Highlands Vacation Packages

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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Clearwater Suites

Clearwater Suites

2.5 out of 5
Price was CA $1,188, price is now CA $727 per person
CA $727
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (23 reviews)
I love the convenient location and a nice staff I'll be excited when the upgrades are done I can't wait to return in November

Reviewed on Sep 10, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $2,460, price is now CA $1,257 per person
CA $1,257
per person
Oct 25 - Nov 1
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,058 reviews)
Hands down one of the best hotels I’ve ever stayed at. Not only is it in a gorgeous location but the suite was incredible, the wine that was waiting for us in our room was phenomenal and the amenities were wonderful. They offer bikes for free as part of your stay, and me and my daughter biked all around the island it was such a good day ☀️. Would absolutely recommend this place to anybody. Perfect for couples but also very family friendly too. Will be staying here again!!

Reviewed on Sep 7, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was CA $2,229, price is now CA $1,206 per person
CA $1,206
per person
Oct 25 - Nov 1
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (618 reviews)
We were very pleased with our 3 night stay at the hotel. The staff graciously offered us an umbrella and chairs to take to the beach from the donation stash. We really appreciated that and returned the items when we left for future guests.

Reviewed on Sep 8, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,656, price is now CA $1,437 per person
CA $1,437
per person
Oct 25 - Nov 1
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (446 reviews)
My stay at the Avalon was great! The staff was really nice and always asked if we needed anything. The room was so nice! It had everything we needed for our stay. Pots, pans, silverware, cup, plates everything. I will definitely be staying here again on my next visit to Clearwater.

Reviewed on Sep 10, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was CA $1,871, price is now CA $1,118 per person
CA $1,118
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,017 reviews)
Loved it Voco hotel was great clean and quiet great place to just sit back and relax place was not busy at all kids are all back in school thank god . Beach’s all near by 10 to 20 minute drive to any beach u wana go too.

Reviewed on Sep 2, 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 $56 per night from Sep 17 to Sep 18
CA $56
CA $62 total
Sep 17 - Sep 18
includes taxes & fees
7.2/10 Good! (1,172 reviews)
"The staff is wonderful here. Rooms are very clean and well taken care of. Conviently located close to shopping . Directly across from Bucaneer Bay and only minutes to the beach. We loved our stay here. Definitely a great experience."

Reviewed on Sep. 4, 2025

Motel 6 Spring Hill, FL - Weeki Wachee
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! (291 reviews)
"Wife, daughter and I had a wonderful experience. Kayaks were easy to get into the water and the water was great."

Reviewed on Aug. 24, 2025

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

Innisbrook Resort

3.5 out of 5
36750 Us Highway 19 N, Palm Harbor, FL
The price is CA $220 per night from Sep 13 to Sep 14
CA $220
CA $311 total
Sep 13 - Sep 14
includes taxes & fees
8.2/10 Very Good! (976 reviews)
"Great spot for holidays when they have their pool parties."

Reviewed on Sep. 2, 2025

Innisbrook Resort
See all 1,619 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 $727, 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.