Oakland Hills holiday rentals
We found 168 holiday rentals — enter your dates for availability
Discover a selection of 75 homes and other holiday rentals in Oakland Hills that are perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as Wi-Fi and parking. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts – Oakland Hills
Showing deals for:4 Dec - 11 Dec
Exceptional
(6 reviews)
Spacious waterfront 6 Bd duplex in lovely Rotonda West near oceans .
Rotonda West
S$4,362
for 7 nights, 1 home
S$623 per night
includes taxes & fees
Exceptional
(14 reviews)
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
Rotonda West
S$1,913
for 7 nights, 1 home
S$273 per night
includes taxes & fees
Exceptional
(28 reviews)
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Rotonda West
S$2,008
for 7 nights, 1 home
S$287 per night
includes taxes & fees
Exceptional
(12 reviews)
Ultimate Privacy: 3BR/2BA Heated Pool, Screened, Green Belt, No Neighbors
Englewood
S$2,222
for 7 nights, 1 home
S$317 per night
includes taxes & fees
Exceptional
(15 reviews)
The Blooming Sanctuary - 3br with pool and EV-Charger
Rotonda West
S$1,538
for 7 nights, 1 home
S$220 per night
includes taxes & fees
Exceptional
(33 reviews)
NewToVRBO RELAX- Own Home Private Pool, Hot Tub, near Beaches, Golf & Pickleball
Rotonda West
S$1,664
for 7 nights, 1 home
S$238 per night
includes taxes & fees
Exceptional
(5 reviews)
South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests
Rotonda West
S$2,140
for 7 nights, 1 home
S$306 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Oakland Hills
Your serene escape - Modern, cozy, and close to the beach.
Sleeps 5 · 3 bedrooms · 2 bathrooms
Golf lovers serene escape - Cozy 3 bed/2 bath, and close to the beach
Sleeps 6 · 3 bedrooms · 2 bathrooms
South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests
Sleeps 6 · 3 bedrooms · 2 bathrooms
Your Dream Getaways Villa only 10 minutes to Boca Grande Beach
Sleeps 6 · 3 bedrooms · 2 bathrooms
Nature's Splendor! Lovely Setting.
Sleeps 6 · 3 bedrooms · 2 bathrooms
Canal Home near Golf Course . 20x32 Heated Pool.15 MIN To BEACHES
Sleeps 9 · 3 bedrooms · 2 bathrooms
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in Oakland Hills?
According to our research, houses are the most in-demand property type in Oakland Hills. But as you know, everyone's idea of the perfect trip differs. Vrbo has holiday homes with every size, shape and budget in mind, and we'll help you to find your perfect match.
How much does it cost to rent a holiday rental in Oakland Hills?
Property type, season and length of stay are some of the things that can determine the price of a holiday home. Simply enter your dates of travel to find your perfect escape. From cosy chalets to sprawling villas, all Vrbo holiday rentals provide amazing value.
How much does it cost to rent a beach house in Oakland Hills?
Prices for beach houses in Oakland Hills may differ depending on the size and type of the property and when you're travelling. Just enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use the filters to narrow down your search by amenities, ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Oakland Hills?
With 45 holiday rentals that allow pets, your furry companion can join in on your Oakland Hills getaway. Use our filter tool to search our pet-friendly holiday rentals and find your pawfect holiday home on Vrbo.
Can I rent a house with a pool in Oakland Hills?
Add a whole other level of fun to your holiday by booking your group into one of the 31 houses with a private pool in Oakland Hills. Use our handy search filter to find the kind of property you want on Vrbo, and then spend your days playing and splashing in a swimming pool that's for your exclusive use.
What are popular rental amenities in Oakland Hills?
The most popular rental amenities guests are looking for in Oakland Hills include a firepit, a nearby waterfront and a garden. Whether you're on the road with family, your besties or even pets, Vrbo holiday rentals feature the best amenities for hanging out with the people that matter most.
Are there large group holiday rentals in Oakland Hills?
You can choose from three holiday properties in Oakland Hills that can accommodate 10 or more people. Whether you're organising a trip with extended family or an event like a birthday party, there's plenty of room to get your group together under the same roof.
Are there holiday rentals in Oakland Hills that welcome kids?
Oakland Hills has 45 family-friendly holiday homes to pick from. And discovering a stay that welcomes little ones is simple with our "Properties good for families" filter. Besides having the entire place to yourselves, you'll also get access to conveniences and perks like dining rooms, full kitchens and private pools.
Can I find two-bedroom holiday rentals in Oakland Hills?
Oakland Hills has 14 two-bedroom properties for you to pick from. Experience a holiday home with all the space and comfort you're looking for at a price that's hard to resist on Vrbo.
Are there holiday rentals with WiFi in Oakland Hills?
Whether you'd like to keep up with the headlines, send a few emails or update your social media accounts, there are 24 holiday homes with WiFi in Oakland Hills. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Oakland Hills?
Oakland Hills has 43 holiday rentals where you can unwind in air-conditioned comfort. To find a stay on Vrbo that has this perk, enter your preferred travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Oakland Hills?
You'll have to check with the Oakland Hills holiday rental you're looking at on Vrbo as the minimum age differs. However, it's normally 16, 18 or 21.
How long can I rent a holiday rental in Oakland Hills for?
It's down to the Oakland Hills property. To look at a list of options offering extended stays, just enter your travel dates and guest number into the Vrbo search page. You can look forward to having the entire place to yourself, along with amenities such as a fully-equipped kitchen, air conditioning and a yard where the kids can burn off energy. Keep an eye out for long-term stays that offer weekly or monthly discounts.