Three Hundred

Sleeps 17 - 5 Bedrooms - 6 Baths
300 E Shipwreck Rd, Santa Rosa Beach, FL 32459

Three Hundred by Oversee 30A | 2025 Diamond Winner-Best Rental Mgmt.

Waterfront, and on the edge of a beautiful bay, welcome to Three Hundred, an exceptional home featuring 5 bedrooms, 5 full baths, 2 half baths, and a large, gorgeous private pool and dock.

📍 Near Miramar Beach on the Choctawhatchee Bay
🚤 Waterfront, with private dock
🛏️ 5 Bedrooms, 5 Full Baths, 2 Half Baths
🪞 Stunning interiors, a coastal masterpiece
👙 Grand entertainment space: private saltwater pool, spillover spa, firepit, gas grill
🚘 Ample parking

A true masterpiece of coastal living, this home is crafted with impeccable attention to detail, with a wealth of features that truly set it apart.

Planning a special event? The driveway offers parking for 10+ cars, so there's plenty of space for guests and family!

Inside, you’ll be awed by the warmth and sophistication of locally sourced pecky wood cypress beams in the kitchen and living areas, and oversized steel windows that flood the home with natural light. French Oak wood floors flow seamlessly throughout, enhancing the timeless appeal of this exquisite home. Gather around the gas fireplace to unwind and create lasting memories with loved ones.

The 20ft accordion doors in the living room effortlessly open to blend indoor and outdoor spaces, allowing you to savor the coastal breeze.

Two primary bedrooms on the first floor offer serene water views, while the guest room features private access to the courtyard and driveway.
Two laundry spaces and a home office, with a separate entry, provide ultimate convenience.

For entertainment, a cinema room awaits your movie nights, and a library passageway upstairs offers quiet escapes. The massive kids' playroom is a versatile space for fun and creativity.

The 1,100-square-foot garage boasts three oversized 10x10 garage doors, a new epoxy floor, and will soon feature a pool table and ping-pong table. Luxury abounds in the primary bath, with deco sliding doors, adding elegance to both the primary closet and bath.

The gourmet kitchen is a culinary dream, complete with two dishwashers and a layout that beckons both seasoned chefs and enthusiastic home cooks alike.

The outdoor space is a true sanctuary, featuring a 20x40 heated saltwater pool and a relaxing spillover spa. Entertain with ease at the outdoor kitchen and gather around the fire pit for cozy evenings under the stars. The expansive backyard offers endless possibilities for outdoor activities and events. Water enthusiasts will appreciate this expansive estate with a deep-water dock capable of accommodating a 35-foot boat

Don't miss the opportunity to enjoy this extraordinary waterfront estate. Embrace the 30A dream in this one-of-a-kind home that seamlessly blends luxury, comfort, and coastal charm. Book your stay today and experience the ultimate in waterfront living!

At Three Hundred, the warmth of hospitality awaits. Our dedicated team at Oversee, 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:
- 5 Bedrooms, 5 Full Baths, 2 Half Baths
- 6240 Sq Ft
- Ample Parking
- Garage has a sitting area, pool table, ping pong table, fridge, microwave, etc.
- Two washers and dryers
- Gas Grill
- Wine cooler
- Fire Pit
- Waterfront
- Private Saltwater Pool (can be heated seasonally for an additional $55.00 per day, contact Oversee for details)
- Spillover Spa

Overnight:
- King in 1st floor primary bedroom; private bath; walk in closet;TV
- King in 1st floor primary bedroom; private bath; TV
- Queen in 1st floor guest room; private bath; Washer/Dryer; TV
- Queen in 1st floor guest room; shared hall bath; TV
- 2 twin over full bunk beds in 1st floor guest room; shared hall bath; TV
- Full daybed with a twin trundle; half bath; TV

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

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House Rules

Who can stay.

  • Guests Maximum17 guests maximum
  • No petsNo pets

What's allowed.

  • Check-inCheck-in after 4:00 PM
  • Check-outCheck-out before 10:00 AM
  • No smokingNo smoking
  • No parties or eventsNo parties or events

Amenities

Indoor

  • Wireless internetWireless internet
  • FireplaceFireplace

Entertainment

  • CableCable
  • Smart TVSmart TV

Safety Features

  • Carbon monoxide detectorCarbon monoxide detector
  • Fire extinguisherFire extinguisher

Kitchen

  • Standard coffee makerStandard coffee maker
  • MicrowaveMicrowave
  • RefrigeratorRefrigerator
  • ToasterToaster
  • DishwasherDishwasher
  • StoveStove

Bed And Bathroom

  • Hair dryerHair dryer
  • Iron & boardIron & board
  • BathtubBathtub

Outdoor

  • GarageGarage
  • Hot tub Hot tub
  • Lake or bay frontLake or bay front
  • Private poolPrivate pool
  • Private heated poolPrivate heated pool
  • Private hot tubPrivate hot tub
  • Private firepitPrivate firepit
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Bed and Baths

1st Floor

Primary Bed Bedroom

1 King bed

full bathroom

 

bedroom

1 Queen bed

full bathroom

 

bedroom

1 Queen bed

full bathroom

 

bedroom

1 Queen bed

full bathroom

 

half bathroom

 

2nd Floor

bedroom

2 Bunk beds

full bathroom

 

half bathroom

 

Location

Upcoming Events

Sun, November 23

Returns to Grand Boulevard

Miramar Beach
Food & Drink Food & Drink

Hello Sugar, the beloved Airstream cotton candy boutique, is returning to Grand Boulevard for a series of pop-up dates in November, December, and March. The event series is called "Hello Sugar Returns to Grand Boulevard!" and features over 25 freshly spun cotton candy flavors, including classic pink vanilla and fun favorites like chocolate, marshmallow, birthday cake, and bubble gum. Additionally, a colorful selection of novelty candies perfect for all ages will be available. The pop-up dates are November 21–30, December 22–January 4, and March 13–22.

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Sun, November 23

La Luna Children’s Boutique Holiday Open House

Miramar Beach
Family Fun Family Fun

La Luna Children’s Boutique is hosting a Holiday Open House at Grand Boulevard. The event series includes dates on Sunday, November 23 from 11:00 AM – 1:00 PM, Friday, November 28 from 12:00 PM – 2:00 PM, and Sunday, November 30 from 12:00 PM – 2:00 PM. Guests are invited to celebrate the season with an enchanting family experience. Attendees can explore a curated collection of festive children’s attire and timeless gifts, enjoy the signature hot cocoa bar, and gather for a charming seasonal storytime. Complimentary professional photos with Santa are available during the first hour of each event.

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Sun, November 23

Sunday Supper

Miramar Beach
Food & Drink Food & Drink

Guests are invited to gather for the timeless southern tradition of Sunday Supper at Ovide, located in Hotel Effie Sandestin, every week from 5-9 p.m. The signature restaurant offers a family-style feast, crafted with heart, and meant to be shared with loved ones. The Sunday Supper is priced at $36 per person (plus tax and gratuity) and features Crispy Skillet Fried Chicken, Mashed Golden Potatoes with Black Pepper Gravy, Country Ham Braised Pole Beans, Effie Biscuits, and House-Made Banana Cream Pie. Reservations are recommended and can be made through OpenTable.

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Sun, November 23

NFL Football

Miramar Beach
Sports & Games Sports & Games

A football game from the NFL will be held.

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Mon, November 24

Returns to Grand Boulevard

Miramar Beach
Food & Drink Food & Drink

Hello Sugar, the beloved Airstream cotton candy boutique, is returning to Grand Boulevard for multiple pop-up dates. Patrons can enjoy over 25 freshly spun flavors, including classic pink vanilla and favorites like chocolate, marshmallow, birthday cake, and bubble gum, along with a colorful selection of novelty candies. Hello Sugar will be back at Grand Boulevard on the following dates: November 21–30, December 22–January 4, and March 13–22.

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Mon, November 24

Free Bonfire

Miramar Beach
Family Fun Family Fun

The venue hosts a complimentary bonfire every Friday and Monday at sunset at their Beach Bar. There is no entrance fee, and resort parking is free. Ample seating is provided, and everyone is welcome. S’mores, drink specials, and the full menu are available. It is an excellent spot for families to enjoy the sunset. Outside food or beverages are not permitted.

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Mon, November 24

Monday Night Football

Miramar Beach
Sports & Games Sports & Games

The event is Monday Night Football.

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Mon, November 24

Live Music

Miramar Beach
Live Music Live Music

Guests can enjoy hand-crafted cocktails while a local artist performs original and cover songs. This event is open to the public, and complimentary validated parking is offered with any food or beverage purchase.

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Tue, November 25

Returns to Grand Boulevard

Miramar Beach
Food & Drink Food & Drink

The "Hello Sugar" event series is returning to Grand Boulevard. Hello Sugar, the Airstream cotton candy boutique, will be back at Grand Boulevard in November, December, and March for a sweet treat. Attendees can enjoy over 25 freshly spun cotton candy flavors, including classic pink vanilla and favorites like chocolate, marshmallow, birthday cake, and bubble gum. A selection of novelty candies will also be available. The pop-up dates are November 21–30, December 22–January 4, and March 13–22.

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Tue, November 25

Almost Famous

Miramar Beach
Live Music Live Music

Almost Famous will be performing live from 5:30 PM to 8:30 PM.

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Tue, November 25

Live Music

Miramar Beach
Live Music Live Music

Guests can enjoy hand-crafted cocktails while listening to a local artist perform original and cover songs. The event is open to the public and includes complimentary validated parking with any food and/or beverage purchase.

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Wed, November 26

Jeff Silvey

Miramar Beach
Live Music Live Music

Jeff Silvey is scheduled to perform live from 5:30 PM to 8:30 PM.

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Wed, November 26

Live Music

Miramar Beach
Live Music Live Music

Guests can enjoy hand-crafted cocktails while listening to a local artist perform original and cover songs. The event is open to the public, and complimentary validated parking is offered with any food or beverage purchase.

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Thu, November 27

Thanksgiving Catering Take Out

Miramar Beach
Food & Drink Food & Drink

Sandestin Golf and Beach Resort offers a stress-free Thanksgiving holiday feast available for purchase. The gourmet meal, which serves 6-8 guests, costs $325 plus tax. It includes an 11-12 pound marinated turkey (smoked, fried, or roasted) with orange cranberry compote and brown gravy, a 7-pound hickory honey-glazed spiral sliced ham, one starter, three sides, and one dessert of choice. Orders must be placed by 5 p.m. on Tuesday, November 25, by calling 850.267.4489 or emailing the provided address. The prepared feast is ready for pickup on Thursday, November 27, between 7 a.m. and noon.

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Thu, November 27

Thanksgiving

Miramar Beach
Food & Drink Food & Drink

Sandestin Golf and Beach Resort invites guests to escape for an unforgettable celebration during the holiday season. The resort offers everything needed for a special season, whether guests are seeking a cozy Thanksgiving gathering or a festive winter getaway. They can experience the magic of the holidays with gourmet feasts and unique seasonal events in a beautiful coastal setting, creating lasting memories with family and friends in the heart of Sandestin. Guests can skip the kitchen hassle this Thanksgiving and let Sandestin Golf and Beach Resort prepare a perfect feast. Orders can be placed by calling 850.267.4489 or emailing Sal Montalto at the provided email address by 5 PM on Tuesday, November 25th, with pickup scheduled for Thursday, November 27th. For $325 plus tax, the meal serves 6-8 hungry guests. The resort will coordinate pickup details, allowing guests to relax while the cooking is handled.

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Thu, November 27

Thanksgiving Lunch Cruise

Miramar Beach
Food & Drink Food & Drink

Thanksgiving celebrations are enhanced when enjoyed on the water. Guests can gather their loved ones for a chef-prepared buffet, offering panoramic views for a truly memorable celebration. Reservations can be made by visiting the company's website.

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Thu, November 27

Thanksgiving

Miramar Beach
Food & Drink Food & Drink

Mezcal Mexican Grill offers a To-Go Thanksgiving Meal for $24.99, which includes a choice of Turkey or Ham, or both for an additional $4.99. Orders can be placed by calling (850) 563-7791 and the meal is available on November 27th from 11 AM to 3 PM.

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Thu, November 27

Thanksgiving

Miramar Beach
Family Fun Family Fun

Guests are invited to bring their friends and family to the Thanksgiving Day celebratory feast.

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Thu, November 27

Thanksgiving Supper

Miramar Beach
Food & Drink Food & Drink

The Ovide restaurant is celebrating Thanksgiving with a coastal-inspired holiday supper. The meal features roasted turkey breast, confit thigh, classic cornbread sourdough stuffing, turkey gravy, sautéed pole beans with Valencia almonds, smashed potatoes, and cranberry chutney. Guests can enhance their feast with a selection of shareable à la carte sides, such as sweet potato casserole with pecans and marshmallows, baked winter squash mac & cheese, and roasted Brussels sprouts with pork belly. The meal concludes with a slice of Dutch apple or pumpkin pie, with the option to add vanilla gelato. The cost is $49 per adult and $19 per child. À la carte sides are $15 each, and desserts are $12.

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Thu, November 27

Thanksgiving Day

Miramar Beach
Food & Drink Food & Drink

The establishment is inviting patrons to celebrate with them, noting that they will be open and ready to serve on Thanksgiving Day.

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Thu, November 27

Thanksgiving

Miramar Beach
Food & Drink Food & Drink

A person might imagine walking into their Thanksgiving celebration and discovering a sushi spread. More information is available on the Shaka 30A website regarding events.

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Fri, November 28

Returns to Grand Boulevard

Miramar Beach
Food & Drink Food & Drink

The "Hello Sugar" event series is returning to Grand Boulevard during November, December, and March. Hello Sugar, an Airstream cotton candy boutique, offers over 25 freshly spun flavors, including classic pink vanilla and favorites like chocolate, marshmallow, birthday cake, and bubble gum, along with novelty candies. Pop-up dates include November 21–30, December 22–January 4, and March 13–22.

Learn More
Fri, November 28

La Luna Children’s Boutique Holiday Open House

Miramar Beach
Family Fun Family Fun

The La Luna Children’s Boutique is hosting a Holiday Open House at Grand Boulevard. The event includes three separate dates: Sunday, November 23 from 11:00 AM to 1:00 PM; Friday, November 28 from 12:00 PM to 2:00 PM; and Sunday, November 30 from 12:00 PM to 2:00 PM. Visitors are invited to embrace the magic of the holidays with an enchanting family experience at La Luna. Guests can explore a curated collection of festive children’s attire and timeless gifts, enjoy the signature hot cocoa bar, and gather for a charming seasonal storytime. Complimentary professional photos with Santa will be available during the first hour of each event.

Learn More
Fri, November 28

Football

Miramar Beach
Sports & Games Sports & Games

The subject is football.

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Fri, November 28

Free Bonfire

Miramar Beach
Live Music Live Music

The beach bar hosts a free bonfire every Friday and Monday at sunset. There is no entrance fee and free resort parking is provided, with plenty of chairs available for everyone. S’mores, drink specials, and the full menu are available. It is a great place to bring children and watch the sunset. Offsite food or beverages are not permitted.

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Fri, November 28

The Polar Express

Miramar Beach
Live Music Live Music

An outdoor showing of The Polar Express is scheduled for 6:00 PM on the Events Plaza Lawn. Attendees are invited to enjoy this holiday film favorite under the stars.

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Fri, November 28

Annie

Miramar Beach
Arts & Culture Arts & Culture

The play runs from November 28 to December 21. Performances are held Thursday through Saturday at 7 PM, and on Sundays and Wednesdays at 2 PM. There is no performance on Wednesday, December 3. Two performances are scheduled for Saturday, December 20, at 2 PM and 7 PM, and two on Sunday, December 21, at 2 PM and 6 PM. Field trips are available on Wednesday, December 3, 10, and 17, at 10 AM. Attendees are invited to join the favorite red-headed orphan Annie, Daddy Warbucks, and the eternally grumpy Miss Hannigan for this feel-good story about finding a forever home. Featuring hits like "You’re Never Fully Dressed Without a Smile," "It’s a Hard Knock Life," and "Tomorrow," the show offers an experience of the magic of the holidays and the spirit of generosity that arrives this time of year.

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Fri, November 28

Live Music

Miramar Beach
Live Music Live Music

Guests can enjoy hand-crafted cocktails while listening to a local artist perform original and cover songs. The event is open to the public, and complimentary validated parking is offered with any food or beverage purchase.

Learn More
Sat, November 29

Farmers Market

Miramar Beach
Markets & Shopping Markets & Shopping

On Saturdays throughout the year, from 9 AM to 1 PM, an outdoor market showcases a variety of unique vendors primarily offering locally sourced food items. These include fresh produce, eggs, milk, butter, grass-fed beef, chicken, local honey, pickled vegetables, and gourmet jams. Additionally, prepared foods such as tomato pies, hummus, pasta, tuna dip, and crab cakes are available for purchase. The market also features vendors selling soap and lotions. This event, known as the Grand Boulevard Farmers’ Market, is held in Grand Park, situated between Cantina Laredo and Tommy Bahama. These lively gatherings are part of the Coastal Culture Calendar of Events, supported by the Grand Boulevard Arts and Entertainment Program.

Learn More
Sat, November 29

Returns to Grand Boulevard

Miramar Beach
Food & Drink Food & Drink

The Hello Sugar cotton candy boutique is returning to Grand Boulevard as part of an event series. This beloved Airstream pop-up will offer sweet treats throughout November, December, and March. Visitors can enjoy over 25 freshly spun flavors, including classic pink vanilla and fun options such as chocolate, marshmallow, birthday cake, and bubble gum. A colorful selection of novelty candies is also available for all ages. The pop-up dates are scheduled for November 21–30, December 22–January 4, and March 13–22.

Learn More
Sat, November 29

Annie

Miramar Beach
Arts & Culture Arts & Culture

Joshua Zook, a local artist, performs live beat creations every Saturday from 2pm until 5pm. He plays popular songs with a unique twist.

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Sat, November 29

College Football

Miramar Beach
Sports & Games Sports & Games

Hops & Harmonies is a November concert series at HarborWalk Village where guests can enjoy the sounds of fall. The event takes place on select Saturdays from 3 PM to 6 PM, featuring an afternoon of live music, craft beer, and a relaxed atmosphere.

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Sat, November 29

Live Music

Miramar Beach
Live Music Live Music

Michael Johnson performs live from 5-7PM, Thursday through Saturday.

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Sun, November 30

Returns to Grand Boulevard

Miramar Beach
Food & Drink Food & Drink

The play runs from November 28 to December 21, with performances scheduled for Thursday through Saturday at 7 PM, and Sundays and Wednesdays at 2 PM. Note that there is no performance on Wednesday, December 3. Special schedules include two performances on Saturday, December 20 (2 PM and 7 PM) and two performances on Sunday, December 21 (2 PM and 6 PM). Field trips are offered on Wednesday, December 3, 10, and 17 at 10 AM. The production features the beloved red-headed orphan Annie, Daddy Warbucks, and the cantankerous Miss Hannigan in a heartwarming tale about finding a permanent family. Attendees can enjoy popular songs such as “You’re Never Fully Dressed Without a Smile,” “It’s a Hard Knock Life,” and “Tomorrow,” bringing the magic of the holidays and the spirit of generosity to the stage.

Learn More
Sat, December 6

Farmers Market

Miramar Beach
Markets & Shopping Markets & Shopping

On Saturdays throughout the year, from 9 AM to 1 PM, an outdoor market showcases a variety of unique vendors primarily offering locally sourced food items. These include fresh produce, eggs, milk, butter, grass-fed beef, chicken, local honey, pickled vegetables, and gourmet jams. Additionally, prepared foods such as tomato pies, hummus, pasta, tuna dip, and crab cakes are available for purchase. The market also features vendors selling soap and lotions. This event, known as the Grand Boulevard Farmers’ Market, is held in Grand Park, situated between Cantina Laredo and Tommy Bahama. These lively gatherings are part of the Coastal Culture Calendar of Events, supported by the Grand Boulevard Arts and Entertainment Program.

Learn More
Sat, December 13

Farmers Market

Miramar Beach
Markets & Shopping Markets & Shopping

On Saturdays throughout the year, from 9 AM to 1 PM, an outdoor market showcases a variety of unique vendors primarily offering locally sourced food items. These include fresh produce, eggs, milk, butter, grass-fed beef, chicken, local honey, pickled vegetables, and gourmet jams. Additionally, prepared foods such as tomato pies, hummus, pasta, tuna dip, and crab cakes are available for purchase. The market also features vendors selling soap and lotions. This event, known as the Grand Boulevard Farmers’ Market, is held in Grand Park, situated between Cantina Laredo and Tommy Bahama. These lively gatherings are part of the Coastal Culture Calendar of Events, supported by the Grand Boulevard Arts and Entertainment Program.

Learn More
Sat, December 20

Farmers Market

Miramar Beach
Markets & Shopping Markets & Shopping

On Saturdays throughout the year, from 9 AM to 1 PM, an outdoor market showcases a variety of unique vendors primarily offering locally sourced food items. These include fresh produce, eggs, milk, butter, grass-fed beef, chicken, local honey, pickled vegetables, and gourmet jams. Additionally, prepared foods such as tomato pies, hummus, pasta, tuna dip, and crab cakes are available for purchase. The market also features vendors selling soap and lotions. This event, known as the Grand Boulevard Farmers’ Market, is held in Grand Park, situated between Cantina Laredo and Tommy Bahama. These lively gatherings are part of the Coastal Culture Calendar of Events, supported by the Grand Boulevard Arts and Entertainment Program.

Learn More

Reviews - 5

jennifer
Sep 2025 Google

The home was stunning and perfect for all ages! We cannot wait to come back! The staff at oversee was amazing and so helpful with anything we needed!

matthew
Apr 2025 Airbnb
paul
Jul 2024 Airbnb
amanda
Jul 2024 Vrbo

Everything was perfect and the house was stunning!

ossie
Jun 2024 Airbnb

Host Family

Grayton Office

Charles McTear
Crystal	Becktel
Ryan Pearson
Gloria Cruz
Triston Luke
Heather Silva
Danny West
Summer McKeon
Right in the heart of Grayton Beach, the Grayton Office lets us offer quick, thoughtful support whenever you need a hand.

Office location:

Grayton Office, Florida

Contact Grayton Office
Guests

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