Southwind Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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 Pensacola

Downtown Pensacola

3 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

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 €151 per night from 17 May to 18 May
€151
17 May - 18 May
includes taxes & fees
8/10 Very Good! (1,517 reviews)
The unit was old and dated. Could tell the property was an off brand hotel before & Hilton put there name on it. My BIGGEST ISSUE WAS wanting to charge us for EVERY SINGLE THING. We’ve stayed at Hiltons and Hampton Inns a lot. Never have signed up for Honors club, so that’s on me, but to pay that ...

Reviewed on 1 May 2026

Hilton Garden Inn Orange Beach Beachfront
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 €263 per night from 6 May to 7 May
€263
6 May - 7 May
includes taxes & fees
9.6/10 Exceptional! (3,070 reviews)
Just beautiful. Everything about it was just perfect.

Reviewed on 3 May 2026

The Pensacola Beach Resort
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 €151 per night from 6 May to 7 May
€151
6 May - 7 May
includes taxes & fees
8.8/10 Excellent! (3,138 reviews)
Great location and lots to do!

Reviewed on 3 May 2026

Surf & Sand Hotel
See all 13,567 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 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.

Popular places to visit

Fort Barrancas NAS Pensacola

Pensacola Naval Air Station

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
C8DBYH Florida, Pensacola, Downtown, Palafox Street, Saenger Theatre, built 1925, performance venue

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
Historic Pensacola Village

Historic Pensacola Village

You can study the exhibits at Historic Pensacola Village, a museum with a story of its own, during your trip to Pensacola. Amble around this family-friendly area's beautiful beaches or experience its great live music.

Historic Pensacola Village

Things to do

Orange Beach: Dolphin-Watching Eco-Boat Tour

Orange Beach: Dolphin-Watching Eco-Boat Tour

€30
per adult
100% of travellers recommend
Orange Beach: Dolphin-Watching Eco-Boat Tour
Dolphin Watching aboard the Cold Mil Fleet

Dolphin Watching aboard the Cold Mil Fleet

€30
per adult
Dolphin Watching aboard the Cold Mil Fleet
2-Hour Dolphin and Nature Eco Tour from Orange Beach

2-Hour Dolphin and Nature Eco Tour from Orange Beach

€33
per adult
96% of travellers recommend
2-Hour Dolphin and Nature Eco Tour from Orange Beach
See all activities in Pensacola
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.