Santa Rosa Island Vacations from $759

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

The Latest Santa Rosa Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Club Wyndham at Majestic Sun

Club Wyndham at Majestic Sun

Save 100% on your flight
$759
per person
Oct 27 - Nov 2
found 2 days ago
Roundtrip flight included
Dallas (DFW) 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

The Bluefin - Ultra Luxury Beach Home

The Bluefin - Ultra Luxury Beach Home

Crystal Beach
Save 100% on your flight
$1,404
per person
Oct 27 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
No reviews
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

Crystal Beach
Save 100% on your flight
$968
per person
Oct 27 - Nov 2
found 2 days ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,008 reviews)
Despite arriving at 11AM and being told we were second in the queue for housekeeping to turn over our room, we had to wait until 3:30 for that to actually happen. I realize check in time is not until 4, but I was told at the front desk that it’s anywhere between 4 and 6 PM. 6?! That seems a little late when you’re wasting your entire day trying to get into your hotel room. In the subsequent days of our stay, I personally witnessed housekeeping still cleaning rooms on our floor at 5:30 at night. I requested with the women I spoke to to please come earlier in the day after we returned a couple of times at the end of a long day on the beach and at the pool expecting a tidied room with fresh towels to instead it still being dirty. For the nightly price to stay here, even in the summer “off season,” I found housekeeping that slow to be unacceptable. On the beach, you must pay extra to rent an umbrella and two lounge chairs. We are a family of three, so this was not exactly convenient with one of us having to be relegated to a towel in the sand. You can rent either morning, afternoon, or a full day session. One morning, we rented for just the morning session, but decided we would rather be back in the afternoon, so I went up to the kiosk and asked if we could just extend our stay to full day and pay the difference between the two prices. I was told that we would have to pay a whole separate afternoon booking fee for a total of $90 instead of the $69 all day fee.

Reviewed on Aug 26, 2026

Sundrift Inn

Sundrift Inn

Okaloosa Island
Save 100% on your flight
$825
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Pensacola (PNS)
9/10 Wonderful! (779 reviews)
Rude and charged you for everything

Reviewed on Aug 25, 2026

Woodland Shores by Avantstay Sleeps 22 Massive Pool + Spa Golf Cart + Game Room + BBQ Near Seaside

Woodland Shores by Avantstay Sleeps 22 Massive Pool + Spa Golf Cart + Game Room + BBQ Near Seaside

Gulfview Heights
Save 100% on your flight
$2,374
per person
Nov 11 - Nov 17
found 2 days ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Santa Rosa Island
View all trips

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.

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.

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.

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.

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.

Stay near popular Santa Rosa Island attractions

A pier with green supports extending into turquoise water.
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
A beach with white sand and tall grasses leading to the ocean.

Pensacola Beach Beaches

9.6/10 (2,160 reviews)
Sink your toes into Pensacola Beach's legendary sugar-white sands along emerald Gulf waters. Explore the vibrant beachfront scene or find serenity in the adjacent Gulf Islands National Seashore preserves.
See properties
A beach with waves, a pier, and a clear sky.

Okaloosa Island Beach

9.4/10 (240 reviews)
Okaloosa Island Beach captivates with powdery white sands and striking emerald waters along Florida's Gulf Coast. Enjoy premium seafood at the Boardwalk restaurants after a day of sunbathing and gentle waves.
See properties
A historic brick staircase leading up to an arched bridge.

Fort Pickens

9.2/10 (1,165 reviews)
This Civil War-era fort showcases 19th-century military engineering through brick corridors and gun batteries. Explore its storied past while enjoying the surrounding Gulf Islands National Seashore.
See properties
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)
This Gulf Coast hub combines waterfront dining with boutique shopping along a lively promenade. Enjoy fresh seafood at sunset or catch live music while overlooking Quietwater Beach's calm waters.
See properties
A coastal road with beach huts and a parking area.
Photo by Brad Taylor

Opal Beach

8.8/10 (314 reviews)
Pristine white sands and crystal-clear waters define this tranquil stretch of Gulf Islands National Seashore. Enjoy the peaceful atmosphere with convenient amenities like picnic shelters and outdoor showers.
See properties
A pier extending into the ocean with waves crashing against it.

Pensacola Beach Gulf Pier

9.0/10 (2,289 reviews)
Extending 1,470 feet into the Gulf of Mexico, this pier offers exceptional fishing without a boat. Spot dolphins and rays while enjoying panoramic views of emerald waters and breathtaking sunsets.
See properties

What to do in Santa Rosa Island

Destin Dolphin and Sunset Cruise

Destin Dolphin Watching and Sunset Cruise

$27
per adult
100% of travellers recommend
Destin Dolphin Watching and Sunset Cruise
Screaming Eagle Speedboat Thrill Ride in Destin

Screaming Eagle Speedboat Thrill Ride in Destin

$68
per adult
Screaming Eagle Speedboat Thrill Ride in Destin
Dolphin & Sunset Cruises

Dolphin & Sunset Cruises

$39
per adult
96% of travellers recommend
Dolphin & Sunset Cruises
See all activities in Santa Rosa Island

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
$178 nightly
$201 total
Sep 7 - Sep 8
Total with taxes and 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
$219 nightly
$246 total
Aug 30 - Aug 31
Total with taxes and fees
The Pensacola Beach Resort
Wyndham Garden Fort Walton Beach Destin

Wyndham Garden Fort Walton Beach Destin

573 Santa Rosa Blvd Fort Walton Beach FL
Fully refundableReserve now, pay when you stay
$126 nightly
$143 total
Sep 27 - Sep 28
Total with taxes and fees
8.2/10 Very Good! (2,547 reviews)
"Muy bonito todo"

Reviewed on Aug 26, 2026

Wyndham Garden Fort Walton Beach Destin
See all 6,240 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.

Find the Best Santa Rosa Island Vacation Packages

Santa Rosa Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Pensacola Intl. Airport (PNS)

More vacations you might like

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.