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29 Oct - 30 Oct
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30 Oct - 31 Oct
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31 Oct - 2 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, (1000)
"All around wonderful stay"
United States
Caleb
The Delaney Hotel
Outdoor pool, pool loungers
Lakeside Inn
Lakeside Inn
3.0 star property
8.8 out of 10, Excellent, (1202)
"Awesome place, we go there every year"
United States
stephen
Lakeside Inn
Front of property
The Eo Inn - Downtown
The Eo Inn - Downtown
3.0 star property
8.0 out of 10, Very good, (1006)
"Love this place! "
United States
Genevieve
The price is ฿4,924
฿5,540 total
includes taxes & fees
27 Nov - 28 Nov
The Eo Inn - 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, (8685)
"Great resort "
United States
Magali
The price is ฿5,471
฿7,612 total
includes taxes & fees
2 Nov - 3 Nov
The Grove Resort & Water Park Orlando
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, (6854)
"Great stay"
United States
Bianca
The price is ฿2,894
฿3,255 total
includes taxes & fees
24 Nov - 25 Nov
DoubleTree by Hilton at the Entrance to Universal 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, (991)
"The breakfast was good and the fresh cinnamon buns was also excellent. "
United States
Rena
The price is ฿3,043
฿3,378 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
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, (2268)
"Great stay!"
United States
Rachana
The price is ฿5,147
฿7,612 total
includes taxes & fees
14 Nov - 15 Nov
Hyatt Regency Grand Cypress
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, (1643)
"Great place to stay"
United States
Maribel
The price is ฿1,977
฿2,244 total
includes taxes & fees
12 Nov - 13 Nov
Kompose Boutique Resort at Theme Parks
View from property
Avanti International Resort
Avanti International Resort
4.0 star property
7.8 out of 10, Good, (4186)
"Wonderful place, really made the holiday and would absolutely stay again if I’m in the area - great pool, regular house keeping, comfortable rooms, happy staff."
United Kingdom
Philip
Avanti International Resort
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, (4098)
"Always a great experience when we stay here. "
United States
Marla
The price is ฿3,470
฿3,904 total
includes taxes & fees
15 Nov - 16 Nov
Rosen Shingle Creek
View from room
Rosen Inn Lake Buena Vista
Rosen Inn Lake Buena Vista
3.5 star property
8.6 out of 10, Excellent, (5513)
"Great hotel!"
Canada
Amanda
The price is ฿2,564
฿2,884 total
includes taxes & fees
2 Nov - 3 Nov
Rosen Inn Lake Buena Vista
Outdoor pool, pool cabanas (surcharge), pool umbrellas
Hyatt Regency Orlando
Hyatt Regency Orlando
4.5 star property
9.2 out of 10, Wonderful, (1805)
"Great beautiful hotel "
United States
Barbara
The price is ฿4,103
฿6,411 total
includes taxes & fees
14 Nov - 15 Nov
Hyatt Regency Orlando
Front of property – evening/night
Rosen Inn International
Rosen Inn International
3.0 star property
8.4 out of 10, Very good, (5851)
"Great value and convenient location. "
United States
Amanda
The price is ฿2,331
฿2,622 total
includes taxes & fees
19 Nov - 20 Nov
Rosen Inn International
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, (2177)
"Always a wonderful stay here, both for business and pleasure. "
United States
Alberto
The price is ฿1,878
฿2,477 total
includes taxes & fees
3 Nov - 4 Nov
Candlewood Suites Orlando - Lake Buena Vista by IHG
Exterior
DoubleTree by Hilton Hotel Orlando at SeaWorld
DoubleTree by Hilton Hotel Orlando at SeaWorld
4.0 star property
7.4 out of 10, Good, (6177)
"Good place to stay."
United States
Alberto
The price is ฿2,246
฿3,437 total
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Hotel Orlando at SeaWorld
Sports court
Caribe Royale Orlando
Caribe Royale Orlando
4.5 star property
9.2 out of 10, Wonderful, (4460)
"Amazing location, friendly staff, great rooms."
United States
Joshua
The price is ฿4,824
฿6,811 total
includes taxes & fees
2 Nov - 3 Nov
Caribe Royale Orlando
Outdoor pool, pool loungers
Wyndham Garden Orlando Airport
Wyndham Garden Orlando Airport
3.0 star property
9.0 out of 10, Wonderful, (3921)
"Wonderful Hotel, would stay here about! "
United States
Gregory
The price is ฿2,823
฿3,176 total
includes taxes & fees
24 Nov - 25 Nov
Wyndham Garden Orlando Airport
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, (3726)
"Clean rooms , kids friendly , pools for all ages "
United States
bashar
The price is ฿2,017
฿2,925 total
includes taxes & fees
2 Nov - 3 Nov
Wyndham I-Drive Avanti Resort & Conference Center
Exterior
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Holiday Inn Resort Orlando Suites - Waterpark by IHG
3.5 star property
7.0 out of 10, Good, (4335)
"Good place to stay"
United States
Yuri
The price is ฿1,959
฿4,592 total
includes taxes & fees
30 Oct - 31 Oct
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Exterior
Wyndham Grand Orlando Resort Bonnet Creek
Wyndham Grand Orlando Resort Bonnet Creek
4.0 star property
8.8 out of 10, Excellent, (2795)
"Great hotel"
United States
Omar
The price is ฿4,500
฿6,519 total
includes taxes & fees
23 Nov - 24 Nov
Wyndham Grand Orlando Resort Bonnet Creek
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 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

Exterior
voco Kissimmee Orlando by IHG
voco Kissimmee Orlando by IHG
4.0 star property
    7.4 out of 10, Good, (1012)
    The price is ฿1,981
    ฿3,351 total
    includes taxes & fees
    2 Nov - 3 Nov
    voco Kissimmee Orlando by IHG
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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

    The Grove Resort & Water Park Orlando

    The Grove Resort & Water Park Orlando

    10/10 Excellent
    "We have stayed here 4 times now, and every time is a truly relaxing vacation. The store is a little over priced but its a tourist location so thats as expected. All in all, wr will be staying again mext year."
    Tyler 3-night trip
    Posted 1 day ago
    The Grove Resort & Water Park Orlando

    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.