Holiday rentals in St. Simons

The exterior of the coastal cottage showcases a welcoming porch with a large American flag hanging. The space features potted plants and a screened-in area, offering a cozy spot for relaxation. Light-colored siding and a metal roof contribute to the charming coastal aesthetic.

4.96 out of 5 average rating, 120 reviews

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

An open kitchen and living area are showcased, featuring dark cabinetry and a central island with seating. Pendant lights above create a modern look. A decorative front door, framed by stained glass panels, complements the space. Natural greenery is positioned in the corner.

5 out of 5 average rating, 161 reviews

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.

Guest house in St. Simons

The cottage treehouse features a modern exterior surrounded by lush greenery, including tall oak trees. A gravel parking area is visible in front, with a staircase leading to a second-floor balcony. Large windows allow for natural light to enter the space.

5 out of 5 average rating, 204 reviews

Private Cottage Treehouse Among Giant Live Oaks

Welcome to your very own island cottage treehouse - all new construction with a beach community theme, laced with Southern charm. To reach your 600 sq/ft studio cottage, use the private entrance to access the stairway. Along with a full bath and a convenient kitchenette, you are welcomed to a large open living space with double sliding glass doors that lead you to your own 180 sq/ft private balcony nestled among the live oaks. All guest bookings w favorable prior history will be considered.

The welcoming entrance of the cottage features a covered porch with two rocking chairs and lush landscaping. A gravel driveway leads to a garage, while the façade showcases shutters and wood accents under a gently sloping roof.

4.89 out of 5 average rating, 61 reviews

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!

A spacious bedding area features a large white bed adorned with decorative pillows. A cozy seating area invites relaxation, accompanied by a light-colored woven side table. Ocean-themed artwork is displayed above the bed, complemented by soft light from two lamps with seashell designs.

4.97 out of 5 average rating, 322 reviews

Perfect Island Private Getaway-Walk2Beach-Village

If you are interested in a great little getaway, this is it. Gated UPDATED BEACHY condo with private gated parking & pool. IDEAL LOCATION. Walk/Bike to the Beach, Pier Village Shopping, Restaurants & Entertainment. Custom made book with local recommendations included. Condo is setup similarly to a hotel suite with Kitchenette *see photos. Relaxing jetted tub&large shower Has washer/dryer, full refrigerator, Keurig coffee, WiFi, Roku Stick, Alexa, Amazon Music, Amazon Prime, Netflix.

4.97 out of 5 average rating, 189 reviews

The exterior of the duplex cottage displays a two-story structure framed by lush trees. A gravel driveway leads to the entrance, with a balcony visible on the upper floor. Landscaping features low shrubs and natural wood accents complementing the serene environment.

Cottage in St. Simons

Top Floor Renovated Cottage by King & Prince Beach

This unique Cottage has just been renovated and redecorated with fine art and features beautiful shiplap walls as well as exposed wood beams and new floors throughout! The kitchen has been overhauled and features quartz countertops and an Italian farm house sink. The unit boasts two bedrooms with one king sized bed and the other being a queen with generous sized closets. In between the bedrooms is a full bathroom with a walk in shower. **This is a duplex and this unit is the top floor.**

A light-filled living room features a sleek entertainment unit with a large TV and a glass coffee table. Comfortable seating options include a woven chair and a sofa visible through the open curtains, enhancing the inviting atmosphere.

4.88 out of 5 average rating, 99 reviews

Newly Renovated Beach Home

Recently renovated quiet condo walking distance to the Village and pier. Your family will be close to everything when you stay at this centrally-located home. This beautiful 2 bedroom and 2 bathroom condo is designed to ensure you're comfortable and relaxed on your vacation. During your stay you will enjoy luxury amenities such as dimmable lights, keyless entry, Smart TV/Roku, marble shower& more. The community features 2 pools one of those are heated for cooler months.

4.91 out of 5 average rating, 11 reviews

Golf Cart | Bikes | Elevator | Ocean View | Roof

Located right across the street from the beach, this luxury home features ocean views from the large, covered balcony and roof top deck. Cruise around the island on the golf cart or any of the 6 new bikes. The huge kitchen and open living area have plenty of room to entertain your whole family. The primary bedroom has a sprawling ensuite bathroom with a soaking tub and large shower. The high ceilings and arched doorways really enhance the elegant feel of the home.

A fully equipped kitchen features stainless steel appliances, including a gas stove and refrigerator. Classic shaker-style cabinets and butcher block countertops are complemented by exposed brick walls. A dining area with a wood table and bright windows is visible in the background.

4.87 out of 5 average rating, 319 reviews

Stanton Apt D - Historic retreat 1 block to beach

Your perfect getaway, just 30 seconds from the beach! This fully restored 1920s 2-bed/2.5-bath cottage beautifully blends historic charm with modern conveniences. Enjoy a quick stroll to the beach, a 5-minute walk to the King & Prince Hotel, and a 15-minute walk to the village. We provide high-quality bedding, towels, and kitchen supplies. Experience ultimate comfort and an unforgettable 5-star stay, with thoughtful amenities and personalized touches throughout.

4.99 out of 5 average rating, 102 reviews

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!

4.94 out of 5 average rating, 132 reviews

Cottage in St. Simons

1940's Beachy Cottage

This 1940s cottage is a a laid back, beachy getaway. Perfect for families! - Located amidst a beautiful canopy of live oaks -Quiet neighborhood, great for walking and biking -6 minute walk to the beach -1 mile from Pier village area -3 bedrooms; 2 bathrooms -Fully stocked kitchen -Washer/Dryer (detergent included) -Wifi and Roku - Screened-in porch - Fenced-in yard -Beach toys, wagon, and charcoal grill all included

A welcoming living area is shown with a spacious sectional sofa and a large television. A soft rug covers the floor, while natural light filters in through windows. A cozy reading nook is visible in the background, adding to the inviting atmosphere.

4.94 out of 5 average rating, 120 reviews

Golden Girls Getaway“Pet Friendly”

Wonderful first floor 3 bedrooms and 2 bathrooms condo available on St. Simons Island. You walk in and see all the upgrades this home has to offer for you and your entourage. 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!

Popular amenities for St. Simons holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in St. Simons

A cozy living area is furnished with a sectional sofa adorned with decorative pillows, accompanied by a modern coffee table. A black armchair adds contrast, while natural light enters through a window, illuminating the neutral palette. A piece of wall art and a round mirror enhance the space.

4.94 out of 5 average rating, 32 reviews

Three-bedroom luxury, central

Superhost

4.86 out of 5 average rating, 7 reviews

Luxury Multi-Level Home Near Pier Village

A swimming pool is positioned in the foreground, featuring crystal-clear water and lounge chairs arranged around its perimeter. Lush green lawns and palm trees are visible in the background, along with a pathway leading toward the beach area.

4.88 out of 5 average rating, 17 reviews

Oceanfront Condo -Private Boardwalk -Pool-Balcony

Superhost

4.67 out of 5 average rating, 3 reviews

Enjoy a Luxury Getaway at this Oceanfront Condo!

5 out of 5 average rating, 3 reviews

Tranquility Place

4.75 out of 5 average rating, 4 reviews

*Beautiful* Folly Flats Just STEPS from the Beach!

Superhost

A spacious back deck features a large umbrella shading a dining area with several black metal chairs and a round table. Lush greenery surrounds the deck, enhancing the outdoor space. The house exterior, adorned with white siding and dark blue shutters, complements the natural setting.

4.88 out of 5 average rating, 8 reviews

Open ranch style home with many great upgrades

An open-concept living area features natural light from multiple windows. A comfortable white sofa is centered on a decorative rug, complemented by a wooden coffee table. The kitchen, visible in the back, showcases stainless steel appliances and a modern design. A large indoor plant adds a touch of greenery.