Downtown Pensacola 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

Top Holiday Package Deals in Downtown Pensacola

Price found within the past 48 hours. Click for updated prices.
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Price was CA $1,607, price is now CA $1,234 per person
CA $1,234
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Walton Beach (VPS)
7.8/10 Good! (3,924 reviews)
I like that it was on a resort I didn’t notice that when I booked it. It came with a lot of unique amenities.

Reviewed on Jun 21, 2026

Sundrift Inn

Sundrift Inn

3 out of 5
Okaloosa Island
Price was CA $1,628, price is now CA $1,236 per person
CA $1,236
per person
Jul 31 - Aug 3
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pensacola (PNS)
9/10 Wonderful! (626 reviews)
We really enjoyed our stay at Sundrift. Our room was very clean and felt spacious. The property is very well-kept, but didn't feel overly formal. We were able to enjoy a nice relaxed beach vacation with a very nice place to stay. The beach access was fantastic and easy to use. The breakfast in the restaurant was also great. Would definitely love to stay again. No complaints whatsoever.

Reviewed on Jun 20, 2026

The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Okaloosa Island
Price was CA $1,638, price is now CA $1,293 per person
CA $1,293
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pensacola (PNS)
8.2/10 Very Good! (3,242 reviews)
If you were looking for a family, friendly beachfront accommodation, The Island is a great choice. Amenities were great and the beachfront is beautiful. There was live music at a beachfront bar every night. Only note is that the two double bed room was pretty snug so if you’re traveling with more than three people, you might consider an upgrade from that.

Reviewed on Jun 20, 2026

Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Price was CA $1,638, price is now CA $1,312 per person
CA $1,312
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Walton Beach (VPS)
9/10 Wonderful! (166 reviews)
Great place, very clean and spacious

Reviewed on Jun 21, 2026

Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Okaloosa Island
Price was CA $1,568, price is now CA $1,259 per person
CA $1,259
per person
Jul 31 - Aug 3
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pensacola (PNS)
9.2/10 Wonderful! (1,027 reviews)
Anthony is the most pleasant personality n I’ve ever met in the hospitality industry. Mae our stay memorable.

Reviewed on Jun 17, 2026

Where to stay in Downtown Pensacola

Find the best Downtown Pensacola areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Pensacola
Southeast Pensacola

Southeast Pensacola

While visiting Southeast Pensacola, you might make a stop by sights like Palafox Shopping Center and Delmar Shopping Center.

Find hotels in Southeast Pensacola

Downtown Pensacola Hotel Deals

Days Inn by Wyndham Pensacola - Historic Downtown

Days Inn by Wyndham Pensacola - Historic Downtown

2 out of 5
710 N Palafox St Pensacola FL
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jun 28 to Jun 29
CA $159
CA $179 total
Jun 28 - Jun 29
includes taxes & fees
7.6/10 Good! (1,004 reviews)
"The hotel staff was very nice and the rooms were also clean. A great pitstop for us."

Reviewed on Jun 19, 2026

Days Inn by Wyndham Pensacola - Historic Downtown
Holiday Inn Express Pensacola Downtown by IHG

Holiday Inn Express Pensacola Downtown by IHG

2.5 out of 5
101 E Main St Pensacola FL
Fully refundable
The price is CA $300 per night from Jun 28 to Jun 29
CA $300
CA $338 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (928 reviews)
"Really great spot to stay!"

Reviewed on Jun 18, 2026

Holiday Inn Express Pensacola Downtown by IHG
Lily Hall- A Boutique Hotel

Lily Hall- A Boutique Hotel

4 out of 5
415 N Alcaniz St Pensacola FL
The price is CA $237 per night from Jul 5 to Jul 6
CA $237
CA $335 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (224 reviews)
"Clean room, cute amenities."

Reviewed on Jun 18, 2026

Lily Hall- A Boutique Hotel
See all 6,147 properties in Downtown Pensacola
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 Downtown Pensacola vacation package cost?
From as low as CA $1,234, you can tailor your Downtown Pensacola vacation package. Simply combine flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Downtown Pensacola?
Our Downtown Pensacola vacation packages promise plenty of savings for the savvy globetrotter. For the best deal, simply combine your flights, hotels and extras (including tours) into a budget-friendly package. But bargain prices are just the beginning of your next memorable adventure. Book with Expedia and you'll have more than 550 airlines and 1,000,000 hotel options worldwide to choose from. No matter your style or budget, there's a vacation package here just for you.
Where should I stay in Downtown Pensacola?
A journey to Downtown Pensacola has to include Pensacola Naval Air Station and Pensacola Bay Center. Stay as close as possible and easily access these fantastic tourist attractions.
What are the top hotels in Downtown Pensacola?
Get your escape off to a good start by locking in a room at Heart Of Downtown On Palafox Place. It's one of most popular hotels in Downtown Pensacola. Another option is Charming Cottage In Downtown Pensacola With Central Ac And Fenced Backyard.
How far in advance should I book my Downtown Pensacola vacation?
Savvy travelers book early. Air carriers usually release flight tickets nearly 12 months prior to departure, and this is a fantastic opportunity to land some rock-bottom prices. Just been told you should take your vacation time next week? No problem! Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Downtown Pensacola travel package include?
Flights, hotels and rental cars — we have them covered. With Expedia, you can shape your Downtown Pensacola package your way. All you have to do is work out what you need. Once you've made your booking, you can add extras like experiences and activities. The more you bundle, the bigger the savings!
What should I know before booking a Downtown Pensacola travel package?
You can save a tidy sum by combining your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or sightseeing tours. Your next awesome adventure is only a couple of clicks away.
Can I choose my airline with a Downtown Pensacola Expedia vacation package?
Yes, and with more than 550 airlines to pick from throughout the world, you have loads of choice. Browse the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Downtown Pensacola vacation package?
You can. We get that life doesn't always go to plan, so we're happy to help if you need to make changes to your Downtown Pensacola vacation package. You may be able to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.