House in Saint Simons Island, GA
16 guests · 7 bedrooms · 7 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
Welcome to HighFlyer Cottage - your home away from home on East Beach, St Simons Island! This wonderful, fully-updated 7 bedroom, 7.5 bath single level beach home features large front and rear screened-in porches, extensive trex decking surrounding the pool with outdoor dining + lounge seating, a pergola-covered pool, 8 beach chairs + toys, and more! It is thoughtfully equipped with families in mind to ensure your visit is enjoyable and memorable.
Nestled under the canopy of a beautiful live oak tree sits High Flyer Cottage in the unique neighborhood of East Beach.
The front of the house features a large screened-in porch, complete with ceiling fans, rocking chairs and a shuffleboard court, if you're so inclined. The front door opens into a spacious family room featuring a vaulted ceiling, shiplap walls, 65” smart TV and ample seating.
Directly behind the living room is the gourmet chefs kitchen with European cabinets, 36'' range with hood, double ovens, microwave and dishwasher, expansive countertop space and storage, center island and eat at 4 person counter seating. Enjoy the coffee or tea from the Keurig single cup coffee/tea maker, 12 cup drip coffee maker or electric tea kettle, perfect for getting your day started. The kitchen sinks directly views the backyard, which is perfect for keeping an eye on your loved ones. Viewing the beautiful live oak tree with sitting area directly underneath it, grill area with pass through window from kitchen, and astro turf - perfect for corn hole.
Beside the kitchen is the dining area featuring a large farm table and spacious seating for 10, with another 65” smart TV. Enjoy the cozy seating nook which integrates the spacious screened-in porch through large windows and expands indoor/outdoor entertaining opportunities. The screened porch features several comfortable seating ensembles that overlook the expansive private pool area, including a dining table and lounge chairs.
High Flyer Cottage features 7 bedrooms, 7.5 bathrooms.
The Master Suite offers a relaxing king bed and large en-suite, complete with freestanding soaking tub and large shower. The master suite has a 55” smart TV and plenty of comfortable space.
The Secondary Master suite, off the living room, also features a king bed, en-suite bathroom with a large shower with a 43” smart TV.
Another King Suite features a king bed with en-suite bath and direct access to the front porch. This suite also has a 43” smart TV.
The Bunk Room features two sets of twin XL bunks, sleeping 4 total. Twin XL beds are full length – same length as a king bed. The bunk room has a 43” smart TV. Next to the bunk room is a bathroom with double vanities and tub/shower combo. The bunk room also has access to the front porch sitting area.
There are an additional 2 guests rooms with a king and queen sized bed, each with an en-suite bathroom. Each bedroom also features a 43” smart TV. One of these bedrooms is only accessible via the screened in porch and features a view of the pool area!
An additional bedroom, located by the pool and independently accessible via both the driveway and pool deck, features a queen sized bed, walk in closet, and en-suite bathroom. This room also has a 43" Smart TV.
Retreat outside to enjoy the 12 X 24 salt pool. The pool has a sunscreen and can be heated or cooled for an additional cost. The pool is surrounded by plentiful seating including lounges, dining table and adirondak rocking chairs. A pool bathroom is also located in this area!
Beside the garage is a beach gear storage shed which can be accessed by the rear gate from the driveway or from the pool deck. A beach shower, located next to the storage shed, features hot/cold water and is perfect for sand and salt water removal from bathers and beach gear. There is also an additional full-sized refrigerator located inside the newly built storage shed, as well as corn hole, games, beach chairs and a beach buggy. Beach towels are provided.
Generous parking is offered at High Flyer Cottage, including front of house paved parking for 3 vehicles and large gravel side parking. No street parking is permitted.
There are wonderful walking and biking opportunities in the East Beach neighborhood including marvelous views of the marsh, which may be easily viewed from the sidewalk and benches. A 5-minute stroll from High Flyer Cottage down 10th Street will bring you to the 10th Street beach access point - a natural path that leads to the beach through the sand dunes. At the end of Bruce Street, Gould's Inlet features a walk-over to the beach. Access to the expansive beach is also reached at the nearby Old Coast Guard Station public access point with lifeguards, parking, sand volleyball courts, snack bar, sailboat rentals and rest rooms.
A short drive or bike ride will take you to dining options such as Crabdaddy's, The Crab Trap, Fiddler's, Southern Soul BBQ, and Beachcomber. There are excellent restaurants and coffee shops around the island to satisfy any taste, and you are sure to find new favorites.
The quaint and lively village area has unique shops, restaurants, and the covered pier where you can fish, crab or watch the shrimp boats and large ships go in and out with the tide. The functioning lighthouse adds to this unique island's feel; and if you are up to it, you can climb the 129 steps to the observation platform for an unforgettable view.
Provided are: linens, house towels, pool towels, and an initial supply of soap, shampoo, conditioner, laundry soap, dish detergent, toilet paper and paper towels. Baby items provided upon request!
We have decorated and furnished our home as we enjoy for our own family, and know you will find it the perfect home for your family and friends! We look forward to welcoming you to St Simons Island and having your family make unforgettable memories at High Flyer Cottage!
East Beach, SSI
Nestled under the canopy of a beautiful live oak tree sits High Flyer Cottage in the unique neighborhood of East Beach.
The front of the house features a large screened-in porch, complete with ceiling fans, rocking chairs and a shuffleboard court, if you're so inclined. The front door opens into a spacious family room featuring a vaulted ceiling, shiplap walls, 65” smart TV and ample seating.
Directly behind the living room is the gourmet chefs kitchen with European cabinets, 36'' range with hood, double ovens, microwave and dishwasher, expansive countertop space and storage, center island and eat at 4 person counter seating. Enjoy the coffee or tea from the Keurig single cup coffee/tea maker, 12 cup drip coffee maker or electric tea kettle, perfect for getting your day started. The kitchen sinks directly views the backyard, which is perfect for keeping an eye on your loved ones. Viewing the beautiful live oak tree with sitting area directly underneath it, grill area with pass through window from kitchen, and astro turf - perfect for corn hole.
Beside the kitchen is the dining area featuring a large farm table and spacious seating for 10, with another 65” smart TV. Enjoy the cozy seating nook which integrates the spacious screened-in porch through large windows and expands indoor/outdoor entertaining opportunities. The screened porch features several comfortable seating ensembles that overlook the expansive private pool area, including a dining table and lounge chairs.
High Flyer Cottage features 7 bedrooms, 7.5 bathrooms.
The Master Suite offers a relaxing king bed and large en-suite, complete with freestanding soaking tub and large shower. The master suite has a 55” smart TV and plenty of comfortable space.
The Secondary Master suite, off the living room, also features a king bed, en-suite bathroom with a large shower with a 43” smart TV.
Another King Suite features a king bed with en-suite bath and direct access to the front porch. This suite also has a 43” smart TV.
The Bunk Room features two sets of twin XL bunks, sleeping 4 total. Twin XL beds are full length – same length as a king bed. The bunk room has a 43” smart TV. Next to the bunk room is a bathroom with double vanities and tub/shower combo. The bunk room also has access to the front porch sitting area.
There are an additional 2 guests rooms with a king and queen sized bed, each with an en-suite bathroom. Each bedroom also features a 43” smart TV. One of these bedrooms is only accessible via the screened in porch and features a view of the pool area!
An additional bedroom, located by the pool and independently accessible via both the driveway and pool deck, features a queen sized bed, walk in closet, and en-suite bathroom. This room also has a 43" Smart TV.
Retreat outside to enjoy the 12 X 24 salt pool. The pool has a sunscreen and can be heated or cooled for an additional cost. The pool is surrounded by plentiful seating including lounges, dining table and adirondak rocking chairs. A pool bathroom is also located in this area!
Beside the garage is a beach gear storage shed which can be accessed by the rear gate from the driveway or from the pool deck. A beach shower, located next to the storage shed, features hot/cold water and is perfect for sand and salt water removal from bathers and beach gear. There is also an additional full-sized refrigerator located inside the newly built storage shed, as well as corn hole, games, beach chairs and a beach buggy. Beach towels are provided.
Generous parking is offered at High Flyer Cottage, including front of house paved parking for 3 vehicles and large gravel side parking. No street parking is permitted.
There are wonderful walking and biking opportunities in the East Beach neighborhood including marvelous views of the marsh, which may be easily viewed from the sidewalk and benches. A 5-minute stroll from High Flyer Cottage down 10th Street will bring you to the 10th Street beach access point - a natural path that leads to the beach through the sand dunes. At the end of Bruce Street, Gould's Inlet features a walk-over to the beach. Access to the expansive beach is also reached at the nearby Old Coast Guard Station public access point with lifeguards, parking, sand volleyball courts, snack bar, sailboat rentals and rest rooms.
A short drive or bike ride will take you to dining options such as Crabdaddy's, The Crab Trap, Fiddler's, Southern Soul BBQ, and Beachcomber. There are excellent restaurants and coffee shops around the island to satisfy any taste, and you are sure to find new favorites.
The quaint and lively village area has unique shops, restaurants, and the covered pier where you can fish, crab or watch the shrimp boats and large ships go in and out with the tide. The functioning lighthouse adds to this unique island's feel; and if you are up to it, you can climb the 129 steps to the observation platform for an unforgettable view.
Provided are: linens, house towels, pool towels, and an initial supply of soap, shampoo, conditioner, laundry soap, dish detergent, toilet paper and paper towels. Baby items provided upon request!
We have decorated and furnished our home as we enjoy for our own family, and know you will find it the perfect home for your family and friends! We look forward to welcoming you to St Simons Island and having your family make unforgettable memories at High Flyer Cottage!
East Beach, SSI
Amenities at Sun-Soaked Luxury: Quintessential Single-Level Beach Cottage With Private Pool!
Non-smoking
No pets allowed
Family friendly
Map of Saint Simons Island, GA
Ratings and reviews
10 / 10Outstanding·Jul 2026
Highflyer Cottage on St. Simon’s Island, Georgia is the perfect getaway. It is such a unique place! There is plenty of room for a big family, is very clean and the beds are so comfortable. It’s close to the beach so we spent much of our time there. When not at the beach, we were in the pool which was a perfect size for all to hangout. The town is also close by and has great shops and restaurants. Lesley manages the cottage and is available and is super responsive in answering questions. Our family had an amazing vacation and hope to return again. Thank you for helping us make great family memories!
10 / 10Outstanding·Jul 2026
We’ve been renting on Saint Simons for years, and High Flyer is hands-down our all-time favorite. Comfortable, well stocked, plenty of spaces to gather whether as a whole family or for smaller groups. The host is super responsive and helpful. First class all the way.
10 / 10Outstanding·Jun 2026
Great house. Perfect for family trips. Great location in relation to the beach. Very responsive owner.
10 / 10Outstanding·Jun 2026
Our family had an absolutely wonderful stay and cannot recommend this home enough. From the moment we arrived, everything felt welcoming, comfortable, and thoughtfully prepared. The home was spotless, spacious, and beautifully maintained. The beds were incredibly comfortable, and we appreciated how everything was clearly labeled and easy to find.
The location was perfect—close to East Beach, restaurants, and everything we wanted to do during our stay. We rented a golf cart and spent our days at the beach and our evenings enjoying dinners with friends who joined us on the trip. Having such a convenient location made everything effortless.
Traveling with children ages 4, 8, and 10 can sometimes be stressful, but this home made our vacation feel completely relaxed. The owners provided beach chairs, beach toys, and so many thoughtful extras that saved us from having to purchase or bring those items ourselves. The pool was clean, warm, and well-maintained, and our kids absolutely loved it. The patio was another favorite spot for our family to unwind.
The neighborhood felt safe, quiet, and family-friendly. We even used a local nanny service one evening so the adults could enjoy dinner out, and having such a comfortable home to return to afterward made the experience even better.
Most importantly, the host was incredibly kind, responsive, and welcoming. Any questions we had were answered quickly, and it truly felt like staying in a home where every detail had been considered.
This was one of those rare vacations where everything went smoothly from start to finish. The house had everything we needed and truly felt like a home away from home. Every penny was worth it, and we are already looking forward to returning. This definitely will not be our last stay.
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Top rated by guests
10Outstanding
(50 Ratings)
"Highflyer Cottage on St. Simon’s Island, Georgia is the perfect getaway. It is such a unique place! There is plenty of room for a big family, is very clean and the beds are so comfortable. It’s clos..."
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