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 family-friendly 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

Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

AU$23
per adult
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
Orlando: 7-D Dark Ride Entry Ticket

Orlando: 7-D Dark Ride Entry Ticket

AU$18
per adult
92% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
I-RIDE Trolley Pass

I-RIDE Trolley Pass

AU$16
per traveller
82% of travellers recommend
I-RIDE Trolley Pass
Titanic : The Artifact Exhibition Ticket in Orlando

Titanic : The Artifact Exhibition Ticket in Orlando

AU$52
per adult
90% of travellers recommend
Titanic : The Artifact Exhibition Ticket in Orlando
Orlando: Chocolate Kingdom Factory Adventure Tour

Orlando: Chocolate Kingdom Factory Adventure Tour

AU$36
per adult
98% of travellers recommend
Orlando: Chocolate Kingdom Factory Adventure Tour
WonderWorks All Access After Dark

WonderWorks All Access After Dark

AU$42
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 Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

4 out of 5
10100 International Drive, Orlando, FL
The price is AU$164 per night from 26 Oct to 27 Oct
AU$164
26 Oct - 27 Oct
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! (6,211 reviews)
"Best hotel. Close to everything. Best breakfast buffet!!"

Reviewed on 15 Oct 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
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 AU$231 per night from 5 Nov to 6 Nov
AU$231
5 Nov - 6 Nov
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! (5,393 reviews)
"Clean room"

Reviewed on 13 Oct 2025

Universal's Cabana Bay Beach Resort
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr, Orlando, FL
The price is AU$158 per night from 17 Nov to 18 Nov
AU$158
17 Nov - 18 Nov
includes taxes & fees
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (3,689 reviews)
"Check in took to long. Otherwise everything was great."

Reviewed on 13 Oct 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
The price is AU$415 per night from 30 Oct to 31 Oct
AU$415
30 Oct - 31 Oct
includes taxes & fees
Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
7.8/10 Good! (8,641 reviews)
"Everything was good"

Reviewed on 13 Oct 2025

The Grove Resort & Water Park Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
The price is AU$164 per night from 12 Nov to 13 Nov
AU$164
12 Nov - 13 Nov
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! (3,336 reviews)
"Very clean room. Accommodating staff and beautiful property with a lot of food and entertainment"

Reviewed on 13 Oct 2025

Marriott's Grande Vista
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 AU$121 per night from 2 Nov to 3 Nov
AU$121
2 Nov - 3 Nov
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! (786 reviews)
"Nice place, clean rooms. Very family oriented."

Reviewed on 13 Oct 2025

Holiday Inn Resort Kissimmee by the Parks by IHG
See all 39,313 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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Horizon West

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

Horizon West
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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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