Oakland Hills Vacations

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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

Oakland Hills Hotel Deals

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 ₩184,495 per night from Feb 16 to Feb 17
₩184,495
₩270,548 total
Feb 16 - Feb 17
includes taxes & fees
9.2/10 Wonderful! (1,761 reviews)
Awesome place

Reviewed on Jan 22, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is ₩326,284 per night from Feb 1 to Feb 2
₩326,284
₩365,447 total
Feb 1 - Feb 2
includes taxes & fees
9.6/10 Exceptional! (1,081 reviews)
Everything good

Reviewed on Jan 19, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites
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 ₩165,346 per night from Jan 25 to Jan 26
₩165,346
₩185,188 total
Jan 25 - Jan 26
includes taxes & fees
7.8/10 Good! (1,225 reviews)
The front desk person was very nice.

Reviewed on Jan 24, 2026

Country Inn & Suites by Radisson, Port Charlotte, FL
See all 6,125 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.
Can I choose my airline with an Oakland Hills Expedia vacation package?
Yes, you're in charge. Expedia has access to more than 550 airlines throughout the world, so you can customize your Oakland Hills escape according to your budget and style.
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.