Your Guide to Planning a Labor Day Vacation at the Beach ~ Southern Vacation Rentals

Labor Day is just around the corner, and with it marks the official end of summer. September is that beautiful sweet spot between summer and fall, where the crowds are smaller but weather is still warm enough to swim and relax on the beach. Labor Day is an annual celebration fo workers and their achievements, so what better way to celebrate than with a Labor Day vacation at the beach? Whether you want to relax in a large beach home with a private pool or take advantage of a condo with a view, our wide inventory of vacation rentals in Northwest Florida and Coastal Alabama has something for everyone.

Consider this your official guide to planning a Labor Day vacation at the beach this September! From activities to properties to stay in, we’ve got you covered.

Labor Day vacation at the beach
Labor Day vacation at the beach

What To Do

Just because it’s the end of summer doesn’t mean there won’t be anything left to do! Many attractions including dolphin cruises, pontoon boat rentals, and fishing charters will be open well into October, giving you plenty of time to plan your trip. After you’ve booked your beach rental, it’s time to start planning your activities. Did you know we partner with local businesses to provide you exclusive discounts on these activities? When you’re visiting, be sure to book your activities through our Southern Perks partners to take advantage of those discounts!

Even if you’re looking for ways to relax on vacation, you can still find ways to unwind during the long weekend. Rent bikes and cruise down Scenic 30A’s 19-mile bike path, or book a golf cart through our Southern Perks partners and take the scenic route to dinner. The humidity won’t be as strong as it is in July and August, so it’s the perfect chance to hike through Big Lagoon State Park in Perdido Key, Gulf State Park in Gulf Shores, or Grayton Beach State Park on 30A.

No matter if you’re a seasoned visitor or it’s your first time, our Gulf Coast Guide has the scoop on everything from dining to local events and adventure to leisure activities. Just pick your favorite area and start exploring!

Where to Stay

We know that narrowing down where to stay for your Labor Day vacation to the beach can be difficult, but it doesn’t have to be! Take a look at some of our top picks below for your trip to the beach. From homes with private pools to condos with incredible amenities, there is something for everyone. And, we’ve got you covered all the way from Panama City Beach, Florida to Gulf Shores and Fort Morgan, Alabama.

Splash – Panama City Beach

Stay beachfront at one of Panama City Beach’s most popular resorts! Splash is a high-rise condominium that overlooks the wide-open beaches of Panama City Beach. Our two-bedroom condos here have enough room 6-8 guests, so it’s perfect for a Labor Day vacation to the beach with friends or family. When you aren’t lounging on the beach, take advantage of the resort amenities including the beachfront pool, lazy river, kids’ play area, and fitness facility.

The Holland House II – 30A

The Holland House II is one of our newest 30A vacation homes, located in the highly desirable Seacrest Beach community. This house is the right size for eight guests, with three bedrooms and three full bathrooms. The well-furnished interior ensures you’ll have everything you need on vacation, and the home even comes with four adult bikes for you to cruise through Scenic 30A on your way to the beach. Don’t forget about Seacrest Beach’s incredible amenities, including a 12,000 square foot lagoon pool and shuttle service to the beach.

DESTINation Sunset – Destin

For a large house the whole family can enjoy during the long weekend, choose DESTINation Sunset in Destin, Florida. Located in the Destiny West neighborhood, this home enjoys access to several community amenities as well as its own private pool and four adult bikes. The large open floor plan on the first floor has lots of space for everyone to gather, and the outdoor grills on the pool deck are an ideal spot for an afternoon cookout while the kids splash about in the pool. There is also a carriage house with one bedroom, one bathroom, a living area, and a kitchenette.

Sea Oats – Fort Walton Beach

Stay beachfront on Okaloosa Island at Sea Oats! These mid-rise condo rentals on Okaloosa Island enjoy the sights and sounds of the Gulf and are about as close as you can get to the beach. Just take the walkover down to the sugary white shoreline! Choose from 2-3 bedroom condo rentals with enough room for 6-11 guests – perfect if you’re traveling with friends, family, or both. Amenities include a beachfront pool, community grills, a fitness center, and more! Plus, Sea Oats in Fort Walton Beach is close to the Okaloosa Island Boardwalk, Gulfarium, and more attractions perfect for your Labor Day getaway.

Portofino Island Resort – Pensacola Beach

Meanwhile, for a truly unforgettable stay at the beach, book your vacation at Portofino Island Resort on Pensacola Beach. This incredible lifestyle center overlooks Pensacola Beach and the Intracoastal Waterway, providing panoramic views all around. You won’t believe it until you see it! Portofino has some of the best amenities on Pensacola Beach, and everything you need is right at your fingertips. Take advantage of indoor and outdoor pools, on-site dining, a poolside bar, spa on-site, and so much more. You can also rent paddleboards, go-carts, bicycles, and so much more.

High Tide – Perdido Key

Or, enjoy a luxurious vacation at High Tide, one of our newest vacation homes in Perdido Key. Tucked back right along the beach, this extraordinary home has four bedrooms, three full bathrooms, and enough room for 12 guests. The unique art-deco decor pairs perfectly with modern furnishings and contemporary architecture. The wide glass windows in the living room curve out onto the ocean, and the oversized balconies are the perfect spot to both start and end your day. You won’t find a better location to enjoy the beach in Perdido Key!

The Wharf – Orange Beach

The Wharf remains one of Orange Beach’s premier destinations for entertainment, and their on-site condos mean that you can enjoy a relaxing beach vacation while still taking advantage of the fun. 1-3 bedroom condos with enough room for 6-9 guests enjoy views of the canal from the living room as well as at-home furnishings that will have you feeling right at home. Whether you’re looking for a game of laser tag, want to visit a local boutique, or are simply craving a sweet treat, you can find it all at The Wharf!

Sol Mates – Gulf Shores

Book your Labor Day vacation at the beach at one of our newest Gulf Shores vacation homes! Sol Mates is a beautiful and large six-bedroom home, well-equipped to suit 19 guests on vacation. It’s full of high-end upgrades including teak hardwood floors, a custom kitchen with exotic granite countertops, and so much more. This home also enjoys its own stretch of white sand beach right on the calming Lagoon waters. In addition, the Lagoon Pass neighborhood has a private boat dock and private beach access right underneath the overpass. In addition, the outdoor patio deck has its own sound system and gas grill – the perfect setup for an outdoor Labor Day cookout!

Labor Day vacation at the beach
Labor Day vacation at the beach