Santa Rosa Island Mountain Vacations and Getaways

Book a Mountain Hotel + Flight or Car together to unlock savings

Top Mountain vacation packages 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
$620
per person
Oct 27 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
8.2/10 Very Good! (3,442 reviews)
Landing Apartments Santa Rosa Beach

Landing Apartments Santa Rosa Beach

Save 100% on your flight
$1,045
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (12 reviews)
 The Pensacola Beach Resort

The Pensacola Beach Resort

Villa Sabine
Save 100% on your flight
$927
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Pensacola (PNS)
9.6/10 Exceptional! (3,458 reviews)
Portofino Island Resort

Portofino Island Resort

$1,161
per person
Nov 5 - Nov 10
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Pensacola (PNS)
8.8/10 Excellent! (493 reviews)
The trolleys were very helpful when going from our condo to the beach. Loved having so many dining options right there, as well as room service.

Reviewed on Aug 17, 2026

Pelican Beach 1418 by Pelican Beach Management

Pelican Beach 1418 by Pelican Beach Management

$1,574
per person
Sep 22 - Sep 27
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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

5* Mountain vacations in Santa Rosa Island

Price found within the past 48 hours. Click for updated prices.
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

Crystal Beach
$846
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,007 reviews)
The hotel overall was good. I traveled with my husband and our 15- and 10-year-old children, and we had a pleasant stay. The valet staff were extremely kind, helpful, and welcoming. However, the valet service is also quite expensive at around $80 per day. The ladies who took care of our room were VERY very kind and attentive as well. The restaurant staff were REALLY wonderful—very friendly, attentive, and accommodating. Unfortunately, the food itself was just okay. It wasn’t bad, but for a hotel of this level, we expected better quality. The most disappointing part of our experience was the beach chair service. We found the chairs to be quite old and honestly very uncomfortable. The cost is around $80 with taxes for the day, from 8:00 a.m. to 5:00 p.m., which felt too expensive for the quality and comfort provided. Unfortunately, the young attendants working at the beach were also far from friendly or helpful. What bothered us the most was the way the seating was assigned. Instead of allowing guests to choose from the available chairs, they seemed to decide where they wanted to place you, regardless of where you preferred to sit. The way this was handled felt unnecessarily unpleasant.

Reviewed on Aug 15, 2026

Don't see what you're looking for?
See all available trips from Columbus to Santa Rosa Island
View all trips

3 Night Mountain vacations in Santa Rosa Island

Price found within the past 48 hours. Click for updated prices.
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

Crystal Beach
$703
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,007 reviews)
The hotel overall was good. I traveled with my husband and our 15- and 10-year-old children, and we had a pleasant stay. The valet staff were extremely kind, helpful, and welcoming. However, the valet service is also quite expensive at around $80 per day. The ladies who took care of our room were VERY very kind and attentive as well. The restaurant staff were REALLY wonderful—very friendly, attentive, and accommodating. Unfortunately, the food itself was just okay. It wasn’t bad, but for a hotel of this level, we expected better quality. The most disappointing part of our experience was the beach chair service. We found the chairs to be quite old and honestly very uncomfortable. The cost is around $80 with taxes for the day, from 8:00 a.m. to 5:00 p.m., which felt too expensive for the quality and comfort provided. Unfortunately, the young attendants working at the beach were also far from friendly or helpful. What bothered us the most was the way the seating was assigned. Instead of allowing guests to choose from the available chairs, they seemed to decide where they wanted to place you, regardless of where you preferred to sit. The way this was handled felt unnecessarily unpleasant.

Reviewed on Aug 15, 2026

 The Pensacola Beach Resort

The Pensacola Beach Resort

Villa Sabine
$1,103
per person
Oct 8 - Oct 11
found 18 hours ago
Roundtrip flight included
Dallas (DAL) to Pensacola (PNS)
9.6/10 Exceptional! (3,458 reviews)
Lily Hall- A Boutique Hotel

Lily Hall- A Boutique Hotel

Downtown Pensacola
$734
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
9.4/10 Exceptional! (228 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Santa Rosa Island
View all trips

4 Night Mountain vacations in Santa Rosa Island

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

Wavecrest Lodge

Okaloosa Island
$691
per person
Sep 27 - Oct 1
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
9.2/10 Wonderful! (1,012 reviews)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

Downtown Pensacola
Save 100% on your flight
$877
per person
Sep 20 - Sep 24
found 14 hours ago
Roundtrip non-stop flight included
New York (NYC) to Pensacola (PNS)
9.6/10 Exceptional! (21 reviews)
Room was amazing and I took photos of the bathroom to get ideas for our future build

Reviewed on Nov 21, 2025

 The Pensacola Beach Resort

The Pensacola Beach Resort

Villa Sabine
$784
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
9.6/10 Exceptional! (3,458 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Santa Rosa Island
View all trips

Find amazing mountains vacations in Santa Rosa Island

How to plan for a mountain vacation in Santa Rosa Island?

The first step to planning your mountain vacation to Santa Rosa Island is to decide what dates you want to go. In the winter months, fresh snowfall means you could hit the slopes at ski resorts near Santa Rosa Island, while summer invites you to enjoy scenic hikes. It's a good idea to choose the type of accommodation you'd prefer, too. On Expedia, you'll encounter a vast array of options in Santa Rosa Island, from famous chain hotels to charming cabins. The vacation planning page has more tips for organizing your Santa Rosa Island mountain vacation.

What amenities should I look for when booking a mountain resort in Santa Rosa Island?

When booking accommodation for your mountain vacation to Santa Rosa Island, check to see if where you're staying has heating. Santa Rosa Island's mountain air means it can feel fresh at night. If you're craving a special stay, look to see if the hotel offers mountain view rooms, or has a pool or hot tub to unwind in the evenings. Expedia's handy search filters include all these amenities and more, making it a breeze to book the right place to stay on your Santa Rosa Island vacation package.

Why should I choose a package for my mountain vacation in Santa Rosa Island?

Choosing a package for your Santa Rosa Island vacation often works out cheaper thanks to the savings you get for bundling up your flights and hotel. You'll typically find it costs more when booking these separately. On Expedia, the green label even shows you how much you're saving. Packages also tend to be more flexible, meaning it's more likely you can cancel for free in case your 2026 plans change. You can usually secure your package by paying a small upfront deposit, whereas booking flights separately requires full payment.

What does a Santa Rosa Island package typically include?

Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to Santa Rosa Island from $620. Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each Santa Rosa Island vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking Santa Rosa Island all-inclusive vacation packages as these include all meals.

How can I book my Santa Rosa Island on Expedia?

Comparing some of the best deals using the search wizard is one of the first steps to booking your Santa Rosa Island mountain vacation on Expedia. Take advantage of the search filters to narrow down hundreds of options at the click of a button. If you've got a strict budget, use the maximum price filter to set your limit. When you've pinned down your Santa Rosa Island package vacation, book it in just a few clicks. You'll also have the option to spread the cost with Expedia's payment plans.

Why book your Santa Rosa Island mountain vacation with Expedia?

With meaty exclusive deals you won't find anywhere else, you'll keep more cash in your pocket when booking your Santa Rosa Island vacation package on Expedia. No matter your preferences or tastes, you'll find the right place to stay thanks to the wide selection of accommodation. There are even last-minute deals, too. And if that's not enough, join One Key for free. Expedia's reward program lets you earn points on eligible trips and also gives you access to juicy member-only discounts.

Can I cancel my mountain vacation package booking?

Yes, as most of Expedia's mountain vacation packages to Santa Rosa Island are flexible, you can often cancel for free. Doing so is easy, too—log in to the “Trips” section and follow the steps. Don't forget to double-check the cancellation policy before booking, as not all Santa Rosa Island vacation packages are flexible. The good news is Expedia will display this to you before payment. Take advantage of the free cancellation search filter so you'll be able to narrow down your search to view only flexible Santa Rosa Island vacation packages.

What types of mountain accommodations are available in Santa Rosa Island?

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Santa Rosa Island. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.

Things to do

Shark Boat Destin Dolphin Watch and Sunset Cruise

Shark Boat Destin Dolphin Watch and Sunset Cruise

$38
per adult
Shark Boat Destin Dolphin Watch and Sunset Cruise
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
See all activities in Santa Rosa Island

More vacations you might like

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