Sun-Soaked Luxury: Quintessential Single-Level Beach Cottage With Private Pool!

Saint Simons Island, Georgia
$1245 avg/night
Minimum Stay 1 Nights
Bed 7

Bed

Bath 7

Bath

Home Private Vacation Home

Property Type

Sleep 16

Max Sleeps

Night 1 nights

Min Stay

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

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    7 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Kitchen Island Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Fenced Yard Garden Patio
  • POOL/SPA

    Heated Pool Private Pool
  • BATHROOMS

    7.5 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • WORKSPACES

    Printer
  • THINGS TO DO

    Birdwatching Nearby Fitness Facilities Nearby Golf Nearby Hiking Nearby Hiking/biking Trails Nearby Sailing Nearby Snorkeling Nearby Surfing/body Boarding Nearby Swimming Nearby Water Park Water Skiing Nearby
  • ENTERTAINMENT

    Books DVD Player Games Smart TV
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    Near A Hospital Near Outlet Shopping Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 16

Map Map

School District Availability

Review Review

  • Mara T.

    Submitted Sep 16, 2025

    Stayed Sep 11, 2025

    Just finished an amazing stay at Highflyer Cottage. The house was charming, in the perfect location and had anything we needed. Lesley was wonderful to work with and the level of hospitality throughout the entire experience was a breath of fresh air. We can’t wait to return!

  • Sara M.

    Submitted Aug 10, 2025

    Stayed Aug 6, 2025

    We enjoyed our stay at this beautiful home so much! It was for a 40th birthday celebration trip and was very spacious with lots of areas to relax. We had 4 couples in the group and loved that everyone had their own bathrooms to spread out and the beds were so comfortable. The pool and screen porch was amazing. We would love to stay here again in the future.

  • Brad C.

    Submitted Aug 5, 2025

    Stayed Aug 2, 2025

    We absolutely loved our stay at the Highflyer Cottage on St. Simon's Island. The owners thought of every aminity one needs in a stay away from home. Truly incredible experience and I would recommend to anyone. It is way more house than we needed, but can comfortable accommodate a larger family or group easily. Amazing experience!

  • Brandon H.

    Submitted Jul 19, 2025

    Stayed Jul 12, 2025

    Simply a perfect property in a great location. Host was responsive and helpful. Strongly recommend!

  • Lee P.

    Submitted Jul 8, 2025

    Stayed Jun 29, 2025

    High Flyer cottage was absolutely outstanding, and perfect for our particular needs. We are a 4-generation family, ranging in age from 1-84. The home was spacious, clean, and incredibly well-outfitted and stocked with everyday items you normally wouldn't expect. The crib was high-quality, sturdy, and easy to use. The kitchen had every imaginable utensil, cookware, and appliance. Beds were comfortable. IT/TVs/technology was user-friendly. Communication was well above average - responsive but not intrusive at all. There were no signs of wear, abuse, or inexpensive furniture that are common in other properties.The home was move-in ready, even for those with the highest standards. Both the home and the host were the best!

  • Pat K.

    Submitted Jun 29, 2025

    Stayed Jun 21, 2025

    We just completed our third vacation at Highflier Cottage. I can’t say enough positive things about this perfect house! It is always clean, comfortable and I have never stayed in a house more equipped, be it in the kitchen, on the big fabulous porch overlooking the pool or with lounge chairs around the pool. There are amenities I would never think of and least of all, expect! Lesley is easily accessible and truly wants your stay to be perfect. We really don’t want to stay anywhere else!

  • Ellen R.

    Submitted Jun 15, 2025

    Stayed Jun 9, 2025

    The house was immaculate and so well stocked for everything you need and more. There are multiple places to sit and visit, large screen porch, around the pool and in the air conditioned family room. There was plenty of room at the big table and bar for all 12 of us to eat. Our 5 grandchildren ages 4-9 would have stayed in the pool all day if we would have let them. They didn't complain at all about walking to the beach for a few hours in the morning because they had the pool to swim in the rest of the day. The pool is perfect in the afternoon because there is plenty of shade. Everyone had a wonderful time and we are looking forward to a week there next summer.

  • Drew P.

    Submitted May 12, 2025

    Stayed May 4, 2025

    Wonderful experience will return.

  • Mary C.

    Submitted Apr 29, 2025

    Stayed Apr 22, 2025

    We loved staying at this home with our extended family. From the large dining table to the screened porches, this is perfect for family time. The home is well maintained, and the hostess is top notch, as well as a great communicator. I would highly recommend!

  • Justin R.

    Submitted Apr 22, 2025

    Stayed Apr 15, 2025

    Beautiful and perfectly functional space. Pool is bigger than it looks in the photos. Great size while not being to big. The owners have provided for every need. Like Disney world, you never have to look far for a wast container. Short walk to the amazing not crowded beach!

  • Heather H.

    Submitted Apr 12, 2025

    Stayed Apr 4, 2025

    This has been our favorite house to rent. We are a huge family and everyone agreed that the house was spacious and met all of our needs. The pool was wonderful and we spent most of our time in the screened in porch. Perfect for watching kids swim in the evening. Location of the house was great. Several of our kids were able tor bike and go to the beach whenever they chose. We will be back again.

  • Deborah H.

    Submitted Sep 17, 2024

    Stayed Sep 11, 2024

    if you are looking for the perfect vacation rental on St. Simons Island, this is it. Great location on a very quiet street. The house has a wonderful layout and a host of amenities that make it a desireable property. We had plenty of room to spread out and made great use of the outdoor spaces. The kitchen is very well stocked and all of the bathrooms are updated and modern. Lesley, our property host was top notch. We had fresh fruit and cupcakes waiting for us upon our arrival. That was a first for me. Very kind. The next time we visit St. Simons we will definitely rent the High Flyer again.

  • John F.

    Submitted Sep 11, 2024

    Stayed Dec 31, 1969

    I couldn't imagine a better experience for our group of 10 guests. Lesley's communication was proactive and kind, and she was exceptionally hospitable. The house itself is also perfect for a group of this size.

  • Susan M.

    Submitted Aug 21, 2024

    Stayed Dec 31, 1969

    Leslie and her family have put together a top-notch home-away-from-home at East Beach. This is without even a close second, the best airb-n-b I have ever stayed in. We came for my birthday weekend and my 2 kids with spouses and babies. This house truly has it all - 2 cribs, a wonderfully stocked kitchen, fabulous screened porches, a CHILLED pool - amazing in steamy August! Plus so much more and that folks have already mentioned. Leslie is wonderful and feels like my newest BFF! Honestly, part of me is tempted to leave a terrible review so that I can make sure there is availability for us to come back next year!! 😂😂😂. Alas, such subterfuge is not in my nature so I can only say, ⭐️⭐️⭐️⭐️⭐️!! Beds, pillows, towels, blow up floaties, shuffle board, great decor…the McCreary family nailed it with this one. We hope to return next year!

  • Alison A.

    Submitted Aug 1, 2024

    Stayed Jul 13, 2024

    High Flyer was the best! This was our sixth year renting in SSI, and we all agreed this was our best house yet. Some of our favorite things about High Flyer: -The owner! Great communication and help when needed. -One story was perfect for the youngest and oldest -Amazing back porch and pool area -Ample parking -Clean and well appointed rooms, each of which felt very private -Plenty of beach and bath towels as well as beach chairs -Kitchen well stocked and with lots of seating -Location…we love East Beach -Baby/toddler items provided for free I could go on and on about this wonderful house. You won’t regret renting it, and we look forward to returning!

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Total

Includes taxes and fees
$1,238+
View details