Highland Oaks Vacation Packages
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Top Holiday Package Deals in Highland Oaks
Price found within the past 48 hours. Click for updated prices.
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
1 out of top 10 points of interest in this area
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.
Downtown St. Petersburg
1 out of top 10 points of interest in this area
Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.
Sand Key
1 out of top 10 points of interest in this area
While visiting Sand Key, you might make a stop by sights like St. Petersburg - Clearwater Beaches and Sand Key Park.
Sunset Beach
Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like St. Petersburg - Clearwater Beaches and Sunset Beach.
Sunshine Beach
If you're spending some time in Sunshine Beach, St. Petersburg - Clearwater Beaches and St. Petersburg Municipal Beach at Treasure Island are top sights worth seeing.
Highland Oaks Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $269
CA $360 total
Aug 26 - Aug 27
includes taxes & fees
9.4/10 Exceptional! (3,726 reviews)
"Loved everything! Would absolutely go back."
Reviewed on Aug 11, 2026
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
CA $200
CA $227 total
Aug 23 - Aug 24
includes taxes & fees
8.6/10 Excellent! (1,504 reviews)
"Staff was very friendly and went out of their way to make us comfortable."
Reviewed on Aug 11, 2026
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $227
CA $312 total
Aug 24 - Aug 25
includes taxes & fees
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 CA $1,256. 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.
Things to do
Sunset Celebration Cruise on Tropics Boat Tours
CA $52
per adult
94% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
CA $52
per adult
90% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
CA $109
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.