Captains Tower

Name: Family Movie Night: Wicked: For Good
Start: 2026-10-21T19:00:00+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)

🕶️

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 Ln 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 situated in the exclusive, gated community of WaterSound West. Featuring a stunning main home and a fully equipped carriage house, this property offers incredible space and privacy for your entire group. Unpacking is a breeze with the included two-car garage. Ready to embrace the Florida sunshine? Step out to your beautiful screened-in porch to lounge by the private pool, or load up the six-seater golf cart for a breezy ride around the neighborhood.

The first floor is anchored by a large, modern kitchen designed for seamless coastal entertaining.

Enjoy meals together at the dining table with seating for five, supported by three additional spots at the breakfast bar. Afterward, settle into the living room's plush, cozy seating for a relaxing evening, with a convenient half bath and laundry room perfectly situated on the main level.

Sleeping arrangements are exceptionally well-planned across the property. The main floor features a magnificent king primary suite offering direct porch access and a spa-inspired bath with double vanity sinks, a walk-in shower, and a deep soaker tub. Also downstairs is a versatile room featuring a queen bed with a twin trundle, complete with its own private bathroom and walk-in shower.

Head up to the second level to find two more elegant sanctuaries—a king guest bedroom and a queen guest bedroom, each with their own private baths.

Ascend the unique spiral staircase to the third floor to discover the lookout tower, where a cozy couch and wrap-around windows create a breathtaking hideaway.

Finally, the detached carriage house serves as a fantastic private oasis, featuring a kitchenette, a queen bedroom with a walk-in shower, and a living area boasting a large TV and balcony.

Outdoor living here is truly top-tier. Step right off your back porch onto the community boardwalk for a peaceful stroll, or grab one of the five included bikes to explore the beautiful neighborhood. You can also spend your afternoons lounging by your very own private pool. When you are ready for the Gulf, a stunningly scenic boardwalk guides you directly to the sand.
Upon your return, wash off in the enclosed outdoor shower before firing up the Big Green Egg or the propane grill for a backyard barbecue. Set in beautiful WaterSound West, you will also enjoy access to a fantastic community pool (heated seasonally) to round out the perfect vacation days.

At Oversee 30A, we keep it simple: clean, comfy stays with a local team always close by. Our office is nearby, open seven days a week, with 24/7 support if you need anything.

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, 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 King bed

full bathroom

bedroom

1 Queen bed

full bathroom

bedroom

Location

Community

Watersound

Upcoming Events

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

Face Paint with Uniquely Clever Art

Watersound

Family Fun

Attendees can participate in face painting hosted by Katlyn of Uniquely Clever. Additional fees apply for this activity, and advance sign-ups are not required.

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

Welded Jewelry Pop-Up with Spark Collection 30A

Watersound

Markets & Shopping

Guests can start their Spark Collection by choosing from a selection of 14K solid yellow or white gold chains, which can be crafted into custom bracelets, necklaces, anklets, and rings. Attendees can experience permanent, welded jewelry by scheduling an appointment at one of the brand's pop-up events.

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.

Tue, October 6

Christon Birge Band

Watersound

Live Music

Guests can enjoy a fun night of live music, food, and treats suitable for the whole family. Florida-born artist Christon Birge grew up in Vernon, near Panama City Beach, with deep country roots that shape his sound alongside various musical influences. Whether performing original songs like "Sunscreen on You" or covering popular tracks, his style crosses genres effortlessly. His passion for music began early when he saved money working on a watermelon farm to buy his first guitar and trick bike. Birge went on to win the 2014 Tootsies Birthday Bash, open for Kid Rock and Trick Pony in Nashville, and earn a finalist spot in the 2019 Pepsi Gulf Coast Jam Southern Original. His recent studio release, "Call Dad," has received national country radio airplay. When he is not performing along the 30A corridor, he enjoys spending time at the beach, building custom parts for his Trans Am, and watching MMA.

Wed, October 7

Welded Jewelry Pop-Up with Spark Collection 30A

Watersound

Markets & Shopping

Customers can launch 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. Individuals are invited to participate in a unique welded jewelry experience by scheduling an appointment at one of the brand's many pop-up events.

Wed, October 7

Family Movie Night: Coco

Watersound

Family Fun

Family Movie Nights are held at The Big Chill, offering an outdoor evening experience for all ages. Guests can gather to watch popular family films displayed on the venue's Jumbotron.

Thu, October 8

NFL on the Jumbotron

Watersound

Sports & Games

The Big Chill hosts NFL watch parties every Thursday throughout the season, displaying live game action 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 surrounding eateries. It offers a prime venue for football fans to follow their favorite teams and track their fantasy lineups.

Fri, October 9

Face Paint with Uniquely Clever Art

Watersound

Family Fun

Guests can participate in face painting hosted by Katlyn of Uniquely Clever. Additional fees apply for the activity, but advance registration is not required.

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

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.