Shady Hills Vacation Packages

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Your Shady Hills Vacation

Organizing your next break is a cinch with a Shady Hills vacation package. The neighborhood of Heritage Pines, which is good for golfing, makes a terrific base to discover the delights of this unique city. If seeing the sights is a must during your trip to Shady Hills, make sure you find your way to leading attractions like Nature Coast Botanical Gardens and Strong Tower Vineyard. Whoever you're taking time off with and whether your budget is big or small, your dream Shady Hills vacation is just a few clicks away with Expedia.

Top Holiday Package Deals in Shady Hills

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,579, price is now CA $979 per person
CA $979
per person
Jan 10 - Jan 16
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (2,471 reviews)
Property had a grateful kitchen with just enough utensils, frying pans things that you would need if you prepare your own food during your stay. The property does not have a lot of amenities, but if you’re not into amenities, it doesn’t matter. It’s in a great location central to all things Sarasota and Siesta key.

Reviewed on Oct 29, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,258, price is now CA $1,333 per person
CA $1,333
per person
Dec 14 - Dec 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)
Everything about the resort is great! I highly recommend to people considering a stay there.

Reviewed on Oct 31, 2026

CW Resort

CW Resort

4 out of 5
Price was CA $2,294, price is now CA $1,384 per person
CA $1,384
per person
Jan 8 - Jan 15
found 1 hour ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
9.4/10 Exceptional! (255 reviews)

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $2,136, price is now CA $1,390 per person
CA $1,390
per person
Jan 7 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9.6/10 Exceptional! (1,532 reviews)
Overall great place to stay

Reviewed on Nov 1, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was CA $2,740, price is now CA $1,797 per person
CA $1,797
per person
Jan 10 - Jan 16
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (614 reviews)

Where to stay in Shady Hills

Find the best Shady Hills areas and neighborhoods for the activities you enjoy most. Learn more about Shady Hills
A field with tall grasses and a line of palm trees under a clear sky.

Weeki Wachee

1 out of top 10 points of interest in this area

Unique features of Weeki Wachee include the shopping and restaurants. Make a stop by Weeki Wachee Springs or Weeki Wachee Springs State Park while you're exploring the area.

Find hotels in Weeki Wachee

Shady Hills Hotel Deals

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
5700 Saddlebrook Way Wesley Chapel FL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 29 to Nov 30
CA $162
CA $225 total
Nov 29 - Nov 30
includes taxes & fees
Saddlebrook Resort
La Vista Inn

La Vista Inn

2 out of 5
11736 US HIGHWAY 19 Port Richey FL
Fully refundableReserve now, pay when you stay
The price is CA $81 per night from Dec 1 to Dec 2
CA $81
CA $91 total
Dec 1 - Dec 2
includes taxes & fees
La Vista Inn
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 $74 per night from Nov 2 to Nov 3
CA $74
CA $82 total
Nov 2 - Nov 3
includes taxes & fees
Motel 6 Spring Hill, FL - Weeki Wachee
See all 2,550 properties in Shady Hills
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 Shady Hills vacation package cost?
The most affordable Shady Hills vacation package is CA $979, so your dream escape can become a reality — without the high price tag. Combine flights, hotels, car rentals and more to custom build a package that matches your traveling style.
How do I get a cheap travel package to Shady Hills?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all covered. Select the combination that best fits you and see your savings stack up. Of course, a travel package is never a one-size-fits-all. That's why we offer more than 550 air carriers and 1,000,000 hotel options throughout the world, which lets you customize your Shady Hills vacation.
Where should I stay in Shady Hills?
A vacation in Shady Hills wouldn't be complete without visiting Strong Tower Vineyard, Bayfront Health Spring Hill and Adventure Coast Fun Park. Stay near these top sights and make sightseeing simple.
What are the top hotels in Shady Hills?
Get your vacation off to a great start by booking a room at Unique Vacation Rv Living, Usd70 Per Nights. It's one of most popular properties in Shady Hills. Another welcoming option is Little Taste Of Country Living.
How far in advance should I book my Shady Hills vacation?
It can be difficult to know exactly when is the ideal time to book your Shady Hills trip. But typically the earlier you book, the lower the prices. In some cases, you can reserve your flights and hotels up to 12 months before departure. If you're thinking of a last-minute getaway, no need to fret! There are fantastic deals featured on Expedia every day.
What does an Expedia Shady Hills travel package include?
Expedia has everything you need to lock in Shady Hills trip, but what your package looks like is up to you. Pick from a combination of flights, hotels and rental cars. Looking for a few activities to keep you on the move? Once you've made your booking, you can add them on too. No matter your style or budget, there's a package deal to suit your needs.
What should I know before booking a Shady Hills travel package?
So many places to venture to, so many things to experience. With a package, you'll be able to cross more of them off your list. Bundle your flights, rental cars and hotels and enjoy big savings.
Can I choose my airline with a Shady Hills Expedia vacation package?
You can, and with more than 550 airlines to pick from worldwide, it's all about choice. Look through the available options and find out which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Shady Hills vacation package?
Yes, you can cancel your Shady Hills booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Stay near popular Shady Hills attractions

Strong Tower Vineyard

7.8/10 (40 reviews)
You can enjoy a tasting or tour at Strong Tower Vineyard during your travels to Spring Hill. While in this family-friendly area, you can savor the top-notch restaurants.
See properties

Things to do

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

CA $112
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
90-Minute Guided Eco Airboat Tour in Homosassa

90-Minute Guided Eco Airboat Tour in Homosassa

CA $133
per adult
90-Minute Guided Eco Airboat Tour in Homosassa
Fast & More Airboat Tour

Fast & More Airboat Tour

CA $101
per adult
80% of travellers recommend
Fast & More Airboat Tour
See all activities in Spring Hill
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.