Highland Oaks Vacation Packages
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Top Holiday Package Deals in Highland Oaks
Price found within the past 48 hours. Click for updated prices.
Westwinds Waterfront Resort
Price was CA $2,066, price is now CA $1,293 per person
CA $1,293
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (742 reviews)
The views and property alone is amazing. Can see dolphins from full wall of windows. Bedroom windows can see ocean side and sun sets. Pool n grills with many tables to enjoy morning swim, your own cooking or drinking coffee with sunrise. I love treasure island and this is a go to place for me now.
Reviewed on Nov 12, 2026
FUSION Resort Waterfront Suites
Price was CA $2,092, price is now CA $1,310 per person
CA $1,310
per person
Jan 30 - Feb 6
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,266 reviews)
Staff were always helpful when we had questions. The condo was nice with a large balcony looking out across the waterway. The tile floors were dirty and needed to be mopped as your feet were black on the bottom after walking around barefoot for a while in the kitchen and living room areas. The kitchen had a basic set of cookware and dishes. The place was quiet at night, even with a wedding going on one night it did not get very loud and the staff were good about ending the festivities at a decent hour. You can walk to the beach, grocery store, and several restaurants from the place.
Reviewed on Nov 11, 2026
Crystal Palms Beach Resort
Sunshine Beach
Price was CA $2,072, price is now CA $1,323 per person
CA $1,323
per person
Feb 1 - Feb 8
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (2,409 reviews)
It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating
Reviewed on Nov 7, 2026
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
A noteworthy feature of Downtown St. Petersburg is its fantastic nightlife. While you're in town, be sure to stop and check out Tampa Bay and The Coliseum.
Highland Oaks Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $292 per night from Dec 13 to Dec 14
CA $292
CA $386 total
Dec 13 - Dec 14
includes taxes & fees
9.4/10 Exceptional! (4,056 reviews)
"We loved the Wyndham Grand. Staff are very friendly and we managed to get a complimentary upgrade to a gulf view room. Parking and the resort fee are extra. Cabanas on the beach are owned by the city and an extra charge. Be prepared to be asked to join a time share presentation which we declined. ..."
Reviewed on Nov 12, 2026
Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $330 per night from Dec 8 to Dec 9
CA $330
CA $430 total
Dec 8 - Dec 9
includes taxes & fees
9.4/10 Exceptional! (2,489 reviews)
"N/A"
Reviewed on Nov 12, 2026
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
The price is CA $209 per night from Nov 22 to Nov 23
CA $209
CA $237 total
Nov 22 - Nov 23
includes taxes & fees
8.6/10 Excellent! (1,648 reviews)
"Was very disappointed with this stay. We have stayed at Westins before and had great experiences; however, this was not one of those times. The best part of the stay was Zachary at the front desk for check in, he was absolutely lovely and kind. The room itself was nice and clean, but the property ..."
Reviewed on Nov 11, 2026
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
Things to do
Starlite Infinity Evening Yacht Cruise Clearwater
CA $52
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
CA $40
per adult
96% of travellers recommend
Dolphin Racer Speedboat Adventure
CA $51
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.