Holiday Harbor Vacations from $288

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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.
Beachside Resort Hotel

Beachside Resort Hotel

2 out of 5
Price was $388, price is now $288 per person
$288
per person
Mar 7 - Mar 11
found 4 hours ago
Roundtrip flight included
Denver (DEN) to Pensacola (PNS)
8/10 Very Good! (1,550 reviews)
Very nice all around Would stay again

Reviewed on Feb 2, 2026

Hotel Indigo Orange Beach - Gulf Shores by IHG

Hotel Indigo Orange Beach - Gulf Shores by IHG

3.5 out of 5
Save 100% on your flight
Price was $2,449, price is now $1,761 per person
$1,761
per person
Apr 8 - Apr 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pensacola (PNS)
9.4/10 Exceptional! (1,001 reviews)
Great staff Beautiful room and everything you would need. Will stay there next year when we come in

Reviewed on Feb 1, 2026

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 $1,418, price is now $1,040 per person
$1,040
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pensacola (PNS)
9.2/10 Wonderful! (1,004 reviews)
Clean, excellent staff, very nice

Reviewed on Feb 3, 2026

Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $2,036, price is now $1,496 per person
$1,496
per person
Apr 24 - May 1
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
8.8/10 Excellent! (470 reviews)
The property set the bar for a relaxing, yet engaging, vacation. The room was spacious, as we were accommodating five people.The food choices were diverse and the pool areas were laid out beautifully. The live music by the pool was such a a nice touch, and there was any activity one could want by the water. A swift walk to the beach for another adventure directly across from the hotel set the tone for a day of fun I. The sun. We will be back.

Reviewed on Jul 29, 2025

The Cabins at Gulf State Park

The Cabins at Gulf State Park

3 out of 5
Save 100% on your flight
Price was $1,105, price is now $833 per person
$833
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pensacola (PNS)
9.8/10 Exceptional! (54 reviews)
Perfect for families, lots to do

Reviewed on Jul 20, 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

3 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
$152 nightly
The price is $171 total per night from Feb 5 to Feb 6
$171 total
Feb 5 - Feb 6
Total with taxes and fees
9.4/10 Exceptional! (2,771 reviews)
Clean room excellent serrvice from check in ro wait staff - house keeping

Reviewed on Feb 2, 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
$89 nightly
The price is $104 total per night from Feb 10 to Feb 11
$104 total
Feb 10 - Feb 11
Total with taxes and fees
7.8/10 Good! (1,398 reviews)
Clean room, quick check-in and very friendly staff

Reviewed on Jan 19, 2026

Hilton Garden Inn Orange Beach Beachfront
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
$70 nightly
The price is $79 total per night from Feb 5 to Feb 6
$79 total
Feb 5 - Feb 6
Total with taxes and fees
8.6/10 Excellent! (3,023 reviews)
Friendly staff, great location.

Reviewed on Jan 31, 2026

Surf & Sand Hotel
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

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 entertainment choices.

Perdido Key Beach
Pensacola_PensacolaCivicCenter_6127819_04

Pensacola Bay Center

After visiting Pensacola Bay Center, make a plan to see the other sights and activities in Pensacola. Stroll along the beautiful beaches or experience the great live music in this family-friendly area.

Pensacola Bay Center

Things to do

2-Hour Dolphin and Nature Eco Tour from Orange Beach

2-Hour Dolphin and Nature Eco Tour from Orange Beach

$38
per adult
96% of travellers recommend
2-Hour Dolphin and Nature Eco Tour from Orange Beach
The Explorer at Sunset

Dolphin and Nature Sunset Cruise from Orange Beach

$50
per adult
100% of travellers recommend
Dolphin and Nature Sunset Cruise 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.