Oakland vacation rentals

Why visit Oakland

1. Outdoor Adventures: Discover the stunning Oakland Hills, offering breathtaking views and opportunities for hiking and nature walks.
2. Family-Friendly Attractions: Engage in a variety of entertainment options, including theme parks and golf courses, perfect for families.
3. Charming Waterfront: Relax by the picturesque waterfront, ideal for leisurely strolls and outdoor seating at local spots.
4. Vibrant West Oakland: Experience the lively atmosphere in West Oakland, filled with shops, eateries, and cultural experiences.
5. Unique Vacation Rentals: Choose from an array of private homes, villas, and condos for a personalized stay.

Popular types of accommodation around Oakland

If you're exploring vacation rentals in Oakland, you're in for a treat! The most popular options include houses, villas, and condos, each offering unique experiences to suit your needs. Whether you're seeking a cozy getaway or a luxurious stay, Oakland vacation rentals provide the perfect base for your adventures. Enjoy transparency, savings, and reassurance as you discover the ideal rental for your next trip to this vibrant city.

• Houses: These spacious and comfortable residences are the top choice for visitors to Oakland, perfect for families or groups seeking a home-away-from-home experience.
• Villas: Offering luxurious amenities and lovely surroundings, villas are a popular selection for those wanting a touch of elegance during their stay.
• Condos: Ideal for convenience and modern living, condos provide a stylish option for vacationers wanting easy access to local attractions.
• Apartments: These versatile living spaces suit solo travellers or couples looking for a well-equipped base in Oakland.
• Cottages: Quaint and charming, cottages offer a cozy retreat, perfect for a peaceful getaway in Oakland.**

Top attractions around Oakland

Oakland, Winter Garden, Florida, is an ideal destination for families seeking entertainment and outdoor adventures. Visitors can enjoy a variety of attractions, including theme parks, golf courses, and arts centres, catering to those interested in cultural experiences. Whether you're exploring with family or friends, there's plenty to discover in and around Oakland that promises a memorable vacation.

1. Walt Disney World® Resort: A magical theme park only 16.1km from Oakland, this iconic destination offers thrilling rides, enchanting attractions, and unforgettable entertainment for the whole family, creating memories that last a lifetime.
2. Orange County Convention Center: Located 20.9km away, this vibrant arts centre showcases a diverse range of cultural events and exhibitions, providing a unique glimpse into the local art scene and community engagement.
3. Arnold Palmer's Bay Hill Golf Club: Just 16.1km from Oakland, this family-friendly golf course and country club offers exciting excursions and a welcoming atmosphere, perfect for both seasoned golfers and beginners alike.

Things to do recommended for couples

For a romantic getaway in Oakland, Florida, consider a ride on The Wheel at ICON Park™ for breathtaking views, indulge in a delightful dinner at Pirate's Dinner Adventure, or enjoy wine tasting at Lakeridge Winery. These experiences promise adventure, romance, and unforgettable memories for couples.

Things to do recommended for families

Your family will love visiting Universal’s Volcano Bay for a splashing good time, exploring Wonderworks for adventurous fun, and catching a game at Camping World Stadium. Each venue promises memorable experiences just a short drive from Oakland, ensuring a fantastic vacation filled with excitement and enjoyment.

Things to do recommended for groups

Explore the scenic West Orange Trail for a lovely hike, challenge your friends at Disney's Palm Golf Course for a fun day outdoors, and catch a captivating show at the Garden Theatre for a taste of local culture and entertainment. Enjoy your group adventure in beautiful Oakland!

What do I need to keep in mind when booking a vacation around Oakland

When planning your trip—whether you're traveling with a group, your family, or pets, or seeking extended stays—be sure to apply the appropriate filters to meet your priorities. Here are some helpful booking tips for using Vrbo.

• Traveling to Oakland with a group: Take into account the number of bedrooms you'll require, along with features like a complete kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
• Traveling to Oakland with young kids: Travelling with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to keep in mind your closeness to family-friendly attractions.
• Taking your pets with you to Oakland: For many families, a vacation wouldn’t feel complete without their beloved furry companions. If you can relate, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels at home.
• Planning for a long term stay visiting Oakland: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Oakland

Oakland, Winter Garden, Florida, offers a delightful blend of family-friendly activities and picturesque outdoor experiences. Explore the stunning Oakland Hills for breathtaking views, enjoy the vibrant atmosphere in West Oakland, or relax at local spots with outdoor seating. The charming waterfront adds to the allure, making it a perfect getaway for both relaxation and adventure. Whether you're seeking romantic excursions or friendly encounters, Oakland is a wonderful destination to create lasting memories.

• Reavills Corner: Nestled approximately 4.8km from Oakland, Reavills Corner is a charming village that offers a delightful blend of family-friendly outdoor activities and entertainment. Visitors can enjoy the nearby resorts and shopping areas, making it a fantastic spot for leisurely strolls and engaging family experiences. The proximity to local landmarks such as a theme park and beautiful beaches adds to the allure, providing ample opportunities for fun in the sun. Whether you’re looking to relax or explore, Reavills Corner is a lovely destination to include in your itinerary.
• Montverde: Located just 6.4km from Oakland, Montverde is a vibrant city known for its outdoor adventures and sports-focused atmosphere. Golf enthusiasts will appreciate the exceptional golf courses and resorts in the area, making it a haven for those who love to hit the greens. Montverde also boasts natural attractions such as a picturesque lake and a film studio, perfect for a unique day out. The city’s inviting environment and recreational offerings make it an ideal spot for families and active travellers alike.
• Ocoee: Situated around 9.7km from Oakland, Ocoee is a lively city that promises a rich family experience filled with entertainment and outdoor activities. With a variety of resorts and shopping centres, visitors have plenty of options for leisure and enjoyment. Ocoee is also close to significant landmarks including a theme park and a film studio, ensuring that there’s never a dull moment. The city’s vibrant atmosphere and accessibility to various attractions make it a must-visit for anyone looking to create lasting memories.

Best time to go to Oakland

If you're planning a trip to Oakland, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

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	Slightly Low
March	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
April	72.5°F (22.5°C)	Light Rain	Mostly Sunny	Average	Average
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	Slightly High
July	82.4°F (28.0°C)	Moderate Rain	Mostly Sunny	Average	Slightly High
August	82.6°F (28.1°C)	Moderate Rain	Mostly Sunny	Slightly Low	Average
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	Slightly Low
November	67.8°F (19.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Average	Slightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, and manage your travel arrangements. You can easily access your previously saved and booked properties under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.