Oakland Hills Trips (flight + hotel)

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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 Don Pedro Island Beach and Little Gasparilla Island Beach are two attractions nearby that you can check out.

Find hotels in Pine Valley

Top hotels in Oakland Hills

Sunseeker Resort Charlotte Harbor
Sunseeker Resort Charlotte Harbor
4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,145 reviews)
"I'll be back..."

Reviewed on Jul 5, 2025

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Sunseeker Resort Charlotte Harbor
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 refundable
The price is P3,933 per night from Jul 14 to Jul 15
P3,933
P4,405 total
Jul 14 - Jul 15
includes taxes & fees
7.6/10 Good! (1,006 reviews)
"Nice pool hours, loved that the bed had a door separating the room in half"

Reviewed on Jul 7, 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
Holiday Inn Express Venice by IHG
Holiday Inn Express Venice by IHG
2.5 out of 5
380 Commercial Ct, Venice, FL
Fully refundable
The price is P5,135 per night from Jul 13 to Jul 14
P5,135
P5,802 total
Jul 13 - Jul 14
includes taxes & fees
7.8/10 Good! (878 reviews)
"I usually stay here when visit Venice, never had any issues."

Reviewed on Jul 6, 2025

Holiday Inn Express Venice by IHG
See all 5,395 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 vacation 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 vacation 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 vacation in Oakland Hills is much closer than you thought!
What are the top hotels in Oakland Hills?
Get your vacation 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 Vacation Home Villa Close To Beaches.
How far in advance should I book my Oakland Hills vacation?
It can be tricky to know exactly when the best time is to book your Oakland Hills vacation. 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 vacation 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 vacation 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 vacation 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.