Watersound Vacation Rentals

Name: MLB on the Jumbotron
Start: 2026-10-20T18:00:00+00:00
Location: The Big Chill

STAY IN Watersound

The Crossings at Watersound Beach C214

Sleeps 6 - Watersound

Roy Diamond

Two Rocking Chairs on a Porch

Sleeps 10 - Watersound

Joseph Diamond

View All Homes On 30A

About Watersound

Everything is perfect here. Including the poolside service. Watersound is like that VIP lounge you secretly wish you could get into. And guess what? You can. Snuggled between two dune lakes, amid waving grasslands and white-sand dunes, Watersound proudly celebrates the best of the best.

Sure, it has the 30A charm, but what sets it apart are the well-planned resort-style pools and those stunning boardwalks, winding through the dunes to the sea. Simply, there’s no getting around it. You’ve arrived.

CLOSE TO PERFECTION.

Central, yet secluded. Easy to get to, but hard to say goodbye. This private 1,400-acre utopia, just off Highway 30A, between Seacrest Beach and Seagrove, is so private, you may just miss it. And if you get a case of the antsy pants, Alys Beach, Rosemary Beach, and Seaside are just minutes away. But let’s get real here. After a few minutes in paradise within a paradise, you won’t be leaving Watersound anytime soon.

NEW KID ON THE 30A BLOCK.

The 30A area was largely undiscovered until the early 20th century, and wasn’t paved until 1961, connecting the area’s small beach communities for the first time! But Watersound? A bonafide “late bloomer”, this utopia didn’t take shape until the early 2000s. And what a beautiful shape it has become! The layout, architecture, and the many dream homes are like nothing else on 30A. Looks like the best came last?

CALM. COOL. CAPTIVATING!

Did you forget where you parked? No problem, you won’t be needing that thing until later. Much later. Getting around on flip-flops, while soaking in the unhurried pace and the gorgeous surroundings, well, the vibe here is next-level luxury. Families, couples, and anyone looking to escape the crowds will love the calm, soothing atmosphere. Truly blissful.

WILD! AND WONDERFULLY DESIGNED.

Privacy? Conservation? Architectural harmony and attention to detail? Hmm. Thank goodness you don’t have to choose. Quite simply, Watersound has it all. With careful planning, this community takes care of its breathtaking seascapes, rolling dunes, and untouched beaches. Yes, Watersound’s natural wonders are a huge draw. But the all-encompassing blend of everything – nature, charm, and design – is what makes this portion of paradise unforgettable.

Nectar Coffee @ The Big Chill

American

$$$$

Duo’s All American Eats @ The Big Chill

American

$$$$

Bruno’s Pizza

AmericanItalian

$$$$

Mile Marker Fifteen @ The Big Chill

AmericanMexican

$$$$

Local Smoke @ The Big Chill

AmericanBbq

$$$$

Tackle Box @ The Big Chill

AmericanSeafood

$$$$

Mr. Freeze @ The Big Chill

American

$$$$

Louie’s Una Pizza

AmericanItalian

$$$$

Dining in Watersound offers a diverse culinary experience with fresh seafood, farm-to-table dishes, and international cuisine at popular spots like The Big Chill. Watersound Club members enjoy private dining options ranging from casual poolside meals to indoor venues and an outdoor sunset bar overlooking the Gulf Coast’s emerald waters. Whether seeking oceanfront dining, casual eateries, or charming cafes, finding delicious food in Watersound is always a sound choice.

Watersound BEACH ACCESSES

Watersound Private Beach Access

Private To Specific Community

EVENTS OF Watersound

Tue, September 29

Words on Wheels

Watersound

Family Fun

The Words on Wheels Bookmobile will be parked at the Watersound Town Center parking lot, located at 170 N. Watersound Parkway in Inlet Beach, FL, from 1:15 PM to 3:30 PM. Attendees can check out or return library materials, collect holds, register for new library cards, and learn about available free resources.

Tue, September 29

Ronni Kay and The Amazing Band

Watersound

Live Music

Attendees can enjoy a live performance by Ronni Kay and The Amazing Band from 6:00 to 9:30 pm.

Wed, September 30

Family Movie Night: Toy Story 4

Watersound

Family Fun

Families can gather for a movie night featuring a screening of Toy Story 4.

Fri, October 2

Discover Watersound Weekend

Watersound

Family Fun

From October 2–4, visitors are invited to experience the Watersound community through a weekend of exploration, relaxation, and local events. The schedule begins Friday evening with a welcome reception at the Watersound Real Estate office from 4 to 6 p.m., followed by the First Friday Concert Series at The Pavilion from 6 to 8 p.m. On Saturday, guests can tour participating communities during regular sales center hours, join the Minto Matchpoint Pickleball Tournament at Latitude Margaritaville Watersound with advance registration, and attend a beachfront bonfire at the Watersound Beach Club from 5:30 to 7:30 p.m. The event wraps up Sunday with ongoing community tours and the Watersound Block Party at The Pavilion from 2 to 6 p.m., featuring live music, food trucks, and activities.

Fri, October 2

DJ Dance Party w/ DJ Dan

Watersound

Family Fun

DJ Dan will be spinning popular hits at the Ultimate Family Dance Party. Families are invited to join in for an energetic night of dancing, fun, and memorable entertainment on the dance floor.

Fri, October 2

First Friday Concert Series: The Mammals

Watersound

Live Music

Presented by the Cultural Arts Alliance of Walton County and The St. Joe Community Foundation, the First Friday Concert Series offers free, family-friendly entertainment on the first Friday of each month throughout the season. The lineup includes performances by The Pink Stones on September 4, featuring an early passport activity, followed by The Mammals on October 2, the Webb Wilder Band on November 6, and Michelle Malone & The Hot Toddies on December 4. Attendees are encouraged to bring chairs and enjoy evenings of live music and community connection.

Sat, October 3

College Football on the Jumbotron

Watersound

Sports & Games

Guests can watch college football games on a 25-foot Jumbotron, with the weekly schedule of featured big-screen games posted by Wednesday each week. Additional top matchups are shown on televisions under the covered pavilion. Furthermore, 10 other TVs are located throughout the property, where specific games can be requested on a first-come, first-served basis by asking a bartender or cashier to contact a manager.

Sat, October 3

Discover Watersound Weekend

Watersound

Family Fun

From October 2-4, visitors are invited to experience the Watersound community through guided tours, lifestyle events, and exclusive access to local amenities. The weekend begins on Friday evening with a welcome reception at the Watersound Real Estate office in Watersound Town Center from 4 to 6 p.m., followed by live music at the First Friday Concert Series at The Pavilion from 6 to 8 p.m. On Saturday, guests can tour participating communities—including Watersound Origins, Watersound Camp Creek, Latitude Margaritaville Watersound, and Watersound Fountains—during regular sales center hours, participate in the Minto Matchpoint Pickleball Tournament with advance registration, and attend a beachfront bonfire at the Watersound Beach Club from 5:30 to 7:30 p.m. The event concludes on Sunday with additional community tours and the Watersound Block Party at The Pavilion from 2 to 6 p.m., featuring live music, food trucks, and family activities.

Sun, October 4

Watersound Block Party

Watersound

Family Fun

Visitors can spend an afternoon outdoors exploring the Watersound community with family and friends. The event features live music

Mon, October 5

NFL on the Jumbotron

Watersound

Sports & Games

The Big Chill hosts an NFL Watch Party every Monday throughout the season. Guests can watch football action on a 25foot Jumbotron while enjoying a fanfriendly atmosphere with outdoor viewing

Tue, October 6

Words on Wheels

Watersound

Family Fun

The Words on Wheels Bookmobile will visit the Watersound Towncenter parking lot, located at 170 N. Watersound Parkway in Inlet Beach, Florida, from 1:15 PM to 3:30 PM. Visitors can check in or check out library materials, collect hold items, register for new library cards, and learn about various complimentary library resources.

Fri, October 9

DJ Dance Party w/ DJ Dan

Watersound

Family Fun

DJ Dan will be spinning popular hits at the Ultimate Family Dance Party, offering a high-energy evening of dancing and family-friendly entertainment. Attendees are encouraged to bring their entire family to enjoy the vibrant event and light up the dance floor.

Sat, October 10

College Football on the Jumbotron

Watersound

Sports & Games

Guests can enjoy college football games broadcast on a 25-foot Jumbotron, with featured matchups posted by Wednesday of each week. Additional top games are shown on televisions located under the covered pavilion. Furthermore, 10 other TVs across the property offer game coverage upon request on a first-come, first-served basis by asking a bartender or cashier to notify a manager.

Sun, October 11

NFL on the Jumbotron

Watersound

Sports & Games

The Big Chill hosts NFL watch parties every Sunday throughout the football season. Guests can catch live game action on a 25-foot Jumbotron while enjoying food options from several eateries alongside full-service bars. Offering a fan-friendly atmosphere with outdoor viewing, it serves as a destination for fans to follow their favorite teams and track fantasy lineups.

Sun, October 11

Watersound Origins Porchfest

Watersound

Live Music

During the annual Watersound Origins Porchfest, front porches are transformed into stages as neighbors and visitors gather together. Guests can enjoy an afternoon of live musical performances held on the porches and lawns throughout the Watersound Origins community, along with food trucks and lawn games.

Mon, October 12

6th Annual Tom Glavine’s Field of Dreams Golf Outing

Watersound

Sports & Games

Registration has opened for Tom Glavine's Field of Dreams Golf Outing, taking place at Camp Creek Golf Course on Monday, October 12. As a premier charity golf event on the Emerald Coast, the tournament brings together community leaders, local businesses, and golf enthusiasts to support SEASIDE SCHOOL students and programs. Interested participants can join by registering a team, becoming a sponsor, or entering the Golf Ball Drop, with all proceeds funding educational opportunities for students. Sponsorship inquiries can be directed to Callie Cox via email at coxc@seasideschools.net.

Mon, October 12

NFL on the Jumbotron

Watersound

Sports & Games

The Big Chill hosts NFL Watch Parties every Monday throughout the football season. Guests can experience wall-to-wall game coverage on a 25-foot outdoor Jumbotron while enjoying a fan-friendly atmosphere. A variety of surrounding eateries and full-service bars offer game day bites and drinks, making it a suitable destination for fans looking to follow their favorite teams or track fantasy lineups.

Tue, October 13

Words on Wheels

Watersound

Family Fun

The Words on Wheels Bookmobile will visit the Watersound Towncenter parking lot from 1:15 PM to 3:30 PM. During this time, the bookmobile will offer circulation services, allowing visitors to check in or check out library materials and collect reserved holds. Staff will also register new patrons for library cards and share information about free library resources. The location for this event is 170 N. Watersound Parkway, Inlet Beach, FL 32413.

Fri, October 16

DJ Dance Party w/ DJ Dan

Watersound

Family Fun

The Ultimate Family Dance Party features DJ Dan spinning popular hits for an energetic evening of dancing and family-friendly entertainment. Guests of all ages are invited to bring their families and hit the dance floor for a fun, memorable night.

Sat, October 17

College Football on the Jumbotron

Watersound

Sports & Games

Guests can watch college football games on a 25-foot Jumbotron, with featured games announced by Wednesday each week. Additional top games are broadcast on televisions under the covered pavilion, and 10 additional TVs across the property offer games upon request on a first-come, first-served basis by asking a bartender or cashier to contact a manager.

Sun, October 18

NFL on the Jumbotron

Watersound

Sports & Games

The Big Chill hosts an NFL Watch Party every Sunday throughout the season, offering wall-to-wall football action on a 25-foot Jumbotron. Guests can enjoy a fan-friendly outdoor viewing atmosphere complete with game day food from various eateries and full-service bars while keeping up with their favorite teams or fantasy lineups.

Mon, October 19

NFL on the Jumbotron

Watersound

Sports & Games

The Big Chill hosts an NFL Watch Party every Monday throughout the entire football season. Guests can watch the live game action on a massive 25-foot Jumbotron while enjoying a fan-friendly atmosphere with outdoor viewing, game day food options from various eateries, and drinks from full-service bars.

Tue, October 20

Words on Wheels

Watersound

Family Fun

The Words on Wheels Bookmobile will be parked at the Watersound Towncenter parking lot, located at 170 N. Watersound Parkway in Inlet Beach, Florida, from 1:15 PM to 3:30 PM. Visitors can check in or check out library materials, collect holds, register for new library cards, and discover various free resources offered by the library.

Tue, October 20

MLB on the Jumbotron

Watersound

Sports & Games

Major League Baseball is displayed on the jumbotron.

Watersound hosts a variety of events celebrating local culture and natural beauty. Enjoy “Sounds Like Summer” with live music every Thursday night and nightly events at The Big Chill. Engage in sports tournaments, beach cleanups, and culinary festivals, all highlighting the vibrant community and scenic charm of Florida’s Emerald Coast.

Watersound STORIES

WHAT MAKES WATERSOUND DIFFERENT FROM OTHER 30A COMMUNITIES?

NOT ALL 30A FEELS THE SAME. AND WATERSOUND KNOWS IT Do most people assume every stretch of 30A is interchangeable? The same coastline, same sand, same vibe? We hope not, […]

Apr 28 Area Highlights

WATERSOUND PHOTOWALKS: THE BEST NATURE BACKDROPS FOR STUNNING SHOTS

Ya think 30A’s beauty starts and ends at the beach? Watersound would like to have a word. Here, the camera roll fills up fast, thanks to mirror-still lakes, towering pines, […]

Nov 12 Area Highlights

EVENING VIBES: BEST SUNSETS, NIGHT WALKS, AND COASTAL STARS

When beach towels head home and the sky starts to blush, the coast finds a new kind of magic. Quieter. Softer. The kind that makes you talk slower and smile […]

Nov 03 Area Highlights

BIRDWATCHING & WILDLIFE AROUND WATERSOUND: NATURE’S QUIET SIDE OF 30A

There’s a whole side of Watersound that doesn’t make it onto postcards. No beach umbrellas, no flip-flop traffic, just the soft flutter of wings and the quiet rustle of something […]

Oct 22 Area Highlights

ADVENTURES IN WATERSOUND: BIKING AND HIKING TRAILS

Watersound isn’t just a quiet coastal paradise. It’s a playground for anyone who loves a good trail, a scenic ride, and a little fresh air. Paved paths and winding nature […]

Mar 10 Area Highlights

WHERE THE GREENS MEET THE GULF. GOLFING IN WATERSOUND.

Watersound isn’t just a stunning, beachside paradise. It’s a golfer’s dream. You’ll love the scenic fairways, flexible courses, and thrilling tournaments. This is a hole-in-one. In the mood for a […]

Feb 26 Area Highlights

EXPLORING WATERSOUND. LUXURY AND LEISURE ON 30A.

So, what’s the Watersound vibe all about? Think upscale meets easygoing, where luxury comes with a side of laid-back charm. It’s the kind of place where you can soak up […]

Oct 28 Area Highlights

30A SONGWRITERS FESTIVAL 2027: DATES, ARTISTS, VENUES, TICKETS & WHERE TO STAY

January on 30A is usually the quieter side of the beach. Then Songwriters Festival weekend arrives. For four days, restaurants become listening rooms, town halls turn into stages, patios fill […]

Sep 09 Plan Your Trip

30A AFTER THE KIDS GO BACK TO SCHOOL: WHO COMES NEXT?

The backpacks are packed. The buses are rolling. And 30A? It doesn’t slow down, it just changes the invitation list. Once summer family season winds down, a different kind of […]

Sep 08 Plan Your Trip

EARLY BIRD OR NIGHT OWL? PICK A 30A RENTAL EVERYONE WILL LOVE

The right rental doesn’t force everyone onto the same schedule. It just gets out of the way. One person’s up before sunrise, coffee in hand, already spotting dolphins from the […]

Aug 12 Plan Your Trip

PLANNING A LARGE GROUP TRIP TO 30A: WHAT MATTERS BEYOND BEDROOM COUNT

A house that sleeps 16 and a house that actually works for 16 are not the same thing. One group arrives, and suddenly three families are sharing two bathrooms, the […]

Jul 29 Plan Your Trip

May 06 2026