Highlands Vacation Packages

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (4,228 reviews)
The staff was amazing

Reviewed on Aug. 5, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.2/10 Wonderful! (1,000 reviews)
The air conditioner made a lot of noise I was unable to sleep well.

Reviewed on Aug. 3, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (557 reviews)
Everything was great. Beautiful view from our room. Surer clean. For sure will stay again.

Reviewed on Aug. 4, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,046 reviews)
Everything is great. Lacking food on the property and roof top bar doesn’t exist anymore

Reviewed on Aug. 1, 2025

Clearwater Suites

Clearwater Suites

2.5 out of 5
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.4/10 Very Good! (9 reviews)
Very conveniently located. Great room size and comfortable bed.

Reviewed on Aug. 5, 2025

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
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Bayonet Point

1 out of top 10 points of interest in this area
3.5/5(5 area reviews)

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.

Find hotels in Bayonet Point

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 $62 per night from Aug 13 to Aug 14
CA $62
CA $69 total
Aug 13 - Aug 14
includes taxes & fees
7.2/10 Good! (1,121 reviews)
"We hated the fact that they closed the pool at 8pm considering we just wanted to swim and our reservation got messed up at the first place so hotels.com put us up in a different one and paid the difference but by the time we got there they were closing the pool. Hotels.com said it closed at 10 so ..."

Reviewed on Aug. 4, 2025

Motel 6 Spring Hill, FL - Weeki Wachee
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
36750 Us Highway 19 N, Palm Harbor, FL
The price is CA $232 per night from Aug 8 to Aug 9
CA $232
CA $325 total
Aug 8 - Aug 9
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Excellent and beautiful stay!!!!"

Reviewed on Aug. 6, 2025

Innisbrook Resort
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
9.8/10 Exceptional! (287 reviews)
"Everything was perfect about this stay! The kitchen is well stocked for cooking and entertaining. Dogs allowed."

Reviewed on Aug. 3, 2025

Get rates
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
See all 1,595 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.
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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 $415, 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

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.