Highland Oaks Vacations from $655
Book a Hotel + Flight or Car together to unlock savings
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 $1,060, price is now $655 per person
$655
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
It was nice to have a gym available and it was always empty. Shower was my favorite park, really big and open, bed was super comfy. The elevators were outnof order though and the coffee machine in the room didnt work, but over all it was a pretty nice hotel. One of the nicest ive been too.
Reviewed on Oct 4, 2025
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $2,296, price is now $1,310 per person
$1,310
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
The place is great, excellent location, close to many outdoor activities, amazing ocean view, staff is very good and attentive to our needs, hotel is clean, parking very convenient, rooms are very nice, clean and confortable.
We’ll definitely come back and recommend Ocean Club.
Reviewed on Oct 13, 2025
The Avalon Club
Save 100% on your flight
Price was $2,638, price is now $1,634 per person
$1,634
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Resort and room were very clean. On the beach a huge bonus. Staff extremely friendly. Downsides: The phrase "Total includes taxes and fees" is not correct. Was hit with a resort and parking fee after booking. Unacceptable. Include them in final price or show "additional fees" prior to booking. Rooftop bar closes too early. Fitness center closes too early. Photo on website shows beautiful Adirondack chairs but resort gave out used/dirty beach chairs. Free towels were also quite harsh. Glad we brought our own.
Bottom line - would stay here again but only when "added fees" are removed.
Reviewed on Oct 13, 2025
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
Price was $1,079, price is now $709 per person
$709
per person
Jan 6 - Jan 12
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (2,173 reviews)
Clean, centrally located, excellent customer service.
Reviewed on Oct 5, 2025
Innisbrook Resort
Save 100% on your flight
Price was $2,137, price is now $1,418 per person
$1,418
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (1,003 reviews)
Staff are wonderful. Rooms and the buildings are a little outdated but still clean. Overall a wonderful experience.
Reviewed on Oct 8, 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
$127 nightly
The price is $144 total per night from Nov 2 to Nov 3
$144 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,039 reviews)
"Great place to stay for an event at the stadium."
Reviewed on Oct 13, 2025
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $242 total per night from Oct 21 to Oct 22
$242 total
Oct 21 - Oct 22
Total with taxes and fees
8/10 Very Good! (2,246 reviews)
"Right on the beach with excellent amenities"
Reviewed on Oct 11, 2025
Hotel Alba, Tapestry Collection by Hilton
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $167 total per night from Oct 26 to Oct 27
$167 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (2,262 reviews)
"Rooms were clean. Staff was friendly and hotel is just a great place to stay."
Reviewed on Oct 12, 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 top-notch restaurants.
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
Sunset Celebration Cruise on Tropics Boat Tours
$37
per adult
88% of travellers recommend
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.