Vacation rentals in St. Simons Island

Heated Pool, Family friendly, Great Location

Welcome to The Ranch SSI! Here you will experience a fully stocked and beautifully designed home with a clean, modern style, located in the heart of St. Simons Island. The Ranch is located in the Kings Terrace area of the island, only a few blocks away from the St. Simons pier village with local shops and restaurants, as well as the lighthouse. The Ranch is only a quick 3 minute drive to the beaches and our favorite local coffee shop-- Wake Up Coffee Co! Enjoy an island retreat at The Ranch SSI!

Starfish on Circle Drive - SSI Cozy Cottage

This traditional cottage on St. Simons offers relaxation, comfort, and proximity to the beach, dining and shopping. A large family room leads out to a backyard sanctuary with two screened-in porches. A fully stocked kitchen provides you opportunity to dine in, or head to the spacious deck to grill dinner or roast s'mores at the fire pit. Three bedrooms and two full baths. Pet-friendly, dogs only. Fenced yard. Secluded for peace and quiet, but conveniently located to visit all of SSI!

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

Jack & Laurel Welcome You To Our Beach Club Condo!

Comfort, relaxation, and beauty await you here - On the quieter and most private side of the Beach Club - with direct, gated beach access . Enjoy our oceanside pool, 2 hot tubs, and lush gardens - in the perfect spot, on one of the prettiest beaches in the South! Primary suite with king bed, walk-in shower/soaking tub. Second bedroom with 1 queen/ 1 twin, full bathroom. Well-equipped kitchen, full balcony... Come on, the dolphins are waiting for you!

Cozy Coastal Cottage

Your home away from home on St. Simons Island! Our house is beautifully updated with 3 private bedrooms, 2 full bathrooms and a spacious common area. The backyard is a private oasis complete with a sitting area, covered patio, large TV and grill. Bonus features include a fire pit and outdoor shower! Ample parking space. The house sits across from a quaint neighborhood park. Few minutes drive to the beach, and a short walk to shops and restaurants. We welcome you to St. Simon’s!

Ocean Vibes Retreat (dog friendly)

This serene ground floor 3 bedrooms and 2 bathrooms condo available on St. Simons Island. We live up to our name “Ocean Vibes Retreat”. You walk in and see all the upgrades and new furnishings this home has to offer for you and your group. The complex is gated and located in walking distance to many restaurants, Redfern Village, and one of our grocery stores. We also offer a pool, workout room, tennis court and play ground. Come stay and let the salt air cure what ails you!

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.

SSI Favorite Showcase Home | Walk to Pier!

Welcome to Miss Georgia Peach — a luxury 4-bedroom, 4-bath St. Simons Island retreat just one block from Pier Village, with a showstopping 3rd-floor crow's nest, two king primary suites, bunk room, whimsical twin bedroom and a chef's kitchen outfitted with Wolf appliances. Perfect for family reunions, golf weekends, girls' trips, and beach getaways, this home sleeps up to 11 in style — steps from the beach, restaurants, shops, and the historic lighthouse.

Perfect cottage ON THE BEACH! Golf Cart for RENT!

Built in 1944 and transformed in 2021, the Mildred Rose Cottage embodies the best of old and new. With direct ocean frontage on two sides, the cottage is uniquely positioned to watch both sunrise and sunset. Luxuriously renovated (all high-end furniture, appliances and fittings), and perfectly situated (bike or walk to town), the Mildred Rose cottage is in a league of its own. Welcome to Saint Simons! 6 SeaterGolf Cart ADD ON available as well!

2BR & 2BA Beach cottage & .5 mi. to Beach!

Welcome to the 1950's historic 'Anguilla Bungalow.' The home is recently renovated and includes 2BR & 2BA. Located on St. Simons Island and only 1/2 mile to the historic Village where you will find great shops and restaurants! The beach is less than 2 miles away. We look forward to having you and please make sure to check out our 5-star reviews and super host status!

Southern Living Cottage in the Village

Welcome to Anastasia’s Burrow! This immaculate custom built Southern Living beach cottage is located in the relaxed south end of the village. This charming 3 bedroom / 4 full bath cottage is nestled in the lush landscape of St. Simons Island under a park of live Oak trees. It is a easy walk to the beach, restaurants, shopping, pier, lighthouse and entertainment.

Robin’s Nest

Welcome to your perfect family getaway on beautiful St. Simons island! This newly renovated 4-bedroom, 3-bathroom beach house has everything you need for a relaxing and memorable coastal escape. Just two miles from the beach and a short 0.3 mile stroll to the Pier Village, you're close to everything, yet tucked into a peaceful spot perfect for unwinding.