Thousand Oaks Vacations from $316

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Spark by Hilton Destin

Spark by Hilton Destin

3 out of 5
Price was $484, price is now $316 per person
$316
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
8.6/10 Excellent! (638 reviews)
Very clean room! Everything in good working order! Nice staff. Loved the location…close to stores and restaurants.

Reviewed on Nov 28, 2025

The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Save 100% on your flight
Price was $1,389, price is now $721 per person
$721
per person
Jan 7 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,000 reviews)
The staff was incredibly friendly. The room was spotless. The pool areas were excellent and well stocked. The private beach was the BEST! Thank you to The Henderson team for a wonderful stay!

Reviewed on Nov 19, 2025

The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Okaloosa Island
Save 100% on your flight
Price was $850, price is now $479 per person
$479
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Pensacola (PNS)
8.4/10 Very Good! (2,910 reviews)
Awesome staff. Awesome place, pool, hot tub, breakfast, location on the beach.

Reviewed on Nov 28, 2025

The Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $602, price is now $364 per person
$364
per person
Feb 21 - Feb 25
found 7 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Pensacola (PNS)
9.2/10 Wonderful! (1,004 reviews)
yes only 3 handicap parking spaces open parking 100 yards away not very handicap friendly

Reviewed on Nov 28, 2025

Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Save 100% on your flight
Price was $873, price is now $540 per person
$540
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
7.8/10 Good! (3,841 reviews)
We love staying here been a couple times always great.

Reviewed on Nov 13, 2025

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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

The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $161 total per night from Dec 10 to Dec 11
$161 total
Dec 10 - Dec 11
Total with taxes and fees
9.4/10 Exceptional! (2,644 reviews)
The hotel and area were beautiful. Rooms large and comfortable.

Reviewed on Nov 27, 2025

The Pensacola Beach Resort
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $67 total per night from Dec 2 to Dec 3
$67 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (2,910 reviews)
Yes . Very nice and friendly!! I booked a 2nd night stay and accidentally booked the wrong night and the staff corrected it for me!!

Reviewed on Nov 25, 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
$97 nightly
The price is $109 total per night from Dec 7 to Dec 8
$109 total
Dec 7 - Dec 8
Total with taxes and fees
8.2/10 Very Good! (2,247 reviews)
Staff was great - breakfast was superb!

Reviewed on Nov 23, 2025

Hampton Inn Pensacola Beach
See all 3,432 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 great live music and fascinating museums.

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 lively bars in this family-friendly area.

National Museum of Naval Aviation

Things to do

2-Hour Dolphin and Nature Eco Tour from Orange Beach

2-Hour Dolphin and Nature Eco Tour from Orange Beach

$38
per adult
92% of travellers recommend
2-Hour Dolphin and Nature Eco Tour from Orange Beach
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
The Explorer at Sunset

Dolphin and Nature Sunset Cruise from Orange Beach

$50
per adult
98% of travellers recommend
Dolphin and Nature Sunset Cruise 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.