Highlands Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Highlands
Price found within the past 48 hours. Click for updated prices.
The Fold Hotels Indian Shores
CA $1,452
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,018 reviews)
Such a nice place! Walking distance to the beach. The staff are very friendly and responsive. Our room was very clean and modern. Great stay!!
Reviewed on Sep 10, 2026
Cedar Cove Resort and Cottages
CA $2,557
per person
Nov 10 - Nov 17
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9.2/10 Wonderful! (604 reviews)
So clean and anything at all that we needed the staff was more than willing to do great experience
Reviewed on Oct 4, 2026
Where to stay in Highlands
Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Bayonet Point
1 out of top 10 points of interest in this area
Shopping, waterfront views, and restaurants highlight some of the notable features of Bayonet Point. Make a stop by Beacon Woods Golf Course while you're exploring.
Gulf Shores
Gulf Shores might not have many top sights, but Hudson Beach and Show Palace Dinner Theater are two attractions nearby that you can check out.
Hudson Beach Estates
1 out of top 10 points of interest in this area
Though Hudson Beach Estates might not have many top sights, you can venture to the surrounding area to see attractions like Hudson Beach and Show Palace Dinner Theater.
Sea Ranch
While Sea Ranch isn't home to many top sights, Hudson Beach and Show Palace Dinner Theater are some notable places to visit nearby.
Signal Cove
When in Signal Cove, you can plan a visit to Hudson Beach and Beacon Woods Golf Course, some noteworthy sights in the nearby area.
Highlands Hotel Deals
La Vista Inn
11736 US HIGHWAY 19 Port Richey FL
Fully refundableReserve now, pay when you stay
CA $68
CA $76 total
Nov 5 - Nov 6
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 $84 total
Oct 13 - Oct 14
includes taxes & fees
Quality Inn & Suites Tarpon Springs South
38724 US Highway 19 North Tarpon Springs FL
Fully refundable
CA $114
CA $129 total
Oct 14 - Oct 15
includes taxes & fees
8/10 Very good! (1,137 reviews)
"The rooms are nice and spacious very clean will stay every trip"
Reviewed on Oct 3, 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
How much does a Highlands vacation package cost?
Our Highlands packages, which start from as low as CA $1,452, are the best way to save big bucks. Choose your favorite hotels, flights and more to create a personalized escape.
How do I get a cheap travel package to Highlands?
Bundle your flights and hotels with Expedia to save big on your next big adventure. With more than 550 airlines and 1,000,000 hotels throughout the world, your Highlands vacation package can be customized exactly to suit your travel style. With all that extra cash, why not throw in a few exciting activities and tours? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Highlands is much closer than you thought!
How far in advance should I book my Highlands vacation?
Reserving your flights early with Expedia means one less thing to worry about. Most carriers display prices up to 12 months in advance. This is typically the cheapest time to book. If circumstances have left you booking late, great deals to Highlands are still known to appear just a few weeks before departure.
What does an Expedia Highlands travel package include?
Rental cars, flights and hotels, or any combination of them — the choice is all yours! Whether you're visiting Highlands with the entire family or traveling by yourself, there's a package to match every budget and style. Once you've made your booking, why not add on a couple of activities?
What should I know before booking a Highlands travel package?
We already have low prices. However, you'll enjoy even more savings when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a huge range of choice.
Can I choose my airline with a Highlands Expedia vacation package?
With a vacation package, you're in control. Whether you want to fly to Highlands in coach or first class, simply pick from the available airline options. Expedia has access to more than 550 airline partners throughout the world.
If I'm not able to travel, can I cancel my Highlands vacation package?
If your travel plans in Highlands have changed, it's comforting to know that you can cancel or amend your booking. If you made your booking less than 24 hours ago, you may be able to receive a refund. If your booking is older than that, your hotel, airline or car rental company may charge a fee. To find out more, visit our Customer Service Portal.
Things to do
Clear Kayak Tours in Weeki Wachee
CA $111
per adult
100% of travellers recommend
Audio Guide to New Port Richey's History and Quirky People
CA $10
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.