Find hotels in Oakland, Winter Garden

Top reasons to visit Oakland

• Outdoor Adventures: Oakland is perfect for outdoor enthusiasts with parks and recreational activities nearby, ideal for family outings.
• Proximity to Theme Parks: Just a short drive from Orlando, enjoy easy access to world-famous theme parks for thrilling fun.
• Family-Friendly Attractions: The area features exciting water parks and entertainment options suitable for all ages.
• Charming Neighborhoods: Explore inviting local neighborhoods that showcase the heart of Florida’s culture and community.
• Diverse Accommodation: A range of lodging options, from family resorts to pet-friendly hotels, cater to every traveler's needs.

Find great hotels near Oakland

Discover a variety of hotel accommodations in Oakland, Florida, designed to meet the needs of every traveler. Whether you're seeking a family-friendly resort, a pet-friendly hotel, or a convenient spot for business travel, Oakland offers an array of options. Enjoy a relaxing vacation experience while exploring the local charm and attractions, with numerous lodging choices available in both Oakland and nearby Oakland Park.

• Universal's Cabana Bay Beach Resort: Universal's Cabana Bay Beach Resort is a vibrant 3.5-star hotel with a guest rating of 9.0, perfect for families seeking a fun-filled vacation. This retro-themed property, just 12 miles from Oakland, immerses guests in a lively atmosphere reminiscent of the 1950s and 60s. Families will appreciate the variety of child-friendly amenities, including an arcade game room, complimentary cribs, and a breakfast fee structure designed for children. With its unique blend of nostalgia and modern comfort, this resort is an excellent choice for family bonding.
• The Grove Resort & Water Park Orlando: The Grove Resort & Water Park Orlando is a family-friendly 4-star resort, boasting a guest rating of 8.0. Located 13 miles from Oakland, this resort features an expansive water park, ensuring endless fun for guests of all ages. Amenities such as a permanent splash pad, children's pool, and arcade game room cater specifically to younger visitors. The resort's focus on family experiences makes it an ideal destination for those looking to create lasting memories in a vibrant and engaging setting.
• DoubleTree by Hilton at the Entrance to Universal Orlando: DoubleTree by Hilton at the Entrance to Universal Orlando is a welcoming 4-star hotel with a guest rating of 8.4, situated 12 miles from Oakland. This property combines convenience for business travelers with family-friendly amenities, making it versatile for various guests. The hotel offers a children's pool, arcade game room, and pet-friendly policies, ensuring a comfortable stay for families and their furry friends. With its warm hospitality, guests can enjoy both relaxation and accessibility to nearby attractions.

Where to stay near Oakland

Oakland, Florida, offers a delightful mix of outdoor family fun and vibrant entertainment. Just a stone's throw from downtown Orlando, visitors can enjoy fresh air while exploring nearby parks and attractions. The friendly atmosphere makes it perfect for excursions with loved ones. Don't miss the charming neighborhoods that showcase the heart of Florida, inviting you to relax and soak in the local culture. Experience the best of both nature and community in this welcoming destination.

• Killarney: Nestled a short distance from Oakland, Killarney offers a blend of family-friendly activities and outdoor experiences. This charming neighborhood is ideal for visitors seeking a cozy atmosphere with convenient access to local resorts and shopping areas. The area is renowned for its nearby theme parks, science museums, and film studios, making it perfect for families and city-themed adventures. Although visitor numbers fluctuate throughout the year, peaks occur in March, July, and December, ensuring that you’ll find plenty of fellow travelers and engaging activities during those months.
• Winter Garden: As a city that envelops Oakland, Winter Garden is a vibrant destination that attracts families and entertainment enthusiasts alike. Known for its lively shopping mall centers and resorts, this city provides a plethora of entertainment options. Visitors flock here in January, February, and September, enjoying attractions such as theme parks, waterparks, and film studios. The welcoming atmosphere and diverse offerings make Winter Garden an excellent base for your vacation, ensuring you experience the best of urban life while still being close to nature.
• Reavills Corner: Located a few miles from Oakland, Reavills Corner is a quaint village that caters to outdoor lovers and sports enthusiasts. With its scenic golf courses and resorts, the area is perfect for families looking to unwind and engage in recreational activities. The village sees a rise in visitors during March, July, and December, making it a lively spot to enjoy the outdoors. Nearby landmarks include a family beach, theme parks, and picturesque lakes, providing ample opportunities for adventure and relaxation.

Things to do near Oakland

Oakland, Florida, is perfect for outdoor and family-friendly vacations, offering a variety of entertainment options. Visitors can enjoy nearby resorts and golf courses, making it a great destination for leisure and recreation. Additionally, families will appreciate the exciting water parks in the area, providing fun activities for all ages. Whether you're looking to relax or have an adventure, Oakland has something for everyone to enjoy.

Shopping

In Oakland, visit the nearby Winter Garden Village, an open-air shopping center with popular retailers and restaurants. For a local experience, check out the West Orange Farmers Market, where you can find unique crafts, fresh produce, and delightful gifts to take home.

Recreation

Experience luxury at Windermere Country Club with upscale amenities and serene surroundings, perfect for relaxation. At Winter Park Tennis Center, enjoy world-class tennis facilities while soaking in the elegant atmosphere. For a unique twist, visit Mount Dora Lawn Bowling Club for a friendly game in a picturesque setting.

Adventure

In Oakland, explore the scenic trails at the Oakland Nature Preserve, where you'll encounter diverse wildlife and stunning views. For water adventures, try kayaking on Lake Apopka, immersing yourself in the tranquil beauty of Florida's wetlands and enjoying the thrill of paddling through nature.

Nightlife

In Oakland, Florida, the nightlife scene is vibrant and welcoming. Enjoy live music at local bars, unwind at cozy lounges, or savor craft cocktails at trendy spots. The atmosphere is lively, perfect for socializing and dancing the night away with friends.

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, though if you're late to the party, have a look at Expedia's last minute deals - the green banner below the hotel's price indicates a discounted rate.
• 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 makes it easy for you to set your budget and choose your ideal location, among other preferences. You can sort your results by price, displaying the most affordable hotels at the top. Additionally, you have the option to narrow down your choices by hotel type; for instance, by selecting the Eco-certified filter, you’ll find a selection of sustainable and eco-friendly hotels ready for booking.
• 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, Florida, offers a delightful vacation experience perfect for families and outdoor enthusiasts. Visitors can explore popular attractions such as theme parks, golf courses, and arts centers. Whether you're seeking fun-filled entertainment or cultural experiences, the local points of interest in and around Oakland cater to all types of travelers, ensuring a memorable getaway for everyone.

• Walt Disney World® Resort: Experience the magic at this iconic theme park, located 10 miles from Oakland. With thrilling rides, enchanting shows, and beloved characters, it’s a family-friendly destination that brings joy and wonder to visitors of all ages.
• Orange County Convention Center: Situated 13 miles away, this arts center is a cultural hub showcasing a variety of exhibitions and events. Immerse yourself in the vibrant arts scene and enjoy engaging performances that highlight the diverse talents of local and international artists.
• Universal CityWalk: Just 12 miles from Oakland, this lively tourist precinct offers an outdoor atmosphere perfect for families. Dine, shop, and enjoy entertainment options, making it a fantastic spot for relaxation and fun after a day at the parks.

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

When visiting Oakland, Winter Garden, Florida, you can fly into three major airports. Orlando International Airport (MCO) is 22 miles away, with nearby hotels like The Ritz-Carlton Orlando, Grande Lakes and Rosen Shingle Creek, both offering airport shuttle services. Tampa International Airport (TPA) is 68 miles away, featuring excellent accommodations such as The Tampa EDITION and JW Marriott Tampa Water Street, also providing easy access to the airport. Daytona Beach International Airport (DAB) is located 56 miles from Oakland, with great options like The Shores Resort & Spa and Hilton Daytona Beach Oceanfront Resort, ensuring convenient transportation to the airport.