Highland Oaks Holidays

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The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Beach Park
per person
11 Apr - 15 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Tampa (TPA)
8.8/10 Excellent! (1,346 reviews)
Rooms are fine. The only negative is when your room faces the office building, therefore no privacy in your room.

Reviewed on 13 Feb 2025

The Saint Hotel

The Saint Hotel

2 out of 5
per person
11 Apr - 15 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Tampa (TPA)
9.6/10 Exceptional! (322 reviews)
Good hotel. Location is a little rough especially after the hurricane and the rooms were not as shown in the online pictures so thats why we give them a 4/5

Reviewed on 2 Feb 2025

Crystal Bay Hotel

Crystal Bay Hotel

3 out of 5
La Vista
per person
11 Apr - 15 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Tampa (TPA)
9.6/10 Exceptional! (1,334 reviews)
It was a nice hotel with a great history.

Reviewed on 10 Feb 2025

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
per person
11 Apr - 15 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Tampa (TPA)
8.4/10 Very Good! (1,177 reviews)
Beautiful property, we had the gulf view twin queen. Small room, but functional with surprisingly outfitted galley kitchen. Site had been damaged from hurricanes, but is certainly an older resort. It could use a face lift, and elevators that move faster than snails on tranquilizers.

Reviewed on 12 Feb 2025

Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
per person
11 Apr - 15 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Tampa (TPA)
7.4/10 Good! (1,005 reviews)
Love being on the ocean

Reviewed on 12 Feb 2025

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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Downtown St. Petersburg

1 out of top 10 points of interest in this area

Downtown St. Petersburg is beloved for its fantastic nightlife. Take some time to explore sights in the area like Tampa Bay and Jannus Live.

Find hotels in Downtown St. Petersburg

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 €544 per night from 23 Feb to 24 Feb
€544
includes taxes & fees
23 Feb - 24 Feb
9.2/10 Wonderful! (1,946 reviews)
"This place was fantastic from the food to the service! The pool was great and so was the hot tub. A hop skip and jump and your on the beach! Don’t forget to try a frozen cocktail. I recommend the Clearwater sunset. It’s delicious."

Reviewed on 11 Feb 2025

Wyndham Grand Clearwater Beach
The Barrymore Hotel Tampa Riverwalk
The Barrymore Hotel Tampa Riverwalk
3 out of 5
111 W Fortune St, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is €244 per night from 17 Feb to 18 Feb
€244
includes taxes & fees
17 Feb - 18 Feb
8.2/10 Very Good! (1,864 reviews)
"Nice stay"

Reviewed on 11 Feb 2025

The Barrymore Hotel Tampa Riverwalk
Hyatt Regency Clearwater Beach Resort & Spa
Hyatt Regency Clearwater Beach Resort & Spa
4 out of 5
301 S Gulfview Blvd, Clearwater Beach, FL
The price is €473 per night from 3 Mar to 4 Mar
€473
includes taxes & fees
3 Mar - 4 Mar
9/10 Wonderful! (1,847 reviews)
"Staff Was Excellent! Room was clean. Food was very good!"

Reviewed on 11 Feb 2025

Hyatt Regency Clearwater Beach Resort & Spa
See all 17,196 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 €909. 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 top-notch restaurants.

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

€31
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Shell Key Island bird's eye view

Shell Key Island Excursion -3hrs.and 30min. trip

€61
per adult
80% of travellers recommend
Shell Key Island Excursion -3hrs.and 30min. trip
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

€35
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.