Description
House Rules
Amenities
Bed and Baths
Location
Community
Upcoming Events
Reviews
Host Family

Out of Office

Name: Myami’s Beach Hair
Start: 2026-05-16T15:00:00+00:00
Location: The Big Chill

Out of Office

Sleeps 10 - 5 Bedrooms - 4 Baths

61 Sheepshank Ln, Santa Rosa Beach, FL 32459

📍

Watersound West!

🏖️

Private beach access via gorgeous boardwalk

🛌

5 bedrooms, 4 bathrooms

👙

Heated community pool, open year-round

🔥

Outdoor grill, kitchen, dining area seats 6

🛺

6-seater golf cart

🚲

4 bikes

☕

Keurig and standard coffee maker

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

The ultimate 30A getaway? Absolutely! Tucked inside an exclusive gated community, Out of Office in Watersound West is a 5-bedroom, 4-bath beauty, that’s all about laid-back luxury and family fun.

Start your day lounging on the dreamy front porch—hammock chairs, cozy seating, and a dining table just waiting for your evenings of al fresco dining. Head out back for grill master vibes on the spacious deck with an outdoor kitchen ready for your BBQs and sunset hangouts.

Inside, you’ll find a welcoming open space with super comfy furniture, perfect for stretching out after a beach day. The kitchen?

Fully stocked, with an island for three—whether you’re whipping up meals or grabbing takeout, it’s all easy breezy.

Upstairs, a second living area makes for the best movie night spot, complete with a big couch, chairs, and a Smart TV for all your streaming marathons.

Ready to make some memories? Your perfect vacation is just a few clicks away. Book now and let Out of Office be your home base for sunshine, relaxation, and lots of beachy fun!

Welcome! Our dedicated team at Oversee 30A, a local company, is committed to ensuring your stay is nothing short of exceptional. We strive for perfection and are just a stone's throw away should you require any assistance. Reach out to us anytime, seven days a week, with the added peace of a 24/7 emergency line.

Overview:
-Private beach access via a scenic boardwalk
-Seasonally Heated community pool (Heated November - February)
-5 bedrooms, 4 bathrooms
-Pack n play and highchair available
-Outdoor grill and dining space
-4 Complimentary bikes
-Complimentary 6 seater golf cart
-Wi-Fi
-2894 sq ft

Overnight:
- King in 1st floor primary; private bath; TV
- Queen in 1st floor guest room (barn door); shared bath; TV
- King in 2nd floor primary; private bath; TV
- King in 2nd floor guest room; shared bath; TV
- Queen in 2nd floor guest room; shared bath; TV

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

Take the 3D walkthrough.

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

House Rules

Who can stay.

10 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

Kitchen

Dishwasher
Stove
Standard coffee maker
Microwave
Refrigerator
Toaster

Indoor

Wireless internet

Outdoor

Garage
Balcony

Complimentary Items

4 Oversee bikes
Golf cart

Community Amenities

Community pool

Safety Features

Carbon monoxide detector
Fire extinguisher

Bed And Bathroom

Hair dryer
Iron & board

Entertainment

Smart TV

Bed and Baths

1st Floor

bedroom

1 Queen bed

Primary Bed Bedroom

1 King bed

full bathroom

2nd Floor

bedroom

1 King bed

bedroom

1 King bed

bedroom

1 Queen bed

full bathroom

Location

Community

Watersound

Upcoming Events

Tue, April 21

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of creative hair services. Guests can enjoy colorful hair wraps, shimmering hair tinsel, and bold mermaid-style waves with color accents. Additionally, the event offers stylish custom braids tailored to each individual's preference. This experience is designed for girls and young ladies looking to express their personal style, and applicable fees will apply for the services provided.

Tue, April 21

Live Music

Watersound

Live Music

The venue features live music for its guests to enjoy.

Wed, April 22

Family Movie Night: A Bug's Life

Watersound

Family Fun

The Big Chill hosts Family Movie Nights, inviting guests of all ages to enjoy popular films on a large Jumbotron. These events offer a memorable experience under the stars where families can simply arrive and enjoy the entertainment.

Thu, April 23

Farmers Market

Watersound

Markets & Shopping

The Farmer’s Market at The Big Chill, managed by Anchored Market Ventures, takes place from 9am to 1pm and features a wide variety of local vendors. Attendees can browse an assortment of goods including fresh produce, farm-fresh eggs, microgreens, and various handmade items like jewelry, soaps, and home decor. This family-friendly event also offers live music, local shops, and onsite food options, inviting everyone in the community to gather and support local businesses.

Thu, April 23

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a day of fabulous fun where guests can enhance their look with various hair services. Attendees can choose from colorful hair wraps, shimmering hair tinsel, and beachy mermaid hair with bold color accents. Custom braids tailored to individual styles are also available, making it an ideal experience for girls and young ladies looking to express their inner magic. Fees apply for these services.

Thu, April 23

Taste of Spice

Watersound

Live Music

Taste of Spice is a musical group that offers a lively performance featuring a blend of soul, blues, and pop. Known for their soulful vocals and engaging stage presence, the band creates an inviting atmosphere for audiences of all ages. Guests are encouraged to dance or sing along while enjoying food and treats, making the event an ideal evening for families.

Fri, April 24

Craft & Canvas Art Class hosted by Uniquely Clever *Must Pre-register

Watersound

Workshops & Classes

Uniquely Clever hosts the Craft and Canvas art class on Fridays from 5:00 PM to 6:00 PM. The class is held in the screened-in area situated to the left of the Jumbotron. Participants are required to pre-register for this event.

Sat, April 25

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a day of fabulous fun featuring various hair styling services. Participants can enjoy colorful hair wraps, shimmering hair tinsel, and beachy mermaid hair with bold color accents. Additionally, custom braids are available for those looking for a stylish, tailored look. These services are ideal for girls and young ladies wanting to express their inner magic, though fees do apply.

Sat, April 25

Family Game Night: MUSIC BINGO

Watersound

Family Fun

The Big Chill is hosting a new family game night featuring Music Bingo, presented by Super Good Trivia. Participants compete by identifying songs and artists on their bingo cards to win various prizes for completing lines or a full house. The event takes place from 6:00 PM to 8:00 PM under a covered and heated pavilion, where guests can also enjoy dinner and drinks.

Sun, April 26

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of hair styling services. Attendees can choose from colorful hair wraps, shimmering hair tinsel, and beachy mermaid hair styles with bold color accents. Custom braids tailored to individual preferences will also be available. This event is designed for girls and young ladies to express their personal style, though service fees do apply.

Mon, April 27

Art Bar Menu Station hosted by Uniquely Clever Art

Watersound

Arts & Culture

Uniquely Clever Art hosts an Art Bar Menu Station at The Big Chill on Mondays, offering guests a variety of art projects to choose from and create. The station is located in the screened-in room to the left of the jumbotron. No prior registration is required, though fees apply and vary by project.

Mon, April 27

Face Paint with Uniquely Clever Art

Watersound

Arts & Culture

Uniquely Clever's Katlyn provides face painting services for attendees. While fees apply for the activity, no prior registration is required to participate.

Mon, April 27

Family Game Night: Trivia

Watersound

Family Fun

The Big Chill is hosting a family trivia night featuring Super Good Trivia, which provides a fun and mind-challenging game for all ages. Guests can enjoy food and drinks from Duos Restaurant and Bar under the covered and heated pavilion from 6:00 PM to 8:00 PM. This free-to-play event includes prizes for the top three teams and provides all necessary materials for participants.

Tue, April 28

Myami’s Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of hair styling services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, mermaid-style waves with bold accents, and personalized custom braids. This event provides a creative way for attendees to express themselves, though fees for the services apply.

Thu, April 30

Farmers Market

Watersound

Markets & Shopping

The Farmer’s Market at The Big Chill, managed by Anchored Market Ventures, takes place from 9am to 1pm and features a wide variety of local vendors. The community-focused event offers assorted goods including fresh produce, farm eggs, pickles, baked goods, and handmade crafts such as jewelry, candles, and home decor. This family-friendly gathering is open to the public and includes live music along with on-site food and shopping. Visitors are encouraged to explore the diverse selection of health, wellness, and artisanal products while enjoying the local atmosphere.

Thu, April 30

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of creative hair services. Attendees can choose from colorful hair wraps, shimmering hair tinsel, beachy mermaid hair with bold color accents, and personalized custom braids. These stylish offerings are designed for girls and young ladies to express their personal style. Please note that fees apply for these services.

Thu, April 30

String Theory

Watersound

Live Music

String Theory is a dynamic band that performs a smooth blend of classic rock, modern rock, pop favorites, and easy listening tunes. They offer an evening of live music perfect for singing along, dancing, or relaxing. Guests can enjoy refreshing drinks and a chill atmosphere while listening to timeless hits and feel-god sounds with friends.

Fri, May 1

Craft & Canvas Art Class hosted by Uniquely Clever *Must Pre-register

Watersound

Workshops & Classes

Uniquely Clever hosts the Craft and Canvas art class on Fridays from 5:00 PM to 6:00 PM. The class is held in the screened-in area to the left of the Jumbotron. Participants are required to pre-register online to attend.

Sat, May 2

Myami’s Beach Hair

Watersound

Family Fun

Myami Henna is hosting a day of fabulous fun featuring a variety of stylish hair services. Participants can enjoy colorful hair wraps, shimmering hair tinsel, and beachy mermaid hair with bold color accents. Custom braids tailored to individual styles are also available, making it an ideal experience for girls and young ladies looking to express their inner magic. Fees apply for these services.

Sun, May 3

Myami's Beach Hair

Watersound

Food & Drink

Myami Henna is hosting a pop-up event featuring a variety of creative hair services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, mermaid-style waves with bold accents, and customized braids. Fees apply for these styling services designed to help participants express their personal magic.

Mon, May 4

Art Bar Menu Station hosted by Uniquely Clever Art

Watersound

Arts & Culture

Uniquely Clever Art is hosting an Art Bar Menu Station at The Big Chill every Monday. Participants can choose from several different art options to create their own projects. The station is situated in the screened-in room located to the left of the jumbotron. No advance registration is necessary, though fees apply and prices vary by project.

Mon, May 4

Face Paint with Uniquely Clever Art

Watersound

Arts & Culture

Katlyn of Uniquely Clever will be hosting a face painting event. Fees apply for the activity, and no advance sign-ups are required for participants.

Tue, May 5

Myami's Beach Hair

Watersound

Family Fun

Tue, May 5

Boukou Groove

Watersound

Live Music

Established in 2010, Boukou Groove is a New Orleans-based musical group specializing in funk, soul, and jam music. The band features veteran vocalist and keyboardist Donnie Sundal, who also plays Moog bass, alongside guitarist Derwin “Big D” Perkins. Known for the synergy between Perkins’ authentic funk guitar style and Sundal’s soulful vocals and keyboard work, the group has performed for global audiences. Their signature sound is captured in their studio albums, A Lil’ Boukou in Your Cup (2012) and Let the Groove Ride (2015), as well as their 2019 single, Never Steal Our Thunder.

Thu, May 7

Farmers' Market

Watersound

Markets & Shopping

The Farmer’s Market at The Big Chill, managed by Anchored Market Ventures, takes place from 9am to 1pm and features a variety of local vendors. The event offers an array of goods including fresh produce, farm eggs, pickles, microgreens, baked items, and handmade crafts such as woodwork, jewelry, and soaps. This family-friendly gathering also includes local shops, food options, and live music. The market is open to the public and encourages community connection through its newsletter and social media updates.

Thu, May 7

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of hair styling services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, mermaid-style beachy waves with bold color accents, and customized braids. This event is designed for those looking to express their personal style with creative and sparkly looks, though fees do apply for the services provided.

Fri, May 8

Craft & Canvas Art Class hosted by Uniquely Clever *Must Pre-register

Watersound

Workshops & Classes

Uniquely Clever is hosting a Craft and Canvas art class on Fridays from 5:00 PM to 6:00 PM. The class takes place in the screened-in area located to the left of the Jumbotron. Participants are required to pre-register online to attend the session.

Sat, May 9

Myami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of hair styling services for girls and young ladies. The offerings include colorful hair wraps, shimmering hair tinsel, mermaid-style waves with bold accents, and personalized custom braids. Fees apply for these services, which are designed to help attendees express their unique style.

Sun, May 10

Miami's Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of creative hair services, including colorful hair wraps, shimmering hair tinsel, and beachy mermaid hair with bold color accents. Attendees can also receive stylish custom braids designed for girls and young ladies wishing to express their inner magic, with fees applying for the services provided.

Mon, May 11

Art Bar Menu Station hosted by Uniquely Clever Art

Watersound

Arts & Culture

Uniquely Clever Art hosts an Art Bar Menu Station every Monday at The Big Chill, located in the screened-in room to the left of the jumbotron. Guests can choose from various art projects to create on-site. No prior registration is required, though fees apply and vary based on the specific project selected.

Mon, May 11

Face Paint with Uniquely Clever Art

Watersound

Family Fun

Katlyn of Uniquely Clever will be offering face painting services. Although fees apply, no advance registration is required for participants to join the activity.

Tue, May 12

Myami’s Beach Hair

Watersound

Family Fun

Myami Henna is offering a day of creative hair styling services tailored for girls and young ladies looking to express their personal style. The pop-up event features colorful hair wraps, shimmering tinsel, mermaid-inspired waves with bold accents, and custom braids. Fees apply for these specialized services.

Thu, May 14

Farmers Market

Watersound

Markets & Shopping

Anchored Market Ventures manages the Farmer’s Market at The Big Chill, which runs from 9 a.m. to 1 p.m. and is open to the general public. This family-friendly event features a variety of local vendors offering fresh produce, handmade crafts, health products, and home decor. Visitors can enjoy live music and local food while supporting the community. Information regarding market news and updates is available through the Farmers Market Junction newsletter and their social media channels.

Thu, May 14

Myami’s Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of creative hair services. Participants can choose from colorful hair wraps, shimmering hair tinsel, beachy mermaid waves, and personalized custom braids. These styling options are ideal for girls and young ladies looking to showcase their unique magic, though fees for the services do apply.

Fri, May 15

Craft & Canvas Art Class hosted by Uniquely Clever *Must Pre-register

Watersound

Workshops & Classes

Uniquely Clever hosts the Craft and Canvas art class every Friday from 5:00 PM to 6:00 PM. The sessions are held in the screened-in space situated to the left of the Jumbotron, and interested participants are required to pre-register for the class.

Sat, May 16

Myami’s Beach Hair

Watersound

Family Fun

Myami Henna is hosting a pop-up event featuring a variety of creative hair services, including colorful hair wraps, shimmering tinsel, mermaid-style waves with bold accents, and custom braids. These offerings are specifically designed for girls and young ladies to showcase their personal style. Please note that fees apply for these services.

Reviews - 8

john

Memphis, TN

Nov 2025

Google

We take multiple trips to Santa Rosa every year and this is hands down our favorite place we’ve ever stayed in!!!

kathy

Sep 2025

Vrbo

jodi

Aug 2025

Airbnb

Darling beach home in a gated community. Sea Grove beach was amazing and perfect and not too populated! Ocean water was clear, blue teal, and of course, gorgeous sand. We stayed at the end of August and it got a lot busier towards Labor Day weekend. The golf cart was an added bonus always fun to get a house with one, made coffee and donut runs to Turbo in morning easy and fun! The Big Chill is right up the road, easy drive in golf cart but we took the Tahoe, amazing ice cream spot in the evening. Alys Beach is one beach over. Ate dinners on Alys beach, it‚’s one of the dreamiest spots in Florida to walk the streets. It feels like Greece. Amazing trip!

kelly

Mccomb, MS

Jul 2025

Google

Loved “Out of Office”
Can’t say enough about this home and experience! The home was immaculate, tastefully decorated, full of personal touches to make you feel at home, and convenient to town and beaches! Excellent responses from management, extras you won’t get anywhere else, like beach chairs, umbrellas and a wagon. And it comes with a beautiful golf cart and 4 bikes! Games are available, they make sure you’re comfortable with a beautifully functioning kitchen, extra supplies like laundry pods, and toiletries, a welcome package, and Oversee quick response for any questions!
In a neighborhood, but the beauty of this is- you can get out of the rat race, and still get to fun things easily. Private neighborhood pool and access to a private beach!
We loved this place and will be back! It was perfect for our family to be able to spend quality time together!!! Win win!!

julie

Bulverde, TX

Jul 2025

Google

Absolutely beautiful home! Super clean and with all the amenities that we could ask for. We will definitely be back and we will definitely recommend

sarah

Jun 2025

Airbnb

This was our 2nd year staying at this beautiful home. We love everything about the home. The neighborhood is quiet and peaceful. Very well maintained. The management company was responsive to us and kept in touch. They fixed any issues very quickly. We would definitely come back again!

julie