Highlands Vacation Packages

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
The Don CeSar

The Don CeSar

4 out of 5
Price was CA $2,038, price is now CA $1,407 per person
CA $1,407
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,173 reviews)
I have one word, WOW!!! You need to go and experience this amazing place for yourself!!!!!!

Reviewed on Jun 19, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,698, price is now CA $1,601 per person
CA $1,601
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,647, price is now CA $1,681 per person
CA $1,681
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (526 reviews)
Beautiful facility. Perfect for families close to all the beaches and fun. Can't wait to return for our next visit!

Reviewed on Jun 18, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,930, price is now CA $1,948 per person
CA $1,948
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (552 reviews)
The staff was very kind and accommodating. We will definitely look to book again.

Reviewed on Jun 19, 2026

The Marker

The Marker

2 out of 5
Price was CA $3,512, price is now CA $2,392 per person
CA $2,392
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
6/10 (3 reviews)
There was no staff due to it being brand new! The owner Jeff was great and very polite and went out of his way to make us feel welcome and valued! It was very quiet and comfortable for my family. Only about a two block walk to the beach but being in the bay was beautiful to wake up to!

Reviewed on Apr 12, 2026

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Pirate ship at St Andrews State Park

Gulf Shores

Gulf Shores might not have many top sights, but Hudson Beach and Cow Creek are two attractions nearby that you can check out.

Find hotels in Gulf Shores

Highlands Hotel Deals

Motel 6 Spring Hill, FL - Weeki Wachee

Motel 6 Spring Hill, FL - Weeki Wachee

2 out of 5
6172 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
The price is CA $81 per night from Jun 25 to Jun 26
CA $81
CA $90 total
Jun 25 - Jun 26
includes taxes & fees
7.2/10 Good! (1,525 reviews)
"The room was just dirty and run down, the grounds were not kept up well, and the staff was odd"

Reviewed on Jun 20, 2026

Motel 6 Spring Hill, FL - Weeki Wachee
Quality Inn & Suites Tarpon Springs South

Quality Inn & Suites Tarpon Springs South

2.5 out of 5
38724 US Highway 19 North Tarpon Springs FL
Fully refundable
The price is CA $120 per night from Jun 24 to Jun 25
CA $120
CA $135 total
Jun 24 - Jun 25
includes taxes & fees
8/10 Very Good! (1,114 reviews)
"At 230 am. Heard car horn a couple times. Then loud banging on front and back patio door. Right below us . Called front desk. Told them. It still went on for over a half hour. Never heard front desk clerk."

Reviewed on Jun 19, 2026

Quality Inn & Suites Tarpon Springs South
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping

Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping

Spring Hill FL
10/10 Exceptional! (319 reviews)
"Family friendly. Wonderful property. And we saw so many manatees at the house & in the river on the provided kayaks."

Reviewed on Jun 12, 2026

Get rates
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
See all 1,771 properties in Highlands
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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Highlands vacation package cost?
Our Highlands packages, which start from as low as CA $1,407, 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.

Discover the most popular places to visit in Highlands

Hudson Beach

Hudson Beach

Why not spend a carefree afternoon at Hudson Beach during your travels in Hudson? Amble around the area's parks or visit its shops.

Hudson Beach

Beacon Woods Golf Course

Enjoy a round of golf in Hudson at Beacon Woods Golf Course. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Beacon Woods Golf Course

Colorama Music

You can make plans for a show at Colorama Music during your stay in Hudson. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Colorama Music

Things to do

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

CA $125
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
Audio Guide to New Port Richey's History and Quirky People

Audio Guide to New Port Richey's History and Quirky People

CA $10
per adult
Audio Guide to New Port Richey's History and Quirky People
See all activities in Hudson
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.