Santa Rosa Island Luxury Vacations

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Flight and Luxury hotel deals in Santa Rosa Island

Price found within the past 48 hours. Click for updated prices.
Hilton Pensacola Beach

Hilton Pensacola Beach

CA $1,053
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pensacola (PNS)
8.2/10 Very good! (1,002 reviews)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

Okaloosa Island
CA $1,427
per person
Sep 19 - Sep 26
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pensacola (PNS)
8.2/10 Very good! (3,442 reviews)
Our stay was just ok , nothing special

Reviewed on Aug 14, 2026

 The Pensacola Beach Resort

The Pensacola Beach Resort

Villa Sabine
CA $1,075
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pensacola (PNS)
9.6/10 Exceptional! (3,458 reviews)
Portofino Island Resort

Portofino Island Resort

CA $1,436
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pensacola (PNS)
8.8/10 Excellent! (493 reviews)
Pros: beautiful view, and the room was nice Cons: a/c issues twice had to move rooms. Website marketing was misleading - numerous dogs on property even though the website said otherwise, and my fiance is allergic to dogs so she had health issues most of the trip. When I messaged the resort about this issue and a possible departure and refund, the resort staff was very rude and the customer service was atrocious. Website advertises resort feel, however only 2 small restaurants and a tiny market. No adult areas or privacy opportunities aside from staying in your room. Room had no soundproof - while my fiancé was sick in bed from dog allergies from your property, we could hear all activity outside the room late at night, and clearly hear our neighbors fighting and slamming doors until 4am. Needless to say, the “resort” and every pool was packed and our only escape was back to our room. I would recommend Portofino island resort only to locals that are looking for a quick getaway with their kids.

Reviewed on Aug 10, 2026

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4 Night Luxury holidays in Santa Rosa Island

Price found within the past 48 hours. Click for updated prices.
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

Okaloosa Island
CA $1,068
per person
Oct 5 - Oct 9
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pensacola (PNS)
8.2/10 Very good! (3,442 reviews)
Our stay was just ok , nothing special

Reviewed on Aug 14, 2026

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Plan the perfect luxury Santa Rosa Island vacation with Expedia

What are some benefits when booking luxury Santa Rosa Island vacations?

When you book a luxury Santa Rosa Island vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Santa Rosa Island?

If you're looking for something luxurious in Santa Rosa Island, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,053, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 0. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Santa Rosa Island. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Santa Rosa Island?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Santa Rosa Island.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Santa Rosa Island. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Santa Rosa Island?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Santa Rosa Island or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Santa Rosa Island. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Santa Rosa Island

Beach Club Resort Residence and Spa

Beach Club Resort Residence and Spa

18 Via De Luna Pensacola Beach FL
  • 24 min drive from Navarre Beach
Book a stay at this luxury aparthotel in Pensacola Beach. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Pensacola Beach Boardwalk ...
8.2/10 Very good! (121 reviews)
"Encantada con el lugar se los recomiendo y el precio aceptable valió la pena mi estancia en Beach club resort&spa. Un hotel bn ubicado y muy bonito. En verano volveré a repetir"

Reviewed on Apr 20, 2026

Beach Club Resort Residence and Spa
Emerald Coast Inn And Suites

Emerald Coast Inn And Suites

1214 Miracle Strip Pkwy Se Fort Walton Beach FL
  • 23 min drive from Navarre Beach
Stay at this hotel in Fort Walton Beach. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions HarborWalk Village and Destin Harbor Boardwalk ...
7.4/10 Good! (1,000 reviews)
"No working phone in room. Didn't feel entirely safe. Staff very accommodating."

Reviewed on Jul 1, 2022

Emerald Coast Inn And Suites
Fairfield Inn & Suites by Marriott Pensacola Beach

Fairfield Inn & Suites by Marriott Pensacola Beach

16 Via de Luna Dr Pensacola Beach FL
  • 24 min drive from Navarre Beach
Book a stay at this beach hotel in Pensacola Beach. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our ...
9.4/10 Exceptional! (1,428 reviews)
"This was our first family trip to Pensacola, and I sure am glad we chose Fairfield Inn & Suites. Check in was a breeze with the friendly staff, who accommodated us with an early check in since a room was available upon our arrival. The room was nice and clean which was a relief plus the ocean view ..."

Reviewed on Aug 15, 2026

Fairfield Inn & Suites by Marriott Pensacola Beach
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.

Things to do

Screaming Eagle Speedboat Thrill Ride in Destin

Screaming Eagle Speedboat Thrill Ride in Destin

CA $95
per adult
Screaming Eagle Speedboat Thrill Ride in Destin
Shark Boat Destin Dolphin Watch and Sunset Cruise

Shark Boat Destin Dolphin Watch and Sunset Cruise

CA $53
per adult
Shark Boat Destin Dolphin Watch and Sunset Cruise
Dolphin & Sunset Cruises

Dolphin & Sunset Cruises

CA $55
per adult
96% of travellers recommend
Dolphin & Sunset Cruises
See all activities in Santa Rosa Island

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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.