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
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Highlands
Price found within the past 48 hours. Click for updated prices.
Where to stay in Highlands
Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Gulf Shores
Gulf Shores might not have many top sights, but Hudson Beach and Beacon Woods Golf Course 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 Gulf View Square.
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.
Sea Ranch
While Sea Ranch isn't home to many top sights, Hudson Beach and Gulf View Square are some notable places to visit nearby.
Gulf Coast Acres
2 out of top 10 points of interest in this area
While visiting Gulf Coast Acres, you might make a stop by sights like Colorama Music and Show Palace Dinner Theater.
Highlands Hotel Deals
Motel 6 Spring Hill, FL - Weeki Wachee
6172 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
CA $74
CA $82 total
Sep 1 - Sep 2
includes taxes & fees
7.2/10 Good! (1,574 reviews)
"Property needs to be cleaned and updated. No microwave, fridge or blow dryer, a/c was not very good and loud."
Reviewed on Aug 14, 2026
Quality Inn & Suites Tarpon Springs South
38724 US Highway 19 North Tarpon Springs FL
Fully refundable
CA $118
CA $133 total
Sep 6 - Sep 7
includes taxes & fees
Innisbrook Resort
36750 Us Highway 19 N Palm Harbor FL
CA $164
CA $256 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"Great property, beautiful and well maintained"
Reviewed on Aug 14, 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 $1,147, 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 $127
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.