Hotels in Oakland

Oakland Oasis: Where Urban Vibes Meet Nature’s Wonder

Nestled just outside Orlando, Oakland, Winter Garden, Florida, is a charming gem that combines small-town warmth with stunning natural beauty. Explore the picturesque landscapes of the nearby lakes and parks, perfect for hiking, biking, and fishing. The historic downtown area invites you to stroll along brick-lined streets, featuring quaint shops and local eateries. With easy access to theme parks and the lush scenery of nearby state parks, Oakland offers a unique blend of adventure and tranquility. Whether you seek a romantic getaway or a family-friendly escape, this enchanting destination promises unforgettable experiences in the heart of Florida.

Discover great hotels in Oakland

Oakland Park offers a variety of hotel accommodations, from cozy inns to luxury stays. You'll find options that combine comfort and convenience, perfect for exploring the area's attractions. Whether you're seeking a boutique experience or family-friendly amenities, Oakland Park hotels cater to diverse traveler needs. Here are some of the most popular hotels with our travelers in Oakland:

1. WoodSpring Suites Orlando West - ClermontOpens in a new window: This inviting 2.5-star hotel is a perfect retreat for travelers seeking a pet-friendly experience. The property features comfortable accommodations and amenities that cater to the needs of pet owners, making it an ideal choice for those traveling with their furry friends. Visitors appreciate the welcoming atmosphere and the ease of bringing their pets along, ensuring a smooth and enjoyable stay. The hotel’s thoughtful pet policies allow guests to enjoy their vacation without leaving their companions behind.
2. Hampton Inn & Suites ClermontOpens in a new window: The 2.5-star Hampton Inn & Suites Clermont is designed with business travelers in mind, offering a seamless blend of comfort and convenience. With a 24-hour business center, meeting rooms, and conference space, this hotel provides everything needed for a productive stay. The family-friendly amenities, such as a secure pool area, complement the overall experience, allowing guests to unwind after a day of meetings. Business travelers frequently highlight the hotel’s strategic location and well-planned facilities, ensuring that their needs are met efficiently.
3. Home2 Suites by Hilton ClermontOpens in a new window: Home2 Suites by Hilton Clermont is a chic 3.0-star hotel that welcomes travelers with a vibrant and inclusive atmosphere. The property features a well-equipped business center and multiple meeting rooms, making it an excellent choice for professionals. Families will appreciate the amenities designed for children, such as cribs available for a fee. Guests rave about the well-thought-out design and the hotel's commitment to creating a welcoming environment for all, ensuring that each stay is both enjoyable and memorable.

Top locations to stay in Oakland

Staying near Walt Disney World® Resort, Universal Studios Florida, and Universal Orlando Resort provides easy access to top attractions, thrilling adventures, and vibrant nightlife. Walt Disney World® Resort is ideal for families with its iconic parks, while Universal Studios Florida offers exhilarating rides and entertainment. For first-time visitors, staying near Walt Disney World® Resort is best for a magical experience.

1. Near Walt Disney World® ResortOpens in a new window: Staying near Walt Disney World® Resort offers a magical experience with access to iconic attractions like Magic Kingdom® Park and Disney Springs™. You'll be surrounded by a fantastic range of entertainment options, including thrilling water parks like Disney's Typhoon Lagoon. Plus, there are plenty of shopping opportunities to indulge in, making it a perfect spot for families and adventure seekers alike.
2. Near Universal Studios FloridaOpens in a new window: When you choose to stay near Universal Studios Florida, you're in for an action-packed getaway. This area boasts exciting attractions such as Universal’s Volcano Bay and the vibrant Orlando Eye at ICON Park. Enjoy a variety of cultural experiences and shopping at top destinations like the Florida Mall and Orlando International Premium Outlets. It's a lively hub that has something for everyone!
3. Near Universal Orlando ResortOpens in a new window: Staying near Universal Orlando Resort places you at the heart of thrilling theme park excitement. With attractions like Aquatica and the bustling Orange County Convention Center nearby, there's no shortage of fun. Disney's Typhoon Lagoon offers additional water adventures, while the nearby shopping at Mall at Millenia provides a stylish retail experience. This area is perfect for those looking to dive into Orlando's vibrant entertainment scene.

Things to do near Oakland

Oakland dazzles with its stunning lakeside views, lush parks, and nearby mountains, inviting outdoor enthusiasts to hike, bike, or paddle. Enjoy vibrant shopping areas and indulge in local arts, while the beautiful beaches provide the perfect backdrop for relaxation and seaside fun. It's a lively spot for all types of travelers!

• Universal Studios FloridaOpens in a new window – Step into the magic of movies at Universal Studios Florida, where you can ride thrilling attractions based on your favorite films. Explore immersive themed areas, meet beloved characters, and enjoy a day filled with excitement and entertainment. Don't miss the chance to experience the adrenaline rush of roller coasters and the charm of live shows!
• Universal Orlando ResortOpens in a new window – A visit to Universal Orlando Resort promises a complete adventure! This expansive destination features multiple theme parks, offering a wide array of attractions for visitors of all ages. Enjoy everything from action-packed rides to relaxing experiences, making it the ideal spot for family fun or a thrilling day out with friends.
• Walt Disney World® ResortOpens in a new window – Dive into a world of imagination and wonder at Walt Disney World® Resort. Whether you're meeting your favorite Disney characters or exploring enchanting lands, there's no shortage of magical experiences. With various parks and attractions, including thrilling rides and captivating shows, the resort is a must-visit for anyone seeking unforgettable memories.
• Magic Kingdom® ParkOpens in a new window – Experience the heart of Disney magic at Magic Kingdom® Park, where iconic attractions like Cinderella Castle await. Enjoy classic rides, delightful parades, and interactive experiences that will bring joy to visitors of all ages. Make sure to catch the evening fireworks for a spectacular end to your day!

5 tips for savvy savings when booking a hotel in Oakland

1. Book for the cheapest times: The most budget-friendly time to visit Oakland is during August, September, and November, when hotel prices may drop. For an affordable yet enriching experience, consider staying at least 3 days to fully explore the city's notable landmarks, cultural sites, and historical attractions. During your visit, you can enjoy a range of places such as historic buildings, parks, museums, theaters, and symbolic landmarks. This allows you to immerse yourself in Oakland's rich heritage while taking advantage of the great value for money that these lower prices offer.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Oakland, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted hotel rates as your travel date approaches. Consider enabling email alerts or push notifications to stay updated on flash sales and last-minute promotions. Additionally, the Smart ShoppingOpens in a new window feature available in the app allows you to compare hotel prices and amenities, helping you make informed decisions. This way, if room availability changes or prices drop, you're more likely to see these opportunities and can quickly book a spontaneous getaway.
3. Be flexible with dates: Prices can fluctuate based on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates might help you save on your stay in an Oakland hotel. For those seeking a unique experience, boutique hotels can provide a more personalized touch and sometimes better value. When you book through Hotels.com, we’ll inform you if the price for your chosen dates is above or below the average. If the price is on the higher end, we’ll recommend alternative dates that could be more affordable, helping you find a better deal.
4. Consider your location: Staying near major attractions or city centers can be convenient, but it often comes with a higher price tag. For more budget-friendly options, you might want to look at hotels in less central neighborhoods, which can help you strike a balance between cost and accessibility to the sites you plan to visit. Additionally, exploring independent hotels a bit further out can offer a more authentic and usually more affordable experience.
5. Become a Member: Join our membership for free and start planning your next stay in Oakland! Enjoy significant savings on over 100,000 hotels worldwide with exclusive member pricing. As a member, you’ll have the opportunity to advance through different membership tiers, unlocking fantastic perks such as complimentary room upgrades when available and discounts on food and beverages at select VIP Access properties. Don’t miss out on these benefits—sign up today and start your journey!

Best time to go to Oakland

Oakland has a varied climate due to its size, so the best time to visit depends on the region and your preferences for weather and crowds. The peak travel months to visit Oakland are January to March, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, August, October, and November are ideal if you're looking for a calmer vacation, marked by light to moderate rainfall and mostly sunny conditions.