Holiday Harbor 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 Holiday Harbor

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Pensacola I-10 & Hwy 29

OYO Hotel Pensacola I-10 & Hwy 29

2 out of 5
Northwest Pensacola
Price was CA $1,655, price is now CA $1,337 per person
CA $1,337
per person
Jul 20 - Jul 25
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Pensacola (PNS)
4.2/10 (729 reviews)
Love it and ac word great

Reviewed on May 14, 2026

Beachfront Townhome With Instant Access to Beach Beachside Kisses by Avantstay

Beachfront Townhome With Instant Access to Beach Beachside Kisses by Avantstay

3 out of 5
Okaloosa Island
Price was CA $6,642, price is now CA $5,008 per person
CA $5,008
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pensacola (PNS)
No reviews
El Matador

El Matador

4 out of 5
Okaloosa Island
Price was CA $3,034, price is now CA $2,380 per person
CA $2,380
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pensacola (PNS)
No reviews
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Okaloosa Island
Price was CA $2,457, price is now CA $1,933 per person
CA $1,933
per person
Jul 27 - Aug 2
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pensacola (PNS)
8.2/10 Very Good! (3,132 reviews)
10/10 I will be coming back with the whole family next spring !! Thank you !!

Reviewed on May 17, 2026

Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Downtown Pensacola
Price was CA $2,909, price is now CA $2,359 per person
CA $2,359
per person
Jul 20 - Jul 25
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Pensacola (PNS)
9.6/10 Exceptional! (21 reviews)
Absolutely beautiful. Will definitely stay here again

Reviewed on Oct 18, 2025

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
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

Holiday Harbor Hotel Deals

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 $322 per night from May 20 to May 21
CA $322
CA $373 total
May 20 - May 21
includes taxes & fees
8/10 Very Good! (1,562 reviews)
Everything was awesome but there is a couple of staff that needs to work on people skills and communication skills

Reviewed on May 17, 2026

Hilton Garden Inn Orange Beach Beachfront
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 $407 per night from May 31 to Jun 1
CA $407
CA $466 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (3,129 reviews)
Room overlooked the beach, great service.

Reviewed on May 18, 2026

The Pensacola Beach Resort
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from May 21 to May 22
CA $181
CA $214 total
May 21 - May 22
includes taxes & fees
8.8/10 Excellent! (3,153 reviews)
This has been our go to for the last few years but it has declined. Property needs basic updates. Swimming area is nice. Staff is also nice.

Reviewed on May 17, 2026

Surf & Sand Hotel
See all 17,701 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 $1,337. 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.

Discover the most popular places to visit in Holiday Harbor

Fort Barrancas NAS Pensacola

Pensacola Naval Air Station

After visiting Pensacola Naval Air Station, make a plan to see the other sights and activities in Pensacola. Wander the beautiful beaches or discover the beautiful sunsets in this family-friendly area.

Pensacola Naval Air Station
Aerial view of the beach at Perdido Key

Perdido Key Beach

Why not spend a lazy afternoon at Perdido Key Beach during your trip to Pensacola? Experience the area's great live music and fascinating museums.

Perdido Key Beach
Pensacola_UniversityofWestFlorida_6127826-10

University of West Florida

Enjoy the collegiate vibe when you visit University of West Florida, during your trip to Ferry Pass. Wander the beautiful beaches in this family-friendly area.

University of West Florida

Things to do

Orange Beach: Dolphin-Watching Eco-Boat Tour

Orange Beach: Dolphin-Watching Eco-Boat Tour

CA $47
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 $53
per adult
98% of travellers recommend
Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour
2-Hour Dolphin and Nature Eco Tour from Orange Beach

2-Hour Dolphin and Nature Eco Tour from Orange Beach

CA $51
per adult
96% of travellers recommend
2-Hour Dolphin and Nature Eco Tour from Orange Beach
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.