Oakland

Winter Garden

At the Oakland Preserve. Nice Boardwalk plus an animal sanctuary
At the Oakland Preserve. Nice Boardwalk plus an animal sanctuary
Panoramic view of Lake Apopka and nature Florida.

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

Surfari Water Park

5/5(7 reviews)

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

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

Things to do

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

RM256
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

RM605
per traveller
86% of travellers recommend
Universal Orlando Resort Express Passes
Aquatica Orlando

Aquatica Orlando

RM215
per traveller
84% of travellers recommend
Aquatica Orlando
Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

RM573
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Orlando: Jet Ski Rentals from Lake Buena Vista Area

Orlando: Jet Ski Rentals from Lake Buena Vista Area

RM321
per traveller
100% of travellers recommend
Orlando: Jet Ski Rentals from Lake Buena Vista Area
WonderWorks All Access After Dark

WonderWorks All Access After Dark

RM112
per traveller
88% of travellers recommend
WonderWorks All Access After Dark
See all activities in Winter Garden

Top hotels in Oakland

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 RM465 per night from 22 Feb to 23 Feb
RM465
RM523 total
22 Feb - 23 Feb
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! (4,382 reviews)
Great property! Had no idea what I was booking, would definitely stay here again. This property had everything!!

Reviewed on 23 Jan 2026

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
Fully refundableReserve now, pay when you stay
The price is RM451 per night from 27 Jan to 28 Jan
RM451
RM508 total
27 Jan - 28 Jan
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! (6,912 reviews)
Excelente

Reviewed on 17 Jan 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
The price is RM324 per night from 8 Feb to 9 Feb
RM324
RM364 total
8 Feb - 9 Feb
includes taxes & fees
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 3 outdoor pools and 2 coffee shops/cafes. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (5,567 reviews)
Daily housekeeping, which was a plus. But the property does not have a drinking water fountain. Neither do they provide any free water bottles to the renter, which is a downside.

Reviewed on 19 Jan 2026

Rosen Inn at Pointe Orlando
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

3.5 out of 5
6515 International Drive Orlando FL
The price is RM287 per night from 25 Jan to 26 Jan
RM287
RM405 total
25 Jan - 26 Jan
includes taxes & fees
Stay at this business-friendly hotel in Orlando. Enjoy free Wi-Fi, free parking and private pools. Our guests praise the pool and the clean rooms in their reviews. ...
7.2/10 Good! (4,084 reviews)
The check in process was smooth. Our room was clean and spacious. The hotel was close to many stores, restaurants and Arcades venues.

Reviewed on 20 Jan 2026

Wyndham I-Drive Avanti Resort & Conference Center
Orlando International Drive North Hotel

Orlando International Drive North Hotel

2 out of 5
5859 American Way Orlando FL
Stay at this business-friendly hotel in Orlando. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
7.2/10 Good! (2,730 reviews)
The room was amazing!

Reviewed on 22 Jan 2026

Get rates
Orlando International Drive North Hotel
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 RM561 per night from 26 Jan to 27 Jan
RM561
RM854 total
26 Jan - 27 Jan
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 ...
8/10 Very Good! (8,989 reviews)
Clean and spacious

Reviewed on 22 Jan 2026

The Grove Resort & Water Park Orlando
See all 39,803 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

Panoramic view of Lake Apopka and nature Florida.

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
March 25, 2023, Winter Garden, FL: The West Orange bicycle trail through Winter Garden, Florida

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