Santa Rosa Island Vacations from ￥227,098

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The Latest Santa Rosa Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Okaloosa Island
Price was ￥249,855, price is now ￥227,098 per person
￥227,098
per person
Sep 18 - Sep 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Pensacola (PNS)
9.2/10 Wonderful! (1,016 reviews)
We had a great stay at Weecrest in Florida! The hotel was very clean, and the staff made our visit enjoyable. Breakfast was included with our stay, which was a nice bonus. While the food could have been a little more seasoned, there was a good variety and we appreciated having it available each morning. The only downside was a strong raw chicken odor when we first parked, but thankfully that didn't affect the rest of our stay. Overall, we had a wonderful experience and would definitely consider staying here again.

Reviewed on Jul 3, 2026

Sundrift Inn

Sundrift Inn

3 out of 5
Okaloosa Island
Price was ￥252,030, price is now ￥238,720 per person
￥238,720
per person
Sep 18 - Sep 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Pensacola (PNS)
9/10 Wonderful! (653 reviews)
Perfect location for a beach vacation.

Reviewed on Jul 3, 2026

The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Price was ￥284,752, price is now ￥270,800 per person
￥270,800
per person
Sep 18 - Sep 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,008 reviews)
Love this place!

Reviewed on Jul 3, 2026

Emerald Isle 706

Emerald Isle 706

3 out of 5
Okaloosa Island
Price was ￥300,966, price is now ￥290,005 per person
￥290,005
per person
Sep 18 - Sep 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Pensacola (PNS)
No reviews
IT HAS BLOOD ON THE COVERS, CEALING FAN WAS DURTY,NOT EVEN A NEW TOILET PAPER... ON THE PICTURES SHOW A DIFFERENT BUILDING THAN WHAT IT WAS.. P

Reviewed on Jul 2, 2026

Completely Coastal

Completely Coastal

3 out of 5
Okaloosa Island
Price was ￥304,167, price is now ￥295,200 per person
￥295,200
per person
Sep 18 - Sep 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Pensacola (PNS)
No reviews

Where to stay in Santa Rosa Island

Find the best Santa Rosa Island areas and neighborhoods for the activities you enjoy most. Learn more about Santa Rosa Island
A lifeguard tower on a sandy beach with a clear blue sky.

Okaloosa Island

1 out of top 10 points of interest in this area

The perfect place for a romantic getaway or a family weekend retreat, this is an unforgettable shoreline delight.

Find hotels in Okaloosa Island

Find the Best Santa Rosa Island Vacation Packages

Santa Rosa Island Hotel Deals

The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Miracle Strip Parkway Southeast, 1500 Fort Walton Beach FL
Fully refundableReserve now, pay when you stay
The price is ￥46,969 per night from Aug 5 to Aug 6
￥46,969
￥59,535 total
Aug 5 - Aug 6
includes taxes & fees
8.2/10 Very Good! (3,321 reviews)
"Todo bien"

Reviewed on Jul 4, 2026

The Island Resort at Fort Walton Beach
Wyndham Garden Fort Walton Beach Destin

Wyndham Garden Fort Walton Beach Destin

3 out of 5
573 Santa Rosa Blvd Fort Walton Beach FL
Fully refundableReserve now, pay when you stay
The price is ￥35,333 per night from Aug 2 to Aug 3
￥35,333
￥39,926 total
Aug 2 - Aug 3
includes taxes & fees
8.2/10 Very Good! (2,430 reviews)
"The room was clean, the view was amazing and the hot tub felt great."

Reviewed on Jul 3, 2026

Wyndham Garden Fort Walton Beach Destin
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
The price is ￥52,129 per night from Jul 19 to Jul 20
￥52,129
￥59,715 total
Jul 19 - Jul 20
includes taxes & fees
9.6/10 Exceptional! (3,339 reviews)
"First time staying here and will definitely stay again!"

Reviewed on Jul 4, 2026

The Pensacola Beach Resort
See all 6,267 properties in Santa Rosa Island
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.

Stay near popular Santa Rosa Island attractions

A pier with green supports extending into turquoise water.
Photo by Brad Taylor
Open Photo by Brad Taylor

Navarre Beach

9.6/10 (1,114 reviews)
Navarre Beach dazzles with pristine sugar-white sands and emerald waters along Florida's Gulf Coast. Explore the longest fishing pier in Florida or snorkel the Marine Sanctuary's underwater ecosystem.
See properties

What to do in Santa Rosa Island

Dolphin & Sunset Cruises

Dolphin & Sunset Cruises

￥6,238
per adult
94% of travellers recommend
Dolphin & Sunset Cruises
4 Hour Destin Harbor Crab Island Excursion

4 Hour Destin Harbor Crab Island Excursion

￥12,636
per adult
100% of travellers recommend
4 Hour Destin Harbor Crab Island Excursion
Destin Dolphin and Sunset Cruise

Destin Dolphin Watching and Sunset Cruise

￥4,319
per adult
100% of travellers recommend
Destin Dolphin Watching and Sunset Cruise
See all activities in Santa Rosa Island

Frequently asked questions

How much does a Santa Rosa Island vacation package cost?
Much less than you might think — from a low ￥227,098, as a matter of fact! By bundling flights, hotels and car rentals into your own tailor-made travel package, your getaway to Santa Rosa Island is only clicks away.
How do I get a cheap travel package to Santa Rosa Island?
One of the simplest ways to save dollars (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all. Select a combination that best fits you and see your savings pile up. Of course, a travel package is never one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 hotel options from all over the world, which lets you customize your Santa Rosa Island getaway.
How far in advance should I book my Santa Rosa Island vacation?
Browse Expedia to compare flights ASAP. You can normally purchase a seat up to a year prior to departure. If it's too early for your preferred air carrier, or you've left things to the last moment, don't worry. Cheap fares to Santa Rosa Island occasionally appear just weeks before the date of departure.
What does an Expedia Santa Rosa Island travel package include?
Choose from any combination of hotels, rental cars and flights. Once you've made your booking, you can add tours and experiences. Want to pick your fare class? That's also possible. The choice is all yours when it comes to arranging your ideal Santa Rosa Island trip.
What should I know before booking a Santa Rosa Island travel package?
When you book your flights, hotels and car rentals together, you'll score incredible discounts. Whether you're organizing a beach escape in a villa or would rather stay in an upscale city hotel, Expedia will make it happen for less.
Can I choose my airline with a Santa Rosa Island Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our vacation packages give you the freedom to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Santa Rosa Island vacation package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Santa Rosa Island vacation package in the last 24 hours? You may be able to make any changes for free. If it's been longer than that, you may be charged a fee by your hotel, airline or car rental company. For more details, look up our Customer Service Portal. We're here to help you each step of the way.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.