Highland Oaks Vacations from $562
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Your Highland Oaks Vacation
Highland Oaks is calling! Whatever type of getaway you're planning, you can experience and see more of this neighborhood with a Highland Oaks vacation 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 vacation into reality, no matter your travel plans or budget.
The Latest Highland Oaks Vacation Packages
Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $1,157, price is now $616 per person
$616
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,006 reviews)
Voco was an excellent choice for a night away from home. The service was top-notch, with a staff that was truly accommodating. Exceptional location with a shuttle that takes you where ever within 3 miles. I want to give a special shout-out to Rich and Tiffany, who went above and beyond to share their favorite local spots for dining and entertainment. Overall. I enjoyed my stay and highly recommend Voco!
Reviewed on Aug 28, 2025
FUSION Resort Waterfront Suites
Save 100% on your flight
Price was $1,936, price is now $1,034 per person
$1,034
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,053 reviews)
The room was fantastic with a big wrap around balcony. Even though the weather did not cooperate, we all enjoyed chilling on the balcony with many trips to the pool. Beach was great. My only disappointment was they did not have any type of grill anywhere. I brought some really expensive steaks, burgers,hot dogs, which we had to cook in a pan.
The staff was fantastic and made sure we had everything we needed
Reviewed on Aug 24, 2025
The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $1,706, price is now $988 per person
$988
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,061 reviews)
It was very noisy. Inside, toilets, doors & cleaning staff. Outside, basic traffic, green car every night
Reviewed on Aug 29, 2025
Ocean Club Treasure Island Hotel
Save 100% on your flight
Price was $1,143, price is now $685 per person
$685
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (609 reviews)
Not your typical resort. It was like a mini-Condo on the beach. Peacefull and relaxing atmosphere. Walking distance to most everything in the area. It was a great getaway for my wife and me.
Reviewed on Aug 29, 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
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.
Highland Oaks Hotel Deals
Hilton Tampa Airport Westshore
2225 N Lois Ave, Tampa, FL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $127 total per night from Sep 1 to Sep 2
$127 total
Sep 1 - Sep 2
Total with taxes and fees
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $250 total per night from Sep 7 to Sep 8
$250 total
Sep 7 - Sep 8
Total with taxes and fees
Hotel Alba, Tapestry Collection by Hilton
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $155 total per night from Sep 7 to Sep 8
$155 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (2,103 reviews)
"Beautiful hotel… very helpful staff… great food and bar and pool area. Daughter goes to U Tampa and I will definitely be staying here again!"
Reviewed on Aug 27, 2025
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.
Discover the most popular places to visit in Highland Oaks
John's Pass Village & Boardwalk
4.5/5(1,625 reviews)
When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the beautiful beaches in this family-friendly area, or check out its lively bars.
Clearwater Beach
4.5/5(44 reviews)
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.
St. Petersburg - Clearwater Beaches
5/5(5 reviews)
Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?
Things to do
StarLite Majesty Evening Yacht Cruise Clearwater
$32
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
$35
per adult
88% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
$37
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.