Southeast Pensacola Vacation Packages

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Top Holiday Package Deals in Southeast Pensacola

Price found within the past 48 hours. Click for updated prices.
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Villa Sabine
Price was CA $1,900, price is now CA $1,540 per person
CA $1,540
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pensacola (PNS)
9.6/10 Exceptional! (3,697 reviews)

Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Price was CA $2,438, price is now CA $1,970 per person
CA $1,970
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Fort Walton Beach (VPS)
9/10 Wonderful! (185 reviews)

Sundrift Inn

Sundrift Inn

3 out of 5
Okaloosa Island
Price was CA $2,105, price is now CA $1,705 per person
CA $1,705
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Pensacola (PNS)
9/10 Wonderful! (889 reviews)
Everything was amazing. They let us get early checked in

Reviewed on Nov 2, 2026

The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Price was CA $2,840, price is now CA $2,330 per person
CA $2,330
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,001 reviews)
Beautiful property. We did not take advantage of all of the amenities but it is a gorgeous property and we loved where it was located.

Reviewed on Nov 4, 2026

Landing Furnished Apartments - Orange Beach 

Landing Furnished Apartments - Orange Beach 

3 out of 5
Price was CA $2,231, price is now CA $1,845 per person
CA $1,845
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pensacola (PNS)
8.8/10 Excellent! (19 reviews)
The apartment was very clean, convenient, and inviting. I will definitely stay here again.

Reviewed on Sep 14, 2026

Where to stay in Southeast Pensacola

Find the best Southeast Pensacola areas and neighborhoods for the activities you enjoy most. Learn more about Southeast Pensacola
A courthouse with columns, a cannon, and a Christmas tree.

Downtown Pensacola

3 out of top 10 points of interest in this area

If you're spending some time in Downtown Pensacola, Saenger Theatre and Historic Pensacola Village are top sights worth seeing.

Find hotels in Downtown Pensacola

Southeast Pensacola Hotel Deals

Tru By Hilton Pensacola Airport Medical Center

Tru By Hilton Pensacola Airport Medical Center

2.5 out of 5
5109 Bayou Blvd Pensacola FL
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Nov 28 to Nov 29
CA $153
CA $172 total
Nov 28 - Nov 29
includes taxes & fees
9.2/10 Wonderful! (573 reviews)
"Overall pretty nice. The only problem for us is they allow dogs to stay in a room"

Reviewed on Oct 30, 2026

Tru By Hilton Pensacola Airport Medical Center
Hilton Garden Inn Pensacola Downtown

Hilton Garden Inn Pensacola Downtown

3 out of 5
8 S 9th Avenue Pensacola FL
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Nov 23 to Nov 24
CA $213
CA $239 total
Nov 23 - Nov 24
includes taxes & fees
9.4/10 Exceptional! (316 reviews)
"Great stay. Wish parking was free but oh well."

Reviewed on Nov 2, 2026

Hilton Garden Inn Pensacola Downtown
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $265 per night from Dec 6 to Dec 7
CA $265
CA $304 total
Dec 6 - Dec 7
includes taxes & fees
The Pensacola Beach Resort
See all 6,862 properties in Southeast 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 Southeast Pensacola vacation package cost?
Our Southeast Pensacola vacation packages, which begin at just CA $1,540, are the perfect way to save loads of cash. Select your preferred hotels, flights and rental car to create a personalized getaway.
How do I get a cheap travel package to Southeast Pensacola?
Our Southeast Pensacola vacation packages promise plenty of savings for the savvy globetrotter. For the best deal, simply bundle your hotel, flights and extras (including tours) into a neat and tidy package. But great bargains are just the beginning of your next amazing adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 properties around the world to pick from. Whatever your style or budget, there's a vacation package here just for you.
Where should I stay in Southeast Pensacola?
Urban explorers come from all corners of the globe to experience Pensacola Naval Air Station and Pensacola Bay Center in Southeast Pensacola. Book yourself a room within walking distance of these must-see attractions and visit them whenever you please.
What are the top hotels in Southeast Pensacola?
Reserve a room at Spacious Comfy Home 15 Mins To Pensacola Beach. It's one of the area's most sought-after properties. Another reputable option in Southeast Pensacola is Lloyd Land, A Restored 1940s East Hill Home.
How far in advance should I book my Southeast Pensacola vacation?
To bag cheap prices, book ASAP. Air carriers typically release flights, along with some of the lowest fares, up to 12 months in advance. Hotels, activities and car rental should also be booked well in advance so you can have the pick of the bunch. If you've decided on a last-minute getaway in Southeast Pensacola, there are always plenty of great deals to be had on Expedia. Check them out now!
What does an Expedia Southeast Pensacola travel package include?
You can choose from any combination of rental cars, hotels and flights. Once you've made your booking, you can add the fun stuff like tours and activities. Want to pick your airfare class? That's also possible. The choice is all yours when it comes to putting together your perfect Southeast Pensacola escape.
What should I know before booking a Southeast Pensacola travel package?
An Expedia travel package can be customized for your budget and is a fantastic way to stretch your dollars further. What you include is up to you. Rental cars, hotels and flights — choose any combination that works with your plans.
Can I choose my airline with a Southeast Pensacola Expedia vacation package?
Yes, you're in control. Expedia has access to more than 550 airlines worldwide, so you can tailor your Southeast Pensacola trip according to your travel preferences.
If I'm not able to travel, can I cancel my Southeast Pensacola vacation package?
Because we know life can be unpredictable, the answer is yes. For further information, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it free of charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.

Stay near popular Southeast Pensacola attractions

Palafox Shopping Center

7.6/10 (4 reviews)
During your trip to Pensacola, you can do some window-shopping at Palafox Shopping Center. Amble around this family-friendly area's beautiful beaches and enjoy its top-notch restaurants.
See properties

Things to do

Picture 1 for Activity Dolphin & Scenic Bay Sightseeing Cruise Up to 49, Pensacola

Dolphin & Scenic Bay Sightseeing Cruise Up to 49, Pensacola

CA $71
per adult
Dolphin & Scenic Bay Sightseeing Cruise Up to 49, Pensacola
Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour

Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour

CA $55
per adult
98% of travellers recommend
Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour
Pensacola's True Crime Walking Tour

Pensacola True Crime Tour: Sweet Tea Murders with a Detective

CA $47
per adult
Pensacola True Crime Tour: Sweet Tea Murders with a Detective
See all activities in Pensacola
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.