Thousand Oaks Vacations from $550

Book a Hotel + Flight or Car together to unlock savings

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.
30A Inn & Suites

30A Inn & Suites

3 out of 5
Dune Allen Beach
Price was $727, price is now $550 per person
$550
per person
Nov 10 - Nov 16
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
9/10 Wonderful! (617 reviews)
Really good place to stay!

Reviewed on Sep 26, 2025

WaterColor Inn & Resort

WaterColor Inn & Resort

4 out of 5
Watercolor
Save 100% on your flight
Price was $2,237, price is now $1,583 per person
$1,583
per person
Nov 10 - Nov 16
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
9.4/10 Exceptional! (252 reviews)
Location and friendly staff

Reviewed on Sep 24, 2025

Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Price was $918, price is now $660 per person
$660
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Fort Walton Beach (VPS)
9/10 Wonderful! (153 reviews)
It was a beautiful place to stay and the staff were so friendly and helpful.

Reviewed on Jul 3, 2025

The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Price was $1,841, price is now $1,335 per person
$1,335
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,005 reviews)
The staff was phenomenal. I have been to 5 continents and stayed in hotels all around the US, and they way I was treated here was in the top 5 of any property I have stayed at in 50 years of living.

Reviewed on Sep 17, 2025

Harborside by Avantstay Expansive Destin Retreat

Harborside by Avantstay Expansive Destin Retreat

3 out of 5
Holiday Isle
Save 100% on your flight
Price was $4,391, price is now $3,249 per person
$3,249
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Fort Walton Beach (VPS)
8/10 Very Good! (1 review)

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
$89 nightly
The price is $100 total per night from Oct 14 to Oct 15
$100 total
Oct 14 - Oct 15
Total with taxes and fees
8.8/10 Excellent! (2,815 reviews)
"Great value for money"

Reviewed on Sep 28, 2025

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
$135 nightly
The price is $152 total per night from Oct 31 to Nov 1
$152 total
Oct 31 - Nov 1
Total with taxes and fees
8.2/10 Very Good! (2,175 reviews)
"Good"

Reviewed on Sep 24, 2025

Hampton Inn Pensacola Beach
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road, Pensacola Beach, FL
$191 nightly
The price is $215 total per night from Oct 29 to Oct 30
$215 total
Oct 29 - Oct 30
Total with taxes and fees
9.4/10 Exceptional! (2,560 reviews)
"We LOVED this property! It was so pretty and clean. The rooms we a good size too."

Reviewed on Sep 28, 2025

The Pensacola Beach Resort
See all 3,377 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

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
Perdido Key Beach

Perdido Key Beach

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

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

National Museum of Naval Aviation

You can spend an afternoon studying the exhibits at National Museum of Naval Aviation in Pensacola. Discover the beautiful sunsets and top-notch restaurants in this family-friendly area.

National Museum of Naval Aviation

Things to do

Alabama Gulf Coast Dolphin Cruise

Alabama Gulf Coast Dolphin Cruise

$30
per adult
92% of travellers recommend
Alabama Gulf Coast Dolphin Cruise
Orange Beach: Dolphin-Watching Eco-Boat Tour

Orange Beach: Dolphin-Watching Eco-Boat Tour

$34
per adult
100% of travellers recommend
Orange Beach: Dolphin-Watching Eco-Boat Tour
Dolphin Watching aboard the Cold Mil Fleet

Dolphin Watching aboard the Cold Mil Fleet

$30
per adult
Dolphin Watching aboard the Cold Mil Fleet
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.