Beach house holiday rentals in Sea Island

Idyllic SSI Beach House

Built in 1944 and sumptuously 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 — while the gentle roar of the ocean serenades every room. Luxuriously renovated (all high-end furniture, appliances and fittings), and perfectly situated (a short bike or walk into town), the Mildred Rose cottage is in a league of its own. Welcome to the joy of Saint Simons!

Luxury family home with private pool - sleeps 8!

Come stay at Live Oak Retreat. Nestled in the heart of St Simon's Island this home is comprised of 3 bedrooms and 2.5 baths with an open floor plan. The welcoming pool allows for family fun time and 4 bicycles are provided for exploring the island. Featuring custom finishes, luxury amenities, and a relaxing screened in porch, this beach house is the perfect place for your next getaway. Located just a quick drive from beaches, popular golf courses, village, historic sites, and so much more.

Hidden Gem

Nestled off the beaten path this hidden gem will tempt you to stick around all day but the beach, village and great restaurants are all within a mile. Bring your bike or rent a golf cart and leave the car parked! Drink your morning coffee in the warm sun of the front screened porch or in the shade of the back screened porch. Enjoy rocking in the garden surrounded by nature's beauty as the fountain provides background music. The comfortable beds will provide a restful night of sleep.

Sleeps 8, Pet-friendly, 1.5 miles from beach

Located a short one-and-a-half mile from the beach, our Peachtree Cottage is comfortable and cozy with 3 bedrooms--2 with queen-size beds and the third bedroom with 2 twin beds and a bunk bed. The master bedroom has a private bathroom with a shower. The hall bathroom has a shower and tub. The kitchen is open with a breakfast nook with a table and chairs. There is also a washer and dryer for your convenience. If you bring a pet, we have a small pet fee and a large fenced in yard.

Steps to East Beach & Pet Friendly w/ 2 King Beds

The sparkling shores of East Beach are just steps away. This condo is located in East Beach Villas about 50 yards from the Olive Way beach access. This Condo is featuring 2 bedrooms and 2.5 bathrooms and sleeps up to 9. Primed to offer you a taste of true island living, this laid-back escape is walking distance to restaurants, bars, and landmarks like Massengale Park and the World War II Museum. Enjoy coffee on the back deck in the mornings and cookouts in the evenings.

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.

Saltlife Below Deck

It's time to kick back and relax at newly renovated Saltlife below deck. Smoke a butt on the Green Egg, hang out in our tiki hut on the hammock, griddle up some pancakes and eggs on the flat top griddle, or just relax on the patio and feel the ocean breeze. 3 blocks to the beach and crab corner (4 popular SSI restaurants). We loved living here and now want to share our place with you.

Vintage-inspired beach bungalow

Welcome to this 1940s beach bungalow! Kick back and relax in this calm, stylish space. Vintage-inspired and fully renovated, and only .5 miles from the beach!

NEW! Pet-Friendly, Great Location, Fenced-In Yard

Relax with the whole family at this cozy home featuring a spacious fully fenced-in yard and newly constructed screened-in back patio.