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Hotels in Oakland, Winter Garden

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Our top choices for Oakland hotels

1. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
19.3 km from Oakland
9.4 out of 10, Exceptional, (5,456 reviews)
"Great location, breakfast was extensive, and the rooms were nice and large."
United States
Andrea
The price is CA $112
CA $126 total
includes taxes & fees
Sep 2 - Sep 3
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

2. DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando
4.0 star property
19.2 km from Oakland
8.6 out of 10, Excellent, (7,044 reviews)
"A very clean and well staffed hotel"
United States
Karrie
The price is CA $98
CA $110 total
includes taxes & fees
Sep 2 - Sep 3
DoubleTree by Hilton at the Entrance to Universal Orlando

3. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
19.3 km from Oakland
9.4 out of 10, Exceptional, (5,975 reviews)
"Great place to stay with the family for Disney vacation! Very clean, great breakfast, close to all the parks and a fun pool!"
United States
Alicia
The price is CA $129
CA $145 total
includes taxes & fees
Sep 8 - Sep 9
Home2 Suites by Hilton Orlando at Flamingo Crossings

4. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
19.3 km from Oakland
9.6 out of 10, Exceptional, (2,240 reviews)
"Location was really close to all the parks, the breakfast was really nice to have before heading out to enjoy the great city of orlando"
Canada
harman
The price is CA $114
CA $128 total
includes taxes & fees
Sep 14 - Sep 15
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

5. Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
18.9 km from Oakland
8.8 out of 10, Excellent, (1,558 reviews)
"Clean room, great staff I love ittt"
United States
Eilyam
The price is CA $112
CA $126 total
includes taxes & fees
Sep 2 - Sep 3
Spark by Hilton Orlando near Universal

6. Holiday Inn Orlando International Dr-ICON by IHG

Holiday Inn Orlando International Dr-ICON by IHG
3.0 star property
20 km from Oakland
9.0 out of 10, Wonderful, (3,457 reviews)
"Great place second time we have stayed there great location"
United States
Heidi
The price is CA $105
CA $138 total
includes taxes & fees
Aug 27 - Aug 28
Holiday Inn Orlando International Dr-ICON by IHG

7. Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
19.3 km from Oakland
9.4 out of 10, Exceptional, (2,666 reviews)
"Breakfast was very nice"
United States
nancy
The price is CA $137
CA $154 total
includes taxes & fees
Sep 6 - Sep 7
Homewood Suites by Hilton Orlando at Flamingo Crossings

8. Courtyard by Marriott across Universal Orlando

Courtyard by Marriott across Universal Orlando
3.0 star property
19.2 km from Oakland
8.8 out of 10, Excellent, (482 reviews)
"Great for families, close to parks and attractions, food on site/nearby."
United States
Karen
The price is CA $101
CA $113 total
includes taxes & fees
Sep 2 - Sep 3
Courtyard by Marriott across Universal Orlando

9. Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

Hilton Garden Inn Orlando I-4 Millenia Blvd Mall
3.0 star property
20.3 km from Oakland
9.0 out of 10, Wonderful, (884 reviews)
"Always a pleasant stay"
United States
Farnishia
The price is CA $118
CA $133 total
includes taxes & fees
Sep 3 - Sep 4
Hilton Garden Inn Orlando I-4 Millenia Blvd Mall

10. Holiday Inn Express & Suites, International Drive by IHG

Holiday Inn Express & Suites, International Drive by IHG
3.5 star property
19.1 km from Oakland
9.0 out of 10, Wonderful, (2,148 reviews)
"Great location and good value for money."
United States
Dietmar Ernst
The price is CA $99
CA $111 total
includes taxes & fees
Sep 3 - Sep 4
Holiday Inn Express & Suites, International Drive by IHG

11. Wyndham Garden Orlando Universal / I Drive

Wyndham Garden Orlando Universal / I Drive
3.0 star property
19.7 km from Oakland
9.4 out of 10, Exceptional, (1,716 reviews)
"The hotel is in great condition well located and have great service."
United States
Manuel
The price is CA $133
CA $150 total
includes taxes & fees
Aug 31 - Sep 1
Wyndham Garden Orlando Universal / I Drive

12. Element by Marriott Orlando Universal Blvd.

Element by Marriott Orlando Universal Blvd.
3.0 star property
20.3 km from Oakland
9.2 out of 10, Wonderful, (2,379 reviews)
"Great stay!!"
United States
Emmanuel
The price is CA $116
CA $131 total
includes taxes & fees
Aug 30 - Aug 31
Element by Marriott Orlando Universal Blvd.

13. Universal's Endless Summer Resort - Surfside Inn and Suites

Universal's Endless Summer Resort - Surfside Inn and Suites
3.0 star property
19.5 km from Oakland
9.4 out of 10, Exceptional, (2,720 reviews)
"Very nice hotel! Food and shuttle to parks made for an easy stay."
United States
Tyler
The price is CA $167
CA $188 total
includes taxes & fees
Aug 27 - Aug 28
Universal's Endless Summer Resort - Surfside Inn and Suites

14. Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area
4.0 star property
20.9 km from Oakland
8.4 out of 10, Very good, (6,965 reviews)
"Great vacation spot"
United States
Tekia
The price is CA $114
CA $175 total
includes taxes & fees
Aug 27 - Aug 28
Westgate Lakes Resort & Spa Universal Studios Area

15. Days Inn by Wyndham Orlando Conv. Center/International Dr

Days Inn by Wyndham Orlando Conv. Center/International Dr
2.0 star property
22.3 km from Oakland
8.2 out of 10, Very good, (2,983 reviews)
"Love this place!"
United States
Manda
The price is CA $83
CA $94 total
includes taxes & fees
Aug 31 - Sep 1
Days Inn by Wyndham Orlando Conv. Center/International Dr

16. Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
24.9 km from Oakland
9.4 out of 10, Exceptional, (5,477 reviews)
"This place was really great and affordable."
United States
Angelina
The price is CA $24
CA $89 total
includes taxes & fees
Aug 30 - Aug 31
Kompose Boutique Resort at Theme Parks

17. Spark by Hilton Orlando Universal Blvd

Spark by Hilton Orlando Universal Blvd
3.0 star property
20 km from Oakland
8.4 out of 10, Very good, (2,274 reviews)
"The room was clean, comfortable bed, available free parking, decent breakfast and nice pool. Overall it was a good stay"
United States
Sam
The price is CA $95
CA $107 total
includes taxes & fees
Aug 30 - Aug 31
Spark by Hilton Orlando Universal Blvd

18. Rosen Inn International

Rosen Inn International
3.0 star property
19.3 km from Oakland
8.4 out of 10, Very good, (6,260 reviews)
"Nice place to stay"
United States
Michael
The price is CA $96
CA $108 total
includes taxes & fees
Aug 27 - Aug 28
Rosen Inn International

19. City Express by Marriott Orlando International Drive

City Express by Marriott Orlando International Drive
3.0 star property
19.7 km from Oakland
8.6 out of 10, Excellent, (1,511 reviews)
"Everything was excellent the parking, room, staff and the breakfast."
United States
Jerry
The price is CA $116
CA $131 total
includes taxes & fees
Aug 31 - Sep 1
City Express by Marriott Orlando International Drive

20. SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
3.0 star property
22.5 km from Oakland
8.8 out of 10, Excellent, (3,599 reviews)
"Breakfast was amazing room was clean for the price everything was great!"
United States
Anabel
The price is CA $107
CA $120 total
includes taxes & fees
Sep 2 - Sep 3
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most.

Horizon West

While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club.

Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

Downtown Winter Garden

While visiting Downtown Winter Garden, you might make a stop by sights like Garden Theatre and Winter Garden Art Association.

Killarney

If you're spending some time in Killarney, Oakland Nature Preserve and Johns Lake are top sights worth seeing.

Top Oakland Hotel Reviews

Find out more about Oakland

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January59.9°F (15.5°C)Light RainMostly SunnySlightly HighAverage
February63.9°F (17.7°C)Light RainMostly SunnySlightly HighAverage
March67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
April72.5°F (22.5°C)Light RainMostly SunnyAverageSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.0°F (27.2°C)Moderate RainMostly SunnyAverageAverage
July82.4°F (28.0°C)Moderate RainMostly SunnyAverageAverage
August82.6°F (28.1°C)Moderate RainMostly SunnySlightly LowSlightly Low
September80.2°F (26.8°C)Moderate RainMostly SunnyAverageSlightly Low
October74.8°F (23.8°C)Light RainMostly SunnySlightly LowAverage
November67.8°F (19.9°C)Light RainMostly SunnySlightly LowSlightly Low
December63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly 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.

Frequently asked questions

When is the best time to go to Oakland?
The best time to visit Oakland, Florida, is from late autumn through to spring, specifically November to May, when the weather is most pleasant.

During these months, you'll experience comfortable temperatures, typically ranging from the low 20s to high 20s Celsius (70s to 80s Fahrenheit), and lower humidity. This makes it ideal for enjoying outdoor activities, exploring the local trails, or visiting nearby attractions without the intense heat and frequent afternoon thunderstorms of the summer. It's a great time for couples seeking a relaxing getaway or families looking for comfortable conditions for day trips.

The summer months, from June to October, are considerably hotter and more humid, with daily chances of rain.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Oakland hotel for you.
How much is the nightly rate at a Oakland hotel?
Hotel prices in Oakland often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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