Westlake Village Vacation Packages

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

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Top Holiday Package Deals in Westlake Village

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 $1,589, price is now CA $1,051 per person
CA $1,051
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (2,333 reviews)
Super bueno y muy cerca de todo

Reviewed on Jun 15, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,872, price is now CA $1,808 per person
CA $1,808
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
No reviews
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Price was CA $3,776, price is now CA $2,551 per person
CA $2,551
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
8.2/10 Very Good! (556 reviews)
Excelente ubicación y 100% recomendado.

Reviewed on May 30, 2026

The Don CeSar

The Don CeSar

4 out of 5
Price was CA $2,041, price is now CA $1,412 per person
CA $1,412
per person
Aug 21 - Aug 26
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,165 reviews)
I have one word, WOW!!! You need to go and experience this amazing place for yourself!!!!!!

Reviewed on Jun 19, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,454, price is now CA $1,704 per person
CA $1,704
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (552 reviews)
The staff was very kind and accommodating. We will definitely look to book again.

Reviewed on Jun 19, 2026

Where to stay in Westlake Village

Find the best Westlake Village areas and neighborhoods for the activities you enjoy most. Learn more about Westlake Village
Pass-a-Grille

Pass-a-Grille

1 out of top 10 points of interest in this area

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

Westlake Village Hotel Deals

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $236 per night from Jul 3 to Jul 4
CA $236
CA $268 total
Jul 3 - Jul 4
includes taxes & fees
8.6/10 Excellent! (1,372 reviews)
"Swimming pool was closed for our stay."

Reviewed on Jun 15, 2026

The Westin Tampa Bay
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $367 per night from Jul 8 to Jul 9
CA $367
CA $471 total
Jul 8 - Jul 9
includes taxes & fees
9.4/10 Exceptional! (3,381 reviews)
"All the staff, front desk, restaurants, pool, housekeeping, etc. were so friendly and welcomely which made the stay wonderful. The hotel is on the beach and we were able to watch the sunset every night."

Reviewed on Jun 19, 2026

Wyndham Grand Clearwater Beach
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $278 per night from Jun 30 to Jul 1
CA $278
CA $370 total
Jun 30 - Jul 1
includes taxes & fees
8.2/10 Very Good! (2,695 reviews)
"Overall the hotel was very nice, the amenities were great, the staff were friendly. Check in was a little rough, but check out was a breeze. Cons: the air conditioner did not work very well, there was mold all over the corner of our room, and everything was incredibly expensive, especially for a ..."

Reviewed on Jun 19, 2026

Hilton Clearwater Beach Resort & Spa
See all 10,756 properties in Westlake Village
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 Westlake Village vacation package cost?
Our Westlake Village packages, which begin at just CA $1,051, are the easiest way to save money. Pick and choose your favorite flights, hotels and rental cars to create your dream trip.
How do I get a cheap travel package to Westlake Village?
You'll save loads of cash if you bundle your car rentals, hotels and flights into a Westlake Village vacation package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 partner airlines and 1,000,000 properties across the world, which means you'll always have plenty of options to choose from. Eager to save even more? Add some exciting activities to your package deal and unlock even more discounts! After all, travel is about more than just getting to your destination.
Where should I stay in Westlake Village?
With loads to discover in Westlake Village, it'd be handy for you to book a hotel near its attractions. Innisbrook Golf Club, Suncoast Primate Sanctuary and Wall Springs Park are some fascinating ones to add to your to-do list.
What are the top hotels in Westlake Village?
Private Pool Near Beaches Palm Harbor is one of Westlake Village's top properties. Book a room here and you'll sleep soundly knowing you're in excellent hands.
How far in advance should I book my Westlake Village vacation?
Browse Expedia to compare flights as soon as you know your travel dates. You can generally purchase a seat up to a year before departure. If it's too early for your preferred air carrier, or you've left things to the last minute, don't worry. Low prices to Westlake Village sometimes occur within weeks of the date of departure.
What does an Expedia Westlake Village travel package include?
It all boils down to what kind of escape you're planning. Westlake Village vacation deals can include hotels, car rentals and flights. You can mix and match to find the package that suits your budget and style. You can also add on experiences and activities after you've booked to get even bigger discounts.
What should I know before booking a Westlake Village travel package?
A travel package can be customized for your circumstances and is a great way to stretch your hard-earned dollars. What you include is your call. Hotels, rental cars and flights — decide on a combination that suits your style.
Can I choose my airline with a Westlake Village Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you definitely can. Simply pick the carrier that suits you and create the perfect Westlake Village trip.
If I'm not able to travel, can I cancel my Westlake Village vacation package?
Yes, you can. We understand that things don't always go to plan, so we're happy to help if you need to make changes to your Westlake Village vacation package. You may be able to change or cancel your itinerary at no cost if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Westlake Village

A coastal cityscape with a prominent waterfront, a bridge, and a distinctive building with a red facade.

John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
Aerial sunset view of Clearwater beach and Sand key in Western Florida on the Mexican Gulf coast with vacation homes, hotels and bridges connecting

Clearwater Beach

Nothing says vacation like spending a carefree day at Clearwater Beach, a popular beach in Clearwater Beach. Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Fort De Soto Park

Fort De Soto Park

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $51
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

CA $62
per adult
94% of travellers recommend
Pirate Adventure Cruise - John's Pass
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.