Oakland Travel Guide

Tourist Guide

Photo by Gregg Yutko
Photo by Gregg Yutko

Popular places to visit

Flamingo Crossings Town Center

You can find the perfect gifts to bring home at Flamingo Crossings Town Center during your stay in Winter Garden. Discover the top-notch restaurants and entertainment choices in this walkable area.

Flamingo Crossings Town Center

Orange County National Golf Club

Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Amble around this family-friendly area's lakeside or experience its entertainment choices.

Orange County National Golf Club

Disney's Palm Golf Course

Enjoy a round of golf in Winter Garden at Disney's Palm Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Palm Golf Course

Disney's Magnolia Golf Course

Enjoy a round of golf in Winter Garden at Disney's Magnolia Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Magnolia Golf Course

AdventHealth Winter Garden

If AdventHealth Winter Garden is what brings you to town, hopefully you'll have a chance to explore more of Winter Garden.

AdventHealth Winter Garden

Surfari Water Park

Enjoy the thrill rides with your children at Surfari Water Park as part of your trip to Four Corners. Make time for the shops and golf courses in this family-friendly area.

Surfari Water Park

Activities

Aquatica Orlando

Aquatica Orlando

NZ$90
per traveller
82% of travellers recommend
Aquatica Orlando
Indoor Karting

Andretti Indoor Karting & Games in Orlando

NZ$52
per adult
82% of travellers recommend
Andretti Indoor Karting & Games in Orlando
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction & Food/Drink Voucher

NZ$25
per adult
74% of travellers recommend
Old Town Kissimmee: Attraction & Food/Drink Voucher
Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

NZ$53
per adult
86% of travellers recommend
Orlando: Museum of Illusions Admission Ticket
Orlando: 7-D Dark Ride Entry Ticket

Orlando: 7-D Dark Ride Entry Ticket

NZ$20
per adult
90% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
WonderWorks All Access After Dark

WonderWorks All Access After Dark

NZ$46
per traveller
84% of travellers recommend
WonderWorks All Access After Dark
See all activities in Winter Garden

Our pick of the best Oakland Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
The price is NZ$176 per night from 10 Sept to 11 Sept
NZ$176
10 Sept - 11 Sept
includes taxes & fees
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (6,528 reviews)
"The property was nice, I like that it had Starbucks and other places to dine."

Reviewed on 15 Aug. 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
The price is NZ$166 per night from 7 Sept to 8 Sept
NZ$166
7 Sept - 8 Sept
includes taxes & fees
Stay at this 4-star spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (2,882 reviews)
"Good sized room unfortunately had a view of trees. Helpful front desk. Didn't explore the grounds or restaurants but the scenery is well kept."

Reviewed on 18 Aug. 2025

Marriott's Grande Vista
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
The price is NZ$264 per night from 1 Sept to 2 Sept
NZ$264
1 Sept - 2 Sept
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.8/10 Excellent! (5,128 reviews)
"Great vacation spot if traveling with kids"

Reviewed on 16 Aug. 2025

Universal's Cabana Bay Beach Resort
DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

4 out of 5
10100 International Drive, Orlando, FL
The price is NZ$174 per night from 26 Aug to 27 Aug
NZ$174
26 Aug - 27 Aug
includes taxes & fees
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
7.4/10 Good! (6,064 reviews)
"I love this property but not a fan of staying in the tower. First experience was not the best since the room did not feel like it was kept nice. Bathroom was not clean and the closet door was broken."

Reviewed on 15 Aug. 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave, Winter Garden, FL
The price is NZ$208 per night from 27 Aug to 28 Aug
NZ$208
27 Aug - 28 Aug
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winter Garden. Enjoy free breakfast, a free theme park shuttle, and a 24-hour fitness center. Our guests praise ...
9.2/10 Wonderful! (4,473 reviews)
"Property was very nice and enjoyable. Spacious rooms and close to Flamingo Crossings Mall with good shopping and food. Loved it. Thank you"

Reviewed on 17 Aug. 2025

Home2 Suites by Hilton Orlando at Flamingo Crossings
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

3.5 out of 5
3011 Maingate Ln, Kissimmee, FL
The price is NZ$135 per night from 24 Aug to 25 Aug
NZ$135
24 Aug - 25 Aug
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free parking, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff ...
8.4/10 Very Good! (437 reviews)
"Nice pool and comfortable bed. Great location for Disney"

Reviewed on 14 Aug. 2025

Holiday Inn Resort Kissimmee by the Parks by IHG
See all 38,426 properties in Oakland
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.

Other neighbourhoods around Oakland

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Killarney

Killarney might not have many top sights, but Bella Collina Golf Club and West Orange Trail are two attractions nearby that you can check out.

Killarney
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Downtown Winter Garden

If you're spending some time in Downtown Winter Garden, West Orange Trail and Central Florida Railroad Museum are top sights worth seeing.

Downtown Winter Garden
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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.

Vista del Lago

Oakland Travel Guide

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