Southwind Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Southwind

Find the best Southwind areas and neighborhoods for the activities you enjoy most. Learn more about Southwind
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Downtown Pensacola

2 out of top 10 points of interest in this area
4/5(1 area review)

While visiting Downtown Pensacola, you might make a stop by sights like Saenger Theatre and Historic Pensacola Village.

Find hotels in Downtown Pensacola

Top hotels in Southwind

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 1.476.773 ₫ per night from 2 Dec to 3 Dec
1.476.773 ₫
1.682.722 ₫ total
2 Dec - 3 Dec
includes taxes & fees
8.6/10 Excellent! (2,895 reviews)
Staf are great super friendly maintenance personnel were extra friendly, only complaint is the soap dispensers in the shower were dirty like they haven’t been cleaned in a while but it was a non issue being that we brought our own

Reviewed on 19 Nov 2025

Surf & Sand Hotel
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 3.535.144 ₫ per night from 24 Nov to 25 Nov
3.535.144 ₫
4.100.768 ₫ total
24 Nov - 25 Nov
includes taxes & fees
9.4/10 Exceptional! (2,614 reviews)
The staff and the hotel were amazing. I will defiantly be coming back!

Reviewed on 19 Nov 2025

The Pensacola Beach Resort
Hampton Inn Pensacola Beach

Hampton Inn Pensacola Beach

2.5 out of 5
2 Via De Luna Drive Pensacola Beach FL
Fully refundableReserve now, pay when you stay
The price is 2.509.662 ₫ per night from 30 Nov to 1 Dec
2.509.662 ₫
2.871.304 ₫ total
30 Nov - 1 Dec
includes taxes & fees
8.2/10 Very Good! (2,238 reviews)
Great view from the balcony overlooking the beach. Beach access was better through neighboring Hilton

Reviewed on 19 Nov 2025

Hampton Inn Pensacola Beach
See all 13,319 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 holiday 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 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 1null000null000 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.

Popular places to visit

Pensacola Naval Air Station

Pensacola Naval Air Station

4.5/5(3 reviews)

After visiting Pensacola Naval Air Station, make a plan to see the other sights and activities in Pensacola. Wander the beautiful beaches or discover the beautiful sunsets in this family-friendly area.

Pensacola Naval Air Station
National Museum of Naval Aviation

National Museum of Naval Aviation

5/5(2 reviews)

You can spend an afternoon exploring the galleries in National Museum of Naval Aviation in Pensacola. Discover the beautiful sunsets and lively bars in this family-friendly area.

National Museum of Naval Aviation
Saenger Theatre

Saenger Theatre

Enjoy a show at Saenger Theatre, a theatre with a story to tell in Pensacola. Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.

Saenger Theatre