Santa Rosa Island Vacation Packages for 2025
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Santa Rosa Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
OYO Hotel Pensacola I-10 & Hwy 29
Price was $619, price is now $472 per person
$472
per person
Oct 20 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Pensacola (PNS)
Stay at this hotel in Pensacola. Enjoy free WiFi, free parking, and room service. Popular attractions Splash City Adventures and Marcus Pointe Golf Club are located nearby.
The Pensacola Beach Resort
Villa Sabine
Price was $1,110, price is now $873 per person
$873
per person
Oct 20 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Pensacola (PNS)
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 reviews. Popular attractions Pensacola Beach Gulf Pier and Casino Beach are located nearby.
SpringHill Suites Pensacola
Price was $724, price is now $573 per person
$573
per person
Oct 20 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Pensacola (PNS)
Book a stay at this business-friendly hotel in Pensacola. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions University Town Plaza and Cordova Mall are located nearby.
Sole Inn and Suites
Downtown Pensacola
Price was $820, price is now $670 per person
$670
per person
Oct 20 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Pensacola (PNS)
Book a stay at this business-friendly motel in Pensacola. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Palafox Market and Civil War Soldiers Museum are located nearby.
Courtyard by Marriott Pensacola I-10 West
Northwest Pensacola
Price was $746, price is now $617 per person
$617
per person
Oct 20 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Pensacola (PNS)
Stay at this 3-star business-friendly hotel in Cantonment. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Five Flags Speedway and DeLuna Lanes Bowling Center are located nearby.
Surf & Sand Hotel
Price was $938, price is now $779 per person
$779
per person
Oct 20 - Oct 26
found 20 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Pensacola (PNS)
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 in our reviews. Popular attractions Pensacola Beach Gulf Pier and Casino Beach are located nearby.
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See all available trips from Columbus to Santa Rosa Island
View all tripsTop Hotel Deals
Wyndham Garden Fort Walton Beach Destin
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
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
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
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
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
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
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
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
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
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
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
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
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 ...
Don't see what you're looking for?
See all available properties in Santa Rosa Island
View all propertiesLowest 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.
Sat, Oct 18 - Sat, Nov 1
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$177 Roundtrip, found 7 hours ago
$177
Roundtrip
found 7 hours ago
Mon, Oct 20 - Mon, Nov 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$184 Roundtrip, found 7 hours ago
$184
Roundtrip
found 7 hours ago
Mon, Oct 20 - Mon, Nov 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$259 Roundtrip, found 7 hours ago
$259
Roundtrip
found 7 hours ago
Mon, Oct 20 - Mon, Nov 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$260 Roundtrip, found 7 hours ago
$260
Roundtrip
found 7 hours ago
Mon, Oct 20 - Mon, Nov 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$261 Roundtrip, found 7 hours ago
$261
Roundtrip
found 7 hours ago