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Winn Pennie | Steps to Beach & Pools | 3BR Cottage

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Terrace/patio - Winn Pennie | Steps to Beach & Pools | 3BR Cottage (St. Simons Island)
Smart TV, books - Winn Pennie | Steps to Beach & Pools | 3BR Cottage (St. Simons Island)
Beach nearby - Winn Pennie | Steps to Beach & Pools | 3BR Cottage (St. Simons Island)
Exterior - Winn Pennie | Steps to Beach & Pools | 3BR Cottage (St. Simons Island)
Property grounds - Winn Pennie | Steps to Beach & Pools | 3BR Cottage (St. Simons Island)
Step into Winn Pennie, a charming St Simons Island cottage just 250 steps from Coast Cottages ocean side pools, pavilion and private beach access boardwalk. With full privileges at Coast Cottage, enjoy the pools, pavilion and beach boardwalk. This cozy retreat offers 3 bedrooms with ensuite bathrooms and an upstairs living area with multiple dining spaces.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms4 bathroomsSleeps 6

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
The current price is NZ$1,246
includes taxes & fees
11 Mar - 12 Mar

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Winn Pennie | Steps to Beach & Pools | 3BR Cottage

Winn Pennie is a meticulously maintained cottage on one of the most sought after rental areas on St Simons Island! This neo-classical cottage is located just 250 steps from Coast Cottages ocean side pools, pavilion and private beach access boardwalk.
Two covered balconies encourage you to rock on the front porch or retreat to back deck with sounds of the ocean in the distance. Winn Pennie has high ceilings and plenty of natural light with pine floors throughout. With two master bedrooms, it is the perfect home for a family getaway!
FIRST FLOOR: Front bedroom is a king suite with plenty of space, tv with cable, ensuite bath with tub/shower. Middle bedroom has twin beds with a trundle pull out available. Bathroom with shower. Perfect room for the kids! Back bedroom is a King suite with walk in closet and private bath with shower.
SECOND FLOOR: Open floor plan allows for dining - cooking and family gathering all together! The kitchen is very well stocked with the family eating at home in mind! The large farmhouse dining table can comfortably seat 8-10 people. A half bath is just off the dining area as well. The living room can comfortably seat the whole family and has a large flat screen tv and dvds for the whole family to enjoy. Also provided are board games, playing cards, puzzles and toys for everyone! The breezy front porch has three rocking chairs that offers a great view of the Coast Cottage neighborhood. The rear porch is just off the living room and opens to a wooded preservation area. This is a large private balcony, perfect for morning coffee or evening cocktails!

Guests enjoy full privileges at Coast Cottage with access to pools, pavilion and beach boardwalk. Our neighborhood is positioned along the Coast Guard beach where the widest stretch of sand is and high tide always provides a place to walk or lounge! (vacation rentals south of Arnold Road do not have any beach access during high tide).

We would love to be our guests at our beloved Win Pennie Cottage! We hope you make lasting memories in our home, just as we have!

3 Bedrooms, Sleeps 7
Bedroom 1 Master - 1 king bed, en suite bath with shower/tub
Bedroom 2 - 3 twin/single, 2 twin beds plus 1 pullout trundle. En suite bath with shower
Bedroom 3 - Master - 1 king bed, en suite bath with shower
3 bathrooms - 1 half bath
Please review the following qualifications before calling for reservations:
Maximum occupants: 7 at a time
Minimum two occupants age 35 or older
No pets
No smoking
No student groups
No wedding events or parties
Parking for two vehicles a the cottage

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car recommended
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the sea

Things to do

  • Heated pool

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)

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  • Air-conditioning
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 30

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Must sign rental agreement upon booking, upload a copy of your driver license
A $500 security hold will be placed 2 days prior to arrival and released 7 days after departure, if no damages are reported
Must follow all house rules including but not limited to not pets, no smoking and no parties.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is recommended for transport to and from this property

Property is also known as

orp5b64ea8x

About the area

Located near the beach, this holiday home is in East End, a neighbourhood in St. Simons Island. World War II Home Front Museum and Glynn Visual Arts are cultural highlights, and some of the area's landmarks include Bloody Marsh Battle Site and St. Simons Lighthouse Museum. Massengale Park and Neptune Park are also worth visiting. Visit our St. Simons Island travel guide
View more Holiday homes in St. Simons Island
Map
St. Simons Island, GA

What's nearby

  • At St Simons Island. Great place to view some birds in the winter and great beaches!
    East Beach
    5 min walk - 0.4 km
  • St. Simons Lighthouse Museum showing a lighthouse and a house
    St. Simons Lighthouse Museum
    3 min drive - 2.3 km
  • World War II Home Front Museum
    1 min walk - 0.2 km
  • Massengale Park
    7 min walk - 0.7 km
  • Demere Park
    16 min walk - 1.4 km

Getting around

  • Brunswick, GA (BQK-Golden Isles)
    28 min drive

Restaurants

  • Chick-fil-A
    3 min drive
  • Starbucks
    3 min drive
  • Wake Up Coffee Company
    3 min drive
  • Mullet Bay
    3 min drive
  • Ziggy’s
    4 min drive

Frequently asked questions

Does Winn Pennie | Steps to Beach & Pools | 3BR Cottage have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Winn Pennie | Steps to Beach & Pools | 3BR Cottage?

As of 25 Feb 2026, prices found for a 1-night stay for 2 adults at Winn Pennie | Steps to Beach & Pools | 3BR Cottage on 11 Mar 2026 start from 1245.92, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Winn Pennie | Steps to Beach & Pools | 3BR Cottage pet-friendly?

No, pets are not allowed at this property.

How much is parking at Winn Pennie | Steps to Beach & Pools | 3BR Cottage?

On-site parking is available at the property.

What time is check-in at Winn Pennie | Steps to Beach & Pools | 3BR Cottage?

Check-in begins at 4:00 PM.

What time is check-out at Winn Pennie | Steps to Beach & Pools | 3BR Cottage?

Checkout is at 10:00 AM.

Where is Winn Pennie | Steps to Beach & Pools | 3BR Cottage located?

Located in East End, this holiday home is within a 5-minute walk of World War II Home Front Museum and East Beach. Massengale Park and Glynn Visual Arts are also within 1 mile (2 km).

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Winn Pennie | Steps to Beach & Pools | 3BR Cottage Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 66 out of 67 reviews
Rating 8 - Good. 1 out of 67 reviews
Rating 6 - Okay. 0 out of 67 reviews
Rating 4 - Poor. 0 out of 67 reviews
Rating 2 - Terrible. 0 out of 67 reviews

10

Cleanliness

10

Location

Reviews

10/10 Excellent

Nicki G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday Celebration

Stayed here for a birthday celebration with friends. Wonderful property that met all our needs. Immaculately decorated warm and cozy.
Stayed 3 nights in Oct 2023

10/10 Excellent

Pamela C.

Liked: Cleanliness, communication, location, listing accuracy

Adult getaway

House very clean and location was wonderful. Had a non functioning coffee maker, but was replaced promptly by management team. Very quiet and comfortable stay…
Stayed 5 nights in Mar 2024

8/10 Good

Michael D.

Liked: Cleanliness, check-in, communication, listing accuracy

Winter Retreat

We had a lovely stay at your charming SSI home! The home was beautiful and had all the kitchen odds and ends to make it feel like you were cooking at home. The home was clean and had lots of space for hanging out together. We walked on the beach, walked to town enjoying the quaint shops and played golf too! We look forward to visiting again in the future!
Stayed 3 nights in Dec 2024

10/10 Excellent

Steve M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

This is a beautiful and comfortable property. Perfect for a family of 5. Everything worked, the host provided a number of thoughtful amenities (beach chairs, umbrellas, agon for ferrying supplies, a well-stocked kitchen with clearly labeled storage), and we had a great week. This was our second stay and we will be back. Highly recommended. Thank you Denise!
Stayed 7 nights in Aug 2023

10/10 Excellent

Julia O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent place made for a wonderful stay!

This was our 3rd time visiting SSI but the first time staying at this place. The add said "Immaculate" which I thought was a strong word but in reality it was just that. A spotless and very well appointed house that is in the best spot possible. Steps from the beach, next to my kids' favorite WW2 museum and a short bike ride away from downtown. So many special touches, spots to gather and everything you could ever need in the kitchen. A very inviting and comfortable place with designer touches. The owner was very prompt to reply to any questions and very accommodating. We have thoroughly enjoyed our stay and can't wait to be back.
Stayed 4 nights in Dec 2023

10/10 Excellent

Mark E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The Perfect Beach Cottage

A family vacation to remember, made possible in no small part to Denise and her beautiful cottage. Her attention to detail was amazing....we wanted for nothing. The house itself is so welcoming and cozy. It was wonderful coming back to it after an outing. Her recommendations on dining, family activities, and shopping were invaluable. An amazing week for all of us. Thank you!
Stayed 7 nights in Jul 2023

10/10 Excellent

Samantha M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed the 3-minute walk to the beach and pools, and the location on St. Simons Island. It was also a nice touch that they had beach/pool toys and kids equipment stocked at the house.
Stayed 4 nights in Aug 2025

10/10 Excellent

Stephanie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Saint Simons

Loved this house! Stocked with everything you need and loved the decor and porches.
Stayed 7 nights in Apr 2023

10/10 Excellent

Lisa V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful beach vacation

Such a wonderful place to stay for a beach vacation! The house had everything we needed for a comfortable stay. Especially liked the bedrooms (each with its own bath) downstairs away from the living area. We were close to everything and had no problems while staying there.
Stayed 7 nights in May 2019

10/10 Excellent

Shira K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

We had a wonderful stay at the Win Pennie. The house is lovely and so well appointed. Denise was extremely responsive to our queries. This is the third place we've stayed in Coast Cottages and by far the nicest. We hope to come again!
Stayed 7 nights in Jul 2023

10/10 Excellent

Christine K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay!

Our family of four had a wonderful time at Denises’s beautiful home. The house was super clean, had tons of room, and had everything we needed to settle in for the week comfortably. It is in a secluded row of beautiful cottages, and a short walk to the beach and pools. Denise was super responsive with questions I had as well. We would definitely come back- 5 stars!
Stayed 7 nights in Mar 2023

10/10 Excellent

Julie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation and awesome host!

I stayed at this rental with my husband and our daughters age 4 and 1.5. This is one of the best rentals we have stayed in with a lovely host. The spot is perfect for young children with books and toys and games and has all the beach gear you need for the week. It's a very quick walk to the beach (very manageable with kids). The front and back porches are great places to relax at the end of the day. We would definitely stay again!
Stayed 5 nights in May 2023

10/10 Excellent

Ginger L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection!

This property is absolutely beautiful. The owner had EVERYTHING you will need to make your stay relaxing and enjoyable. The location is perfect, and the house is stocked full of beautiful decor and amenities for the family. The communication and friendliness from the owner was above and beyond. She gave us recommendations that made our vacation so enjoyable. Truly the best daily vacation in years!
Stayed 5 nights in Jul 2023

10/10 Excellent

Krissy V., Avon, OH

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved everything about our stay at Winn Pennie

Denise is a wonderful host and the property was perfect for our family. The cottage home was very clean, well stocked with everything we could possibly need, plenty of space and great location. Denise was responsive to all questions and provided great suggestions. The location is central on East Beach, with a nice beach and pool just for Coast Cottages. No problem for our teens to bike to the Village but also easy drive to many restaurants and things to do. Wonderful experience overall!
Stayed 7 nights in Apr 2023

10/10 Excellent

Leah P., Cartersville, GA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Get away without worry or hassle

I have booked places to stay prior and then found myself at a nearby grocery store supplementing. Everything has truly already been thought out for you at this property…which means that it is impossible to not have what you need. It is so clean and organized that everything is easily located. I booked this quick getaway based on all of the positive reviews, and this place did not disappoint. We will definitely book again in future.
Stayed 3 nights in Feb 2023

10/10 Excellent

Holly P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another great vacation!

Wonderful property in a wonderful location! We really love our stay each summer and look forward to it all year. We love the new addition to the beach access - it makes getting everyone and everything out to the beach a breeze!
Stayed 6 nights in Aug 2022

10/10 Excellent

Laura L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls’ Weekend

This was the perfect place for four women enjoying a week away. So we’ll appointed and so clean! We will definitely be back. Denise was wonderful!
Stayed 7 nights in Aug 2022

10/10 Excellent

Elizabeth D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun and charming beach house.

Win Pennie was such a fun place to celebrate the 4th of July. We enjoyed strolling on the beach and biking around the island. The house is comfy and spacious, with a well-stocked kitchen. We grilled on the 4th, and got a kick out of watching the decorated golf carts driving by. Thanks for hosting us!
Stayed 7 nights in Jul 2022

10/10 Excellent

Nathan C., Charlotte, NC

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Vacation

We have stayed at our fair share of beach houses around the country and this was one of our absolute favorites. The cottage is beautiful, just a short walk to the pools/private beach access. It is wonderfully decorated and updated. Inside you’ll find everything you would need for an island getaway. We and the kids had an incredible experience. Denise and her family were so welcoming and engaging. We would highly recommend this place and look forward to visiting again in the future.
Stayed 7 nights in Jun 2022

10/10 Excellent

Peter P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house

The house was perfect in every way. Lovely and quiet neighborhood. Photos were accurate, the house was clean, comfortable, bright and beautifully decorated. Short walk to the pool and beach. Kitchen was well stocked. The owner was very helpful in recommending restaurants prior to our arrival.
Stayed 4 nights in Apr 2022

10/10 Excellent

Sara A., Mooresville, NC

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

Our stay here was wonderful! It was probably the best rental we've stayed in and I definitely hope we'll be back. The house was very clean, furnished beautifully, and the location was great. There were a lot of small touches that made things even better - beach towels, paper towels, toilet paper, bathroom toiletries, beach wagon and tons of toys, games, books, crockpot, etc. These things make the vacation easier. The house was super comfortable and we loved both porches. The walk down to the pool and beach was easy and the pool facilities were very nice. The owner was super responsive and accommodating. I would not hesitate to recommend this house to anyone and plan to come back!
Stayed 3 nights in Apr 2022

10/10 Excellent

Kristy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We had a fantastic week!!

What a great week in St. Simons. Property was everything we needed and can’t wait to come back. Great location, great pool and the beach was perfect!! Can’t wait to come back.
Stayed 6 nights in Mar 2022

10/10 Excellent

Michael F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Every single little thing was PERFECT

My family and I spent 5 days at this property and I can’t say enough wonderful things about it! Where do I start because so many things to comment on… First, Denise was truly amazing to work with right from the beginning. She gave numerous recommendations for dining, bike rentals (Bike Dude just awesome to work with), grocery shopping, fishing charter, horseback riding etc. Denise was extremely responsive and really went above and beyond sharing her knowledge of the area as we were first time visitors. Now onto the house, let me start by saying my family and I travel a lot and I’ve never written a glowing review like this one. The house was absolutely spotless and I am extremely picky. The bed linens, towels, furniture were all in as new condition. The decor of the house was something out of a magazine. The house had everything you would need which was so nice not to have to run out and buy garbage bags, toilet paper, tissues, paper towels, dishwasher pods, travel size toiletries and even laundry detergent, she has really thought of everything! We were traveling with 3 young children and the house had everything you would need for the beach, towels, chairs, beach toys, umbrellas … everything! Location, the street the house is located on is right out of a movie. Every house is cuter than the next. The pool and beach are a super short walk from the house, you can see the entrance to pool and beach from the house it’s that close. We rode our bikes into town every day ! We cannot thank Denise enough for a wonderful vacation. We will for sure rent this house again the next time we are in the area.
Stayed 5 nights in Oct 2021

10/10 Excellent

Kate K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A wonderful week at a wonderful home!

We had the best time at Winn Pennie. One of the cleanest prosperities we’ve ever rented. So warm and welcoming with everything you could possibly need for a perfect beach week. We can’t wait to stay again!
Stayed 7 nights in Sep 2021

10/10 Excellent

Bradley w. W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wanderful Vacation.

Extremely CLEAN!!
Stayed 3 nights in Aug 2021