Santa Rosa Island Vacation Packages

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Top Santa Rosa Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Bay Club of Sandestin

Bay Club of Sandestin

CA $1,244
per person
Dec 18 - Dec 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Walton Beach (VPS)
9/10 Wonderful! (182 reviews)
We had a good stay overall. The property is on the bay side, so there is no direct beach access, but the free shuttle to the beach across the road was convenient. Driving to the beach is also an option. One thing to note is that a golf cart is not included with the package, so plan accordingly. The property itself is a bit dated, including some of the appliances, but it is very well maintained and comfortable for a short family trip. We enjoyed the pool and the proximity to the beaches and nearby attractions. Overall, it was a pleasant and practical stay for the price.

Reviewed on Sep 12, 2026

The Bluefin - Ultra Luxury Beach Home

The Bluefin - Ultra Luxury Beach Home

Crystal Beach
Save 100% on your flight
CA $3,351
per person
Dec 18 - Dec 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Walton Beach (VPS)
No reviews
Club Wyndham at Majestic Sun

Club Wyndham at Majestic Sun

CA $1,374
per person
Dec 18 - Dec 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Walton Beach (VPS)
8.2/10 Very good! (65 reviews)
Perfect location great staff and tons around to shop and dine

Reviewed on Jan 15, 2026

Harbor Suites at Harborwalk Village

Harbor Suites at Harborwalk Village

CA $1,463
per person
Dec 18 - Dec 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Walton Beach (VPS)
9.4/10 Exceptional! (93 reviews)
The front desk staff was very friendly, and I was very satisfied with both the room condition and the location. The hotel layout was a little confusing at first, but it became easier once we got used to it. Unfortunately, the towels we requested were never delivered, and the conditioner bottle appeared to contain body lotion instead. The pool was also very small.

Reviewed on Sep 23, 2026

The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

Crystal Beach
CA $1,816
per person
Dec 18 - Dec 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,012 reviews)
Hospitality at its best staff went above and beyond COD, location perfect next to naturally preserved state park, beach area perfect

Reviewed on Sep 24, 2026

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
A diver holding a large shell underwater.

Villa Sabine

1 out of top 10 points of interest in this area

While visiting Villa Sabine, you might make a stop by sights like Casino Beach and Pensacola Beach Beaches.

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A sandy beach with a pathway leading to a signpost labeled '25E'.

Villa Segunda

If you're spending some time in Villa Segunda, Opal Beach and Santa Rosa Sound are top sights worth seeing.

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A coastal cityscape with a long beach, a marina, and a prominent hotel.

Toilla Segunda

While Toilla Segunda might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Pensacola Beach Boardwalk and Quietwater Beach.

Find hotels in Toilla Segunda
A coastal town with a marina, a bridge, and a beach.

Villa Primera

While visiting Villa Primera, you might make a stop by sights like Pensacola Beach Beaches and Santa Rosa Sound.

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Ready to book your vacation to Santa Rosa Island?

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Santa Rosa Island Hotel Deals

The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

Miracle Strip Parkway Southeast, 1500 Fort Walton Beach FL
Fully refundableReserve now, pay when you stay
CA $146
CA $216 total
Oct 25 - Oct 26
includes taxes & fees
The Island Resort at Fort Walton Beach
The Pensacola Beach Resort

The Pensacola Beach Resort

165 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
CA $291
CA $333 total
Sep 30 - Oct 1
includes taxes & fees
The Pensacola Beach Resort
Surf & Sand Hotel

Surf & Sand Hotel

40 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
CA $154
CA $182 total
Oct 26 - Oct 27
includes taxes & fees
8.8/10 Excellent! (3,272 reviews)
"Kayaks and paddle boards and bikes where awesome to use, everything within walking distance didn’t even have to drive the car anywhere,"

Reviewed on Sep 24, 2026

Surf & Sand Hotel
See all 6,241 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.
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Stay near popular Santa Rosa Island attractions

A beach with clear turquoise water, white sand, and a pier extending into the ocean.
Photo by mlur_RN

Navarre Beach

9.6/10 (1,114 reviews)
Head over to Navarre Beach, a favorite beach in Navarre to enjoy the surf and sand, along with fishing. Wander the seaside or discover the sunsets in this relaxing area.
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A sandy beach with a pathway leading to a signpost labeled '25E'.
Photo by Susan Shope

Pensacola Beach Beaches

9.6/10 (2,160 reviews)
Why not spend a lazy afternoon at Pensacola Beach Beaches during your trip to Pensacola Beach? Stroll along the area's seaside, or simply savor its top-notch restaurants.
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A beach with waves, a pier, and a clear sky.

Okaloosa Island Beach

9.4/10 (240 reviews)
Why not spend a lazy afternoon at Okaloosa Island Beach during your trip to Fort Walton Beach? Wander the beautiful beaches and seaside in this relaxing area.
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A large cannon on a circular platform with a brick wall and a bench in the foreground, set against a clear sky and distant buildings.

Fort Pickens

9.2/10 (1,165 reviews)
You can find out about the history of Pensacola Beach with a stop at Fort Pickens. Experience the great live music or attend a sporting event in this family-friendly area.
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A wooden pier extending into a body of water with a cloudy sky above.
Photo by mlur_RN

Pensacola Beach Boardwalk

8.8/10 (928 reviews)
You can search for that perfect souvenir at Pensacola Beach Boardwalk during your visit to Pensacola Beach. Wander the beautiful beaches and seaside in this family-friendly area.
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A sunset over the ocean with a pier extending into the water.

Fort Walton Beaches

9.4/10 (821 reviews)
Why not spend a lazy afternoon at Fort Walton Beaches during your trip to Fort Walton Beach? Wander the beautiful beaches and seaside in this relaxing area.
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A modern building with a brick-paved entrance, steps leading up to the entrance, and three flags on flagpoles.

Destin-Fort Walton Beach Convention Center

8.4/10 (441 reviews)
Learn about the events happening at Destin-Fort Walton Beach Convention Center during your trip to Fort Walton Beach. Wander the beautiful beaches and seaside in this family-friendly area.
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A coastal road with beach huts and a parking area.
Photo by Brad Taylor

Opal Beach

8.8/10 (314 reviews)
Why not spend a lazy afternoon at Opal Beach during your trip to Pensacola Beach? Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
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What to do in Santa Rosa Island

SeaQuest Daytime Dolphin Cruise in Destin

SeaQuest Daytime Dolphin Cruise in Destin

CA $38
per adult
100% of travellers recommend
SeaQuest Daytime Dolphin Cruise in Destin
Crab Island Explorer Catamaran Tours to Crab Island

Crab Island Explorer Catamaran Tours to Crab Island

CA $55
per adult
100% of travellers recommend
Crab Island Explorer Catamaran Tours to Crab Island
SunVenture I and SunVenture II at Crab Island in Destin, FL

4 Hour Destin Harbor Crab Island Excursion

CA $111
per adult
100% of travellers recommend
4 Hour Destin Harbor Crab Island Excursion
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 CA $1,244, 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.

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