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Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992
Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

Win Pennie Cottage ~ Immaculate Coast Cottage along St Simons' Finest Beach

Bedrooms 3
Separate WC's1
Space 1,830 sq. ft.
Property type cottage
Minimum Stay 3 - 14 nights


About the property

3 bedroom, 3.5 bath beach house 250 steps from Coast Cottages' ocean side pools

NOTE: If you encounter any error messages after clicking "Request to Book," please contact the property manager Patrick Anderson by clicking "Ask Manager a Question."

Win Pennie Cottage is pristine! ... seldom rented and meticulously maintained since it was built in 1997. This neo-classic beach cottage is located just 250 steps from Coast Cottages' fabulous ocean side pools, pavilion and beach boardwalk. And, you'll have private access to St. Simons Island's widest and best beach area. And this home has two king master suites!

You'll love the front and rear covered balconies where you'll always have a shady place to sit outside, whether it's morning or afternoon. Win Pennie has high ceilings, tall windows for plenty of natural light, and solid pine floors throughout.

FIRST FLOOR: Bedroom 1 is a king master suite, with plenty of space and its own private bath. Bedroom 2 has two twin beds, with a pull out trundle ... perfect for the kids. It also has its own full bath. Bedroom 3 is also king master suite with walk in closet, and private bath.

SECOND FLOOR: You'll love the open living, dining and kitchen arrangement where everyone can join together for family gatherings. The kitchen area is spacious and well equipped, just in case you're planning to cook in. You'll find plenty of comfortable seating in the living room, along with a large flat screen TV. And the dining area easily seats 8. There's a convenient 1/2 bath on the second floor as well. The interior decor is carefully planned for comfort and style, with whimsical flourishes throughout.

The breezy front porch faces beautiful Coast Cottage Lane and features a collection of sturdy rocking chairs ... perfect for reading a good book. The rear porch is just off the living room and opens to a wooded preservation area. This very private balcony is spacious and has plenty of outdoor seating for morning coffee or evening cocktails.

You and your family will enjoy full privileges at Coast Cottages' beach front pools and shady pavilion. Our award winning neighborhood sits front and center on St. Simons Island's magnificent Coast Guard beach, the widest stretch of sand on the island. This is a place where you can walk on the beach at high tide, low tide, any tide! (Note: vacation rentals south of Arnold Road cannot make this claim.)

Win Pennie Cottage will inspire a lifetime of memories for you and your family! Please review the following qualifications before calling for reservations:

Maximum occupants: 7 at any time

Minimum two occupants age 35 or older

No pets

No smoking

No student groups

No parties or wedding events

Parking for two vehicles at the cottage

More Details

Property Manager
Patrick Anderson
Member since: 2003
Speaks English
Response time:
Within a few days
Response rate:
Calendar last updated:
23 March, 2018

About Patrick Anderson

Patrick Anderson is sometimes called the 'Mayor of Coast Cottages' ... St. Simons Island's favorite beach side community. Since 1998, Anderson has been involved in sales, development, management, and vacation rentals. His devotion to excellence and responsiveness are recognized by friends and customers alike . Patrick Anderson is broker/owner of Patrick Anderson & Associations, Inc., a Georgia licensed real estate firm.


Accommodation and facilities for this holiday cottage in St Simons Island in Glynn County

Property Type:
  • cottage
  • Self-catering
  • Housekeeper Optional
Floor Area:
  • 1830 sq. ft.
House Rules:
  • Check-in: 16:00
  • /
  • Check-out: 10:00
  • Max. occupancy: 7
  • Min. age of primary renter: 35
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
Location Type:
  • Beachfront ...
  • Adventure
  • Family
  • Historic
  • Romantic
  • Air Conditioning ...
  • Clothes Dryer
  • Hair Dryer
  • Heating ...
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Hob
  • Toaster
  • Dining Area
  • seating for 8 people
  • 3 Bathrooms
  • 1 Separate WC
  • Bathroom 1 - Toilet , Shower Enclosure , Has tub/shower
    Bathroom 2 - Toilet , Shower Enclosure
    Bathroom 3 - Toilet , Shower Enclosure
    Bathroom 4 - Toilet , On living/dining/kitchen floor
  • 3 Bedrooms, Sleeps 7
  • Bedroom 1 Master - 1 Extra Lg. Double Bed , King bed, en suite bath with shower tub
    Bedroom 3 (second Master) - 1 Extra Lg. Double Bed , King bed, walk in closet, en suite bath with shower
    Bedroom 2 - 3 Single Bed , 2 twin beds plus1 pull-out trundle. En suite bath w/shower
  • First floor has all bedrooms. Second floor has living/dining/kitchen and two balconies.
  • Satellite / Cable
  • Television ...
  • Balcony ...
  • Barbecue ...
  • Long-term Renters Welcome
  • wheelchair inaccessible
Pool / Spa:
  • Communal Pool ...
Onsite Services:
  • Private Chef
  • churches
  • cinemas
  • Health/Beauty Spa
  • library
  • live theatre
  • marina
  • museums
  • playground
  • restaurants
  • ruins
  • water parks
Leisure Activities:
  • antique hunting
  • beachcombing
  • bird watching
  • Boating
  • eco tourism
  • horse riding
  • Miniature golf
  • photography
  • Shelling
  • Shopping
  • sight seeing
  • walking
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • Basketball Court
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • Kayaking
  • pier fishing
  • Racquetball
  • roller blading
  • sailing
  • bay fishing
  • surf fishing
  • swimming
  • tennis
  • wind-surfing


Exceptional! 5/5 -
(6 traveller reviews)

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Win Pennie Cottage ~ Immaculate Coast Cottage along St Simons' Finest Beach
average rating of 5.0 based on 6 reviews

A wonderful rental on St Simons Island

  • 5 of 5

Win Pennie is a lovely, comfortable cottage in a great location on St Simons. Everything that you might need for your stay is in the house. The interior is well maintained and charming and two outside porches have comfortable seating to enjoy the outside. A delightful rental!

  • Review Submitted: 19-Mar-2018
  • Date of Stay: January 2018
  • Source: VRBO, from HomeAway
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0 0

Perfect Getaway

  • 5 of 5

This place is spectacular! Beautifully furnished. Inviting. Comfortable. Spotless. Upscale linens. Beach towels provided. A few steps to the pool area and the pier. Great value too. We loved it!

  • Review Submitted: 18-Mar-2018
  • Date of Stay: March 2018
  • Source: VRBO, from HomeAway
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0 0

Win Pennie

  • 5 of 5

We thoroughly enjoyed our visit to your beautiful home. It was well-equipped, bright, and cheerful. The furnishings are beautiful, and we had a relaxing stay.

  • Review Submitted: 18-Jan-2016
  • Date of Stay: December 2015
  • Source: VRBO, from HomeAway
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2 0
Sarasota, FL

Great stay at Win Pennie!!!

  • 5 of 5

The Win Pennie was an excellent choice for a wonderful beach vacation away! The house was so well equipped....we could have shown up with just our swim suits and would have been all set!!! Just a short walk to the beach and pool! The house was so clean and so beautifully furnished! There was even toys and books for the children! It will definitely be a place we stay at for future vacations!!

  • Review Submitted: 11-Aug-2015
  • Date of Stay: July 2015
  • Source: VRBO, from HomeAway
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3 0

Win Pennie Cottage -- Sun, Sand, Surf and so much more!

  • 5 of 5

Our family started vacationing on SSI three years ago. Of all of the places we've stayed so far, Win Pennie Cottage outshines them all. Our family enjoyed our stay at Win Pennie Cottage immensely. East Beach is beautiful. The location is convenient to the Village and destinations farther north. The house was clean and well-appointed. The owners have truly thought of everything. Traveling with small children means eating in a lot. I was able to easily prepare meals in the well equipped kitchen. Direct access to the beach made it just that much easier to hike the kids and ALL of their stuff/toys to and from the beach daily. This was the perfect place for our family vacation. We look forward to visiting SSI and Win Pennie Cottage again next year.

  • Review Submitted: 03-Aug-2015
  • Date of Stay: July 2015
  • Source: VRBO, from HomeAway
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4 0
Atlanta, GA

Win Pennie Review

  • 5 of 5

My girlfriends and I had a getaway weekend to St Simons and loved our stay at Win Pennie! The house is great and the owners have thought of everything. We stayed in for dinner one night and the kitchen was well equipped much better than any beach rental I have stayed at in the past. I would definitely recommend this house for your vacation.

  • Review Submitted: 15-Apr-2015
  • Date of Stay: February 2015
  • Source: VRBO, from HomeAway
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6 0


St. Simons Island is sometimes described as a little piece of paradise. Scarcely known outside Georgia, it is quite possibly the best kept secret along the coastal Southeast. The island's majestic entrance over miles of unspoiled marshland was memorialized by Sidney Lanier in his poem The Marshes of Glynn. It's a place where an unpretentious low country meets the great ocean ... where huge tidal changes breathe life into the grassy expanse flourishing in wildlife. Somewhere in between you will discover the magic of St. Simons Island. Upon arrival, visitors are enveloped by a feeling of calm amidst ancient moss-draped oaks standing alongside glorious palms and tall southern pines. Many miles of bike paths connect a variety of shopping, eating, cultural and recreational areas within the island. There's always something fun and interesting to do. The beach at St. Simons Island is like no other. As the 7-foot tide shifts from high to low, it pulls the shoreline 1/2 mile out to sea uncovering a breathtaking system sandbars and shoals. Development is largely unseen along the north end of the beach where an abundant shrub forest has been protected and allowed to expand naturally. Acres of young dune fields nurture sensitive Sea Oats while thousands of shore birds migrate from one sand bar to the next with the receding tide. The owners and guests of Coast Cottages at St. Simons cherish their unrestricted view and enjoyment of this ecological wonderland.

Things to do on St. Simons Island:

Kayak through the marsh streams, walk the beach, eat at many great restaurants, climb the lighthouse, golf, tennis, miniature golf, small skate board park, go shopping at many quaint shops, go antique hunting, tour Fort Frederica, tour the Old Coast Guard Station (right next door to Coast Cottages), walk the sandbars at low tide, go skim boarding along the shoreline, take a trolley tour of the island, hang out at the Coast Cottages pool, go to a water park on Jekyll Island, take paddle board lessons, go crabbing or fishing right off the pier.


Prices & Availability

Ask Manager a Question


  • Rates vary by season
  • US Dollar
  • Minimum night stay varies by season from 3 - 7 nights