Holiday rentals in Sea Island

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.

Family · Location · Outdoor spaces

Bosch Huis Goldie - Luxury Victorian Retreat

• A stunning Victorian home set in an unforgettable destination. • Elevated luxury and a thoughtfully curated experience — we’ve anticipated everything you need to make your stay truly special. • Just a short walk or drive to exceptional dining, shopping, pristine beaches, and tranquil waters. • Your stay helps support the ongoing restoration of this beautiful historic property and the vibrant community around it. • Flexible, guest-first policies — if it’s possible, we’ll make it happen.

Family · Location · Outdoor spaces

Riverfront 3 Bd, Renov. Home, 2 Blk to Cloister

This gorgeous home is perfectly located on Sea Island to provide you with stunning sunsets and breathtaking river and marsh views. 1106 River Club epitomizes quintessential Sea Island living and recently underwent a complete renovation and is newly furnished. This professionally decorated, 3 bedroom / 3.5 bathroom, waterfront home is nestled in the safe haven of River Club and only a 2 block walk from the private, 5-star Cloister Hotel, Beach Club and the Tennis, Spa and Fitness facilities.

Value · Family · Kitchen

Private Pool | Pet-Friendly | Fenced-in Yard

Bring the whole family! Pet-friendly four bedroom home with fenced-in yard and oversized private pool (NOT HEATED). Great location near beaches, golf, dining, and FLETC. Please note: We do not accept events or gatherings of any kind. This spacious home is in a quiet neighborhood just 15 minutes from St. Simons and 30 minutes from Jekyll Island. Enjoy the in-home gym with a treadmill, wall-mounted barre, and Peloton. Enjoy all the Golden Isles has to offer without island prices!

Value · Location · Walkability

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!

Family · Location · Decor

Dunn's Creek

Relax and breathe at this 3/2.5 home which offers a beautiful mid island location, large screen porch & fenced sideyard w/ deck. Outdoor shower, fire pit, grill. Washer & dryer, crib, Wi-Fi, 3 TVs. Enjoy St. Simon's eclectic shops, classic fishing pier, beaches. Natural island environment with the charm of old coastal towns - no looming high-rise condos or hotels here. Sea Palms Resort golf across the street. I respect diversity & inclusion & the home is a welcoming space.

Location · Family · Outdoor spaces

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!

Value · Family · Pets

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.

Family · Location · Decor

Oceanfront Condo w/view! | Free Bikes! | Updated!

Welcome to your luxurious coastal getaway! Our newly updated condo is located in the exclusive Beach Club gated community on SSI offering guests access to *private* beaches, oceanside pool, and more. Our condo is fully equipped with everything you need for a comfortable stay. Unit 315 is situated on the 3rd floor giving this condo a lovely view of the beach, courtyard and pool. We are a short walk to restaurants, shops, and a quick bike ride to so much more!

Location · Family · Decor

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!

Family · Location · Check-in

Coastal Cottage

Coastal Cottage is less than a mile from the Jekyll And Saint Simon's Island causeways and Historic Downtown Brunswick. Savannah and Jacksonville and their airports are an easy hour away. Come love what we love about our adopted hometown! We are pet lovers! So your pets are welcome. There is a $25 one time pet fee per pet to help cover the cost of the extra cleaning needed when our furry guests check out.

Value · Location · Cleanliness

The Nest | Steps to beach and dining

Welcome to our charming guest cottage privately nestled behind a quaint 1940s home. Situated within walking distance to the beach and a variety of restaurants, this cozy retreat offers a peaceful getaway with modern amenities. Relax in comfort and convenience while enjoying the coastal breeze and exploring the vibrant, tree canopied neighborhood. Your seaside escape awaits!

Family · Location · Laundry