Santa Rosa Island Vacation Packages for 2025

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Wyndham Garden Fort Walton Beach Destin

Wyndham Garden Fort Walton Beach Destin

3 out of 5
573 Santa Rosa Blvd, Fort Walton Beach, FL
10.95 km from city center
Stay at this 3-star beach hotel in Fort Walton Beach. Enjoy free WiFi, 2 outdoor pools, and a beach locale. Our guests praise the pool and the helpful staff ...
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
13.44 km from city center
Stay at this 4-star beach resort in Fort Walton Beach. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road, Pensacola Beach, FL
40.33 km from city center
Book a stay at this beach hotel in Pensacola Beach. Enjoy free breakfast, free WiFi, and free bicycles on site. Our guests praise the breakfast and the pool ...
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road, Pensacola Beach, FL
40.84 km from city center
Book a stay at this beach hotel in Pensacola Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our ...
Hampton Inn Pensacola Beach

Hampton Inn Pensacola Beach

2.5 out of 5
2 Via De Luna Drive, Pensacola Beach, FL
39.96 km from city center
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 ...
Fairfield Inn & Suites by Marriott Pensacola Beach

Fairfield Inn & Suites by Marriott Pensacola Beach

3.5 out of 5
16 Via de Luna Dr, Pensacola Beach, FL
39.59 km from city center
Stay at this 3.5-star beach hotel in Pensacola Beach. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our ...
Holiday Inn Resort Pensacola Beach by IHG

Holiday Inn Resort Pensacola Beach by IHG

3 out of 5
14 Via De Luna Drive, Pensacola Beach, FL
39.69 km from city center
Stay at this 3-star beach hotel in Pensacola Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
SpringHill Suites by Marriott Navarre Beach

SpringHill Suites by Marriott Navarre Beach

4 out of 5
8375 Gulf Blvd, Navarre, FL
13.97 km from city center
Stay at this 4-star beach hotel in Navarre. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the restaurant in our reviews. ...
Hilton Garden Inn Ft. Walton Beach

Hilton Garden Inn Ft. Walton Beach

3 out of 5
1297 Miracle Strip PKWY SE, Fort Walton Beach, FL
12.63 km from city center
Stay at this 3-star beach hotel in Fort Walton Beach. Enjoy free WiFi, a beach locale, and room service. Our guests praise the pool and the helpful staff in ...
Hilton Pensacola Beach

Hilton Pensacola Beach

4 out of 5
12 Via De Luna Dr, Pensacola Beach, FL
39.81 km from city center
Stay at this 4-star beach resort in Pensacola Beach. Enjoy 2 outdoor pools, 2 restaurants, and a beach locale. Our guests praise the pool and the bar in our ...
Four Points by Sheraton Destin-Fort Walton Beach

Four Points by Sheraton Destin-Fort Walton Beach

3 out of 5
1325 Miracle Strip Pkwy SE, Fort Walton Beach, FL
12.82 km from city center
Stay at this 3-star beach hotel in Fort Walton Beach. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the helpful staff and the clean ...
Fairfield Inn & Suites Fort Walton Beach-West Destin

Fairfield Inn & Suites Fort Walton Beach-West Destin

2.5 out of 5
540 Santa Rosa Blvd, Fort Walton Beach, FL
10.85 km from city center
Book a stay at this beach hotel in Fort Walton Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Resort Fort Walton Beach by IHG

Holiday Inn Resort Fort Walton Beach by IHG

3 out of 5
1299 Miracle Strip Parkway SE, Fort Walton Beach, FL
12.69 km from city center
Stay at this 3-star beach resort in Fort Walton Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Waterscape Condominiums

Waterscape Condominiums

3.5 out of 5
1110 Santa Rosa Blvd, Fort Walton Beach, FL
12.5 km from city center
Stay at this 3.5-star beach condo in Fort Walton Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Okaloosa Island Beach and HarborWalk ...
Hampton Inn Ft. Walton Beach

Hampton Inn Ft. Walton Beach

2.5 out of 5
1112 Santa Rosa Blvd, Fort Walton Beach, FL
12.35 km from city center
Book a stay at this beach hotel in Fort Walton Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff ...
Don't see what you're looking for?
See all available properties in Santa Rosa Island
View all properties
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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Oct 18 - Sat, Nov 1
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$177 Roundtrip, found 10 hours ago
$177
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Pensacola Intl., returning Sat, Nov 1, priced at $177 found 10 hours ago
Spirit Airlines
Mon, Oct 20 - Mon, Nov 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$184 Roundtrip, found 10 hours ago
$184
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Mon, Oct 20 from O'Hare Intl. to Pensacola Intl., returning Mon, Nov 3, priced at $184 found 10 hours ago
American Airlines
Mon, Oct 20 - Mon, Nov 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$259 Roundtrip, found 10 hours ago
$259
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Mon, Oct 20 from O'Hare Intl. to Pensacola Intl., returning Mon, Nov 3, priced at $259 found 10 hours ago
United
Mon, Oct 20 - Mon, Nov 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$260 Roundtrip, found 10 hours ago
$260
Roundtrip
found 10 hours ago
Select United flight, departing Mon, Oct 20 from O'Hare Intl. to Pensacola Intl., returning Mon, Nov 3, priced at $260 found 10 hours ago
Frontier Airlines
Mon, Oct 20 - Mon, Nov 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$261 Roundtrip, found 10 hours ago
$261
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Mon, Oct 20 from O'Hare Intl. to Pensacola Intl., returning Mon, Nov 3, priced at $261 found 10 hours ago