Highlands Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Southbank Apartments by Landing

Southbank Apartments by Landing

4 out of 5
Downtown Jacksonville
Price was CA $1,363, price is now CA $1,111 per person
CA $1,111
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Jacksonville (JAX)
10/10 Exceptional! (1 review)
The check in process was very confusing but the visa

Reviewed on Apr 4, 2026

Hammock Beach Golf Resort & Spa

Hammock Beach Golf Resort & Spa

4 out of 5
Price was CA $2,950, price is now CA $2,237 per person
CA $2,237
per person
Aug 27 - Sep 3
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Jacksonville (JAX)
8.6/10 Excellent! (1,018 reviews)
Everything was amazing

Reviewed on Jun 19, 2026

The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Price was CA $1,529, price is now CA $1,229 per person
CA $1,229
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Jacksonville (JAX)
8.4/10 Very Good! (1,212 reviews)
The space was immaculate, beautifully renovated, and thoughtfully appointed. We had everything we needed to enjoy our stay comfortably. The beach views were spectacular, and watching both the sunrise and sunset from the property was truly a highlight of our trip. A couple of minor suggestions for improvement: * The barn doors in the primary bathroom did not fully close, which limited privacy when using the restroom. * Providing beach towels (separate from the bath towels) would be a nice addition. We noticed the villa pool did not have towels available either, so we’re not sure if they were intended to be provided. Overall, we had a wonderful stay and would gladly return.

Reviewed on Jun 19, 2026

Landing Apartments near JAX

Landing Apartments near JAX

3.5 out of 5
Northside
Price was CA $1,422, price is now CA $1,149 per person
CA $1,149
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Jacksonville (JAX)
No reviews
Marriott Jacksonville Downtown

Marriott Jacksonville Downtown

4 out of 5
Downtown Jacksonville
Price was CA $1,700, price is now CA $1,403 per person
CA $1,403
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Jacksonville (JAX)
8.4/10 Very Good! (1,007 reviews)
Generally convenient location. Drainage issues in bathroom Bed uncomfortably low

Reviewed on Jun 20, 2026

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
A coastal town at dusk with a prominent clock tower, waterfront, and illuminated buildings.

Amelia City

While visiting Amelia City, you might make a stop by sights like American Beach and Fernandina Beach.

Find hotels in Amelia City

Highlands Hotel Deals

Margaritaville Jacksonville Beach

Margaritaville Jacksonville Beach

2.5 out of 5
715 1st St N Jacksonville Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $237 per night from Jun 24 to Jun 25
CA $237
CA $269 total
Jun 24 - Jun 25
includes taxes & fees
9/10 Wonderful! (4,058 reviews)
"Great location nice beach vibes easy to walk to"

Reviewed on Jun 21, 2026

Margaritaville Jacksonville Beach
Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
225 E Coastline Dr Jacksonville FL
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Jul 2 to Jul 3
CA $255
CA $292 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (1,656 reviews)
"Very pleasant hotel. Love the Morton’s and the bar there."

Reviewed on Jun 19, 2026

Hyatt Regency Jacksonville
Wyndham Garden Jacksonville

Wyndham Garden Jacksonville

3 out of 5
4660 Salisbury Road Jacksonville FL
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Jul 5 to Jul 6
CA $111
CA $126 total
Jul 5 - Jul 6
includes taxes & fees
8/10 Very Good! (1,917 reviews)
"Unfortunately, our experience was very disappointing. During our stay we encountered multiple cockroaches in the room, including inside the dresser drawers where our family’s clothing was stored. Traveling with a 16-month-old and a 6-year-old, we ended up staying awake until around 2:00 AM dealing ..."

Reviewed on Jun 21, 2026

Wyndham Garden Jacksonville
See all 3,947 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Highlands vacation package cost?
From just CA $1,111. Yes, you read that correctly. Our Highlands packages are an easy way to make your budget last longer. Combine your favorite hotels, flights and car rentals and get out and see this lively destination.
How do I get a cheap travel package to Highlands?
You'll save a pile of money if you combine your car rentals, flights and hotels into a Highlands vacation package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer more than 550 airlines and 1,000,000 hotels all over the world, which means you'll always have plenty of options to choose from. Eager to save even more? Add some interesting activities to your package deal to unlock even bigger bargains! After all, travel is about more than just getting to your destination.
Where should I stay in Highlands?
Visitors come from all over to see Cummer Museum of Art and Gardens and Jacksonville Museum of Modern Art in Highlands. Book a hotel within a stone's throw of these wonderful attractions and visit them at your leisure.
What are the top hotels in Highlands?
If it's your first time staying in Highlands, reserve a room at Red Roof Inn Jacksonville - Cruise Port or Stayable Suites Jacksonville North. Both offer friendly service and are popular options with many savvy travelers.
How far in advance should I book my Highlands vacation?
While not all airlines advertise ticket prices early, you can normally look up international airfares on Expedia up to a year in advance. This is the time when you'll nab some incredible deals. If you're booking last minute, you could still be in luck. Sometimes the cheapest prices emerge a few weeks before departure.
What does an Expedia Highlands travel package include?
You can select from any combination of hotels, flights and rental cars. Once you've made your booking, you can also add on activities and tours. Want to pick your fare class? That's also easy to do. The choice is yours when it comes to putting together your dream Highlands getaway.
What should I know before booking a Highlands travel package?
Bundling your bookings into a Highlands vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Highlands Expedia vacation package?
With a vacation package, you're in control. Whether you'd like to fly to Highlands in economy or first class, simply choose from the available airline options. Expedia has access to over 550 airline partners across the world.
If I'm not able to travel, can I cancel my Highlands vacation package?
We get that sometimes life doesn't go according to plan. If you've locked in a Highlands vacation package and have to cancel or change it, we're here to help. It's always worth having a look at our Customer Service Portal first for information. But in general, if you've taken out your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's more than 24 hours, your hotel, airline or car rental company may impose a charge.

Discover the most popular places to visit in Highlands

Big Talbot Island State Park

Big Talbot Island State Park

4/5(2 reviews)

Go wildlife spotting and admire great views across marshes and the Atlantic Ocean in this nature reserve on the east coast of Florida.

Big Talbot Island State Park
EverBank Stadium

EverBank Stadium

4.5/5(8 reviews)

Capable of seating over 80,000 fans, this modern football stadium is the exciting home of the Jacksonville Jaguars, international soccer games and music events.

EverBank Stadium
Jacksonville Zoo and Gardens

Jacksonville Zoo and Gardens

5/5(4 reviews)

Admire thousands of animals and plants across entertaining exhibits in this family-friendly zoo that also has a children’s play area and a 4-D experience.

Jacksonville Zoo and Gardens

Things to do

St. Augustine: St. Johns River Airboat Safari with a Guide

St. Augustine: St. Johns River Airboat Safari with a Guide

CA $72
per adult
100% of travellers recommend
St. Augustine: St. Johns River Airboat Safari with a Guide
Gummy Making Class

Gummy Making Class

CA $28
per traveller
Gummy Making Class
CraigCat Boat Tour from Fernandina Beach

CraigCat Boat Tour from Fernandina Beach

CA $201
per adult
98% of travellers recommend
CraigCat Boat Tour from Fernandina Beach
See all activities in Jacksonville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.