Description

This captivating cabin-like cottage provides an enchanting trip back in time and can even become your own "little house on the prairie." However, in this case, you're not on the prairie, but right down the street from the shimmering white shoreline beside the dazzling emerald green waters of the gorgeous Gulf of Mexico. This beguiling abode was one of the first early cabins to be built in Old Grayton Beach back in the 1880s. It has been updated with a new kitchen, central heat and air, comfortable furnishings and a new queen-sized bed - all while preserving its original character. The rental cottage is nestled among towering pines, clusters of palmetto palms and natural indigenous plants.

A gracious front porch spans across the width of Shepherd Cottage and includes a couple of rocking chairs and a hanging bench swing decorated with hand-carved hearts overlooking the lovely setting. Wide double glass French doors lead indoors to an open living area with original hardwood flooring brightened by lots of windows on three sides and canned lighting above. One side of the room has a cozy seating ensemble that includes a comfortable pale blue couch, tables for drinks or snacks, and an antique dresser with a mirror. A large flatscreen TV is provided for entertainment that is perched above an old cargo trunk in the corner. The dining area is centered with a round maple table beneath a candled chandelier accented by four dark elegantly carved stylish antique chairs for a charming dining experience.

The ample country kitchen has cream-colored cottage cabinetry as well as an electric stove with an oven on one side of the open area and a refrigerator along with a microwave on the other side. Deep double farm sinks sit beside a double window for natural light. There is an enchanting bedroom that resembles a small sunroom with a queen-sized bed that features a decorative metal headboard. The bathroom has a classic white pedestal sink and a convenient walk-in glass shower. An additional twin bed is tucked away off the living area. A raised deck in the back has a table with chairs for drinks or dining al fresco and an outdoor shower to rinse sand off after the beach. This intimate comfy cottage is ideal as a time forgotten getaway for a loving couple to create romantic, magical memories in the here and now. 

Besides the beautiful beach you can also enjoy a nice stroll down to the historic coastal village center of Grayton for some delightful diversions that include the amazing Zoo Gallery, which represents talented artists from all over the nation, Spanish style Tapas at Chiringo along with drinks, dining and live music at the famed soon to be reopened Red Bar. You may try your luck fishing on the small village dock or go kayaking on Western Lake. This precious coastal dune lake is a rare treasure since they are found hardly anywhere else in the world and support abundant wildlife with lots of fish.  A wide assortment of restaurants, friendly beach bars, galleries, boutiques, concerts, and seasonal festivals are also minutes away in nearby villages like Seaside and WaterColor.

First Floor: Living Room, Kitchen, Dining, Queen Bedroom, Hall Bath with Walk-In Shower, Nook with Twin Bed, Exterior Laundry.

Amenities
  • Amenity Icon Internet
  • Amenity Icon Laundry
  • Amenity Icon Nightly
  • Amenity Icon No Pets Allowed
  • Amenity Icon Parking Spaces: 3
  • Amenity Icon Security Cameras
  • Amenity Icon Walk to Beach: 9-10 Minutes
Calendar
December 2024
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1 2 3 4 5 6 7
8 9 10 11 $150 12 13 14
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29 30 31        
January 2025
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      1 2 $174 3 4
5 6 7 8 9 $177 10 $177 11
$169 12 $169 13 $169 14 $169 15 16 17 18
19 20 $169 21 $169 22 $169 23 $177 24 $177 25
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February 2025
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            $177 1
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March 2025
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$239 2 $239 3 $239 4 $239 5 $239 6 $266 7 $266 8
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$243 16 $243 17 $243 18 $243 19 $243 20 $243 21 $300 22
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April 2025
Su Mo Tu We Th Fr Sa
    $300 1 $300 2 $300 3 $328 4 $328 5
$300 6 $300 7 $300 8 $300 9 $300 10 $328 11 $344 12
$280 13 $280 14 $280 15 $280 16 $280 17 $321 18 $290 19
$254 20 $254 21 $254 22 $254 23 $254 24 $290 25 26
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May 2025
Su Mo Tu We Th Fr Sa
        $280 1 $321 2 $290 3
$254 4 $254 5 $254 6 $254 7 $254 8 $290 9 $369 10
$322 11 $322 12 $322 13 $322 14 $322 15 $369 16 $352 17
$322 18 $322 19 $322 20 $322 21 22 23 24
25 $310 26 $310 27 $310 28 $310 29 $340 30 $340 31
June 2025
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$310 1 $310 2 $310 3 $310 4 $310 5 $340 6 $356 7
$325 8 $325 9 $325 10 $325 11 $325 12 $356 13 $340 14
$310 15 $310 16 $310 17 $310 18 $310 19 $340 20 $372 21
$340 22 $340 23 $340 24 $340 25 $340 26 $372 27 $407 28
$372 29 $372 30          
July 2025
Su Mo Tu We Th Fr Sa
    $372 1 $372 2 $372 3 $407 4 $355 5
$324 6 $324 7 $324 8 $324 9 $324 10 $355 11 $355 12
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August 2025
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          $355 1 $283 2
$259 3 $259 4 $259 5 $259 6 $259 7 $283 8 $257 9
$235 10 $235 11 $235 12 $235 13 $235 14 $257 15 $257 16
$235 17 $235 18 $235 19 $235 20 $235 21 $257 22 $257 23
$235 24 $235 25 $235 26 $235 27 $235 28 $285 29 $285 30
$261 31            
September 2025
Su Mo Tu We Th Fr Sa
  $252 1 $252 2 $252 3 $252 4 $275 5 $275 6
$252 7 $252 8 $252 9 $252 10 $252 11 $275 12 $275 13
$252 14 $252 15 $252 16 $252 17 $252 18 $275 19 $275 20
$252 21 $252 22 $252 23 $252 24 $252 25 $275 26 $275 27
$252 28 $252 29 $252 30        
October 2025
Su Mo Tu We Th Fr Sa
      $252 1 $252 2 $275 3 $288 4
$264 5 $264 6 $264 7 $264 8 $264 9 $264 10 $264 11
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$264 19 $264 20 $264 21 $264 22 $264 23 $264 24 $264 25
$264 26 $264 27 $264 28 $264 29 $264 30 $264 31  
November 2025
Su Mo Tu We Th Fr Sa
            $193 1
$193 2 $193 3 $193 4 $193 5 $193 6 $193 7 $193 8
$193 9 $193 10 $193 11 $193 12 $193 13 $193 14 $193 15
$193 16 $193 17 $193 18 $193 19 $193 20 $193 21 $210 22
$210 23 $210 24 $210 25 $210 26 $210 27 $210 28 $193 29
$193 30            
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Bedding
First Floor:
Queen
Queen
Twin
Twin
Total: Queen, Twin
Reviews
Rating 5
Amazing birthday weekend
We had the best time. Communication was perfect in all needs. Perfect for 2 people.
Ali D from Madison TN - Stayed October 2023
Rating 5
Ideal location for anniversary celebration!
Being in this super cute cottage and walking to the beach and local restaurants for quick food or live music was easy and ideal. The additional outdoor shower was a bonus for in-between beach trips. The locals and visitors were all very friendly. I highly recommend this experience.
Shawna C from Fort Collins CO - Stayed September 2023
Rating 5
Shepherd Cottage Grayton Beach
The cottage was everything we were looking for. Simple, cozy, laid back, close to the beach and restaurants. We will definitely be back, more likely in the fall of the year rather than blistering heat of August.
Felicia C from Crawfordville FL - Stayed August 2023
Rating 5
Wonderful
My wife and I stayed here for a couple of nights before family arrived for vacation. This property was perfect! Great location, cute decor, very comfortable, quite, very clean and in a great location. We had several people pass by and say cute house!
Tom S from Jenks OK - Stayed August 2023
Rating 5
Perfect
Cool place, unbeatable location.
K.C. H from Ocean Springs MS - Stayed July 2023
Rating 5
This is the sweetest little cottage.
Perfect for a getaway. 2nd time staying here and it will not be our last. Half a mile walk to the beach. Love this town and working with the Ocean Reef team was a breeze.
Zarah F from Southaven, MS - Stayed April 2023
Rating 5
Exceeded our expectations
If you’re looking for convenience and a change of pace from a traditional, conventional resort stay- Ocean Reef Vacation Rentals is the way to go!! Our rental and entire experience at The Sheppard Cottage in Grayton Beach exceeded our expectations. It was a cozy, homey cottage while still feeling like a tropical getaway. All the living essentials were provided (be forewarned no beach towels or chairs are provided!). It was the perfect backdrop to a romantic proposal, as well! The backyard and landscape felt like a tropical jungle oasis while being just minutes away (about an 8 minute walk!) from the sugary sand of Grayton beach. It’s walking distance from the Grayton convenience store, coffee shops, plenty of food, the beach…AKA absolute perfection. The check in/check out process is a BREEZE and perfect for young couples who are very tech-orientated. Everything takes place right on your phone. Check in/check out is a literal press of a button. The rental company also provided text updates regarding trash pick up and your upcoming arrivals/departures. There’s a detailed info sheet provided in the rental listing out all the important info you may need, like maintenance, address, housekeeping needs, etc. SUPER effortless experience all around, and plenty of great discounts and coupons offered in the guest portal—which is great for self-sufficient couples who are used to everything being digital/mobile-based! We’ll absolutely be back at the Sheppard Cottage!!
Vanessa P from Elgin IL - Stayed April 2023
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FAQs

We welcome all of your questions! Most property-specific details can be answered in the AMENITIES tab, for example, "Is beach service included?", "Is there a community pool?" and "How far is the beach?". Additional answers may be found in our Rental Policies.

Still have unanswered questions? We invite you to ask below. Our vacation specialists look forward to providing you with a detailed response to help you find the best place by the beach!

What is the cancellation policy?
Dana R - Posted: 01/31/2022

Answer:

You can view details about cancellations and all of our rental policies here.

Does this home allow a small dog?
Janet G - Posted: 02/11/2022

Answer:

We love our dogs here at Ocean Reef, however - Shepherd Cottage is a non-pet-friendly property.  If you are unable to board your pup, you may want to consider one of these Pet Friendly Rentals.

What beach chair rental service can you recommend for this property?
Lauren R - Posted: 05/17/2022

Answer:

Beach chairs and umbrellas are most certainly available at this location. Once you have secured your reservation, we will provide you with the beach services contact information. You can reserve chairs and umbrellas over the phone, or directly on the sand. See you soon!

Average walk time to the beach please?
Kellie W - Posted: 07/24/2022

Answer:

The Grayton Beach public access is a leisurely 6-7 minute stroll away from Shepherd Cottage. Don't forget the sunscreen!

Does this property have air conditioning?
Vanessa P - Posted: 09/06/2022

Answer:

All Ocean Reef properties include air conditioning and heating. We want to ensure your stay is as cool as possible while vacationing at the beach!

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