Southwind Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$5,067 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Southwind

Find the best Southwind areas and neighborhoods for the activities you enjoy most. Learn more about Southwind
Downtown showing heritage elements and heritage architecture

Downtown Pensacola

3 out of top 10 points of interest in this area
4/5(314 area reviews)

If you're spending some time in Downtown Pensacola, Saenger Theatre and Historic Pensacola Village are top sights worth seeing.

Find hotels in Downtown Pensacola

Southwind Hotel Deals

The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
The price is NT$3,950 per night from Jan 28 to Jan 29
NT$3,950
NT$4,525 total
Jan 28 - Jan 29
includes taxes & fees
9.4/10 Exceptional! (2,758 reviews)
Everything from rhe view was perfect

Reviewed on 2026/1/26

The Pensacola Beach Resort
Hilton Garden Inn Orange Beach Beachfront

Hilton Garden Inn Orange Beach Beachfront

3 out of 5
23092 Perdido Beach Blvd Orange Beach AL
Fully refundableReserve now, pay when you stay
The price is NT$2,648 per night from Jan 29 to Jan 30
NT$2,648
NT$3,071 total
Jan 29 - Jan 30
includes taxes & fees
7.8/10 Good! (1,397 reviews)
Clean room, quick check-in and very friendly staff

Reviewed on 2026/1/19

Hilton Garden Inn Orange Beach Beachfront
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
The price is NT$2,120 per night from Feb 1 to Feb 2
NT$2,120
NT$2,500 total
Feb 1 - Feb 2
includes taxes & fees
8.6/10 Excellent! (3,019 reviews)
Nice clean walking distance to beach and restaurants

Reviewed on 2026/1/25

Surf & Sand Hotel
See all 13,306 properties in Southwind
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 vacation package cost?
Tailor make your Southwind package from as little as . 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 vacation 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 Center 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 vacation?
Reward yourself with the biggest variety at the cheapest prices by booking your vacation 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 vacation!
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 vacation 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 vacation package?
Whether it's your hotel or flight, you can cancel or amend it. Booked your Southwind vacation 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.

Discover the most popular places to visit in Southwind

Pensacola_PensacolaCivicCenter_6127819_04

Pensacola Bay Center

After visiting Pensacola Bay Center, make a plan to see the other sights and activities in Pensacola. Stroll along the beautiful beaches or experience the great live music in this family-friendly area.

Pensacola Bay Center
Pensacola_UniversityofWestFlorida_6127826-10

University of West Florida

Enjoy the collegiate vibe when you visit University of West Florida, during your trip to Ferry Pass. Wander the beautiful beaches in this family-friendly area.

University of West Florida
National Museum of Naval Aviation which includes interior views

National Museum of Naval Aviation

You can spend an afternoon studying the exhibits at National Museum of Naval Aviation in Pensacola. Discover the beautiful sunsets and top-notch restaurants in this family-friendly area.

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