Captains Tower

Name: NFL on the Jumbotron
Start: 2026-10-22T19:00:00+00:00
Location: The Big Chill

Captains Tower

Sleeps 11 - 5 Bedrooms - 5.5 Baths

21 Clove Hitch Ln, Santa Rosa Beach, FL 32459

📍

WaterSound West (gated community)

🏖️

Private beach access via a scenic boardwalk

👙

Private pool! (optional heat)

🕶️

Seasonally heated community pool!

🛺

6-seater golf cart!

🚗

2-car garage

🚲

5 bikes!

🔥

Big Green Egg & propane grill

🛌

5 bedrooms, 5.5 baths (main house + carriage house)

🌅

3rd-floor lookout tower with panoramic windows

Captains Tower by Oversee 30A | Perfect in Walton County Awards – Three-Time Diamond Winner – Best Rental Mgmt. 2026, 2025, 2024

Welcome to Captains Tower, an elegantly decorated retreat in the gated WaterSound West community. With a spacious main house and a fully equipped carriage house, there’s plenty of room, and privacy, for everyone to spread out and get comfortable.

The two-car garage makes unloading easy, while the screened-in porch and stunning private pool are ready when it’s time to relax… or time for a cannonball contest. For a breezy ride around the neighborhood, hop on the six-seater golf cart or one of the bikes. Trips to the beach are about to become a vacation highlight.

The first floor is anchored by a large, modern kitchen, designed for seamless entertaining, comfortably seating eight. The living room is super comfy, and there's a half bath and laundry room close by.

The gorgeous primary suite has a king bed, porch access, and a private bath, double vanity, walk-in shower, and soaker tub. A guest room has a queen bed, a twin trundle, and its own bath.

Upstairs, a guest room with a king bed, and a guest room with a queen bed, each have their own private baths. And then there’s the lookout tower.. Climb the spiral staircase to the best seat in the house, where wraparound windows and a cozy couch are your new headquarters for gawking at sunsets.

The carriage house is a fantastic private oasis and includes a guest room with a queen bed and full bath, a kitchenette, living area, TV, and balcony. Grandma gets her own place. Everybody wins.

A stunningly scenic boardwalk runs from the back porch through the neighborhood to the beach. Absolutely dreamy. Back home, take a rinse with the outdoor shower, then fire up the Big Green Egg or the propane grill. The community pool is heated seasonally, and the private pool can be heated too for an additional fee.

With plenty of house, plenty of toys, and zero shortage of ways to spend the day, the Captains Tower is next level!

At Oversee 30A, we keep it simple: clean, comfortable stays with a local team nearby. Our office is open seven days a week, with 24/7 support whenever you need us.

Overview:
- Private beach access via a scenic boardwalk
- Private pool (can be heated seasonally for additional $55.00 per day, contact Oversee for details)
- Seasonally Heated community pool (Heated November - February)
- Detached Carriage House with kitchenette, living room, and balcony
- 3rd-floor lookout tower accessed via spiral staircase
- 6-seater golf cart included
- 5 bikes!
- 2-car garage included
- Enclosed outdoor shower
- Big Green Egg and propane grill
- Wi-Fi

Overnight:
FIRST FLOOR
- Primary Bedroom: king bed, w/ a private bathroom, walk-in shower, soaker tub, double vanity, and porch access
- Guest Room: queen bed with twin trundle, private bathroom, walk-in shower
- Half bath
SECOND FLOOR
- Guest Room: king bed, private bathroom
- Guest Room: queen bed, private bathroom
CARRIAGE HOUSE
- Guest Room: queen bed
- Full bathroom w/walk-in shower

Check-in is 4:00 PM CST. Checkout is 10:00 AM CST.

Hassle-free check-in.
Add your trip dates to get the cancellation details for this stay.

House Rules

Who can stay.

11 guests maximum
No pets

What's allowed.

Check-in after 4:00 PM
Check-out before 10:00 AM
No smoking
No parties or events

Amenities

Bed And Bathroom

Bathtub
Hair dryer
Iron & board

Kitchen

Dishwasher
Stove
Standard coffee maker
Microwave
Refrigerator
Toaster

Indoor

Wireless internet

Complimentary Items

5 Oversee bikes
Golf cart

Outdoor

Garage
Balcony
Private pool
Private heated pool

Community Amenities

Community pool

Safety Features

Carbon monoxide detector
Fire extinguisher

Entertainment

Smart TV

Bed and Baths

1st Floor

Primary Bedroom

1 King bed

full bathroom

bedroom

1 Queen bed 1 Single bed

full bathroom

half bathroom

2nd Floor

bedroom

1 Queen bed

bedroom

1 King bed

full bathroom

bedroom

1 Queen bed

full bathroom

Location

Community

Watersound

Upcoming Events

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

Welded Jewelry Pop-Up with Spark Collection 30A

Watersound

Markets & Shopping

Customers can start their Spark Collection by selecting from a curated array of 14K solid yellow or white gold chains, which can be crafted into custom bracelets, necklaces, anklets, and rings. Interested individuals can book an appointment to attend a welded jewelry experience at one of the brand's many pop-up events.

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.

Tue, October 13

Loose Cannon

Watersound

Live Music

Loose Cannon is a high-energy musical group operating out of the Florida Panhandle, performing popular hits spanning classic rock, country, southern rock, and modern genres. Recognized for their impressive musicianship, powerful vocals, and captivating stage performance, the group delivers an entertaining atmosphere at every event. Whether playing at festivals, private gatherings, pubs, or concert venues, Loose Cannon continuously engages crowds with lively music that keeps audiences singing and dancing.

Wed, October 14

Family Movie Night- Hotel Transylvania 3: Summer Vacation

Watersound

Family Fun

The Big Chill hosts Family Movie Nights, offering guests of all ages an enjoyable evening under the stars. Families and friends can gather to watch favorite films displayed on the venue's Jumbotron for a fun and relaxed night out.

Thu, October 15

NFL on the Jumbotron

Watersound

Sports & Games

Sports fans can attend the weekly Thursday NFL Watch Party throughout the season at The Big Chill. The venue features a 25-foot Jumbotron for wall-to-wall football action, surrounded by full-service bars and various eateries offering game-day bites in a fan-friendly, outdoor viewing atmosphere.

Fri, October 16

Face Paint with Uniquely Clever Art

Watersound

Family Fun

Attendees can participate in face painting with Katlyn of Uniquely Clever. Fees apply for the activity, and no advance sign-ups are necessary.

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

Welded Jewelry Pop-Up with Spark Collection 30A

Watersound

Markets & Shopping

Customers can begin their custom jewelry experience with The Spark Collection by choosing from a curated selection of 14K solid yellow or white gold chains. These pieces can be custom-crafted into bracelets, necklaces, anklets, and rings. Interested individuals can participate in a welded jewelry session by booking an appointment at one of the brand's pop-up events.

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.

Wed, October 21

Family Movie Night: Wicked: For Good

Watersound

Family Fun

Families and groups of all ages can gather at The Big Chill for Family Movie Nights under the stars. The venue features popular family films on its Jumbotron, offering a night out where guests can simply arrive and enjoy the entertainment.

Thu, October 22

NFL on the Jumbotron

Watersound

Sports & Games

The Big Chill hosts an NFL Watch Party every Thursday throughout the season, broadcasting every play on a 25-foot Jumbotron. Attendees can enjoy a fan-friendly atmosphere with outdoor viewing, full-service bars, and game-day food options from multiple on-site eateries while cheering for their favorite teams.