Holiday Harbor Vacations from $394

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Your Holiday Harbor Vacation

Lock in your vacation package to Holiday Harbor and prepare to explore its watersports and more. Whether you're craving adventure or fun, you'll find it in this appealing neighborhood. Kick off your trip to Holiday Harbor by visiting nearby attractions such as Perdido Key State Park, Big Lagoon State Park and Lost Key Golf Club. No matter what your dream Holiday Harbor vacation looks like, you can make it a reality with Expedia.

The Latest Holiday Harbor Vacation Packages

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
Price was $526, price is now $394 per person
$394
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
4.2/10 (698 reviews)
It was decent nice staff nice room quite easy check in etc

Reviewed on Oct 4, 2025

The Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $877, price is now $589 per person
$589
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
9.2/10 Wonderful! (1,004 reviews)
Hotel was empty but I got the worst room in the hotel. Because I booked through a 3rd party I had the room next to the elevator no balcony but it was away from the construction at least.

Reviewed on Dec 6, 2025

Eagle Cottages at Gulf State Park

Eagle Cottages at Gulf State Park

3 out of 5
Save 100% on your flight
Price was $1,937, price is now $1,409 per person
$1,409
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Pensacola (PNS)
8.6/10 Excellent! (38 reviews)
Woodside Restaurant at Gulf State Park is the best kept secret of Gulf Shores. Emma at breakfast and Issac at dinner, made our meals welcoming and special.

Reviewed on Jul 29, 2025

Hotel Indigo Orange Beach - Gulf Shores by IHG

Hotel Indigo Orange Beach - Gulf Shores by IHG

3.5 out of 5
Price was $629, price is now $465 per person
$465
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
9.4/10 Exceptional! (1,001 reviews)
Only booked because it was pet friendly and we were pleasantly surprised. Super friendly staff - shout out to Julie who we met when we checked in and Mike who helped us with dinner. All the rest of the staff was great as well! Very clean, spacious rooms and an amazing view of the gulf from our room! Unfortunately we were unable to use the pools and gym but we did get coffee at the attached coffeehouse and gift shop. Definitely recommend!!!

Reviewed on Nov 28, 2025

Perdido Beach Resort

Perdido Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $904, price is now $669 per person
$669
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Pensacola (PNS)
9.8/10 Exceptional! (1,789 reviews)
The room,property, and staff were great! The fire alarm went off in our building at 5:00 am Thanksgiving morning. I must admit that really freaked my wife and me out. It was so load and thank God it was a false alarm.Really disturbed our sleep that morning.

Reviewed on Dec 9, 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 showing heritage elements and heritage architecture

Downtown Pensacola

2 out of top 10 points of interest in this area
4/5(314 area reviews)

Contemporary components integrated in a historical city keep visitors’ interests high. Walk this pedestrian-friendly sector to get to know its diversity.

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
$152 nightly
The price is $171 total per night from Dec 14 to Dec 15
$171 total
Dec 14 - Dec 15
Total with taxes and fees
9.4/10 Exceptional! (2,656 reviews)
Loved this place so much! It was clean, pretty, the perfect costal vibes. The staff were the sweetest and perfectly located next to everything. The best beach access. Bed super comfy.

Reviewed on Dec 5, 2025

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
$58 nightly
The price is $65 total per night from Dec 18 to Dec 19
$65 total
Dec 18 - Dec 19
Total with taxes and fees
8.6/10 Excellent! (2,936 reviews)
Room was great staff friendly. Only downfall eas a nus of high schoolers was there for 2 day and the poor lady that was cooking breakfast couldnt keep up so we had to go and get breakfast for 2 days.

Reviewed on Dec 9, 2025

Surf & Sand Hotel
Hampton Inn Pensacola Beach

Hampton Inn Pensacola Beach

2.5 out of 5
2 Via De Luna Drive Pensacola Beach FL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $91 total per night from Dec 18 to Dec 19
$91 total
Dec 18 - Dec 19
Total with taxes and fees
8.2/10 Very Good! (2,260 reviews)
We enjoyed our stay both days; we were greeted and taken care of by James. He was helpful and provided us with excellent service. Our stay was great.

Reviewed on Dec 5, 2025

Hampton Inn Pensacola Beach
See all 17,311 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Holiday Harbor

Florida Panhandle showing a statue or sculpture and interior views

Pensacola Naval Air Station

4.5/5(697 reviews)

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
Perdido Key Beach

Perdido Key Beach

4.5/5(283 reviews)

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
National Museum of Naval Aviation which includes interior views

National Museum of Naval Aviation

5/5(488 reviews)

You can spend an afternoon studying the exhibits at National Museum of Naval Aviation in Pensacola. Discover the beautiful sunsets and top-notch restaurants in this family-friendly area.

National Museum of Naval Aviation

Things to do

Orange Beach: Dolphin-Watching Eco-Boat Tour

Orange Beach: Dolphin-Watching Eco-Boat Tour

$34
per adult
100% of travellers recommend
Orange Beach: Dolphin-Watching Eco-Boat Tour
2-Hour Dolphin and Nature Eco Tour from Orange Beach

2-Hour Dolphin and Nature Eco Tour from Orange Beach

$38
per adult
92% of travellers recommend
2-Hour Dolphin and Nature Eco Tour from Orange Beach
Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour

Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour

$39
per adult
98% of travellers recommend
Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour
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.