Thousand Oaks Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Jun 25 - Jun 30

    Holiday Inn Express Orange Beach by IHG + Flight

    Orange Beach
    5 nights
    2.5 star property
    8.8/10 - Excellent (1,007 reviews)
    "Staff was excellent and helpful."
    Reviewed May 18, 2026
    Roundtrip • Toronto (YYZ) - Pensacola (PNS)
    YYZ - PNS • 1 stop PNS - YYZ • 1 stop
    CA $1,853
    CA $1,258
    per traveller
    found 13 hours ago
    Holiday Inn Express Orange Beach by IHG
  • Exterior
    Jun 25 - Jun 30

    Hotel Indigo Orange Beach - Gulf Shores by IHG + Flight

    Orange Beach
    5 nights
    3.5 star property
    9.4/10 - Exceptional (1,006 reviews)
    "We absolutely loved the family room we had with the bunkbed for the kids. The set up was fantastic! Such kind staff and love that the coffee /restaurant was right next door. Great location and service. Would stay again."
    Reviewed May 18, 2026
    Roundtrip • Toronto (YYZ) - Pensacola (PNS)
    YYZ - PNS • 1 stop PNS - YYZ • 1 stop
    CA $2,191
    CA $1,565
    per traveller
    found 13 hours ago
    Hotel Indigo Orange Beach - Gulf Shores by IHG
  • House (3 Bedrooms) | Front of property
    Jul 24 - Aug 14

    Beachfront Townhome With Instant Access to Beach Beachside Kisses by Avantstay + Flight

    Okaloosa Island
    21 nights
    3.0 star property
    Roundtrip • Toronto (YYZ) - Fort Walton Beach (VPS)
    YYZ - VPS • 1 stop VPS - YYZ • 1 stop
    CA $20,828
    CA $15,095
    per traveller
    found 1 day ago
    Beachfront Townhome With Instant Access to Beach Beachside Kisses by Avantstay
  • Condo, 2 Bedrooms, Patio, Courtyard View | Terrace/patio
    Jul 24 - Aug 14

    El Matador + Flight

    Okaloosa Island
    21 nights
    4.0 star property
    10/10 - Exceptional (1 review)
    "Great room. "
    Reviewed May 15, 2026
    Roundtrip • Toronto (YYZ) - Fort Walton Beach (VPS)
    YYZ - VPS • 1 stop VPS - YYZ • 1 stop
    CA $7,574
    CA $5,532
    per traveller
    found 1 day ago
    El Matador
  • Desk, iron/ironing board, free WiFi
    Jul 24 - Aug 14

    OYO Hotel Pensacola I-10 & Hwy 29 + Flight

    Northwest Pensacola
    21 nights
    2.0 star property
    4.2/10 - (732 reviews)
    "Love it and ac word great "
    Reviewed May 14, 2026
    Roundtrip • Toronto (YYZ) - Pensacola (PNS)
    YYZ - PNS • 1 stop PNS - YYZ • 1 stop
    CA $3,974
    CA $2,903
    per traveller
    found 1 day ago
    OYO Hotel Pensacola I-10 & Hwy 29

Where to stay in Thousand Oaks

Find the best Thousand Oaks areas and neighborhoods for the activities you enjoy most. Learn more about Thousand Oaks
Downtown Pensacola

Downtown Pensacola

3 out of top 10 points of interest in this area

If you're spending some time in Downtown Pensacola, Saenger Theatre and Historic Pensacola Village are top sights worth seeing.

Find hotels in Downtown Pensacola

Thousand Oaks Hotel Deals

The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road Pensacola Beach FL
The price is CA $432 per night from May 31 to Jun 1
CA $432
CA $494 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (3,135 reviews)
"We really enjoyed our stay here . Close to everything but not in the mix of the overly crowded beach area. Very nice hotel . Clean rooms . Just wish there was a microwave."

Reviewed on May 19, 2026

The Pensacola Beach Resort
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
The price is CA $210 per night from May 21 to May 22
CA $210
CA $248 total
May 21 - May 22
includes taxes & fees
8.8/10 Excellent! (3,161 reviews)
"Clean rooms , friendly staff and great breakfast"

Reviewed on May 19, 2026

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
The price is CA $327 per night from May 31 to Jun 1
CA $327
CA $375 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (2,409 reviews)
"Breakfast was fresh but didn't have grits"

Reviewed on May 18, 2026

Hampton Inn Pensacola Beach
See all 3,451 properties in Thousand Oaks
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
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Family Vacations
Family Vacations

Frequently asked questions

How much does a Thousand Oaks vacation package cost?
Perhaps much less than you think — from a low , actually! By bundling flights, hotels and car rentals into your own custom-made package, your trip to Thousand Oaks is just clicks away.
How do I get a cheap travel package to Thousand Oaks?
Our Thousand Oaks vacation packages offer plenty of savings for the savvy traveler. For the best deal, simply combine your hotel, flights and activities into a neat and tidy package. But cheap prices are only the start of your next awesome adventure. Book with Expedia and you'll have more than 550 airlines and 1,000,000 hotel options throughout the world to select from. No matter your budget, there's a package to suit you.
Where should I stay in Thousand Oaks?
Make sightseeing a breeze by staying someplace just a stone's throw away from Thousand Oaks's big attractions. Pensacola Naval Air Station and Pensacola Bay Center are two of the most popular.
How far in advance should I book my Thousand Oaks vacation?
Travelers are normally able to compare international airfares on Expedia up to a year in advance of departure. Booking at the last minute? With a stroke of luck, it's still possible to nab an affordable ticket just weeks before your journey.
What does an Expedia Thousand Oaks travel package include?
Travel packages include flights, rental cars and hotels, but you can combine any of them to create your perfect Thousand Oaks escape. You can also add on a few activities and tours once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Thousand Oaks travel package?
So many places to wander around, so many things to experience. With a package, you can cross more of them off your list. Combine your flights, hotels and rental cars and get ready to save.
Can I choose my airline with a Thousand Oaks Expedia vacation package?
With a vacation package, you're in control. Whether you'd like to fly to Thousand Oaks in coach or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Thousand Oaks vacation package?
Don't stress if you're rethinking your Thousand Oaks vacation package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We know life can occasionally throw a spanner in the travel works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.

Discover the most popular places to visit in Thousand Oaks

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 fascinating museums.

Perdido Key Beach
Pensacola_UniversityofWestFlorida_6127826-10

University of West Florida

Enjoy the collegiate vibe when you visit University of West Florida, during your trip to Ferry Pass. Wander the beautiful beaches in this family-friendly area.

University of West Florida

Things to do

Orange Beach: Dolphin-Watching Eco-Boat Tour

Orange Beach: Dolphin-Watching Eco-Boat Tour

CA $47
per adult
100% of travellers recommend
Orange Beach: Dolphin-Watching Eco-Boat Tour
Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour

Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour

CA $53
per adult
98% of travellers recommend
Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour
2-Hour Dolphin and Nature Eco Tour from Orange Beach

2-Hour Dolphin and Nature Eco Tour from Orange Beach

CA $51
per adult
96% of travellers recommend
2-Hour Dolphin and Nature Eco Tour from Orange Beach
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.