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.