Highland Oaks Vacations

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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
Downtown St. Petersburg

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.

Find hotels in Downtown St. Petersburg

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 NT$11,329 per night from May 10 to May 11
NT$11,329
NT$14,060 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (3,148 reviews)
The place is beautiful, the hot tub is way too crowded. But the location of the hotel is perfect, and the place was spotless , my family and I loved our stay and are looking to come back

Reviewed on 2026/4/11

Wyndham Grand Clearwater Beach
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is NT$4,838 per night from May 11 to May 12
NT$4,838
NT$7,445 total
May 11 - May 12
includes taxes & fees
8.2/10 Very Good! (1,787 reviews)
The rooms are not updated, but are very clean. The staff were very friendly and helpful. The transportation around the area is free if you stay at Tradewinds. That saved us a lot in transportation costs for the week. The restaurants were all very good and tasty.

Reviewed on 2026/4/11

RumFish Beach at TradeWinds
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
200 N Ashley Dr Tampa FL
The price is NT$4,653 per night from May 3 to May 4
NT$4,653
NT$5,336 total
May 3 - May 4
includes taxes & fees
7/10 Good! (1,833 reviews)
Not what I expected for almost $300 a night Staff was friendly but couldn’t get a straight answer out of anyone regarding where/what we could use our $30/day credit on. The “restaurant” was open limited hours breakfast was premade items heated up in an air fryer, no ice machine on any floor. Room ...

Reviewed on 2026/4/11

Hotel Tampa Riverwalk
See all 18,805 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 vacation package cost?
Say yes to new adventures with our Highland Oaks vacation 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 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.

Discover the most popular places to visit in Highland Oaks

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the marina in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.