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

$33
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$128
per traveler
80% of travellers recommend
Universal Orlando Resort Express Passes
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

$31
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Orlando: Jet Ski Rentals from Lake Buena Vista Area

Orlando: Jet Ski Rentals from Lake Buena Vista Area

$79
per adult
80% of travellers recommend
Orlando: Jet Ski Rentals from Lake Buena Vista Area
Orlando: Polynesian Fire Luau with Dinner and Live Show

Orlando: Polynesian Fire Luau with Dinner and Live Show

$75
per adult
94% of travellers recommend
Orlando: Polynesian Fire Luau with Dinner and Live Show
Orlando: 7-D Dark Ride Entry Ticket

Orlando: 7-D Dark Ride Entry Ticket

$12
per adult
84% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
See all activities in Winter Garden

Oakland Hotel Deals

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
$137 nightly
The price is $154 total per night from Oct 18 to Oct 19
$154 total
Oct 18 - Oct 19
Total with taxes and fees
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 ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Avanti International Resort

Avanti International Resort

4 out of 5
8738 International Dr Orlando FL
$90 nightly
The price is $102 total per night from Sep 29 to Sep 30
$102 total
Sep 29 - Sep 30
Total with taxes and fees
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Avanti International Resort
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista Orlando FL
$96 nightly
The price is $108 total per night from Oct 18 to Oct 19
$108 total
Oct 18 - Oct 19
Total with taxes and fees
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 ...
9/10 Wonderful! (5,047 reviews)
"Not as expected and we were locked out of our room"

Reviewed on Sep 27, 2026

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
$150 nightly
The price is $169 total per night from Sep 29 to Sep 30
$169 total
Sep 29 - Sep 30
Total with taxes and fees
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 ...
Universal's Cabana Bay Beach Resort
Walt Disney World Dolphin

Walt Disney World Dolphin

4 out of 5
1500 Epcot Resort Blvd Lake Buena Vista FL
$277 nightly
The price is $312 total per night from Oct 28 to Oct 29
$312 total
Oct 28 - Oct 29
Total with taxes and fees
Book a stay at this beach hotel in Lake Buena Vista. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant ...
9/10 Wonderful! (4,682 reviews)
"I loved this hotel so much from the staff to the amenities. My kids also enjoyed it and can’t wait to go back. The rooms are super clean and well taken care of. Food was amazing and the staff is also amazing. I can not wait to go back."

Reviewed on Sep 27, 2026

Walt Disney World Dolphin
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
$219 nightly
The price is $246 total per night from Oct 27 to Oct 28
$246 total
Oct 27 - Oct 28
Total with taxes and fees
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 ...
The Grove Resort & Water Park Orlando
See all 40,781 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 West Orange Trail.

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

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