Highland Oaks Holidays

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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
A beach with people, a city skyline, and a distinctive pink building.

Pass-a-Grille

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

Top hotels in Highland Oaks

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 Rp4.556.952 per night from 2 Aug to 3 Aug
Rp4.556.952
Rp5.858.196 total
2 Aug - 3 Aug
includes taxes & fees
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 Rp2.630.444 per night from 2 Aug to 3 Aug
Rp2.630.444
Rp2.985.555 total
2 Aug - 3 Aug
includes taxes & fees
8.6/10 Excellent! (1,441 reviews)
"The breakfast could've been better for the price"

Reviewed on 20 Jul 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 Rp3.494.953 per night from 2 Aug to 3 Aug
Rp3.494.953
Rp4.658.074 total
2 Aug - 3 Aug
includes taxes & fees
8.2/10 Very good! (2,826 reviews)
"Oceanfront location was wonderful. Rooms were clean and comfortable. All of the staff from housekeeping to valet were terrific. Check in and check out was not great. Checked in and had to wait about 40 minutes. When they text that room was ready had to stand in line again instead of being helped ..."

Reviewed on 20 Jul 2026

Hilton Clearwater Beach Resort & Spa
See all 18,999 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 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.

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

Rp663.462
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

Starlite Infinity Evening Yacht Cruise Clearwater

Rp655.337
per adult
90% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

Rp1.190.660
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
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.