Hotels in Oakland, Winter Garden

Top reasons to visit Oakland

• Outdoor Adventures: Oakland offers a variety of outdoor activities, including scenic hiking trails and beautiful parks, perfect for nature lovers.
• Family-Friendly Attractions: With nearby theme parks and amusement options, Oakland is ideal for families seeking fun and entertainment.
• Charming Neighborhoods: Explore friendly local communities filled with relaxing atmospheres and unique shops.
• Wine and Dine: Enjoy delightful winery tours and local dining experiences, showcasing Florida's culinary delights.
• Relaxing Accommodations: Choose from a range of well-appointed hotels and serene resorts for a comfortable stay.

Find great hotels near Oakland

In Oakland, Winter Garden, Florida, you'll discover a variety of lodging options, including inviting resorts and hotels that cater to families, pets, and business travellers alike. With excellent accommodations available at places like Oakland Resort, Oakwood Resort, and Oakridge Resort, you’re sure to find the perfect spot for your vacation experience. Whether you seek relaxation or adventure, Oakland has something to offer every visitor.

• Universal's Cabana Bay Beach Resort: Universal's Cabana Bay Beach Resort is a vibrant 3.5-star hotel that captures the essence of a classic 1950s and 60s beach vacation. With a fantastic guest rating of 9.0, this family-friendly resort is situated 19.3km from Oakland. The property features a playful atmosphere with amenities tailored for children, including a complimentary crib service and an exciting arcade game room. Guests can start their day with a hearty breakfast that caters to young ones, making it an ideal choice for families seeking a fun-filled getaway.
• The Grove Resort & Water Park Orlando: The Grove Resort & Water Park Orlando is a luxurious 4-star resort boasting a guest rating of 8.0 and located 20.9km from Oakland. This resort is designed for family vacations, offering a range of amenities such as a mini-golf course and a children’s club, making it an excellent choice for families. The on-site water park provides endless fun for all ages, while the well-appointed accommodations ensure a comfortable stay. With a focus on family entertainment, this resort elevates the vacation experience for children and parents alike.
• DoubleTree by Hilton at the Entrance to Universal Orlando: This 4-star hotel, rated 8.4 by guests, is conveniently located 19.3km from Oakland. The DoubleTree by Hilton is perfect for families and business travellers alike, featuring pet-friendly policies for those travelling with furry companions. The hotel provides a welcoming atmosphere with amenities like an arcade game room and a children’s pool, ensuring fun for the whole family. Guests appreciate the comfortable accommodations and the hotel’s commitment to service, making it a great base for exploring Orlando.

Where to stay near Oakland

Oakland, nestled in Winter Garden, Florida, offers a delightful blend of outdoor activities and family-friendly experiences. Explore nearby charming neighborhoods, each brimming with friendly locals and relaxing atmospheres. From vibrant event venues to unforgettable excursions, Oakland is perfect for a weekly getaway. Enjoy scenic parks and local attractions that promise memorable moments for visitors of all ages, making it an ideal destination for a laid-back yet engaging vacation.

• Killarney: Located a mere 1.3km from Oakland, Killarney is a charming neighbourhood that caters to families and outdoor enthusiasts alike. With a steady flow of visitors year-round, Killarney sees peaks in traveller arrivals during March, July, and December. Guests flock to this area for its resort amenities, vibrant shopping areas, and scenic golf courses. Notable local attractions include a thrilling theme park, an engaging science museum, and a captivating film studio, all within easy reach.
• Winter Garden: As the city where Oakland is situated, Winter Garden is a bustling hub with a vibrant atmosphere. Travellers often visit throughout the year, with peak seasons in January, February, and September. Families and entertainment seekers are drawn to the city for its diverse array of resorts and shopping centres. Highlights include a renowned theme park, a dynamic film studio, and a fun-filled waterpark, making Winter Garden a must-visit for those seeking both leisure and excitement.
• Reavills Corner: A quaint village located 6.4km from Oakland, Reavills Corner offers a delightful escape for those looking to immerse themselves in outdoor activities and family-friendly experiences. Similar to its neighbouring areas, visitor numbers peak in March, July, and December. The village is well-known for its golf courses and resorts, providing ample opportunities for recreation. Residents and visitors alike can enjoy the nearby theme park, charming streets, and expansive urban parks, all contributing to the area's inviting atmosphere.

Things to do near Oakland

Oakland, Florida offers a delightful blend of outdoor adventures, family-friendly activities, and entertainment options. Visitors can enjoy relaxing retreats at local resorts, tee off at scenic golf courses, and immerse themselves in live music events. For those seeking thrill, water sports and nearby hot springs provide the perfect escape. Whether you're looking for recreation or relaxation, Oakland has something for everyone to enjoy.

Shopping

In Oakland, immerse yourself in a delightful shopping experience at the charming local boutiques and markets. Don't miss the diverse offerings at the West Oaks Mall and the unique finds at the nearby Winter Garden Farmers Market, perfect for gifts and souvenirs to take home.

Recreation

At Windermere Country Club, indulge in upscale amenities and serene surroundings, perfect for relaxation. The Winter Park Tennis Center offers a refined atmosphere for tennis enthusiasts, while the Mount Dora Lawn Bowling Club provides a charming setting for socializing and enjoying leisurely games in a luxurious environment.

Adventure

Explore the scenic trails at Oakland Nature Preserve, where you can hike and experience Florida's natural beauty. For a thrilling outdoor adventure, try kayaking on Lake Apopka, where you can spot diverse wildlife and enjoy the serene waters.

Nightlife

In Oakland, Winter Garden, Florida, the nightlife is vibrant with local pubs and live music venues. The Crooked Can Brewing Company is popular for its craft beers, while the Winter Garden Theatre hosts performances that captivate audiences, ensuring a lively evening for visitors.

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: Utilize Expedia's search tool to narrow down your options based on your budget, desired location, and preferred type of accommodation. To find the best prices and deals, 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 by booking a package through Expedia.

Find the best attractions near Oakland

Oakland, Winter Garden, Florida, is perfect for families and outdoor enthusiasts, offering a range of attractions such as theme parks, golf courses, and amusement parks. Visitors can explore the Oakland Museum, enjoy nearby attractions, take in ocean views, or visit charming fishing villages. With a blend of entertainment and cultural experiences, Oakland ensures a memorable vacation for everyone.

• Walt Disney World® Resort: Experience the magic at this iconic theme park, located 16.1km from Oakland. With enchanting rides, character interactions, and vibrant entertainment, it offers endless family fun and unforgettable memories.
• Universal CityWalk: A lively outdoor tourist precinct located 19.3km away, Universal CityWalk is perfect for family outings. Enjoy dining, shopping, and entertainment in a vibrant atmosphere, making it a great spot for relaxation and adventure.
• Arnold Palmer's Bay Hill Golf Club: Just 16.1km from Oakland, this renowned golf course and country club provides a family-friendly atmosphere. Engage in exciting excursions and enjoy friendly interactions while experiencing the thrill of the game.

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 visit Oakland, Winter Garden, Florida, the nearest major airport is Orlando International Airport (MCO), located 35.4km away. Nearby hotel options include The Ritz-Carlton Orlando, Grande Lakes, a luxurious 5-star aparthotel, and Rosen Shingle Creek, a 4.5-star hotel, both 12.9km from MCO, offering convenient airport shuttle services. Tampa International Airport (TPA) is another option, situated 109.4km away, with excellent accommodations like The Tampa EDITION and ROOST Tampa, both 9.7km from TPA. Daytona Beach International Airport (DAB) is 90.1km from Oakland, with comfortable stays at The Shores Resort & Spa and Daytona Grande Oceanfront Resort, each only 6.4km from DAB.