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 Westin Sarasota
Central Sarasota
CA $1,260
per person
Dec 7 - Dec 13
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,150 reviews)
Breakfasts wonderful- staff exceedingly helpful. I would change the bed comforters- much to heavy and lumpy
Reviewed on Sep 25, 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
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.
Pass-a-Grille
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.
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 Belleair Beach and Sand Key Park.
Sunset Beach
Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like Sunset Beach and St. Petersburg - Clearwater Beaches.
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 $332
CA $431 total
Sep 30 - Oct 1
includes taxes & fees
9.4/10 Exceptional! (3,925 reviews)
"This hotel was located in the perfect spot you can walk to restaurants and to shops the beach and the pier was easy to get to I enjoyed my stay there the views of the sunset were amazing the staff was very friendly and accommodating I would definitely recommend this place"
Reviewed on Sep 25, 2026
Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $347
CA $448 total
Sep 27 - Sep 28
includes taxes & fees
9.4/10 Exceptional! (2,403 reviews)
"The staff was very welcoming and nice to talk to . They made my stay way better"
Reviewed on Sep 25, 2026
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
CA $211
CA $278 total
Sep 27 - Sep 28
includes taxes & fees
9.4/10 Exceptional! (2,586 reviews)
"We had a wonderful stay in the hotel. We were able to check in early and was given an upgrade room. The property is clean & beautiful. Also, shout out to Dawn, a wonderful lady, who greeted us every morning with a smile at the breakfast area. Thank you for a wonderful stay while visiting AMI"
Reviewed on Sep 25, 2026
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 $898. 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
Starlite Infinity Evening Yacht Cruise Clearwater
CA $51
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
CA $39
per adult
94% of travellers recommend
Dolphin Racer Speedboat Adventure
CA $50
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.