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Search Hotels in Oakland, Winter Garden

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27 Dec - 28 Dec
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Our top choices for Oakland hotels

4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
24.2 km from Oakland
9.4 out of 10, Exceptional, (4386)
"Great place to stay. Definitely will stay here again.."
United States
Donnell
The price is ฿3,699
฿4,162 total
includes taxes & fees
23 Jan - 24 Jan 2026
Rosen Shingle Creek
Property grounds
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
30.2 km from Oakland
8.8 out of 10, Excellent, (3315)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is ฿1,955
฿2,219 total
includes taxes & fees
4 Jan - 5 Jan 2026
Seasons Florida Resort
Lobby lounge
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
22.5 km from Oakland
8.8 out of 10, Excellent, (1921)
"Good place to stay "
United States
victor
The price is ฿2,421
฿2,723 total
includes taxes & fees
4 Jan - 5 Jan 2026
Aloft Orlando Lake Buena Vista
Room, 2 Queen Beds | Laptop workspace, blackout curtains, iron/ironing board
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport
3.0 star property
29.4 km from Oakland
8.0 out of 10, Very good, (296)
"The hotel was very clean and the customer.service was great. "
United States
Heather
The price is ฿2,762
฿3,108 total
includes taxes & fees
26 Jan - 27 Jan 2026
Sonesta Essential Orlando Airport
Outdoor pool, pool umbrellas, pool loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
19.2 km from Oakland
7.4 out of 10, Good, (3936)
"Excellent room and the beds were very comfortable, also very clean "
United States
Daisy
The price is ฿1,934
฿2,804 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wyndham I-Drive Avanti Resort & Conference Center
Business centre
Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
18.9 km from Oakland
9.0 out of 10, Wonderful, (489)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is ฿2,677
฿3,012 total
includes taxes & fees
26 Jan - 27 Jan 2026
Spark by Hilton Orlando near Universal
Outdoor pool, pool cabanas (surcharge), pool umbrellas
Hyatt Regency Orlando

Hyatt Regency Orlando

Hyatt Regency Orlando
4.5 star property
21.4 km from Oakland
9.2 out of 10, Wonderful, (1889)
"Clean and beautifully maintained hotel . "
United States
Puneet
The price is ฿4,166
฿6,410 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hyatt Regency Orlando
Outdoor pool
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando
4.0 star property
19.2 km from Oakland
8.4 out of 10, Very good, (6882)
"Great hotel great food"
United States
Malika
The price is ฿2,774
฿3,121 total
includes taxes & fees
15 Jan - 16 Jan 2026
DoubleTree by Hilton at the Entrance to Universal Orlando
Free daily buffet breakfast
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
20.6 km from Oakland
9.4 out of 10, Exceptional, (1402)
"Good location, good breakfast "
United States
Andrea
The price is ฿3,662
฿4,120 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt House Orlando International Drive
6 outdoor pools, free pool cabanas, pool umbrellas
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
24.3 km from Oakland
9.4 out of 10, Exceptional, (4180)
"Great stay "
United States
Jude
The price is ฿3,451
฿3,882 total
includes taxes & fees
19 Jan - 20 Jan 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Exterior
Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport

Cambria Hotel Orlando Airport
3.0 star property
31.4 km from Oakland
8.8 out of 10, Excellent, (1939)
"Clean room and pleasant staff. "
United States
Mariama Velinique
The price is ฿3,139
฿3,532 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cambria Hotel Orlando Airport
2 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
3.5 star property
18.5 km from Oakland
9.0 out of 10, Wonderful, (5874)
"Excelente resort."
Brazil
RONALDO
The price is ฿4,128
฿4,644 total
includes taxes & fees
6 Jan - 7 Jan 2026
Universal's Cabana Bay Beach Resort
Lobby
Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG
3.5 star property
24 km from Oakland
8.4 out of 10, Very good, (3589)
"Very convenient and liked the hotel"
United States
Melanie
The price is ฿2,048
฿3,352 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Outdoor pool, pool loungers
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
3.0 star property
23.1 km from Oakland
9.8 out of 10, Exceptional, (5459)
"Great stay!"
United States
Kiran
The price is ฿5,012
฿5,638 total
includes taxes & fees
4 Jan - 5 Jan 2026
Drury Plaza Hotel Orlando - Disney Springs Area
In-room safe, laptop workspace, blackout curtains, iron/ironing board
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
28.9 km from Oakland
8.2 out of 10, Very good, (5148)
"Beautiful place to stay."
United States
Mohammad
The price is ฿1,209
฿2,429 total
includes taxes & fees
4 Jan - 5 Jan 2026
Palazzo Lakeside Hotel
Outdoor pool, pool umbrellas, pool loungers
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
24.9 km from Oakland
9.4 out of 10, Exceptional, (2102)
"Very nice place to stay in, we love it!!"
United States
Basim
The price is ฿2,142
฿3,664 total
includes taxes & fees
6 Jan - 7 Jan 2026
Kompose Boutique Resort at Theme Parks
Exterior
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway
3.0 star property
25.2 km from Oakland
8.0 out of 10, Very good, (3902)
"Phenomenal hotel for the price point as well as the children. "
United States
Destiny
The price is ฿1,564
฿2,409 total
includes taxes & fees
20 Jan - 21 Jan 2026
Ramada by Wyndham Kissimmee Gateway
Property amenity
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
19.6 km from Oakland
8.6 out of 10, Excellent, (748)
"What a wonderful stay! "
United States
Lucia
The price is ฿2,612
฿2,938 total
includes taxes & fees
26 Jan - 27 Jan 2026
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
View from room
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista
3.5 star property
22.9 km from Oakland
8.6 out of 10, Excellent, (5646)
"Great property to stay"
United States
Deepankar
The price is ฿2,541
฿2,859 total
includes taxes & fees
23 Jan - 24 Jan 2026
Rosen Inn Lake Buena Vista
Outdoor pool, open 9 AM to 10 PM, pool loungers
Orlando Palms Hotel

Orlando Palms Hotel

Orlando Palms Hotel
2.5 star property
25.8 km from Oakland
7.6 out of 10, Good, (2245)
"Accommodation was great , clean and not too expensive "
United States
Jossy
The price is ฿1,509
฿2,068 total
includes taxes & fees
4 Jan - 5 Jan 2026
Orlando Palms Hotel
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.
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Where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.

Horizon West

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

Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Flamingo Crossings Town Center are some notable places to visit nearby.

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.

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.

Top Oakland Hotel Reviews

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent
"Great experience. Buffet was elaborate. "
Olakunle 3-night trip
Posted 16 hours ago
DoubleTree by Hilton Hotel Orlando at SeaWorld

Frequently asked questions

What's it like in Oakland?
Travellers will be sure to enjoy their time in Winter Garden's Oakland neighbourhood. Consider a visit to Oakland Nature Preserve as part of your Oakland travel plans.
How many hotels can I expect to find in Oakland?
When you want to put your feet up after a day of exploring the sights in Winter Garden, you can choose from 12 Expedia hotels and other accommodation options in Oakland.
If I need to cancel my hotel reservation in Oakland, will I receive a refund?
Yes, you'll find most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to review the best options available in Oakland.
What is there to do in this Winter Garden neighbourhood?
Oakland Nature Preserve is an attraction you might want to check out while you're in Oakland. While you're out sightseeing in Winter Garden, make sure that you visit other sights such as Plant Street Market or Garden Theatre.

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