Thousand Oaks Vacations from $647

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Your Thousand Oaks Vacation

Make travel planning hassle-free by snapping up a vacation package to Thousand Oaks. We'll handle the minutiae, so you can focus on appreciating everything this neighborhood can offer. Start your trip to Thousand Oaks by visiting nearby attractions such as University of West Florida, DeLuna Lanes Bowling Center and Uncle Sandys Macaw Bird Park. No matter what your ideal Thousand Oaks vacation may look like, you can make it a reality with Expedia.

The Latest Thousand Oaks Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Fort Walton Beach (VPS)
7.8/10 Good! (3,717 reviews)
Lots of great food options. Comfortable Bed.

Reviewed on Jul 28, 2025

The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Save 100% on your flight
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,007 reviews)
Overall, i loved our stay at the henderson, most staff were helpful and accommodating. Renting a spot on the now private beach was a nightmare and we were never confirmed and that was our only issue. The pools were beautifully kept and our room as well. The younger valet men were also great and helpful, we enjoyed conversing with then.

Reviewed on Jul 27, 2025

Priv Heated Pool + Hot Tub, Boat-friendly, Sleeps 16! Good Times by Avantstay

Priv Heated Pool + Hot Tub, Boat-friendly, Sleeps 16! Good Times by Avantstay

3 out of 5
Seagrove Beach
Save 100% on your flight
per person
Oct 5 - Oct 10
just found
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
No reviews
Gulf-view Retreat w/ Rooftop Deck + Private Pool Villa Anesi by Avantstay

Gulf-view Retreat w/ Rooftop Deck + Private Pool Villa Anesi by Avantstay

3 out of 5
Dune Allen Beach
Save 100% on your flight
per person
Sep 4 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MCI) to Fort Walton Beach (VPS)
No reviews
30A Seaclusion by Avantstay Walk to Beach, Pool

30A Seaclusion by Avantstay Walk to Beach, Pool

3 out of 5
Seagrove Beach
Save 100% on your flight
per person
Oct 5 - Oct 10
just found
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
No reviews

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 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

Thousand Oaks Hotel Deals

Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road, Pensacola Beach, FL
$161 nightly
The price is $181 total per night from Aug 12 to Aug 13
$181 total
Aug 12 - Aug 13
Total includes taxes and fees
8.6/10 Excellent! (2,669 reviews)
"We were very impressed by the hotel, the food, surroundings and cleanliness!! We will definitely be back"

Reviewed on Jul 29, 2025

Surf & Sand Hotel
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road, Pensacola Beach, FL
$242 nightly
The price is $272 total per night from Aug 10 to Aug 11
$272 total
Aug 10 - Aug 11
Total includes taxes and fees
9.2/10 Wonderful! (2,366 reviews)
"Beautiful place right on the beach!"

Reviewed on Jul 27, 2025

The Pensacola Beach Resort
Quality Inn & Suites Pensacola Bayview

Quality Inn & Suites Pensacola Bayview

2.5 out of 5
7601 Scenic Highway, Pensacola, FL
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $82 total per night from Jul 30 to Jul 31
$82 total
Jul 30 - Jul 31
Total includes taxes and fees
7/10 Good! (1,031 reviews)
"Good hotel with cheap rate!"

Reviewed on Jul 27, 2025

Quality Inn & Suites Pensacola Bayview
See all 3,371 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
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Thousand Oaks

Florida Panhandle showing a statue or sculpture and interior views

Pensacola Naval Air Station

4.5/5(697 reviews)

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

4.5/5(283 reviews)

Why not spend a lazy afternoon at Perdido Key Beach during your trip to Pensacola? Experience the area's fascinating museums and entertainment choices.

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

National Museum of Naval Aviation

5/5(488 reviews)

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
Pub Crawl of Pensacola by Pedal Trolley

Party Bike Pub Crawl of Downtown Pensacola

$45
per adult
Party Bike Pub Crawl of Downtown Pensacola
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
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.