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.
The Don CeSar

The Don CeSar

4 out of 5
Price was CA $2,038, price is now CA $1,407 per person
CA $1,407
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,173 reviews)
I have one word, WOW!!! You need to go and experience this amazing place for yourself!!!!!!

Reviewed on Jun 19, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,698, price is now CA $1,601 per person
CA $1,601
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,647, price is now CA $1,681 per person
CA $1,681
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (526 reviews)
Beautiful facility. Perfect for families close to all the beaches and fun. Can't wait to return for our next visit!

Reviewed on Jun 18, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,930, price is now CA $1,948 per person
CA $1,948
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (552 reviews)
The staff was very kind and accommodating. We will definitely look to book again.

Reviewed on Jun 19, 2026

The Marker

The Marker

2 out of 5
Price was CA $3,512, price is now CA $2,392 per person
CA $2,392
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
6/10 (3 reviews)
There was no staff due to it being brand new! The owner Jeff was great and very polite and went out of his way to make us feel welcome and valued! It was very quiet and comfortable for my family. Only about a two block walk to the beach but being in the bay was beautiful to wake up to!

Reviewed on Apr 12, 2026

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

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.

Find hotels in Pass-a-Grille

Highland Oaks Hotel Deals

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Jul 5 to Jul 6
CA $227
CA $258 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,376 reviews)
"Clean room, friendly staff. For the price, parking should be included."

Reviewed on Jun 20, 2026

The Westin Tampa Bay
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 CA $365 per night from Jul 16 to Jul 17
CA $365
CA $469 total
Jul 16 - Jul 17
includes taxes & fees
9.4/10 Exceptional! (3,392 reviews)
"Amazing experience. Highly recommended"

Reviewed on Jun 20, 2026

Wyndham Grand Clearwater Beach
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 CA $296 per night from Jun 28 to Jun 29
CA $296
CA $390 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very Good! (2,705 reviews)
"Gross. Run down. Needs a major update. Promotes a private beach but open to the public. I’ll never stay here again."

Reviewed on Jun 20, 2026

Hilton Clearwater Beach Resort & Spa
See all 18,828 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.
All Inclusive Vacations
All Inclusive Vacations
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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 $1,407. 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

A coastal cityscape with a prominent waterfront, a bridge, and a distinctive building with a red facade.

John's Pass Village & Boardwalk

4.5/5(141 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
Aerial sunset view of Clearwater beach and Sand key in Western Florida on the Mexican Gulf coast with vacation homes, hotels and bridges connecting

Clearwater Beach

4.5/5(5 reviews)

Nothing says vacation like spending a carefree day at Clearwater Beach, a popular beach in Clearwater Beach. Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Fort De Soto Park

Fort De Soto Park

4.5/5(28 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $51
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

CA $62
per adult
94% of travellers recommend
Pirate Adventure Cruise - John's Pass
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.