Out of Office
Out of Office
Out of Office
Out of Office
Out of Office by Oversee 30A | 2025 Diamond Winner-Best Rental Mgmt.
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.
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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
Outdoor
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Garage
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Balcony
Complimentary Items
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4 Oversee bikes
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Golf cart
Community Amenities
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Community pool
Entertainment
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Cable
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Smart TV
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
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 Basketball on the Jumbotron
Watersound
Sports & Games
Guests can enjoy dinner and drinks while watching their favorite team on the big screen.
Olympics on the Jumbotron
Watersound
Sports & Games
The venue is hosting an Olympics Watch Party, inviting attendees to watch their favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, lasting all day long.
College Basketball on the Jumbotron
Watersound
Sports & Games
Guests can enjoy dinner and drinks while watching their favorite team on the big screen.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted to watch favorite Olympic sports on a massive 25-ft Jumbotron, advertised as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere all day long.
Brunch by the Lake
Watersound
Food & Drink
AJ's Grayton Beach is hosting a job fair on February 2nd and February 9th from 12 PM to 5 PM. Interested applicants are encouraged to attend, ready to interview and bring their resume. The restaurant group is currently hiring for all departments, including Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers. Candidates have the opportunity to meet face-to-face with hiring managers to learn about the many opportunities available with the locally owned and operated restaurant group, which has been part of the community for over 42 years. Furthermore, the community is invited to celebrate the grand opening of the new location at Shops at the Hub on February 7th from 10 AM to 6 PM.
College Basketball on the Jumbotron
Watersound
Sports & Games
Guests can enjoy dinner and drinks while watching their favorite team on the big screen.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted, offering an opportunity to enjoy favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, available all day long.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being held, inviting attendees to watch their favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, lasting all day long.
College Basketball on the Jumbotron
Watersound
Sports & Games
Attendees are invited to enjoy dinner and drinks while watching their preferred team on the large screen.
Olympics on the Jumbotron
Watersound
Sports & Games
The venue is hosting an Olympics Watch Party, inviting attendees to prepare for the Olympics by watching their favorite sports on a massive 25-ft Jumbotron, advertised as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere all day long.
College Basketball on the Jumbotron
Watersound
Sports & Games
Attendees can grab some dinner and drinks and join the group to watch their favorite team on the big screen.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics watch party is being hosted to view favorite Olympic sports on a massive 25-ft Jumbotron, which is described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere that will last all day long.
College Basketball on the Jumbotron
Watersound
Sports & Games
Guests are invited to enjoy dinner and drinks while watching their favorite team on the big screen.
Olympics on the Jumbotron
Watersound
Sports & Games
The venue is hosting an Olympics Watch Party, inviting attendees to experience the games on their massive 25-ft Jumbotron, which is described as the biggest screen in town. The event features multiple restaurants and bars, cold drinks, outdoor seating, and promises an electric atmosphere that lasts all day long.
College Basketball on the Jumbotron
Watersound
Sports & Games
Attendees are invited to enjoy dinner and drinks while watching their favorite team on the big screen.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted for fans to enjoy their favorite Olympic sports on a massive 25-ft Jumbotron, touted as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, continuing all day long.
Family Game Night: TRIVIA
Watersound
Family Fun
Attendees are invited to enjoy drinks and dinner while participating in family trivia night, which will take place from 6-8 pm under the covered and heated pavilion. Participants must have an electronic device to play.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted to allow attendees to view their favorite Olympic sports on a massive 25-ft Jumbotron. The venue is promoted as having the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, and outdoor seating, promising an electric atmosphere that will last all day long.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being held, inviting people to join and watch their favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, an electric atmosphere, and lasts all day long.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being held to prepare for the Olympics. Attendees are invited to watch their favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The venue features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere for the all-day event.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being held, inviting people to get ready for the Olympics by watching their favorite sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, an electric atmosphere, and lasts all day long.
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted for fans to enjoy their favorite Olympic sports on the massive 25-foot Jumbotron, which is touted as the biggest screen in town. Attendees can look forward to multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, with the celebration lasting all day long.
Olympics on the Jumbotron
Watersound
Sports & Games
The venue invites attendees to an Olympics Watch Party to view their favorite Olympic sports on a massive 25-ft Jumbotron, touted as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere that lasts all day long.
College Basketball on the Jumbotron
Watersound
Sports & Games
Attendees are invited to enjoy dinner and drinks while watching their favorite team on the big screen.
Olympics on the Jumbotron
Watersound
Sports & Games
A massive 25-ft Jumbotron—the biggest screen in town—will show the Olympics. Attendees can enjoy multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere throughout the day while watching their favorite Olympic sports.
Family Game Night : BINGO
Watersound
Family Fun
Attendees are invited to enjoy drinks and dinner while participating in family bingo night, which is scheduled from 6-8 pm under the covered and heated pavilion. Each person must have an electronic device to play, and only one device per person is allowed.
Olympics on the Jumbotron
Watersound
Sports & Games
The venue is hosting an Olympics Watch Party, inviting attendees to join them to watch their favorite Olympic sports on their massive 25-ft Jumbotron, which they claim is the biggest screen in town. They offer multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere all day long.
Thu, February 5
College Basketball on the Jumbotron
Watersound
Sports & Games
Guests can enjoy dinner and drinks while watching their favorite team on the big screen.
Fri, February 6
Olympics on the Jumbotron
Watersound
Sports & Games
The venue is hosting an Olympics Watch Party, inviting attendees to watch their favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, lasting all day long.
Fri, February 6
College Basketball on the Jumbotron
Watersound
Sports & Games
Guests can enjoy dinner and drinks while watching their favorite team on the big screen.
Sat, February 7
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted to watch favorite Olympic sports on a massive 25-ft Jumbotron, advertised as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere all day long.
Sat, February 7
Brunch by the Lake
Watersound
Food & Drink
AJ’s Grayton Beach is hosting a job fair on February 2nd and February 9th from 12 PM to 5 PM. Interested applicants are encouraged to attend, ready to interview and bring their resume. The restaurant group is currently hiring for all departments, including Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers. Candidates have the opportunity to meet face-to-face with hiring managers to learn about the many opportunities available with the locally owned and operated restaurant group, which has been part of the community for over 42 years. Furthermore, the community is invited to celebrate the grand opening of the new location at Shops at the Hub on February 7th from 10 AM to 6 PM.
Sat, February 7
College Basketball on the Jumbotron
Watersound
Sports & Games
Guests can enjoy dinner and drinks while watching their favorite team on the big screen.
Sun, February 8
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted, offering an opportunity to enjoy favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, available all day long.
Mon, February 9
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being held, inviting attendees to watch their favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, lasting all day long.
Mon, February 9
College Basketball on the Jumbotron
Watersound
Sports & Games
Attendees are invited to enjoy dinner and drinks while watching their preferred team on the large screen.
Tue, February 10
Olympics on the Jumbotron
Watersound
Sports & Games
The venue is hosting an Olympics Watch Party, inviting attendees to prepare for the Olympics by watching their favorite sports on a massive 25-ft Jumbotron, advertised as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere all day long.
Tue, February 10
College Basketball on the Jumbotron
Watersound
Sports & Games
Attendees can grab some dinner and drinks and join the group to watch their favorite team on the big screen.
Wed, February 11
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics watch party is being hosted to view favorite Olympic sports on a massive 25-ft Jumbotron, which is described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere that will last all day long.
Wed, February 11
College Basketball on the Jumbotron
Watersound
Sports & Games
Guests are invited to enjoy dinner and drinks while watching their favorite team on the big screen.
Thu, February 12
Olympics on the Jumbotron
Watersound
Sports & Games
The venue is hosting an Olympics Watch Party, inviting attendees to experience the games on their massive 25-ft Jumbotron, which is described as the biggest screen in town. The event features multiple restaurants and bars, cold drinks, outdoor seating, and promises an electric atmosphere that lasts all day long.
Thu, February 12
College Basketball on the Jumbotron
Watersound
Sports & Games
Attendees are invited to enjoy dinner and drinks while watching their favorite team on the big screen.
Fri, February 13
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted for fans to enjoy their favorite Olympic sports on a massive 25-ft Jumbotron, touted as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, continuing all day long.
Fri, February 13
Family Game Night: TRIVIA
Watersound
Family Fun
Attendees are invited to enjoy drinks and dinner while participating in family trivia night, which will take place from 6-8 pm under the covered and heated pavilion. Participants must have an electronic device to play.
Sat, February 14
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted to allow attendees to view their favorite Olympic sports on a massive 25-ft Jumbotron. The venue is promoted as having the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, and outdoor seating, promising an electric atmosphere that will last all day long.
Sun, February 15
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being held, inviting people to join and watch their favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, an electric atmosphere, and lasts all day long.
Mon, February 16
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being held to prepare for the Olympics. Attendees are invited to watch their favorite Olympic sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The venue features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere for the all-day event.
Tue, February 17
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being held, inviting people to get ready for the Olympics by watching their favorite sports on a massive 25-ft Jumbotron, described as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, an electric atmosphere, and lasts all day long.
Wed, February 18
Olympics on the Jumbotron
Watersound
Sports & Games
An Olympics Watch Party is being hosted for fans to enjoy their favorite Olympic sports on the massive 25-foot Jumbotron, which is touted as the biggest screen in town. Attendees can look forward to multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere, with the celebration lasting all day long.
Thu, February 19
Olympics on the Jumbotron
Watersound
Sports & Games
The venue invites attendees to an Olympics Watch Party to view their favorite Olympic sports on a massive 25-ft Jumbotron, touted as the biggest screen in town. The event features multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere that lasts all day long.
Thu, February 19
College Basketball on the Jumbotron
Watersound
Sports & Games
Attendees are invited to enjoy dinner and drinks while watching their favorite team on the big screen.
Fri, February 20
Olympics on the Jumbotron
Watersound
Sports & Games
A massive 25-ft Jumbotron—the biggest screen in town—will show the Olympics. Attendees can enjoy multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere throughout the day while watching their favorite Olympic sports.
Fri, February 20
Family Game Night : BINGO
Watersound
Family Fun
Attendees are invited to enjoy drinks and dinner while participating in family bingo night, which is scheduled from 6-8 pm under the covered and heated pavilion. Each person must have an electronic device to play, and only one device per person is allowed.
Sat, February 21
Olympics on the Jumbotron
Watersound
Sports & Games
The venue is hosting an Olympics Watch Party, inviting attendees to join them to watch their favorite Olympic sports on their massive 25-ft Jumbotron, which they claim is the biggest screen in town. They offer multiple restaurants and bars, ice-cold drinks, outdoor seating, and an electric atmosphere all day long.
Reviews - 8
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