St. Simons Island South Island Rentals
26 properties available
Welcome to Under the Oaks! Located in a brand new community - Orchard Place, this private cottage has everything your group will want for your next vacation to St. Simons Island! Minutes to the best beaches, shopping, and restaurants on St. Simons Island, Under the Oaks is a special getaway right in the middle of everything. Guest
Under the Oaks
Home
$492.50 / per night avg

4
bedrooms
3
baths
8
guests
5
(19)
Welcome to Circle Cottage! Located in the quiet and convenient St. Simon Heights neighborhood, this designer-decorated cottage offers guests a private pool (14x24) and spa (8x8) tucked into a secluded backyard. Guests of Circle Cottage will enjoy quick access to the beaches, shopping, and restaurants! Take a quick bike ride or walk to t
Circle Cottage
Home
$466.00 / per night avg

4
bedrooms
3
baths
8
guests
4.8
(37)
Welcome to the Island Pearl! This beautifully updated vacation rental offers guests the perfect St. Simons Island escape with a private pool and tons of outdoor space for guests to relax and play. Fully renovated in 2021, the Island Pearl is a short 5-minute drive to the beach (1.5 miles), the island's best restaurants and shopping.
Island Pearl
Home
$587.00 / per night avg

4
bedrooms
3
baths
10
guests
4.9
(34)
Oleander Cottage is what beach vacation dreams are made of! This newly decorated home exudes coastal style at it`s finest. It`s attractive & sophisticated, yet oh so comfortable! The plush furnishings will make your stay a relaxed experience! Any group gatherings and events at this property are limited to the number of occupants (10
Oleander Cottage
Home
$442.50 / per night avg

3
bedrooms
3
baths
10
guests
5
(33)
Welcome to Houdini by the Sea! This wonderful island escape is centrally located just a short walk to the beaches and the best village area shops, restaurants and sites on St. Simons Island. Guests of Houdini by the Sea will have their own private heated pool (heated upon request for $45/day) with plenty of pool side seating and lounging for
Houdini by the Sea
Home
$533.50 / per night avg

5
bedrooms
3
baths
10
guests
4.8
(19)
Welcome to 30 Waterfront Dr. #332, a sophisticated coastal retreat nestled in the South Island area of Saint Simons Island, Georgia. This pet-friendly rental offers breathtaking marsh views, creating a serene and private sanctuary for your stay. Spanning 1,550 square feet, this elegant three-bedroom, three-bathroom condo comfortably accommoda
30 Waterfront Dr. #332
Condo
$202.50 / per night avg
3
bedrooms
3
baths
6
guests
4.9
(20)
Welcome to the More Fun Cottage! This immaculate 4 bedroom / 3 bathroom island beach cottage is located in a quiet neighborhood just a few minutes away from beaches, restaurants and shopping of St. Simons Island! The wraparound front porch and the chic coastal décor will lure guests into island living at its finest! Re
More Fun Cottage
Home
$427.50 / per night avg

4
bedrooms
3
baths
8
guests
4.9
(38)
Welcome to High Tide! This hidden gem is THE perfect villa to relax and enjoy some of the best marsh views on St. Simons Island! Situated in a secluded and quiet three home neighborhood on the marsh, High Tide has everything guests will want to enjoy island time. The large pool area and backyard space along with multi-level porche
High Tide
Home
$597.50 / per night avg

4
bedrooms
4
baths
10
guests
4.8
(32)
If you’re the type of traveler that sets your sights on St. Simons Island in the name of fun and relaxation, then Stones Throw Cottage has your name on it. This home away from home is a fan-favorite thanks to its incredible location. Only 80 yards away from the beach, this south island hot spot is a new two-story option on the rental market.&
Stones Throw Cottage
Home
$347.50 / per night avg

2
bedrooms
2
baths
8
guests
4.7
(78)
Welcome to Island Whimsy!Built in 2021, this breathtaking vacation rental home is ready to welcome guests! Located in the quaint cul-de-sac neighborhood of Couper Place, Island Whimsy is the perfect island escape for guests to enjoy time away from it all but minutes to the beaches, shopping, and restaurants on St. Simons Island. The outdoor s
Island Whimsy
Home
$645.00 / per night avg

4
bedrooms
3
baths
10
guests
5
(32)
Welcome to the Atlantic Cottage! Newly constructed and professionally furnished, the Atlantic Cottage has everything guests are looking for in the next St. Simons Island getaway! Offering 4 spacious bedrooms and 3.5 bathrooms, the Atlantic Cottage will allow guests to put their toes in the sand after a convenient 200 step walk 
Atlantic Cottage
Home
$650.00 / per night avg

4
bedrooms
3
baths
9
guests
5
(32)
Welcome to Latitude Adjustment! Any group gatherings and events at this property are limited to the number of occupants (13 persons). Events such as weddings, rehearsal dinners, receptions, etc. are not permitted. Pets are NOT allowed Linens (bath towels, beach towels & bed sheets) provided Check In: 4:00pm 
Latitude Adjustment
Home
$695.00 / per night avg

4
bedrooms
3
baths
13
guests
5
(42)
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