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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Take the 3D walkthrough.
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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
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill is the ultimate destination for catching every NFL game, hosting an NFL Watch Party every Sunday throughout the season. Visitors can watch the wall-to-wall football action on the 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites. The event features game day bites from various eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing options. Whether attendees are rooting for their favorite team or tracking their fantasy lineup, this location provides the ultimate NFL experience. The specific games displayed on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under a covered pavilion, and requests for specific games can be made to a manager at the bars on a first-come basis.
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Monday throughout the season, offering the best place to catch every play. Attendees can enjoy wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites, including game day bites. The atmosphere is fan-friendly, with full-service bars and outdoor viewing options, making it the ultimate destination for cheering on a home team or tracking a fantasy lineup.
College Football on the Jumbotron
Watersound
Sports & Games
A college football watch party is being held all season long. Attendees are invited to watch their favorite college football teams compete on a massive 25-ft Jumbotron. Multiple restaurants and bars will be available, offering ice-cold drinks and an electric atmosphere with outdoor seating. All the big games will be shown all day long. This is the ideal spot for fans to represent their alma mater or enjoy the rivalries. Guests are encouraged to bring their friends, wear their team colors, and cheer loudly for a proper college football experience. The specific games shown on the Jumbotron will be posted weekly by Wednesday. All other games will be shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Guests should ask a manager at the bars for any requests.
NYE Celebration! College Football and Beach Ball Drop!
Watersound
Family Fun
The event organizers are hosting a family-friendly New Year's Eve Celebration to ring in 2026. The celebration will feature college football bowl games displayed on a Jumbotron, as well as an early New Year's Eve countdown and beach ball drop. The Beach Ball Drop will take place on stage with DJ Dan Davis during halftime of the game that begins at 6:30 p.m. The precise timing of the countdown and ball drop is dependent upon the progression of the game.
Rooftop Soirée
Watersound
Food & Drink
A New Year’s Eve Rooftop Soirée is scheduled to take place, offering attendees a chance to enjoy the final sunset of 2025 with breathtaking views over the Emerald Coast. The ticket price is $89 per person, exclusive of fees, and includes two select beverages and passed appetizers. The event is scheduled from 4:00 PM to 6:00 PM. Additional beverages will be charged at the menu price upon consumption. The event concludes at 6:00 PM, after which Pescado will close until dinner service begins at 7:00 PM for reservations only. All ticket sales are non-refundable and non-transferable, and all guests must be 21 years of age or older to attend.
NYE 'Wickedly' Celebration
Watersound
Food & Drink
Pescado’s NYE celebration, titled "Wickedly," invites guests to step into the new year with sparkle, mystery, and rebellion, rising above the ordinary for a night that feels defyingly wicked. Reservations are available from 7 PM to 10 PM. The celebration begins with a glass of wine before sweeping guests into the new year. The "Wickedly" celebration tickets include a three-course dinner and amuse, entry to The Courtyard Studio 54 Party, and a DJ performing spells from 11 PM to 1 AM on the Rooftop. The cost is $259.00 plus a 22% service charge and 7% state tax. All beverages, except for the arrival glass, will be charged on consumption.
Calling All Songwriters: The Songwriters Showdown Returns
Watersound
Live Music
The Cultural Arts Alliance of Walton County (CAA) has announced the return of The Made in Walton County – Songwriters Showdown, and submissions are currently open for local songwriters. This live showcase is a celebration of homegrown talent, original music, and the narratives behind the songs. Songwriters across all genres are encouraged to apply for the chance to perform, engage with an audience, and compete for cash prizes, including a guaranteed spot in the 2027 30A Songwriters Festival lineup. Up to ten finalists will be chosen from submissions received by the deadline on Friday, February 20, 2026, to perform live on Thursday, March 26, 2026, at The Pavilion at Watersound Town Center. Each finalist will have up to 10 minutes on stage to present their original songs and stories before a live audience and a panel of judges. Reflecting on the previous year, the inaugural Songwriters Showdown was described as a memorable evening showcasing raw talent and heartfelt performances. Finalists from that year included Sammi Accola, Emily Bass, Gage Cowart, Marc Harris, Nate Kelly, Tom Pritchett, and Nathan Worthey, with Sammi Accola securing the top prize. The event was hosted by Wyatt Espalin, a favorite from the 30A Songwriters Festival, and featured an esteemed panel of judges: Jessica Sharman, Gretchen Peters, and Jennifer Steele, who provided valuable industry insight and feedback. The evening concluded with the announcement of first, second, and third-place winners, alongside a People’s Choice Award decided by the audience. The Made in Walton County – Songwriters Showdown is considered more than just a contest; it is a celebration of creativity, community, and original music. It offers both emerging and seasoned performers an opportunity to share their voice, tell their story, and contribute to a growing tradition that highlights the vibrant music scene in Walton County. Songwriters selected as finalists will perform for an audience of music lovers, arts supporters, and fellow creatives, an experience intended to foster connection and elevate local talent. Songwriters who believe they have a song worth sharing are encouraged to submit their entry no later than Friday, February 20, 2026, for a chance to be in the spotlight. Guidelines and the application are available online.
Mon, December 29
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill is the ultimate destination for catching every NFL game, hosting an NFL Watch Party every Sunday throughout the season. Visitors can watch the wall-to-wall football action on the 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites.
The event features game day bites from various eateries, full-service bars, and a fan-friendly atmosphere with outdoor viewing options. Whether attendees are rooting for their favorite team or tracking their fantasy lineup, this location provides the ultimate NFL experience.
The specific games displayed on the Jumbotron are posted weekly by Wednesday. All other games are shown on TVs under a covered pavilion, and requests for specific games can be made to a manager at the bars on a first-come basis.
Mon, December 29
NFL on the Jumbotron
Watersound
Sports & Games
The Big Chill hosts an NFL Watch Party every Monday throughout the season, offering the best place to catch every play. Attendees can enjoy wall-to-wall football action on a 25-foot Jumbotron, surrounded by multiple restaurants and bars serving game day favorites, including game day bites. The atmosphere is fan-friendly, with full-service bars and outdoor viewing options, making it the ultimate destination for cheering on a home team or tracking a fantasy lineup.
Tue, December 30
College Football on the Jumbotron
Watersound
Sports & Games
A college football watch party is being held all season long. Attendees are invited to watch their favorite college football teams compete on a massive 25-ft Jumbotron. Multiple restaurants and bars will be available, offering ice-cold drinks and an electric atmosphere with outdoor seating. All the big games will be shown all day long. This is the ideal spot for fans to represent their alma mater or enjoy the rivalries. Guests are encouraged to bring their friends, wear their team colors, and cheer loudly for a proper college football experience. The specific games shown on the Jumbotron will be posted weekly by Wednesday. All other games will be shown on TVs under a covered pavilion, with several TVs available for requests on a first-come basis. Guests should ask a manager at the bars for any requests.
Wed, December 31
NYE Celebration! College Football and Beach Ball Drop!
Watersound
Family Fun
The event organizers are hosting a family-friendly New Year’s Eve Celebration to ring in 2026. The celebration will feature college football bowl games displayed on a Jumbotron, as well as an early New Year’s Eve countdown and beach ball drop. The Beach Ball Drop will take place on stage with DJ Dan Davis during halftime of the game that begins at 6:30 p.m. The precise timing of the countdown and ball drop is dependent upon the progression of the game.
Wed, December 31
Rooftop Soirée
Watersound
Food & Drink
A New Year’s Eve Rooftop Soirée is scheduled to take place, offering attendees a chance to enjoy the final sunset of 2025 with breathtaking views over the Emerald Coast. The ticket price is $89 per person, exclusive of fees, and includes two select beverages and passed appetizers. The event is scheduled from 4:00 PM to 6:00 PM. Additional beverages will be charged at the menu price upon consumption. The event concludes at 6:00 PM, after which Pescado will close until dinner service begins at 7:00 PM for reservations only. All ticket sales are non-refundable and non-transferable, and all guests must be 21 years of age or older to attend.
Wed, December 31
NYE 'Wickedly' Celebration
Watersound
Food & Drink
Pescado’s NYE celebration, titled “Wickedly,” invites guests to step into the new year with sparkle, mystery, and rebellion, rising above the ordinary for a night that feels defyingly wicked. Reservations are available from 7 PM to 10 PM. The celebration begins with a glass of wine before sweeping guests into the new year. The “Wickedly” celebration tickets include a three-course dinner and amuse, entry to The Courtyard Studio 54 Party, and a DJ performing spells from 11 PM to 1 AM on the Rooftop. The cost is $259.00 plus a 22% service charge and 7% state tax. All beverages, except for the arrival glass, will be charged on consumption.
Thu, March 26
Calling All Songwriters: The Songwriters Showdown Returns
Watersound
Live Music
The Cultural Arts Alliance of Walton County (CAA) has announced the return of The Made in Walton County – Songwriters Showdown, and submissions are currently open for local songwriters. This live showcase is a celebration of homegrown talent, original music, and the narratives behind the songs. Songwriters across all genres are encouraged to apply for the chance to perform, engage with an audience, and compete for cash prizes, including a guaranteed spot in the 2027 30A Songwriters Festival lineup.
Up to ten finalists will be chosen from submissions received by the deadline on Friday, February 20, 2026, to perform live on Thursday, March 26, 2026, at The Pavilion at Watersound Town Center. Each finalist will have up to 10 minutes on stage to present their original songs and stories before a live audience and a panel of judges.
Reflecting on the previous year, the inaugural Songwriters Showdown was described as a memorable evening showcasing raw talent and heartfelt performances. Finalists from that year included Sammi Accola, Emily Bass, Gage Cowart, Marc Harris, Nate Kelly, Tom Pritchett, and Nathan Worthey, with Sammi Accola securing the top prize. The event was hosted by Wyatt Espalin, a favorite from the 30A Songwriters Festival, and featured an esteemed panel of judges: Jessica Sharman, Gretchen Peters, and Jennifer Steele, who provided valuable industry insight and feedback. The evening concluded with the announcement of first, second, and third-place winners, alongside a People’s Choice Award decided by the audience.
The Made in Walton County – Songwriters Showdown is considered more than just a contest; it is a celebration of creativity, community, and original music. It offers both emerging and seasoned performers an opportunity to share their voice, tell their story, and contribute to a growing tradition that highlights the vibrant music scene in Walton County. Songwriters selected as finalists will perform for an audience of music lovers, arts supporters, and fellow creatives, an experience intended to foster connection and elevate local talent. Songwriters who believe they have a song worth sharing are encouraged to submit their entry no later than Friday, February 20, 2026, for a chance to be in the spotlight. Guidelines and the application are available online.
Reviews - 5
Google
We take multiple trips to Santa Rosa every year and this is hands down our favorite place we’ve ever stayed in!!!
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
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