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3 Nov - 4 Nov
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Top Trending Hotels Near Oakland, Winter Garden

Terrace/patio
The Delaney Hotel
The Delaney Hotel
3.5 star property
9.6 out of 10, Exceptional, (1011)
"All around wonderful stay"
United States
Caleb
The Delaney Hotel
6 outdoor pools, free pool cabanas, pool umbrellas
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
9.4 out of 10, Exceptional, (3838)
"Always a great property to stay at. Been going since i was a toddler and back at 44 for another amazing stay. "
United States
Laura
The price is ฿2,949
฿3,317 total
includes taxes & fees
1 Dec - 2 Dec
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
5 outdoor pools, pool umbrellas, pool loungers
Summer Bay Orlando by Exploria Resorts
Summer Bay Orlando by Exploria Resorts
3.5 star property
8.8 out of 10, Excellent, (2073)
"We loved our stay here. "
Canada
Andrew
The price is ฿3,346
฿4,791 total
includes taxes & fees
16 Nov - 17 Nov
Summer Bay Orlando by Exploria Resorts
Property amenity
Courtyard by Marriott Orlando Downtown
Courtyard by Marriott Orlando Downtown
3.0 star property
9.6 out of 10, Exceptional, (1009)
"The bed was extremely comfortable! The room was amazing! Staff was very nice! Will stay here again!"
United States
Jerry
The price is ฿4,106
฿4,619 total
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott Orlando Downtown
Aerial view
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4.0 star property
8.0 out of 10, Very good, (8721)
"Great place to stay!!!"
United States
Darick
The price is ฿5,334
฿7,456 total
includes taxes & fees
1 Dec - 2 Dec
The Grove Resort & Water Park Orlando
Property amenity
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
2.5 star property
8.4 out of 10, Very good, (997)
"The breakfast was good and the fresh cinnamon buns was also excellent. "
United States
Rena
The price is ฿2,721
฿3,020 total
includes taxes & fees
6 Nov - 7 Nov
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Outdoor pool
DoubleTree by Hilton at the Entrance to Universal Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando
4.0 star property
8.4 out of 10, Very good, (6897)
"Great hotel "
United States
Meghan
The price is ฿3,155
฿3,549 total
includes taxes & fees
10 Nov - 11 Nov
DoubleTree by Hilton at the Entrance to Universal Orlando
Lobby lounge
Aloft Orlando Lake Buena Vista
Aloft Orlando Lake Buena Vista
3.0 star property
8.8 out of 10, Excellent, (1840)
"Great stay "
United States
Melissa
The price is ฿2,263
฿2,546 total
includes taxes & fees
23 Nov - 24 Nov
Aloft Orlando Lake Buena Vista
Meeting facility
Hampton Inn & Suites Orlando Intl Dr N
Hampton Inn & Suites Orlando Intl Dr N
2.5 star property
9.2 out of 10, Wonderful, (1094)
"Great food great room "
United States
David
The price is ฿2,757
฿3,102 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn & Suites Orlando Intl Dr N
View from property
Avanti International Resort
Avanti International Resort
4.0 star property
7.8 out of 10, Good, (4191)
"The Best ! "
United States
Oscar
Avanti International Resort
View from room
Rosen Inn Lake Buena Vista
Rosen Inn Lake Buena Vista
3.5 star property
8.6 out of 10, Excellent, (5532)
"I really liked how quiet the hotel was and how close everything is "
United States
Victor
The price is ฿2,560
฿2,880 total
includes taxes & fees
5 Nov - 6 Nov
Rosen Inn Lake Buena Vista
Suite, 1 King Bed with Sofa bed, Balcony | 1 bedroom, premium bedding, minibar, in-room safe
Kompose Boutique Resort at Theme Parks
Kompose Boutique Resort at Theme Parks
3.0 star property
9.4 out of 10, Exceptional, (1681)
"Great place to stay"
United States
Maribel
The price is ฿2,008
฿2,279 total
includes taxes & fees
1 Dec - 2 Dec
Kompose Boutique Resort at Theme Parks
3 outdoor pools, open 7 AM to 10:00 PM, pool cabanas (surcharge)
Hyatt Regency Grand Cypress
Hyatt Regency Grand Cypress
4.0 star property
9.2 out of 10, Wonderful, (2273)
"Great stay!"
United States
Rachana
The price is ฿5,140
฿7,602 total
includes taxes & fees
14 Nov - 15 Nov
Hyatt Regency Grand Cypress
Front of property – evening/night
Rosen Inn International
Rosen Inn International
3.0 star property
8.4 out of 10, Very good, (5862)
"I have always stayed in the rosen inn, its the best affordable hitel in Orlando. "
United States
Joao Ricardo
The price is ฿2,327
฿2,618 total
includes taxes & fees
30 Nov - 1 Dec
Rosen Inn International
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)
Rosen Shingle Creek
Rosen Shingle Creek
4.5 star property
9.4 out of 10, Exceptional, (4130)
"Always a great experience when we stay here. "
United States
Marla
The price is ฿3,466
฿3,899 total
includes taxes & fees
15 Nov - 16 Nov
Rosen Shingle Creek
Suite, Multiple Beds | In-room safe, desk, laptop workspace, blackout curtains
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
3.0 star property
8.8 out of 10, Excellent, (2209)
"I love this hotel and definitely will stay again. It is conveniently located between Walt Disney World and Universal Resort and offer shuttle transportation to both areas by schedule. In addition it has complimentary hot breakfast, which is good, and the staff is very helpful and attentive."
United States
Yamaris
The price is ฿2,619
฿2,946 total
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG
Business centre
Spark by Hilton Orlando near Universal
Spark by Hilton Orlando near Universal
2.5 star property
9.0 out of 10, Wonderful, (260)
"Nice place to stay specially if you have dog(s) "
United States
Grismilda
The price is ฿2,625
฿2,953 total
includes taxes & fees
10 Nov - 11 Nov
Spark by Hilton Orlando near Universal
1 bedroom, premium bedding, desk, laptop workspace
Candlewood Suites Orlando - Lake Buena Vista by IHG
Candlewood Suites Orlando - Lake Buena Vista by IHG
2.5 star property
9.0 out of 10, Wonderful, (2192)
"Always a wonderful stay here, both for business and pleasure. "
United States
Alberto
The price is ฿2,295
฿2,946 total
includes taxes & fees
11 Nov - 12 Nov
Candlewood Suites Orlando - Lake Buena Vista by IHG
Sports court
Caribe Royale Orlando
Caribe Royale Orlando
4.5 star property
9.2 out of 10, Wonderful, (4466)
"Great place to stay"
United States
Bernardo
The price is ฿4,817
฿6,802 total
includes taxes & fees
23 Nov - 24 Nov
Caribe Royale Orlando
Outdoor pool, pool umbrellas, pool loungers
Wyndham I-Drive Avanti Resort & Conference Center
Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
7.4 out of 10, Good, (3753)
"I love this place the food and the pool was amazing and the rooms was clean…"
United States
Monique
The price is ฿2,014
฿2,921 total
includes taxes & fees
10 Nov - 11 Nov
Wyndham I-Drive Avanti Resort & Conference Center
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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Hotels in Oakland with free breakfast

Outdoor pool, pool cabanas (surcharge), pool umbrellas
Hyatt Regency Orlando
Hyatt Regency Orlando
4.5 star property
  • Breakfast included
9.2 out of 10, Wonderful, (1823)
The price is ฿4,098
฿6,402 total
includes taxes & fees
14 Nov - 15 Nov
Hyatt Regency Orlando
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Hotels in Oakland with a pool

Outdoor pool
The Oak View Place..
The Oak View Place..
  • Pool
9.2 out of 10, Wonderful, (10)
The Oak View Place..
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Top guest rated hotels in Oakland

Front of property – evening/night
SPOT X Hotel Orlando/Intl Dr by The Red Collection
SPOT X Hotel Orlando/Intl Dr by The Red Collection
3.0 star property
    8.6 out of 10, Excellent, (2877)
    The price is ฿1,938
    ฿2,762 total
    includes taxes & fees
    24 Nov - 25 Nov
    SPOT X Hotel Orlando/Intl Dr by The Red Collection
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    Where to stay in Oakland

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

    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.

    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.

    Horizon West

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

    Top Oakland Hotel Reviews

    Marriott's Grande Vista

    Marriott's Grande Vista

    10/10 Excellent
    "Clean room, very comfortable bed, really enjoyable stay. Pleasant staff. "
    Lori 1-night trip
    Posted 16 hours ago
    Marriott's Grande Vista

    Explore a world of travel with Expedia

    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.