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
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Pass-a-Grille

5/5(3 area reviews)

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

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 €215 per night from 28 Jul to 29 Jul
€215
28 Jul - 29 Jul
includes taxes & fees
8/10 Very Good! (2,030 reviews)
"Its location. Right on the beach and near shops and restaurants"

Reviewed on 20 Jul 2025

Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is €124 per night from 5 Aug to 6 Aug
€124
5 Aug - 6 Aug
includes taxes & fees
8.6/10 Excellent! (1,997 reviews)
"It was a nice hotel the pool was bery nice and clean but the elevator wasnt working needed to use the stairs so carrying luggage down was hard"

Reviewed on 19 Jul 2025

Hotel Alba, Tapestry Collection by Hilton
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 €301 per night from 10 Aug to 11 Aug
€301
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (2,395 reviews)
"Wonderful staff!"

Reviewed on 19 Jul 2025

Wyndham Grand Clearwater Beach
See all 17,647 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.

Popular places to visit

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4/5(33 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 visit its lively bars.

John's Pass Village & Boardwalk
Fort De Soto Park featuring a beach

Fort De Soto Park

4.5/5(25 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
Salvador Dali Museum showing modern architecture and night scenes

Salvador Dali Museum

5/5(20 reviews)

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

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

€27
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

€31
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
Sea Screamer boat in Orlando

Day Trip to Clearwater Beach with Sea Screamer Ride

€106
per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
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.