Oak Vacations from $507

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Your Oak Vacation

Book a custom vacation package to Oak and prepare to experience this fascinating city your way. Consider spending time in the neighborhood of Oyster Bay, which is good for fishing and tons more. Gulf Shores Beach, The Wharf and Gulf State Park are just a few of the attractions you'll want to see during your trip to Oak. Expedia can help you escape your daily routine. Tailor your vacation to Oak to suit your style of travel, whatever that may be!

The Latest Oak 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 $656, price is now $507 per person
$507
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Pensacola (PNS)
9.4/10 Exceptional! (2,609 reviews)
Everything was great. Off-season made it even better!

Reviewed on Jan 29, 2026

Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $2,145, price is now $1,513 per person
$1,513
per person
Apr 6 - Apr 12
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Price was $823, price is now $637 per person
$637
per person
Apr 12 - Apr 15
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to Pensacola (PNS)
9.2/10 Wonderful! (1,004 reviews)
Comfortable and spotless room. Beautiful lobby area. Great staff

Reviewed on Jan 16, 2026

Beachside Resort Hotel

Beachside Resort Hotel

2 out of 5
Price was $695, price is now $544 per person
$544
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Pensacola (PNS)
8/10 Very Good! (1,550 reviews)
Great location, easy access and friendly staff.

Reviewed on Jan 29, 2026

Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Downtown Pensacola
Price was $933, price is now $734 per person
$734
per person
Apr 25 - Apr 27
found 1 hour ago
Roundtrip non-stop flight included
Denver (DEN) to Pensacola (PNS)
9.4/10 Exceptional! (19 reviews)
Absolutely beautiful. Will definitely stay here again

Reviewed on Oct 18, 2025

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Discover the most popular places to visit in Oak

Gulf Shores Beach showing a coastal town, general coastal views and a beach

Gulf Shores Beach

4.5/5(1,223 reviews)

For the complete beach experience, visit this well-groomed swath of sand on the Gulf Coast, with thoughtful amenities and a convenient and central location.

Gulf Shores Beach
Fort Morgan

Fort Morgan

4/5(220 reviews)

Experience southern United States military history, lounge on soft white-sand beaches and explore quiet natural parks in this beautiful Mobile Bay destination.

Fort Morgan
Aerial view of beach houses at Fort Morgan, Alabama

Fort Morgan Beach

5/5(1 review)

Why not spend a lazy afternoon at Fort Morgan Beach during your trip to Fort Morgan?

Fort Morgan Beach

What to do in Oak

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
Dolphin Cruise in Orange Beach Alabama

Dolphin Cruise in Orange Beach Alabama

$34
per adult
Dolphin Cruise in Orange Beach Alabama
See all activities in Oak

Oak Hotel Deals

Staybridge Suites Gulf Shores by IHG

Staybridge Suites Gulf Shores by IHG

3 out of 5
3947 Gulf Shores Parkway Gulf Shores AL
Fully refundable
$100 nightly
The price is $116 total per night from Feb 2 to Feb 3
$116 total
Feb 2 - Feb 3
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Great stay ! Close to everything ! Pet friendly , can’t wait to come back .

Reviewed on Dec 31, 2025

Staybridge Suites Gulf Shores by IHG
Hilton Garden Inn Orange Beach Beachfront

Hilton Garden Inn Orange Beach Beachfront

3 out of 5
23092 Perdido Beach Blvd Orange Beach AL
$93 nightly
The price is $107 total per night from Feb 8 to Feb 9
$107 total
Feb 8 - Feb 9
Total with taxes and fees
7.8/10 Good! (1,397 reviews)
Clean room, quick check-in and very friendly staff

Reviewed on Jan 19, 2026

Hilton Garden Inn Orange Beach Beachfront
Hampton Inn & Suites Orange Beach/Gulf Front

Hampton Inn & Suites Orange Beach/Gulf Front

2.5 out of 5
25518 Perdido Beach Blvd Orange Beach AL
$106 nightly
The price is $123 total per night from Feb 8 to Feb 9
$123 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,313 reviews)
Great say. The place is really nice. Front desk awesome. My only thing is that's it's pet friendly. That should only be on certain floors because Some of us have allergies. The rug in room looked like a pet stain. But besides that. Great breakfast and the most comfortable beds

Reviewed on Jan 29, 2026

Hampton Inn & Suites Orange Beach/Gulf Front
See all 18,776 properties in Oak
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.

Find the Best Oak Vacation Packages

Oak Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
60ºF
Max Temp Summer
90ºF
Top Sights
Waterville USA, Alabama Gulf Coast Zoo and The Track Family Recreation Center

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Frequently asked questions

How much does an Oak vacation package cost?
You'll find cheap prices from $507 on Expedia for your Oak getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Oak costs.
What are the cheapest months to go to Oak?
March, May and August are the best times to look for cheap Oak vacation packages. Traveling in quieter periods means you can typically find reduced prices on flights and accommodations.
How many days is enough for Oak?
With a well-organized itinerary, you can easily hit the main Oak attractions in a handful of days. But if you prefer to explore off the beaten track or take day trips, consider booking your Oak vacation for longer.
How to find the best Oak package deals?
Use Expedia's filters to find some unbeatable Oak package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Oak package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book an Oak vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can customize your Oak getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Oak?
If you're considering an impromptu Oak adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Oak vacation packages?
Jet off on your perfect trip to Oak with our Book Now, Pay Later vacations. No need to scrimp and save or wait for your next payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stay on budget and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.