Highland Oaks Vacations

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Where to stay in Highland Oaks

Find the best Highland Oaks areas and neighborhoods for the activities you enjoy most. Learn more about Highland Oaks
Pass-a-Grille

Pass-a-Grille

5/5(26 area reviews)

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

Highland Oaks Hotel Deals

Hilton Clearwater Beach Resort & Spa
Hilton Clearwater Beach Resort & Spa
4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is NT$5,439 per night from Aug 11 to Aug 12
NT$5,439
NT$7,301 total
Aug 11 - Aug 12
includes taxes & fees
8/10 Very Good! (2,002 reviews)
"Great resort"

Reviewed on 2025/7/12

Hilton Clearwater Beach Resort & Spa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is NT$4,417 per night from Aug 7 to Aug 8
NT$4,417
NT$5,014 total
Aug 7 - Aug 8
includes taxes & fees
8.6/10 Excellent! (1,654 reviews)
"Nice overnight stay! Super comfortable"

Reviewed on 2025/7/12

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Wyndham Grand Clearwater Beach
Wyndham Grand Clearwater Beach
4 out of 5
100 Coronado Drive, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is NT$8,388 per night from Aug 3 to Aug 4
NT$8,388
NT$10,634 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (2,375 reviews)
"Great location with convenient stores, restaurants,very clean the hotel with excellent guest service. Overall everything was great at our stay."

Reviewed on 2025/7/13

Wyndham Grand Clearwater Beach
See all 17,653 properties in Highland Oaks
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 a Highland Oaks vacation package cost?
Say yes to new adventures with our Highland Oaks vacation packages, which start from only . Pick the hotels and flights that match your travel plans. Then, add on one or two enriching experiences for a memorable adventure.
How do I get a cheap travel package to Highland Oaks?
Book everything all in one place with our Highland Oaks vacation packages. You'll find deals on flights, hotels and more that'll keep your budget happy and adventurous side satisfied. And, with more than 550 partner airlines and 1,000,000 properties around the world to choose from, you have countless opportunities to mix and match your own way.
Where should I stay in Highland Oaks?
A visit to Highland Oaks isn't complete without seeing Salvador Dali Museum and Tropicana Field. Stay somewhere right nearby and easily access these popular tourist attractions.
How far in advance should I book my Highland Oaks vacation?
Reserving your seat early with Expedia means one less thing to worry about. A number of air carriers advertise tickets up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, great deals to Highland Oaks will sometimes occur just a few weeks before departure.
What does an Expedia Highland Oaks travel package include?
Hotels, flights and rental cars --- you'll find them all here. With Expedia, you can shape your Highland Oaks package the way you like it. All you have to do is decide what you need. Once you've made your booking, you can add on extras like activities and experiences. The more you bundle, the bigger the savings!
What should I know before booking a Highland Oaks travel package?
Bundling your bookings into a Highland Oaks vacation package is the easiest way to organize your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Highland Oaks Expedia vacation package?
You sure can. We have more than 550 airline partners worldwide, so select the carrier that best suits your needs.
If I'm not able to travel, can I cancel my Highland Oaks vacation package?
You sure can, and we're here to help. You may be able to cancel or change your Highland Oaks vacation package at no cost if you booked in the last 24 hours. However, you may incur a fee from your hotel, airline or car rental company for older bookings. If your circumstances suddenly change, have a look at our Customer Service Portal for further information.

Discover the most popular places to visit in Highland Oaks

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(1,625 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
Salvador Dali Museum showing night scenes and modern architecture

Salvador Dali Museum

4.5/5(1,166 reviews)

Browse the surrealistic masterpieces of a world-famous Spanish painter in a remarkable building that perfectly suits the style of the art exhibits.

Salvador Dali Museum
Vinoy Park

Vinoy Park

4.5/5(227 reviews)

While area beaches are abundant, it’s convenient to have this lovely spot right in the city. Lounge under a palm tree and enjoy the frequent entertainment.

Vinoy Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.