Out of Office
Out of Office
Out of Office
Out of Office
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 built for super chill days, great meals, and plenty of time together. Grab one of the complimentary bikes or hop in the six-seater golf cart and head out to explore the neighborhood. An absolute vacation highlight!
The front porch might steal the show.
Hammock chairs, comfortable seating, and an outdoor dining table make it the kind of place for slow mornings and even slower evenings.
Around back, the spacious deck features an outdoor kitchen and grill, ready for burgers, seafood, or whatever sounds good after a day at the beach.
Inside, everyone has room to relax. The living area is warm, comfortable, and perfect for swapping beach stories or settling in for the evening. The fully equipped kitchen keeps meals simple, with an island that seats three for coffee, snacks, or a quick bite before heading out.
Upstairs, a second living room gives kids, teens, or night owls their own place to spread out. Sink into the oversized sofa, pick a movie, and let the Smart TV handle the entertainment.
Out of Office makes it easy to slow down, spend time together, and enjoy everything that makes 30A special. You’re gonna love it.
At Oversee 30A, we're local, nearby, and here when you need us. Our team is available seven days a week, with 24/7 emergency support, so you can focus on enjoying your vacation while we take care of the rest.
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:
FIRST FLOOR
- Primary Bedroom: king bed, private bath, TV
- Guest Room: queen bed, barn door, shared bath, TV
SECOND FLOOR
- Primary Bedroom: king bed, private bath, TV
- Guest Room: king bed, shared bath, TV
- Guest Room: queen bed, shared bath, TV
Check-in is 4:00 PM CST. Checkout is 10:00 AM CST.
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Hassle-free check-in.
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Add your trip dates to get the cancellation details for this stay.
House Rules
Who can stay.
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10 guests maximum
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No pets
What's allowed.
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Check-in after 4:00 PM
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Check-out before 10:00 AM
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No smoking
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No parties or events
Amenities
Kitchen
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Dishwasher
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Stove
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Standard coffee maker
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Microwave
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Refrigerator
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Toaster
Indoor
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Wireless internet
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Fireplace
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Workspace
Complimentary Items
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4 Oversee bikes
- Beach chairs
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Golf cart
Outdoor
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Garage
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Balcony
Community Amenities
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Community pool
Safety Features
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Carbon monoxide detector
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Fire extinguisher
Bed And Bathroom
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Hair dryer
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Iron & board
Entertainment
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Smart TV
Bed and Baths
1st Floor
bedroom
1 Queen bed
Primary Bed Bedroom
1 King bed
full bathroom
full bathroom
2nd Floor
bedroom
1 King bed
bedroom
1 King bed
bedroom
1 Queen bed
full bathroom
full bathroom
Location
Upcoming Events
College Football on the Jumbotron
Watersound
Sports & Games
The Jumbotron schedule for Thursday, September 3 features a matchup between Colorado and Georgia Tech at 7 PM.
Welded Jewelry Pop-Up with Spark Collection 30A
Watersound
Markets & Shopping
Customers can start their Spark Collection by choosing from a curated selection of 14K solid yellow or white gold chains, which can be crafted into custom bracelets, necklaces, anklets, and rings. Guests are invited to participate in a custom welded jewelry experience by scheduling an appointment at one of the brand's many pop-up events.
DJ Dance Party w/ DJ Dan
Watersound
Family Fun
Families can enjoy an energetic evening of dancing and music at the Ultimate Family Dance Party, featuring popular hits played live by DJ Dan.
Welded Jewelry Pop-Up with Spark Collection 30A
Watersound
Markets & Shopping
Customers can start their Spark Collection by choosing from a curated selection of 14K solid yellow or white gold chains, which can be crafted into custom bracelets, necklaces, anklets, and rings. Guests are invited to join a unique welded jewelry experience by booking an appointment at one of their pop-up events.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday throughout the football season. Guests can watch every game day play on a 25-foot Jumbotron while enjoying full-service bars and food options from several nearby eateries. It offers an outdoor viewing experience and a fan-friendly environment suitable for following fantasy lineups or supporting local teams.
College Football on the Jumbotron: Louisville vs. Ole Miss
Watersound
Sports & Games
Louisville will play against Ole Miss on the Jumbotron at 6:30 PM.
Monday Art Studio with Sparkleberry
Watersound
Workshops & Classes
Monday Art Studio offers a weekly homeschool art experience for children ages 5 to 12 at Stage Right inside The Big Chill in Watersound, Florida. Held on Mondays from 10:00 AM to 12:00 PM starting August 17th, the program allows participants to explore famous artists, experiment with different materials, and work on meaningful projects in a collaborative environment. Pricing options include $60 per class, $240 monthly, or $780 for the 13-week Fall Semester. While individual sessions stand on their own, consistent attendance helps foster deeper artistic growth and creative confidence. Step Up for Students Direct Pay is accepted.
College Football: FSU vs SMU
Watersound
Sports & Games
Florida State University faces Southern Methodist University in a college football matchup.
MLB on the Jumbotron
Watersound
Sports & Games
Major League Baseball is displayed on the massive video screen.
NFL on the Jumbotron
Watersound
Sports & Games
The National Football League is featured on the large video screen.
Farmer’s Market
Watersound
Markets & Shopping
The Farmer’s Market at The Big Chill, managed by Anchored Market Ventures, takes place from 9:00 a.m. to 1:00 p.m. This family-friendly event is open to the public and features a wide variety of local vendors offering items such as fresh produce, farm-fresh eggs, pickles, microgreens, baked goods, jellies, and jams. Visitors can also explore health and wellness products, woodwork, home decor, lavender items, beard oils, handmade jewelry, candles, soaps, art, and crafts. In addition to shopping, the event offers local food options on-premise and great music. Attendees are encouraged to stay connected through the Farmers Market Junction newsletter and watch market videos online.
College Football on the Jumbotron: Florida A&M vs Miami
Watersound
Sports & Games
A college football game featuring Florida A&M versus Miami is displayed on the jumbotron.
DJ Dance Party w/ DJ Dan
Watersound
Family Fun
Guests are invited to attend the Ultimate Family Dance Party, featuring DJ Dan playing popular hits. The event offers a high-energy, family-friendly evening filled with music and dancing for attendees of all ages.
NFL on the Jumbotron
Watersound
Sports & Games
Every Sunday throughout the season, The Big Chill hosts an NFL Watch Party featuring wall-to-wall football action on a 25-foot Jumbotron. Attendees can enjoy a fan-friendly atmosphere with outdoor viewing, full-service bars, and game day bites from multiple eateries while watching their favorite teams or tracking fantasy lineups.
Monday Art Studio with Sparkleberry
Watersound
Workshops & Classes
Monday Art Studio is a weekly homeschool art experience for children ages 5 to 12, held on Mondays from 10:00 AM to 12:00 PM starting August 17th at Stage Right inside The Big Chill in Watersound, Florida. Each week, participants explore celebrated artists, experiment with diverse materials, and work on meaningful projects within a collaborative studio environment. The program offers flexibility with options to attend individual classes at $60 per class, monthly at $240, or for the full 13-week fall semester at $780. While each session functions independently, consistent attendance encourages deeper artistic growth, creative confidence, and community building. Step Up for Students Direct Pay is accepted for payment.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill is hosting an NFL Watch Party every Monday throughout the season. Attendees can watch all the football action on a 25-foot Jumbotron while enjoying food and drinks from multiple eateries and full-service bars in a fan-friendly outdoor atmosphere.
MLB on the Jumbotron
Watersound
Sports & Games
Major League Baseball is displayed on the large video screen.
MLB on the Jumbotron
Watersound
Sports & Games
Major League Baseball is displayed on the giant video screen.
College Football on the Jumbotron: Miami vs Wake Forest
Watersound
Sports & Games
A college football matchup featuring Miami versus Wake Forest is displayed on the large video screen.
College Football on the Jumbotron
Watersound
Sports & Games
College football action is broadcast on a 25-foot Jumbotron, with featured games posted by Wednesday each week. Additional top games of the day are shown on televisions under the covered pavilion. Guests can also request specific games on 10 other TVs located across the property on a first-come, first-served basis by asking a bartender or cashier to contact a manager.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Sunday throughout the football season. Attendees can watch game day action on a 25-foot Jumbotron while enjoying outdoor viewing, a fan-friendly atmosphere, full-service bars, and food options from various eateries. It offers a great destination for sports fans looking to catch every play and track their fantasy lineups.
Monday Art Studio with Sparkleberry
Watersound
Workshops & Classes
Monday Art Studio offers a weekly homeschool art experience for children ages 5 to 12 at Stage Right inside The Big Chill in Watersound, Florida. Held on Mondays from 10:00 AM to 12:00 PM starting August 17th, the program allows young artists to explore celebrated figures, experiment with various mediums, and build creative confidence in a collaborative environment. Tuition options include $60 per class, $240 monthly, or $780 for the 13-week Fall Semester, with Step Up for Students Direct Pay accepted. While individual class attendance is welcome, consistent participation encourages deeper artistic growth and community connection. Registration is available online.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Monday throughout the football season. Attendees can watch every play on a 25-foot Jumbotron while enjoying food from multiple eateries and drinks from full-service bars in a fan-friendly outdoor atmosphere. It is an ideal destination for fans to support their team or follow their fantasy football lineups.
Mind Plays
Watersound
Live Music
Mind Plays will perform live from 6:00 to 9:30 pm.
Thu, September 3
College Football on the Jumbotron
Watersound
Sports & Games
Fri, September 4
Welded Jewelry Pop-Up with Spark Collection 30A
Watersound
Markets & Shopping
Fri, September 4
DJ Dance Party w/ DJ Dan
Watersound
Family Fun
Sat, September 5
Welded Jewelry Pop-Up with Spark Collection 30A
Watersound
Markets & Shopping
Sun, September 6
NFL on the Jumbotron
Watersound
Sports & Games
Sun, September 6
College Football on the Jumbotron: Louisville vs. Ole Miss
Watersound
Sports & Games
Mon, September 7
Monday Art Studio with Sparkleberry
Watersound
Workshops & Classes
Mon, September 7
College Football: FSU vs SMU
Watersound
Sports & Games
Tue, September 8
MLB on the Jumbotron
Watersound
Sports & Games
Wed, September 9
NFL on the Jumbotron
Watersound
Sports & Games
Thu, September 10
Farmer’s Market
Watersound
Markets & Shopping
Thu, September 10
College Football on the Jumbotron: Florida A&M vs Miami
Watersound
Sports & Games
Fri, September 11
DJ Dance Party w/ DJ Dan
Watersound
Family Fun
Sun, September 13
NFL on the Jumbotron
Watersound
Sports & Games
Mon, September 14
Monday Art Studio with Sparkleberry
Watersound
Workshops & Classes
Mon, September 14
NFL on the Jumbotron
Watersound
Sports & Games
Tue, September 15
MLB on the Jumbotron
Watersound
Sports & Games
Wed, September 16
MLB on the Jumbotron
Watersound
Sports & Games
Fri, September 18
College Football on the Jumbotron: Miami vs Wake Forest
Watersound
Sports & Games
Sat, September 19
College Football on the Jumbotron
Watersound
Sports & Games
Sun, September 20
NFL on the Jumbotron
Watersound
Sports & Games
Mon, September 21
Monday Art Studio with Sparkleberry
Watersound
Workshops & Classes
Mon, September 21
NFL on the Jumbotron
Watersound
Sports & Games
Tue, September 22
Mind Plays
Watersound
Live Music
Reviews - 11
Airbnb
We had a water issue at another place and needed a new place with virtually zero notice. Oversee was very understanding of our position and really saved our trip. The house was great. The location was ideal. Loved the semi-private beach and pool. Loved the ability to bike to the beach. I hope to return to the same place this fall.
Google
Oversee did an excellent job managing my vacation home rental in 30A. Their team was professional, responsive, and made the entire process stress-free. Communication was clear, and they took great care of both the property and questions I had. I highly recommend them to anyone looking for reliable vacation rental management services.
Vrbo
Absolutely beautiful house – perfect stay!
Google
We take multiple trips to Santa Rosa every year and this is hands down our favorite place we’ve ever stayed in!!!
Vrbo
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!
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!!
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
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!
Airbnb
Airbnb
Host Family
Diamond Office at Sunnyside
Office location:
Diamond Office at Sunnyside, Florida
Contact Diamond Office at Sunnyside
Out of Office
Santa Rosa Beach - Sleeps 10
5 bedrooms - 5 beds - 4 baths
Prices include all fees and taxes