Oakland Hills Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Where to stay in Oakland Hills

Find the best Oakland Hills areas and neighborhoods for the activities you enjoy most. Learn more about Oakland Hills
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Pine Valley

Pine Valley might not have many top sights, but Gasparilla Marina and Don Pedro Island Beach are two attractions nearby that you can check out.

Find hotels in Pine Valley

Top hotels in Oakland Hills

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is S$264 per night from 21 Dec to 22 Dec
S$264
21 Dec - 22 Dec
includes taxes & fees
9.2/10 Wonderful! (1,665 reviews)
Great stay. Pool was very nice and warm with many choices and staff was great.

Reviewed on 14 Dec, 2025

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL

2.5 out of 5
24244 Corporate Ct Port Charlotte FL
Fully refundableReserve now, pay when you stay
The price is S$108 per night from 21 Dec to 22 Dec
S$108
21 Dec - 22 Dec
includes taxes & fees
7.8/10 Good! (1,151 reviews)
Nothing to complain or brag about

Reviewed on 14 Dec, 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
Motel 6 Venice, FL

Motel 6 Venice, FL

2 out of 5
281 US 41 Bypass North Venice FL
Fully refundableReserve now, pay when you stay
The price is S$97 per night from 16 Dec to 17 Dec
S$97
16 Dec - 17 Dec
includes taxes & fees
8.2/10 Very Good! (363 reviews)
Pleasantly surprised! Newly renovated so everything was pretty nice. It was affordable which let me stay for 2 nights and I was able to get some good rest to go back to my drive back home. I totally recommend staying here for convenience and especially price. They could clean up the grounds a bit ...

Reviewed on 8 Dec, 2025

Motel 6 Venice, FL
See all 6,036 properties in Oakland Hills
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.

Frequently asked questions

How much does an Oakland Hills holiday package cost?
Perhaps much less than you think — from only , as a matter of fact! By bundling flights, hotels and car rentals into your own tailor-made travel package, your getaway to Oakland Hills is just clicks away.
How do I get a cheap travel package to Oakland Hills?
Bundle your bookings with Expedia to save on your next adventure. With over 550 air carriers and 1,000,000 properties across the globe, your Oakland Hills holiday package can be customized exactly to suit your travel style. With all those extra dollars, why not include some interesting tours and experiences? It's an easy way to unlock even more discounts. Your dream holiday in Oakland Hills is much closer than you thought!
What are the top hotels in Oakland Hills?
Get your holiday off to a great start by reserving a room at Designer Home On Fresh Water Canal20x32 Heated Poolclose To Manasota Key Beach. It's one of most popular properties in Oakland Hills. Another comfortable option is Water Front Boundary Holiday Home Villa Close To Beaches.
How far in advance should I book my Oakland Hills holiday?
It can be tricky to know exactly when the best time is to book your Oakland Hills holiday. But generally the earlier you book, the lower the prices. In some cases, you can reserve your flights and hotels nearly 12 months before departure. If you're eager to escape on a last-minute getaway, no need to stress! There are terrific bargains advertised on Expedia all the time.
What does an Expedia Oakland Hills travel package include?
Expedia has everything you need to lock in Oakland Hills escape, but what goes into your package is your call. Pick from a combination of hotels, rental cars and flights. In search of some experiences or tours to fill in your time? Once you've made your booking, you can add them too. Whatever your budget, there's a package to meet your needs.
What should I know before booking an Oakland Hills travel package?
A package can be more affordable than separately booking all you need for your trip. For example, bundle your hotels, flights and rental cars and save a tidy sum. Whatever type of holiday you have in mind, you're sure to find a package within your budget.
If I'm not able to travel, can I cancel my Oakland Hills holiday package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can change or cancel your Oakland Hills holiday package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.