Gulf Highlands Vacation Packages
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Top Holiday Package Deals in Gulf Highlands
Price found within the past 48 hours. Click for updated prices.
Westwinds Waterfront Resort
CA $1,084
per person
Nov 26 - Dec 3
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (737 reviews)
Excellent time at this property. Only thing I wish was a little bit later checkout time as our flight wasn’t until 9pm at night and we had to be out by 10am. I understand it was most likely due to cleaning for incoming guest so we made it work. Overall I would definitely stay at this property again if we ever returned to Clearwater.
Reviewed on Oct 15, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
CA $1,738
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
Very clean place, great staff but had bathroom issues which they will fix! But overall good.
Reviewed on Oct 16, 2026
Sunrise Garden Resort
CA $2,203
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
4/10 (2 reviews)
The hotel was conveniently located near the beach and restaurants. The interior and exterior were immaculately clean, and the pool was a lovely feature. It was a peaceful and relaxing getaway.
Reviewed on Oct 15, 2026
Where to stay in Gulf Highlands
Find the best Gulf Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Gulf Highlands
Jasmine Estates
While Jasmine Estates isn't home to many top sights, Gulf View Square and Regal Hollywood - Port Richey are some notable places to visit nearby.
Embassy Hills
Embassy Hills might not have many top sights, but Gulf View Square and Regal Hollywood - Port Richey are two attractions nearby that you can check out.
Marthas Vineyard
Though Marthas Vineyard might not have many top sights, you can venture to the surrounding area to see attractions like Gulf View Square and Werner Boyce Salt Springs State Park.
Regency Park
If you're looking for some top things to see and do in Regency Park and surrounding area, you can visit Gulf View Square and Regal Hollywood - Port Richey.
Jasmine Lakes
While Jasmine Lakes isn't home to many top sights, Regal Hollywood - Port Richey and Gulf View Square are some notable places to visit nearby.
Gulf Highlands Hotel Deals
La Vista Inn
11736 US HIGHWAY 19 Port Richey FL
Fully refundableReserve now, pay when you stay
CA $89
CA $100 total
Oct 22 - Oct 23
includes taxes & fees
Motel 6 Spring Hill, FL - Weeki Wachee
6172 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
CA $75
CA $83 total
Oct 22 - Oct 23
includes taxes & fees
7.4/10 Good! (1,593 reviews)
"We had a really big room, but did not have a microwave or a fridge inside which we thought it was really weird. I think the thing that bothered us the most we had roaches as soon as you put on the lights, you saw three roaches in the bathroom one walking over the TV it’s a really nice big place. ..."
Reviewed on Oct 16, 2026
Quality Inn & Suites Tarpon Springs South
38724 US Highway 19 North Tarpon Springs FL
Fully refundable
CA $113
CA $128 total
Oct 25 - Oct 26
includes taxes & fees
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 Gulf Highlands vacation package cost?
Perhaps less than you imagined — from only CA $953, actually! By bundling hotels, flights and car rentals into a customized package, your trip to Gulf Highlands is just a few clicks away.
How do I get a cheap travel package to Gulf Highlands?
You'll save loads of cash if you bundle your hotels, car rentals and flights into a Gulf Highlands vacation package. Sometimes cheap means fewer options. But not with Expedia. We offer over 550 partner airlines and 1,000,000 properties throughout the world, so you'll always have plenty of options to choose from. Want to save even more? Add some fun activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
Where should I stay in Gulf Highlands?
With popular attractions such as Werner Boyce Salt Springs State Park and Gulf View Square in this area, look for a hotel located near either one. Beacon Woods Golf Course is another sight in Gulf Highlands that travelers flock to.
How far in advance should I book my Gulf Highlands vacation?
It depends on the air carrier, but it's usually possible to look up international airfares on Expedia nearly a year in advance. While it's advisable to book ahead of time, lucky customers occasionally score a cheaper flight just weeks prior to the date of departure.
What does an Expedia Gulf Highlands travel package include?
Hotels, flights and rental cars, or any combination of the three — it's your pick! Whether you're headed to Gulf Highlands with the entire family or enjoying a solo break, there's a package to match every style and budget. Once you've made your booking, why not add on one or two tours and experiences?
What should I know before booking a Gulf Highlands travel package?
Get set to save with an Expedia travel package. Bundle your airfares, rental cars and hotels and unlock fantastic discounts. You're not restricted to hotels, however. We have beachside condos, city apartments and even houseboats and castles!
Can I choose my airline with a Gulf Highlands Expedia vacation package?
You can, and with over 550 airlines to choose from worldwide, you're spoiled for choice. Scroll through the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Gulf Highlands vacation package?
If your travel plans in Gulf Highlands have changed, it's a relief to know that it is possible to cancel or amend your booking. If you booked in the last 24 hours, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a cancellation fee. To learn more, check our Customer Service Portal.
Things to do
Tarpon Springs: Evening Dolphin Cruise
CA $40
per adult
100% of travellers recommend
Tarpon Springs Ghost Tour: Haunted History & True Crime
CA $56
per adult
2 Hours Kayak Eco Tour in Tarpon Springs
CA $76
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.