Oakland Hills Holidays

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Our guide on 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

Our pick of the best Oakland Hills Hotel Deals

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Rotonda West
The price is NZ$541 per night from 22 Aug to 23 Aug
NZ$541
22 Aug - 23 Aug
includes taxes & fees
9.8/10 Exceptional! (57 reviews)
Amazing
"This is the second time in a year that we have rented this home. It is so well kept, clean and supplies wirh all you need for a trip to the beach. The host is very attentive to any issues that might pop up, dealing with them that day. I would highly recommend this home and host."

Reviewed on 5 May 2025

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
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! (1,218 reviews)
"We had a rough check in. Wasn't told we were in bldg 3 that was a very long walk w tons of luggage and extreme heat . Found out later we cld have checked in there or got a golf cart ride there.we had a good time but a bit of trouble w the air conditioning at night too. Thats why i gave it a 4"

Reviewed on 21 Jul. 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 NZ$139 per night from 3 Aug to 4 Aug
NZ$139
3 Aug - 4 Aug
includes taxes & fees
7.6/10 Good! (1,010 reviews)
"Amazing stay"

Reviewed on 19 Jul. 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
See all 5,396 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.