Vacation rentals in Oakland
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Top-rated vacation rentals in Oakland
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Oakland vacation rentals
Other great vacation rentals in Oakland
Guest favourite
Guesthouse in Winter Garden
4.94 out of 5 average rating, 53 reviewsBlue Heron Bungalow
Jul. 14 – 21
$169 CAD per night
Guest favourite
Farm stay in Winter Garden
4.96 out of 5 average rating, 46 reviewsCarriage House Studio Apt Peaceful & Private Ranch
Oct. 25 – Nov. 1
$216 CAD per night
Superhost
Apartment in Windermere
4.83 out of 5 average rating, 54 reviewsPrivate Garage Apt., 5 Miles from Disney World
May 30 – Jun. 6
$199 CAD per night
Guest favourite
Home in Winter Garden
4.94 out of 5 average rating, 18 reviewsCozy home in Winter Garden
Oct. 7 – 14
$216 CAD per night
Guest favourite
Home in Montverde
4.95 out of 5 average rating, 20 reviewsCottage in the Hills
Oct. 30 – Nov. 6
$198 CAD per night
Guest favourite
Home in Winter Garden
4.91 out of 5 average rating, 43 reviewsWinter Garden Experience
Dec. 4 – 11
$258 CAD per night
Guest favourite
Guest suite in Clermont
5.0 out of 5 average rating, 45 reviewsTraveling med staff,pro athletes & remote worker
Aug. 22 – 29
$113 CAD per night
Guest favourite
Villa in Clermont
4.9 out of 5 average rating, 42 reviewsCute N Cozy Villa near Disney, pool, Wi-Fi
Aug. 11 – 18
$213 CAD per night
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