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.
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 18 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 18 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 Southeast Pensacola

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

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

Courtyard Pensacola Downtown

Courtyard Pensacola Downtown

3 out of 5
700 E Chase St Pensacola FL
Fully refundableReserve now, pay when you stay
The price is CA $317 per night from Jun 28 to Jun 29
CA $317
CA $357 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (782 reviews)
"Nice facility"

Reviewed on Jun 12, 2026

Courtyard Pensacola Downtown
Charming pink 2-bedroom cottage in gorgeous Pensacola with AC

Charming pink 2-bedroom cottage in gorgeous Pensacola with AC

Pensacola FL
The price is CA $195 per night from Jun 23 to Jun 24
CA $195
CA $292 total
Jun 23 - Jun 24
includes taxes & fees
10/10 Exceptional! (2 reviews)
"Jenny was amazing and very accommodating! Will definitely use her again!"

Reviewed on May 24, 2026

Charming pink 2-bedroom cottage in gorgeous Pensacola with AC
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 $508 per night from Jun 28 to Jun 29
CA $508
CA $582 total
Jun 28 - Jun 29
includes taxes & fees
9.6/10 Exceptional! (3,290 reviews)
"Grade A Service"

Reviewed on Jun 21, 2026

The Pensacola Beach Resort
See all 6,820 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 $1,234, 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.

Discover the most popular places to visit in Southeast Pensacola

Bayview Dog Beach Park

Bayview Dog Beach Park is just one of the places to see in Pensacola, so why not enjoy the other things to explore during your travels? Amble around the area's beaches or visit its shops.

Bayview Dog Beach Park

Barnes Shopping Center

During your visit to Brent, you can enjoy retail therapy at Barnes Shopping Center. Stroll along the beautiful beaches or experience the great live music in this family-friendly area.

Barnes Shopping Center

Things to do

Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour

Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour

CA $54
per adult
98% of travellers recommend
Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour
Picture 1 for Activity Dolphin & Scenic Bay Sightseeing Cruise Up to 49, Pensacola

Dolphin & Scenic Bay Sightseeing Cruise Up to 49, Pensacola

CA $69
per adult
Dolphin & Scenic Bay Sightseeing Cruise Up to 49, Pensacola
Ghosts and Graveyard Tour of Pensacola

Ghosts and Graveyard Tour of Pensacola

CA $55
per adult
100% of travellers recommend
Ghosts and Graveyard Tour of Pensacola
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.