Westside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Westside Vacation

A great way to experience this city is with a customized Westside vacation package. Stay in the neighborhood of Murray Hill, which is great for distilleries and craft breweries, bars and pubs and dining or go someplace else — our package deals are all about you. Jacksonville Equestrian Center, Crystal Springs Park and Bent Creek Golf Course are just a few of the many sights you'll want to check out during your trip to Westside. Browse Expedia's wide range of travel options and start planning your ultimate vacation to Westside now.

Top Holiday Package Deals in Westside

Price found within the past 48 hours. Click for updated prices.
Southbank Apartments by Landing

Southbank Apartments by Landing

Downtown Jacksonville
CA $1,314
per person
Dec 4 - Dec 11
found 24 hours ago
Roundtrip flight included
Calgary (YYC) to Jacksonville (JAX)
10/10 Exceptional! (2 reviews)
The Villas of Amelia Island

The Villas of Amelia Island

CA $1,414
per person
Dec 4 - Dec 11
found 24 hours ago
Roundtrip flight included
Calgary (YYC) to Jacksonville (JAX)
8.4/10 Very good! (1,249 reviews)
Landing Apartments near Downtown Jacksonville

Landing Apartments near Downtown Jacksonville

Downtown Jacksonville
CA $1,576
per person
Dec 4 - Dec 11
found 24 hours ago
Roundtrip flight included
Calgary (YYC) to Jacksonville (JAX)
No reviews
Close to ball. Park. Convenient parking

Reviewed on Sep 3, 2026

Holiday Inn Express & Suites Fleming Island by IHG

Holiday Inn Express & Suites Fleming Island by IHG

CA $1,350
per person
Dec 4 - Dec 11
found 24 hours ago
Roundtrip flight included
Calgary (YYC) to Jacksonville (JAX)
9.2/10 Wonderful! (1,002 reviews)
Made sure we had what we needed towels, trash, etc

Reviewed on Sep 12, 2026

Landing Jacksonville

Landing Jacksonville

Sunbeam
CA $1,416
per person
Dec 4 - Dec 11
found 24 hours ago
Roundtrip flight included
Calgary (YYC) to Jacksonville (JAX)
7/10 Good! (2 reviews)
Room hardwares and cleaness very good, but Landing App did not properly work, not easy to link up with the landlord/agent for check-in/check-out process.

Reviewed on Mar 25, 2026

Where to stay in Westside

Find the best Westside areas and neighborhoods for the activities you enjoy most. Learn more about Westside
A city skyline with modern skyscrapers, a prominent Wells Fargo building, and a blue bridge over a river.

Downtown Jacksonville

2 out of top 10 points of interest in this area

Historic core with major corporations, Downtown Jacksonville offers diverse culinary and nightlife experiences at The Elbow. Explore attractions like Florida Theatre, TIAA Bank Field, and museums, while enjoying convenient transportation options.

A coastal town at dusk with a prominent clock tower, waterfront, and illuminated buildings.

Amelia City

While visiting Amelia City, you might make a stop by sights like American Beach and Fernandina Beach.

A sunset over a beach with waves and a pier.

Oceanfront

1 out of top 10 points of interest in this area

If you're spending some time in Oceanfront, Oceanfront Park and Northeast Florida Beaches are top sights worth seeing.

A river with a bridge, a marina with boats, and a city skyline with high-rise buildings.

Southside

1 out of top 10 points of interest in this area

If you're spending some time in Southside, St. Johns Town Center and Orange Park Place Shopping Center are top sights worth seeing.

A golf course with a pond, trees, and buildings in the background.

Sawgrass

Visitors to Sawgrass like its beaches and riverfront, and Mickler Beach is a sight worth a stop.

Westside Hotel Deals

Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station

Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station

8001 PARRAMORE ROAD Jacksonville FL
Fully refundable
CA $144
CA $164 total
Oct 11 - Oct 12
includes taxes & fees
Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station
StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park

8045 Parramore Road Jacksonville FL
Fully refundableReserve now, pay when you stay
CA $106
CA $121 total
Sep 23 - Sep 24
includes taxes & fees
StudioRes by Marriott Jacksonville Orange Park
Margaritaville Jacksonville Beach

Margaritaville Jacksonville Beach

715 1st St N Jacksonville Beach FL
Fully refundableReserve now, pay when you stay
CA $209
CA $237 total
Oct 11 - Oct 12
includes taxes & fees
Margaritaville Jacksonville Beach
See all 3,186 properties in Westside
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 Westside vacation package cost?
Browse and book everything in one place with our Westside vacation packages, which start from a low CA $1,314. Pick the flights and hotels that suit your plans. Then, add on one or two tours or activities for a one-of-a-kind adventure.
How do I get a cheap travel package to Westside?
Browse and lock in everything in the one place with our Westside vacation packages. We have deals on flights, hotels, tours and more that'll keep your travel budget happy and your sense of adventure alive. And, with more than 550 airlines and 1,000,000 hotels all over the world to choose from, you'll have endless opportunities to mix and match as you want.
Where should I stay in Westside?
Most visitors to Westside include Cummer Museum of Art and Gardens and Jacksonville Museum of Modern Art on their itineraries. Why not go for a hotel as close as possible to these top attractions?
What are the top hotels in Westside?
If it's comfort and convenience you're after, you can't beat Jax Home With Yard - 10 Mi To Adventure Landing. Spend your nights unwinding here and your days wandering around Westside's best sights.
How far in advance should I book my Westside vacation?
It's tricky picking the perfect time for airfares, but we generally suggest the earlier, the better. Most international flights on Expedia become available to compare up to a year in advance. If you're booking last minute, don't stress. Cheap prices occasionally appear within a few weeks of departure dates.
What does an Expedia Westside travel package include?
Expedia has all you need to arrange your Westside trip, but how your package is structured is your choice. Choose from a combination of hotels, flights and rental cars. Looking for some tours or experiences to keep you busy? Once you've made your booking, you can add them too. Whatever your budget or style, there's a deal to meet your needs.
What should I know before booking a Westside travel package?
A travel package can be customized for your circumstances and is a great way to stretch your hard-earned dollars. How little or much you include is totally up to you. Hotels, rental cars and flights — choose any combination that suits your plans.
Can I choose my airline with a Westside Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You're the boss! We have more than 550 airline partners around the world, so you have options galore when arranging your Westside escape.
If I'm not able to travel, can I cancel my Westside vacation package?
If your travel plans in Westside have changed, it's good to know that it is possible to cancel your booking. If your booking was made in the last 24 hours, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may impose fees. For more details, check our Customer Service Portal.

Stay near popular Westside attractions

Jacksonville Equestrian Center

7.6/10 (18 reviews)
You can take time to visit Jacksonville Equestrian Center during your travels to Jacksonville. Attend a sporting event in this family-friendly area.
See properties

Crystal Springs Park

7.4/10 (6 reviews)
After visiting Crystal Springs Park, make a plan to see the other sights and activities in Jacksonville. Experience the acclaimed theater scene or attend a sporting event in this family-friendly area.
See properties

Florida Yacht Club Marina

Explore the waterfront in Jacksonville with a trip to Florida Yacht Club Marina. Amble around this family-friendly area's riverfront or experience its acclaimed theater scene.
See properties

Pope Duval Park

2.0/10 (1 review)
Explore the great outdoors at Pope Duval Park, a lovely green space in Jacksonville. Wander the riverfront in this family-friendly area.
See properties

Normandy Lane Plaza Shopping Center

You can search for that perfect souvenir at Normandy Lane Plaza Shopping Center during your visit to Jacksonville. Experience the area's lively festivals and great live music.
See properties

Ringhaver Park

6.0/10 (1 review)
Explore the great outdoors at Ringhaver Park, a lovely green space in Jacksonville. Stroll along the riverfront or attend a sporting event in this family-friendly area.
See properties

Normandy Mall Shopping Center

You can find the perfect gifts to bring home at Normandy Mall Shopping Center during your visit to Jacksonville. Experience the area's acclaimed theater scene or attend a sporting event.
See properties

Ortega Yacht Club Marina

Explore the waterfront in Jacksonville with a trip to Ortega Yacht Club Marina. Amble around the area's riverfront or attend a sporting event.
See properties

Things to do

Half-Day City Tour in Downtown Jacksonville

Half-Day City Tour in Downtown Jacksonville

CA $158
per adult
100% of travellers recommend
Half-Day City Tour in Downtown Jacksonville
The Escape Game at St. John's Town Center in Jacksonville

The Escape Game at St. John's Town Center in Jacksonville

CA $58
per adult
100% of travellers recommend
The Escape Game at St. John's Town Center in Jacksonville
1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports

1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports

CA $201
per traveller
90% of travellers recommend
1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports
See all activities in Jacksonville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.