Holiday Harbor Vacation Packages

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  • Better together

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

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

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Top Holiday Package Deals in Holiday Harbor

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Orange Beach - Gulf Shores by IHG

Hotel Indigo Orange Beach - Gulf Shores by IHG

3.5 out of 5
Price was CA $1,471, price is now CA $1,049 per person
CA $1,049
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pensacola (PNS)
9.4/10 Exceptional! (1,005 reviews)
Great place to stay with a shuttle to the beach access

Reviewed on Jul 9, 2026

Landing Furnished Apartments - Orange Beach 

Landing Furnished Apartments - Orange Beach 

3 out of 5
Price was CA $2,380, price is now CA $1,648 per person
CA $1,648
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pensacola (PNS)
8/10 Very good! (11 reviews)
The check-in process and automatic locks at the property were very confusing. I could not get through to an actual person. Also, the access to the beach is not nearly as close as it looks on a map. Other than that, it’s a beautiful property, with nice accommodations.

Reviewed on Jul 1, 2026

Landing Apartments Gulf Shores

Landing Apartments Gulf Shores

3.5 out of 5
Price was CA $1,693, price is now CA $1,296 per person
CA $1,296
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pensacola (PNS)
9.8/10 Exceptional! (7 reviews)
2bdrm 2bath..very nice,bed was comfortable, we loved the adult pool..only wish the pool was open later than 7pm in the evening.old management was at least 9pm.. Nice dog park.. My husband and his cousin enjoyed the golf course there too.

Reviewed on Jul 6, 2026

Palm Beach Resort Orange Beach a Ramada by Wyndham

Palm Beach Resort Orange Beach a Ramada by Wyndham

3.5 out of 5
Price was CA $2,041, price is now CA $1,707 per person
CA $1,707
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pensacola (PNS)
9/10 Wonderful! (414 reviews)
A great location and the accommodations were perfect! Very clean!

Reviewed on Jun 14, 2026

Seaside Beach 5417- Two Bedrooms Waterfront Condo With Pool Sauna Amazing Ocean View Balcony

Seaside Beach 5417- Two Bedrooms Waterfront Condo With Pool Sauna Amazing Ocean View Balcony

2 out of 5
Price was CA $2,149, price is now CA $1,804 per person
CA $1,804
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pensacola (PNS)
9/10 Wonderful! (2 reviews)
Make sure you bring extra TP, dish soap and paper towels. I for sure thought we would have more than one roll of TP for the week. The shower is tiny. It was very clean and homey. We loved the pool and it being right at beach. It was kind of hard to remember all the codes. But we managed it. All in all a great stay!

Reviewed on Jun 13, 2026

Where to stay in Holiday Harbor

Find the best Holiday Harbor areas and neighborhoods for the activities you enjoy most. Learn more about Holiday Harbor
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

Holiday Harbor Hotel Deals

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 $432 per night from Aug 9 to Aug 10
CA $432
CA $495 total
Aug 9 - Aug 10
includes taxes & fees
9.6/10 Exceptional! (3,371 reviews)
"An amazing hotel. Very friendly staff. A great beach view. Wonderful dinning experience. Highly recommend"

Reviewed on Jul 9, 2026

The Pensacola Beach Resort
Hilton Garden Inn Orange Beach Beachfront

Hilton Garden Inn Orange Beach Beachfront

3 out of 5
23092 Perdido Beach Blvd Orange Beach AL
Fully refundableReserve now, pay when you stay
The price is CA $262 per night from Aug 9 to Aug 10
CA $262
CA $304 total
Aug 9 - Aug 10
includes taxes & fees
8/10 Very good! (1,688 reviews)
"Ask for a balcony with view of the beach. From the pictures I thought I was getting a view of the beach but it was the hotel next door. Other than that rooms were okay kinda small."

Reviewed on Jul 9, 2026

Hilton Garden Inn Orange Beach Beachfront
Beachside Resort Hotel

Beachside Resort Hotel

2 out of 5
610 W Beach Blvd Gulf Shores AL
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Aug 9 to Aug 10
CA $131
CA $152 total
Aug 9 - Aug 10
includes taxes & fees
8/10 Very good! (1,676 reviews)
"Was a pretty good stay."

Reviewed on Jul 9, 2026

Beachside Resort Hotel
See all 17,712 properties in Holiday Harbor
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 Holiday Harbor vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Holiday Harbor from just CA $1,049. And the more you bundle, the more you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Holiday Harbor?
Combine your hotels and flights, throw in extras such as tours, and save with a Holiday Harbor vacation package. You won't just land big discounts on your escape — you'll have plenty of choice at your fingertips too. When you book through Expedia, you'll have your pick of over 550 airlines and 1,000,000 hotels worldwide. Your next affordable adventure starts right here, right now!
Where should I stay in Holiday Harbor?
Travelers come from near and far to see Pensacola Naval Air Station and Pensacola Bay Center in Holiday Harbor. Book yourself a room near these fantastic attractions to make sightseeing a breeze.
What are the top hotels in Holiday Harbor?
If it's comfort and convenience you're looking for, you can't beat Low As 185/nt Aug 6 - 18 @ Terrific Waterfront Home With Sugar Sand Beach. Spend your evenings relaxing here and your days discovering Holiday Harbor's best sights.
How far in advance should I book my Holiday Harbor vacation?
It can be hard to know when the best time is to book your vacation to Holiday Harbor. But usually the earlier you book, the cheaper the prices. Sometimes, you can book your flights and hotels nearly 12 months prior to your departure date. If you're thinking of a last-minute getaway, no need to worry! There are fantastic deals featured on Expedia every day.
What does an Expedia Holiday Harbor travel package include?
Hotels, flights and a reliable car for all your road trip adventures. Simply select your preferred bundle and get access to incredible deals. Once you've made your booking, add on some sightseeing tours and watch your savings stack up. When it comes to crafting your Holiday Harbor break, you're the one in control!
Can I choose my airline with a Holiday Harbor Expedia vacation package?
Yes, of course. We have more than 550 airline partners globally, so pick the carrier that fits your budget needs.
If I'm not able to travel, can I cancel my Holiday Harbor vacation package?
Yes, you can. We understand that life happens, so we're happy to help if you need to make changes to your Holiday Harbor vacation package. You may be able to cancel or amend your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

Things to do

Orange Beach: Dolphin-Watching Eco-Boat Tour

Orange Beach: Dolphin-Watching Eco-Boat Tour

CA $39
per adult
100% of travellers recommend
Orange Beach: Dolphin-Watching Eco-Boat Tour
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
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
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.