Oakland, FL

Winter Garden

A calm lake with lily pads and reeds in the foreground, surrounded by trees and a cloudy sky.
A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.

Things to do

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$42
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

$184
per adult
84% of travellers recommend
Walt Disney World® Resort Theme Park Tickets
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

$157
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$234
per traveler
80% of travellers recommend
Universal Orlando Resort Express Passes
Aquatica Orlando

Aquatica Orlando

$66
per traveler
84% of travellers recommend
Aquatica Orlando
Exterior of WonderWorks

WonderWorks Orlando Admission Tickets

$36
per adult
88% of travellers recommend
WonderWorks Orlando Admission Tickets
See all activities in Winter Garden

Oakland Hotel Deals

Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista Orlando FL
Book a stay at this spa aparthotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Get rates
Marriott's Grande Vista
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
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Get rates
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
Get rates
DoubleTree by Hilton at the Entrance to Universal Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Get rates
Universal's Cabana Bay Beach Resort
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
9500 Turkey Lake Rd Orlando FL
Book a stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Get rates
Westgate Lakes Resort & Spa Universal Studios Area
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Get rates
The Grove Resort & Water Park Orlando
See all 42,489 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.

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland
A city skyline at dusk with illuminated buildings reflecting on a calm body of water.

Horizon West

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

A sunset over a body of water with silhouetted land in the distance and tall grasses in the foreground.

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.

A tree-lined sidewalk with parked cars and a clear sky.

Downtown Winter Garden

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

A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.

Killarney

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

Oakland, FL

Choose two or more items and save on your trip: