Americana with its colourful décor and family-friendly atmosphere. Located 19.3km from Oakland, this resort is ideal for families seeking a fun-filled vacation. The property features a range of amenities for children, including a breakfast option for kids, an arcade game room, and complimentary cribs for the little ones. Guests can enjoy a relaxing pool area and a lazy river, making it a perfect choice for those looking to unwind after a day of adventure.
• The Grove Resort & Water Park Orlando: This 4-star resort, boasting a guest rating of 8.0, offers a thrilling family adventure experience just 20.9km from Oakland. The Grove Resort & Water Park immerses guests in a world of excitement, featuring an impressive water park, fishing, boat tours, and surf lessons. Children will love the dedicated kids' club (for a fee) and the onsite mini-golf, while parents can unwind by the pool or take advantage of the water sports equipment available nearby. This resort is a perfect blend of recreation and relaxation, appealing to families seeking an action-packed holiday.
• DoubleTree by Hilton at the Entrance to Universal Orlando: A refined 4-star hotel rated 8.4, situated 19.3km from Oakland, DoubleTree by Hilton is perfect for families, business travellers, and pet owners alike. Guests are greeted with the signature warm chocolate chip cookie upon arrival, setting a welcoming tone. The hotel boasts amenities for children, such as an arcade game room and a dedicated children's pool. With a pet-friendly policy, this hotel allows dogs and cats, making it a convenient choice for those travelling with furry companions. Enjoy a blend of comfort and convenience at this well-appointed property.

Where to stay near Oakland

Oakland, Winter Garden, Florida, offers a delightful blend of outdoor activities and family-friendly entertainment. Visitors can enjoy the vibrant atmosphere of downtown Oakland, explore the charming neighbourhoods, and experience the local culture. Just a short distance from the Oakland Arena, this thriving area is perfect for excursions, relaxation, and making lasting memories with friendly locals. Whether you're seeking adventure or a peaceful retreat, Oakland has something for everyone.

• Winter Garden: Nestled within the vibrant city of Winter Garden, this area offers a delightful blend of family-friendly activities and entertainment. With its peak visitor seasons in January to February and September, you can expect a lively atmosphere filled with attractions such as theme parks, film studios, and water parks. The local shopping area and mall are perfect for those looking to indulge in some retail therapy. Strolling through the charming streets, you'll discover a welcoming community spirit that makes Winter Garden a fantastic base for your Florida adventure.
• Reavills Corner: Located a mere 6.4km from Oakland, Reavills Corner is a quaint village that attracts visitors year-round, especially in March, July, and December. Ideal for outdoor enthusiasts and families, this area boasts excellent golf courses and a lovely resort. The nearby urban park provides a serene setting for leisurely walks or picnics, while the proximity to thrilling theme parks ensures there's never a dull moment. Enjoy the relaxed vibe of this charming village as you immerse yourself in its sporting and recreational offerings.
• Montverde: A picturesque city just 6.4km from Oakland, Montverde is renowned for its outdoor activities and family-oriented experiences. With a peak in visitor numbers from January to March, this city invites you to explore its splendid golf courses and nearby resorts. Nature lovers will appreciate the local lake and beach, perfect for a day of relaxation or adventure. Montverde's welcoming atmosphere and beautiful landscapes provide an ideal backdrop for creating lasting memories during your vacation.

Things to do near Oakland

Oakland, Florida, is perfect for outdoor family getaways, offering various activities such as golf and leisure resorts. Visitors can enjoy sightseeing tours around the area, making it ideal for those who appreciate the great outdoors. Tennis enthusiasts will also find ample opportunities to play and enjoy the sport. With its blend of entertainment and relaxation, Oakland is an excellent destination for a memorable holiday.

Shopping

In Oakland, visit the charming Winter Garden Village at Fowler Groves, featuring a delightful mix of shops and eateries. For a local touch, explore the historic downtown area where you’ll find unique boutiques and markets brimming with gifts and souvenirs that reflect the area’s culture.

Recreation

Experience the luxury of Alaqua Country Club, offering serene golf courses and upscale amenities. Alternatively, unwind at Ridgewood Lakes Golf and Country Club, where you can indulge in fine dining and leisure activities. Windermere Country Club, a mere 8.0km away, provides a tranquil escape amidst stunning surroundings.

Adventure

In Oakland, explore the scenic trails of the nearby Lake Apopka Wildlife Drive, where you can observe diverse wildlife. For a thrilling experience, try zip-lining at the Orlando Tree Trek Adventure Park, offering exhilarating courses amidst the treetops.

Nightlife

In Oakland, Winter Garden, Florida, the nightlife is vibrant, with venues like the historic Garden Theatre showcasing live performances and local bands. The nearby Downtown area features charming bars and restaurants, offering a relaxed atmosphere for socialising and enjoying delicious food and drinks.

Booking tips and Expedia advantages for Oakland

• 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 enables you to set your budget, choose your desired location, and more. You can organise your results to display prices from the lowest to the highest, ensuring you see the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
• Consider bundling your trip: You can save money by combining your hotel booking in Oakland with your flights and activities through an Expedia package.

Find the best attractions near Oakland

Oakland, Winter Garden, Florida, offers a delightful blend of outdoor activities and family-friendly entertainment. Explore popular attractions such as theme parks, golf courses, and amusement parks, catering to those seeking both adventure and cultural experiences. Don't miss the nearby Oakland Museum, historic buildings, the Oakland Zoo, the Paramount Theatre, and the scenic Oakland Hills, ensuring a memorable visit filled with diverse activities for all ages.

• Walt Disney World® Resort: Experience the magic at this iconic theme park, located 16.1km from Oakland. With thrilling rides, enchanting shows, and beloved characters, it offers a delightful atmosphere for families and visitors of all ages.
• Universal CityWalk: Just 19.3km away, this vibrant tourist precinct boasts an outdoor setting filled with shops, restaurants, and entertainment. Perfect for family outings, it provides a lively ambience with plenty of options to explore.
• Arnold Palmer's Bay Hill Golf Club: Situated 16.1km from Oakland, this prestigious golf course and country club offers family-friendly excursions. With its scenic views and welcoming staff, it makes for an adventurous day out.

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 nearest major airport is Orlando International Airport (MCO), situated 35.4km away. Nearby hotel options include the luxurious 5-star Ritz-Carlton Orlando, Grande Lakes and the 4.5-star Rosen Shingle Creek, both approximately 12.9km from MCO, offering various transportation services. For a slightly longer journey, Tampa International Airport (TPA) is located 109.4km away, with top accommodations like the 5-star Tampa EDITION and the 4.5-star JW Marriott Tampa Water Street, both 9.7km from TPA. Daytona Beach International Airport (DAB) is 90.1km from Oakland, with excellent hotels such as The Shores Resort & Spa, just 8.0km from DAB.