Holiday Harbor Vacations from $409

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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.
Holiday Inn Express & Suites Pensacola Airport North – I-10 by IHG

Holiday Inn Express & Suites Pensacola Airport North – I-10 by IHG

2.5 out of 5
Price was $529, price is now $409 per person
$409
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Pensacola (PNS)
9.2/10 Wonderful! (762 reviews)
I loved the cleanliness of the room.

Reviewed on Sep 1, 2025

LUXURY Penthouse Style Condo 2

LUXURY Penthouse Style Condo 2

4 out of 5
Save 100% on your flight
Price was $2,240, price is now $1,520 per person
$1,520
per person
Nov 3 - Nov 7
found 13 hours ago
Roundtrip flight included
Denver (DEN) to Pensacola (PNS)
8/10 Very Good! (2 reviews)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Downtown Pensacola
Save 100% on your flight
Price was $1,553, price is now $1,088 per person
$1,088
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Pensacola (PNS)
9.4/10 Exceptional! (17 reviews)
Clean, quiet and absolutely beautiful inside and out! Staff was super friendly! Would definitely stay there again!

Reviewed on Mar 11, 2025

The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Price was $682, price is now $518 per person
$518
per person
Nov 7 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Pensacola (PNS)
8.4/10 Very Good! (2,786 reviews)
Very friendly staff! Lot of amenities. Walk to the beach. It has everything we needed.

Reviewed on Aug 31, 2025

Embassy Suites By Hilton Gulf Shores Beach Resort

Embassy Suites By Hilton Gulf Shores Beach Resort

3.5 out of 5
Price was $1,197, price is now $925 per person
$925
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Pensacola (PNS)
10/10 Exceptional! (18 reviews)
Everything was great! The 2% milk was spoiled at breakfast. People/Staff were awesome.

Reviewed on Sep 1, 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

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
$110 nightly
The price is $127 total per night from Sep 29 to Sep 30
$127 total
Sep 29 - Sep 30
Total with taxes and fees
Hilton Garden Inn Orange Beach Beachfront
Beachside Resort Hotel

Beachside Resort Hotel

2 out of 5
610 W Beach Blvd, Gulf Shores, AL
Fully refundable
$83 nightly
The price is $96 total per night from Sep 3 to Sep 4
$96 total
Sep 3 - Sep 4
Total with taxes and fees
Beachside Resort Hotel
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road, Pensacola Beach, FL
$212 nightly
The price is $238 total per night from Sep 28 to Sep 29
$238 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (2,338 reviews)
"Very nice workers. Nice views. Not an overcrowded area."

Reviewed on Sep 1, 2025

The Pensacola Beach Resort
See all 17,250 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

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
You can't see it in this picture, but there is a waterfall in the middle of the pool. This is an awesome place for families.

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 acclaimed theater scene.

Perdido Key Beach
National Museum of Naval Aviation which includes interior views

National Museum of Naval Aviation

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

National Museum of Naval Aviation

Things to do

Come see Pensacola like you never have heard tales of death and bring the city's history back to life.

Haunted Pensacola Walking Tour

$26
per adult
90% of travellers recommend
Haunted Pensacola Walking Tour
Private Yacht Cruise with Beach Stop and Swimming/Paddle Boarding

Private Luxury Yacht with Beach Stop and Swimming/Paddle Boarding

$1,200
per traveler
Private Luxury Yacht with Beach Stop and Swimming/Paddle Boarding
Pub Crawl of Pensacola by Pedal Trolley

Party Bike Pub Crawl of Downtown Pensacola

$45
per adult
Party Bike Pub Crawl of Downtown 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.