Oriole Beach Vacations from $652

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Your Oriole Beach Vacation

Say farewell to the stress of planning and hello to a Oriole Beach vacation package. With your travel details organized before you take off, you can focus on discovering this city, starting with Downtown Pensacola, which is great for shopping, festivals and bars and pubs. Fill up your itinerary with tours of Tiger Point Golf and Country Club, Shoreline Park and Naval Live Oaks Nature Preserve, some of the things you simply have to see during your trip to Oriole Beach. Your Oriole Beach vacation is a few clicks away. Search flights, accommodations and more on Expedia for an adventure that's tailored to suit your style.

The Latest Oriole Beach vacation packages

Price found within the past 48 hours. Click for updated prices.
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Villa Sabine
Price was $838, price is now $652 per person
$652
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pensacola (PNS)
9.4/10 Exceptional! (2,472 reviews)
The hotel staff was excellent very helpful.

Reviewed on Sep 8, 2025

Portofino Island Resort

Portofino Island Resort

4 out of 5
Price was $1,210, price is now $939 per person
$939
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pensacola (PNS)
8.8/10 Excellent! (468 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

Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Downtown Pensacola
Save 100% on your flight
Price was $1,584, price is now $1,234 per person
$1,234
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

Windward Pointe 104

Windward Pointe 104

3.5 out of 5
Save 100% on your flight
Price was $1,254, price is now $985 per person
$985
per person
Oct 27 - Nov 2
found 24 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Pensacola (PNS)
No reviews
Emerald Isle

Emerald Isle

3 out of 5
Villa Primera
Price was $1,107, price is now $872 per person
$872
per person
Nov 22 - Nov 26
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
8.6/10 Excellent! (79 reviews)
We enjoyed our stay here so much we booked a condo again for next summer.

Reviewed on Aug 8, 2025

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Discover the most popular places to visit in Oriole Beach

A few gators at the Gulf Breeze Zoo.

Gulf Breeze Zoo

Meet the animals who call Gulf Breeze Zoo home during your travels in Gulf Breeze. Wander the beautiful beaches or discover the beautiful sunsets in this family-friendly area.

Gulf Breeze Zoo
sunrise on the beach in Alabama. #trovember

Naval Live Oaks Nature Preserve

Explore the great outdoors at Naval Live Oaks Nature Preserve, a lovely green space in Gulf Breeze. Stroll along the area's beautiful beaches, or simply savor its top-notch restaurants.

Naval Live Oaks Nature Preserve

Gulf Breeze Shopping Center

You can search for that perfect souvenir at Gulf Breeze Shopping Center during your visit to Gulf Breeze. Stroll along the seaside or experience the great live music in this family-friendly area.

Gulf Breeze Shopping Center

What to do in Oriole Beach

Destin: Buccaneer Pirate Cruise

Destin: Buccaneer Pirate Cruise

$55
per adult
100% of travellers recommend
Destin: Buccaneer Pirate Cruise
Destin: Snorkeling Cruise with 2 Stops and Dolphin Watching

Destin: Snorkeling Cruise with 2 Stops and Dolphin Watching

$45
per adult
100% of travellers recommend
Destin: Snorkeling Cruise with 2 Stops and Dolphin Watching
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 Oriole Beach

Oriole Beach Hotel Deals

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
The Pensacola Beach Resort
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road, Pensacola Beach, FL
$90 nightly
The price is $102 total per night from Sep 11 to Sep 12
$102 total
Sep 11 - Sep 12
Total with taxes and fees
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
$128 nightly
The price is $144 total per night from Sep 15 to Sep 16
$144 total
Sep 15 - Sep 16
Total with taxes and fees
Hampton Inn Pensacola Beach
See all 4,974 properties in Oriole Beach
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.

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Frequently asked questions

How much does an Oriole Beach vacation package cost?
Offering great value package deals from $652 on Expedia, you'll be thrilled with how little a vacation to Oriole Beach costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Oriole Beach?
If you'd like to snag a cheap Oriole Beach vacation package, consider visiting in October, November and December. You'll generally find better prices on airfares and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Oriole Beach?
The ideal duration for your Oriole Beach vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you time to hit all the top sights and explore some hidden gems along the way.
How to find the best Oriole Beach package deals?
Begin your search for an Oriole Beach package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Oriole Beach package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oriole Beach escape off to a flying start.
Is it cheaper to book an Oriole Beach vacation as a package?
You can enjoy significant savings on your next Oriole Beach retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Oriole Beach?
If you have your Oriole Beach vacation dates locked in, book early to score some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for quick escapes.
Does Expedia offer Book Now, Pay Later Oriole Beach vacation packages?
Your Oriole Beach trip is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.