House holiday rentals in St. Simons Island

Summer Special, Family Cottage w/ Bikes | Sleeps 9

The Freddie is a newly updated 3-bedroom, 3.5-bathroom coastal cottage in the heart of St. Simons Island. It features an open floor plan with a fully equipped kitchen, dining area for six, living room with a fireplace, and a screened porch for relaxing. The master bedroom with a king bed is on the first floor, and upstairs offers a bunk room that sleeps five, a king guest bedroom, and a sitting area with a coffee station. All bedrooms have ensuite bathrooms. The home comfortably sleeps nine gues

The East Inn - Hip Hideout Blocks from Beach

Tucked behind the historic Hazel's Cafe, this 4 bedroom hideout is rooted in and captures the "South End" living. Tall ceilings and large rooms make this Modern-Spanish style house the perfect oasis for taking it slow. Moments away you can be walking on our natural beaches, viewing our famous marshes, or catching magical sunsets. It is located 1 mile from The Village-the island's traditional "downtown" area and 5 blocks from the beach. This house is perfect for 2 families or large friend groups.

Woodford’s Reserve Estate on Saint Simons Island

​Woodford's Reserve: Kentucky's Bourbon & Bluegrass in the gentle beauty of Georgia's Golden Isles. At St Simon's Park, blocks to the beach, this nicely appointed retreat with outdoor dining, 4 bdrms, all with ensuite bathrooms & a Barrel Bistro Bunk Room, gives everyone space. The spacious kitchen/dining/HD media room is large enough for everyone. Relax in hammock chairs under a canopy of towering Live Oaks draped in Spanish moss as worries carelessly drift away with the gentle ocean breeze.

The Peachy Palm

Charming beach house in the heart of St. Simons Island, just a short 2 min. walk to the Village, shopping, restaurants, lighthouse, fishing pier, and nightlife. The island’s stunning beaches are minutes away(2 mile drive from condo). This spacious one-bedroom retreat features a king-size bed, sofa sleeper, private balcony, and access to a complex pool. Fully equipped with WiFi, kitchen essentials, 4 beach chairs/towels, for a stress-free stay. Perfect for a romantic getaway or family escape.

Charming Home near downtown & beaches.

It's a Beauty! Forget your worries in this extremely well insulated charming home located in a quiet and safe neighborhood. The hard wood floors in this 1900's refurbished home are spectacular. This beautiful cottage is walking distance to downtown and a short 10-min drive to the beaches. This place is exactly what you are looking for & has all the amenities. Super clean and new. Enjoy a relaxing swing on the porch and if you listen close, you might even hear a ship's horn in the distance.

My Ocean Getaway Yards from beach! Pets! Location!

Actually minute walk to beach! 3 bedroom 2.5 bath -Beautiful fenced in back yard with a patio area covered ,with grill, Beach kart and towels chairs included! Located in the heart of popular beach community Restaurants shops markets and more! Block to beach access and minute from Village. Guest favorite on South end . Great king beds and Smart tvs in bedrooms Fully stocked kitchen. Great outdoor space private yard . Beach Restaurants Markets shopping in Popular Beach Community !

Renovated 3BR w/ Pool–Sleeps 10, Walk to Beach

Are you ready for an escape? How about The Grace Escape! Come enjoy St. Simon’s Island in this newly renovated beach house! Located a short walk to the beach, Pier Village and the King & Prince. Bring all of your toys as this house features a large two car garage complete with 50A EV charging outlet. Or stay in and enjoy a relaxing day by the heated pool (extra charge). Rinse off in the outdoor shower and cook a wonderful meal in the fully stocked kitchen and grill. No pets allowed

Cater Cove - private pool, 1 mile to beach, quiet!

This home was fully renovated, top to bottom, in 2025 – everything is brand new! Welcome to your island escape on beautiful Saint Simons! This charming coastal retreat features a private backyard oasis with a pool, grill, and plenty of room to unwind. With 3 cozy bedrooms, Roku TVs throughout, and modern amenities, you'll have everything you need for a relaxing getaway. Just a short golf cart ride from shops, dining, and the beach—your perfect vacation starts here.

The Fig House | Mid Century, Pool, Mins from Beach

The Fig House is a newly renovated 3-bedroom, 2-bathroom Mid-Century Modern ranch style vacation home set on 1 level. It comprises: a living room/dining room with a wood-burning fireplace, 8-seater table and connection to the kitchen, which also has a breakfast table. There is a sitting room and a sun room off the kitchen with access to the pool courtyard. There are two masters with king size beds and a bunk room that has 2 sets of bunk (twin) beds.

Mid-Island Beach Cottage "Heron's Hideaway" Pets!

This 3-bed, 2-bath home was recently renovated from top to bottom! Open living/dining/kitchen perfect for gatherings and entertaining. Granite countertops, stainless steel appliances, and luxury vinyl flooring throughout. Mid-island location offers easy access to tourist destinations, shopping, and FLETC. This beach house is pet-friendly with a fully fenced backyard. Enjoy evenings around the fire pit or 8-minute drive to the beach!

Live like a local on SSI! Bike to BEACH! Pool/Spa

Y’all we added an all season POOL/SPA! This home is local beach living at its finest and newly renovated, decorated and furnished for comfort. Enjoy all the south end has to offer from our beautiful beach to quaint shops and restaurants. Our home is less than a mile from the public beach access and is an easy walk or bike ride! The outdoor living is awesome here - plenty of room to park a boat and a fully fenced yard.

Coco’s Cottage

This is a dream cottage with a yard that envelops you as you walk into the gate. If charming is what you are looking for with all the modern conveniences you found the perfect location. This tranquil cottage has two bedrooms and one bath decorated beautifully. The large deck begs for you to sit outside with a sweet tea and breathe in the wonderful salt air. Let me say Welcome Home!