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Summer Special! Cute Cottage Steps to Beach & Pool

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King bedroom 1
Welcome to Winn Pennie
Exterior
King bedroom 1
King bedroom 1

Reviews

10 out of 10
Exceptional
3 bedrooms3+ bathroomsSleeps 6

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
St. Simons Island, GA
  • Place, World War II Home Front Museum
    ‪1 min walk‬
  • Place, East Beach
    ‪5 min walk‬
  • Place, Massengale Park
    ‪7 min walk‬
  • Airport, Brunswick, GA (BQK-Golden Isles)
    ‪26 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Twin Beds

3 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony

About this property

Summer Special! Cute Cottage Steps to Beach & Pool

Welcome to Winn Pennie, a meticulously maintained Coast Cottage located in one of the most sought-after vacation rental communities on St. Simons Island. Perfectly positioned just 250 steps from the ocean-side pools, pavilion, and private gated beach boardwalk, this home offers the ideal blend of comfort, convenience, and coastal charm.

Our neighborhood sits along Coast Guard Beach, known for having the widest stretch of sand on the island. Even at high tide, there is always plenty of room to walk, relax, or lounge by the shore.

The home features a thoughtfully designed layout with 3 bedrooms and 3.5 bathrooms. All bedrooms are located on the ground level and include private ensuite bathrooms. Upstairs, you will find a spacious living area, a fully equipped kitchen with a drip coffee maker, and both front and back porches. Multiple dining and sitting areas throughout the home provide ample space to gather together or spread out and relax.

For your comfort, each bathroom is equipped with a hair dryer, and guests enjoy full access to the community pools, pavilion, and private gated beach access.

Pool heating information:
At least one community pool is heated every weekend from Friday afternoon through Sunday, during Spring Break from March 15 through April 15, Thanksgiving week, and from Christmas through New Year’s Day. Pool heating may be requested outside of these dates for $50 per day. Pool heat is not available during the warmer season from May 21 through September 21.

Easy online check-in is required prior to arrival. Similar to a hotel check-in, guests complete a rental agreement, ID verification, and a security hold through our secure web-based system, Happy Guest. This process is quick, mobile-friendly, and must be completed in order to receive arrival instructions. Failure to complete check-in may result in cancellation without refund.

You will also receive a personalized digital guidebook with helpful information about the home, local favorites, early check-in notifications when available, and occasional late checkout opportunities. The guidebook can be shared with friends and family for easy trip planning.

If you have any questions before or during your stay, feel free to message us anytime.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
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.

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
Onsite 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 there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

St. Simons Island

Located near the beach, this vacation home is in East End, a neighborhood 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.
View more Vacation Homes in St. Simons IslandOpens in a new window
Map
St. Simons Island, GA

What's nearby

  • World War II Home Front Museum - 1 min walk - 0.2 km
  • East Beach - 5 min walk - 0.4 km
  • Massengale Park - 7 min walk - 0.7 km
  • Demere Park - 16 min walk - 1.4 km
  • St. Simons Lighthouse Museum - 3 min drive - 2.3 km

Getting around

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

Restaurants

  • ‪Chick-fil-A - ‬3 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Ziggy’s - ‬4 min drive
  • ‪Wake Up Coffee Company - ‬3 min drive
  • ‪Mullet Bay - ‬3 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 Summer Special! Cute Cottage Steps to Beach & Pool?

As of Apr 15, 2026, prices found for a 1-night stay for 2 adults at Summer Special! Cute Cottage Steps to Beach & Pool on May 2, 2026 start from $727, 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?

Onsite 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?

Check-out is at 10:00 AM.

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

Located in East End, this vacation 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 mi (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 67 out of 68 reviews
Rating 8 - Good. 1 out of 68 reviews
Rating 6 - Okay. 0 out of 68 reviews
Rating 4 - Poor. 0 out of 68 reviews
Rating 2 - Terrible. 0 out of 68 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

natalie k.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house perfect for family!
Stayed 2 nights in Feb 2026
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Krissy V.

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
Verified

10/10 Excellent

Leah P.

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
Verified

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
Verified

10/10 Excellent

Michael L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful house for our family of 4 for a spring break getaway. Beautifully decorated and organized, kitchen has everything you could ever need. Loved spending time on both porches, playing games around the big table, and spending time at the pool and beach just a short walk down the road. Lovely location, close to restaurants and parks.
Stayed 5 nights in Mar 2026
Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Nathan C.

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
Verified

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
Verified

10/10 Excellent

Sara A.

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
Verified

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
Verified

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

About the host

Hosted by Ashley Fassnacht

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