Highland Oaks Holidays

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Your Highland Oaks Holiday

Highland Oaks is calling! Whatever type of getaway you're planning, you can experience and see more of this neighbourhood with a Highland Oaks holiday package. Eager to do some sightseeing during your trip to Highland Oaks? Don't miss nearby attractions like Salvador Dali Museum, Tropicana Field and Museum of Fine Arts. Expedia can help you turn your ideal Highland Oaks holiday into reality, no matter your travel plans or budget.

Our guide on 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

As you view this neighborhood’s iconic pink hotel it feels as if you’ve crossed into the past. Find beautiful beaches and serene enjoyment here.

Find hotels in Pass-a-Grille

Our pick of the best Highland Oaks Hotel Deals

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 AU$537 per night from 22 June to 23 June
AU$537
22 June - 23 June
includes taxes & fees
9.4/10 Exceptional! (3,330 reviews)
"Close to beach"

Reviewed on 8 June 2026

Wyndham Grand Clearwater Beach
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 AU$296 per night from 18 June to 19 June
AU$296
18 June - 19 June
includes taxes & fees
8.6/10 Excellent! (1,353 reviews)
"Nice view to south from our room overlooking the causeway. Enjoyed seeing the planes landing in the evening. Did not use any of the “amenities “. The pool was closed. Would choose another hotel for future stays."

Reviewed on 8 June 2026

The Westin Tampa Bay
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
The price is AU$401 per night from 28 June to 29 June
AU$401
28 June - 29 June
includes taxes & fees
8.2/10 Very Good! (2,681 reviews)
"Ok la limpieza es todos los dias eso si lo q pasa q para el precio deberían de darle ya mantenimiento al hotel tiene cosas como la puerta. Del balcón casi ni habría muy recia y para el precio mínimo el desayuno debería de incluirlo pero por todo lo demás bien una experiencia"

Reviewed on 8 June 2026

Hilton Clearwater Beach Resort & Spa
See all 18,850 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Highland Oaks holiday package cost?
Say yes to new adventures with our Highland Oaks holiday 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 holiday 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 holiday?
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 holiday package is the easiest way to organise 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 holiday 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 holiday package?
You sure can, and we're here to help. You may be able to cancel or change your Highland Oaks holiday 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

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

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Salvador Dali Museum

Salvador Dali Museum

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

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

Activities

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

AU$52
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

AU$50
per adult
94% of travellers recommend
Dolphin Racer Speedboat Adventure
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

AU$63
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.