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

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

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

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

West Orange Trail

Enjoy a trip to West Orange Trail and popular activities such as taking adventure tours in Winter Garden. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.

West Orange Trail

Activities

Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

AU$299
per adult
Walt Disney World® Resort Theme Park Tickets
Orlando: 7-D Dark Ride Entry Ticket

Orlando: 7-D Dark Ride Entry Ticket

AU$18
per adult
90% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

AU$23
per adult
80% of travellers recommend
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
I-RIDE Trolley Pass

I-RIDE Trolley Pass

AU$16
per traveller
82% of travellers recommend
I-RIDE Trolley Pass
WonderWorks All Access After Dark

WonderWorks All Access After Dark

AU$43
per traveller
84% of travellers recommend
WonderWorks All Access After Dark
The Outta Control Magic Dinner Show

The Outta Control Magic Dinner Show

AU$61
per adult
84% of travellers recommend
The Outta Control Magic Dinner Show
See all activities in Winter Garden

Our pick of the best Oakland Hotel Deals

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$225 per night from 15 Dec to 16 Dec
AU$225
15 Dec - 16 Dec
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their ...
8.8/10 Excellent! (5,697 reviews)
The lazy river was fantastic!

Reviewed on 8 Dec 2025

Universal's Cabana Bay Beach Resort
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 AU$166 per night from 15 Dec to 16 Dec
AU$166
15 Dec - 16 Dec
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the pool and the helpful staff in their ...
8.4/10 Very Good! (6,884 reviews)
Very nice hotel. Beautiful and convenient.

Reviewed on 8 Dec 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Avanti International Resort

Avanti International Resort

4 out of 5
8738 International Dr Orlando FL
The price is AU$148 per night from 14 Dec to 15 Dec
AU$148
14 Dec - 15 Dec
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, an outdoor pool and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
7.8/10 Good! (4,289 reviews)
clean, great parking.

Reviewed on 8 Dec 2025

Avanti International 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
Fully refundableReserve now, pay when you stay
The price is AU$188 per night from 4 Jan to 5 Jan
AU$188
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 6 outdoor pools and 3 restaurants. Our guests praise the pool and the helpful staff in their ...
9.2/10 Wonderful! (4,069 reviews)
The rooms were clean and recently renovated Staff was extremely helpful

Reviewed on 9 Dec 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$335 per night from 11 Dec to 12 Dec
AU$335
11 Dec - 12 Dec
includes taxes & fees
Stay at this family-friendly resort in Four Corners. Enjoy free Wi-Fi, 6 outdoor pools and 3 restaurants. Our guests praise the pool and the helpful staff in ...
7.8/10 Good! (8,788 reviews)
Clean and spacious condos . Easy to get in and out staff was very friendly.

Reviewed on 8 Dec 2025

The Grove Resort & Water Park Orlando
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$160 per night from 17 Dec to 18 Dec
AU$160
17 Dec - 18 Dec
includes taxes & fees
Stay at this family-friendly resort in Orlando. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the breakfast and the pool in their reviews. ...
7.4/10 Good! (6,239 reviews)
Yes

Reviewed on 5 Dec 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
See all 39,608 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

Default Image

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
Default Image

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

Oakland Travel Guide

Choose two or more items and save on your trip: