Southwind Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Landing Apartments Pensacola - Belleview Heights
€639
per person
9 Oct - 11 Oct
found 11 hours ago
Return flight included
Chicago (ORD) to Pensacola (PNS)
2/10 (1 review)
We had an infestation of ants all over the apartment. We had them in the bed on the coach in the kitchen crawling all over the floor. We had to go and buy some mop cleaner to try to get them out of the kitchen. The property was pretty but the actually air b n b was a night mare. We got bitten by ants.
Reviewed on 24 May 2026
Where to stay in Southwind
Find the best Southwind areas and neighborhoods for the activities you enjoy most. Learn more about Southwind
Downtown Pensacola
3 out of top 10 points of interest in this area
While visiting Downtown Pensacola, you might make a stop by sights like Saenger Theatre and Historic Pensacola Village.
Southeast Pensacola
If you're spending some time in Southeast Pensacola, Palafox Shopping Center and Beach Road Shopping Center are top sights worth seeing.
South Pensacola
While visiting South Pensacola, you might make a stop by sights like Palafox Shopping Center and Pensacola Outlet Mall.
Northeast Pensacola
2 out of top 10 points of interest in this area
While visiting Northeast Pensacola, you might make a stop by sights like Cordova Mall and Roger Scott Athletic Complex.
Northwest Pensacola
If you're spending some time in Northwest Pensacola, Five Flags Speedway and Marcus Pointe Golf Club are top sights worth seeing.
Top hotels in Southwind
The Pensacola Beach Resort
165 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
€222
18 Aug - 19 Aug
includes taxes & fees
Hilton Garden Inn Orange Beach Beachfront
23092 Perdido Beach Blvd Orange Beach AL
Fully refundableReserve now, pay when you stay
€131
30 Aug - 31 Aug
includes taxes & fees
7.8/10 Good! (1,786 reviews)
"No towels for two day, even though we called several times. Ice machine on fifth floor did not work. Just one elevator was working and extremely slow. No beach towels were available. Thanks"
Reviewed on 16 Aug 2026
Surf & Sand Hotel
40 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
€119
13 Sept - 14 Sept
includes taxes & fees
8.8/10 Excellent! (3,257 reviews)
"The rooms was nice and clean the staff was very friendly. They had good breakfast and the beach view was great,"
Reviewed on 16 Aug 2026
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.
Frequently asked questions
How much does a Southwind holiday package cost?
Tailor make your Southwind package from as little as €639. Choose from any combination of flights, hotels and rental cars to build the escape you've been dreaming about. Don't forget to add on a few experiences or activities!
How do I get a cheap travel package to Southwind?
Bundling your hotel and flight with Expedia won't just save you time — it'll save you a pretty penny too. A Southwind holiday package makes it easy to create the perfect trip. With more than 550 airlines worldwide to select from, finding convenient flights that fit your busy schedule won't be a problem. In addition to that, we have over 1,000,000 properties globally to pick from. Talk about choice! Whatever your budget, Expedia will help show you the world.
Where should I stay in Southwind?
Urban explorers come from all corners of the globe to see Pensacola Naval Air Station and Pensacola Bay Centre in Southwind. Stay within walking distance of these popular attractions and visit them at your leisure.
How far in advance should I book my Southwind holiday?
Reward yourself with the biggest variety at the cheapest prices by booking your holiday to Southwind early. Airlines typically advertise flights anywhere up to 12 months in advance, so start your planning ASAP. That being said, Expedia is constantly working to give you the best deals around, so it's always a good time to book your dream holiday!
What does an Expedia Southwind travel package include?
You can select from any combination of rental cars, hotels and flights. Once you've made your booking, you can add the fun stuff like activities and experiences. Want to pick your airfare class? That's also easy to do. The choice is yours when it comes to planning your perfect Southwind getaway.
What should I know before booking a Southwind travel package?
We already have low prices. However, you'll snap up even more savings if you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Southwind Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the flexibility to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Southwind holiday package?
Whether it's your hotel or flight, you can cancel or amend it. Booked your Southwind holiday package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings older than that, you may be charged a fee by your hotel, airline or car rental company. For more details, look up our Customer Service Portal. We're here to help you every step of the way.
Things to do
Orange Beach: Dolphin-Watching Eco-Boat Tour
€24
per adult
100% of travellers recommend
Dolphin Cruise in Orange Beach Alabama
€30
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.