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Holiday houses in St. Simons Island

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Top-rated holiday rentals in St. Simons Island

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Top Guest favourite
The exterior showcases a light-colored building with multiple windows, allowing natural light to filter in. A wooden deck is visible, leading to a covered seating area. Nearby, a grill is situated on the deck, surrounded by trees for added privacy.
Tiny home in St. Simons

Tiny Turtle, 1 queen, full bath and kitchenette

Tiny Turtle is perfect for a couple or small family with one child. Tiny Turtle is a cozy place to spend your nights after exploring the Islands. You will love the beach and nautical décor. It has one bedroom that can only be accessed up a spiral staircase, kitchenette and private bath. Start your island adventure with beach bikes, beach chairs, wagon & umbrella all included! Tiny Turtle was designed to have an interior similar to a light house quarters! It truly is a special little place.

4.95 out of 5 average rating, 215 reviews
Top Guest favourite
A well-lit bedroom features two queen beds adorned with white linens and tropical-themed pillows. Colorful bird art hangs on the walls above the beds, while a lighted side table to one side adds functionality. Natural light filters through white sheer curtains.
Guest suite in St. Simons

Lovely, central village area, cozy coastal cottage

Enjoy a stylish experience at the centrally-located Cottages at Neptune Way. Cottage #1 (this listing) features 2 bed/2 bath, a full kitchen, dining, and living area with a separate laundry room. Fully renovated with a beautiful color story and details, this cottage is a perfect getaway spot. Walk to breakfast at Sandcastle Cafe, then take a stroll by the ocean before hitting the local shops… *Please note this unit is part of a 3-unit home. No pets, or parties please. Parking for 2 cars only.

4.97 out of 5 average rating, 175 reviews
Guest favourite
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.
Home in St. Simons

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!

4.89 out of 5 average rating, 76 reviews
Guest favourite
Cottage in St. Simons

Historic Beach Cottage - Steps to Beach & Dining

Experience a serene escape in this beautifully restored 1928 beach cottage. Blending historic charm with modern comforts, this home features an open floor plan, a fully equipped kitchen, and a comfortable living area. The cozy bedroom offers a peaceful retreat, and the modern bathroom includes a marble shower. Relax on the screened porch with a swinging daybed or take a short, two-block walk to the beach. Located in a vibrant neighborhood, you'll be steps away from dining and shopping.

4.89 out of 5 average rating, 214 reviews
Top Guest favourite
A bright living area features a light-colored sofa adorned with decorative pillows. Soft sunlight illuminates the space, highlighting a round coffee table made of natural wood. In the background, a modern kitchen with bar seating is visible, contributing to a welcoming open-concept design.
Home in St. Simons

The Peachy Palm

Charming beach house in the heart of St. Simons Island, just a short 2 min. walk to the Village, shopping, restaurants, lighthouse, fishing pier, and nightlife. The island’s stunning beaches are minutes away. This spacious one-bedroom retreat is in a gated area and features a king-size bed, sofa sleeper, private balcony, and access to a complex pool. Fully equipped with WiFi, kitchen essentials, 4 beach chairs/towels, and free parking. Perfect for a romantic getaway or family escape.

4.94 out of 5 average rating, 70 reviews
Top Guest favourite
A serene swimming pool is framed by lounge chairs and palm trees, with an inviting sunset casting warm colors over the water. Umbrellas provide shade, creating a tranquil ambiance adjacent to the beach.
Condo in St. Simons

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!

4.98 out of 5 average rating, 248 reviews
Top Guest favourite
A contemporary living area is showcased, featuring a comfortable sofa, two accent chairs, and a coffee table. Natural light enters through large windows, illuminating the space. A piece of artwork is displayed on the wall, and a neutral-colored area rug is laid on the floor.
Condo in St. Simons

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!

4.98 out of 5 average rating, 150 reviews
Top Guest favourite
A charming beach house is nestled close to the shoreline, surrounded by lush palm trees and rocky formations. The clear blue sky complements the sandy beach and calm waters, creating a serene coastal atmosphere. Nearby homes reflect a mix of architecture, adding to the scenic view.
Home in St. Simons

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!

5.0 out of 5 average rating, 50 reviews
Top Guest favourite
A cozy bedroom features a spacious bed dressed with striped linens and decorative pillows. Two windows allow natural light to fill the room, while a four-poster bed adds a touch of elegance. A seating area with soft armchairs and a small table completes the inviting space.
Apartment in St. Simons

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!

4.98 out of 5 average rating, 102 reviews
Guest favourite
Bungalow in St. Simons

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!

4.85 out of 5 average rating, 151 reviews
Top Guest favourite
A modern coastal home is framed by lush greenery, featuring a welcoming entrance with large windows and a distinctive angled roofline. A 6-seater golf cart is parked in the foreground, accompanied by a gravel driveway and manicured landscape elements.
Home in St. Simons

Flying Turtle SSI

Coastal comfort meets island adventure at The Flying Turtle! This 3BR/2BA home includes porches, a stocked kitchen, and a 6-seater golf cart for exploring the island. Stays of 5+ nights include complimentary cart use; shorter stays may add it for a fee. Rental agreement required after booking. Cart use requires additional terms and valid license.

4.94 out of 5 average rating, 71 reviews
Superhost
A serene outdoor space features a decorative fountain surrounded by lush greenery, offering views of the water and distant shoreline. Comfortable seating is positioned beneath the shade of a large tree, creating an inviting area to relax and enjoy the natural surroundings.
Home in St. Simons

Ocean Views and Tuscany Charm, Luxury Home

Feel the enchanting embrace of Old World Italy, nestled on the pristine shores of St. Simons Island. Inspired by the timeless beauty of the Amalfi Coast, this stunning private waterfront home offers an unforgettable escape with spectacular views and luxurious amenities. All located a short walk to the village!

4.75 out of 5 average rating, 44 reviews

Popular amenities for St. Simons Island holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in St. Simons Island

Top Guest favourite
Condo in St. Simons

Golf Cart | Bikes | Elevator | Ocean View | Roof

4.96 out of 5 average rating, 24 reviews
Top Guest favourite
A sprawling live oak tree provides shade over a private Airstream, surrounded by vibrant tropical vegetation. Pathways of gravel lead through lush greenery, while a wooden pergola offers an inviting outdoor seating area, blending seamlessly with the natural landscape.
Campervan/RV in St. Simons

BeachCamp - Renovated Airstream, Walk to Beach!

5.0 out of 5 average rating, 39 reviews
Top Guest favourite
The modern beach cottage is showcased at dusk, featuring large windows that allow natural light to fill the interior. Stylish landscaping with palm plants enhances the entrance, while soft exterior lighting highlights the structure's clean lines and inviting facade.
Guesthouse in St. Simons

N̈ew stylish 1250 sq ft beach cottage. St Simons

4.94 out of 5 average rating, 79 reviews
Top Guest favourite
Condo in St. Simons

Beachy Keen

4.97 out of 5 average rating, 29 reviews
Top Guest favourite
The exterior of a French Country Estate is showcased, featuring a paved driveway leading to a two-story home surrounded by well-maintained landscaping. Lush green grass and tall trees provide privacy, complemented by elegant lampposts flanking the entrance.
Island in St. Simons

Robin's Nest, Saint Simons Island, GA

4.98 out of 5 average rating, 100 reviews
Guest favourite
A modern kitchen features sleek white cabinetry and open shelving. A coffee maker and various kitchenware are neatly arranged on the shelves. Countertops are finished in a dark, smooth material, and natural light is highlighted through multiple windows.
Home in St. Simons

Atlantic Breeze

4.88 out of 5 average rating, 86 reviews
Top Guest favourite
Home in St. Simons

Cozy Coastal Cottage

4.95 out of 5 average rating, 22 reviews
Top Guest favourite
A multi-story cottage features a light blue and white exterior, with multiple spacious porches adorned with white railings. Tropical palm trees and landscaped greenery surround the property, situated in a tranquil neighborhood. A white picket fence and a sign marked 'Information' are visible in the foreground.
Home in St. Simons

Family-Run Cottage | Beach+Pool+Golf Cart Add On

5.0 out of 5 average rating, 33 reviews

Frequently Asked Questions

  • Where is Saint Simons Island located?

    Saint Simons Island is on the southeastern coast of Georgia, United States, nestled along the Atlantic Ocean. It is known for its maritime forests, sandy beaches, and welcoming coastal communities.

  • When is the best time to visit Saint Simons Island?

    Mild temperatures and lower rainfall in spring and fall make those seasons frequently suggested for visiting Saint Simons Island. Summer is popular for beach activities but brings warmer weather and higher humidity.

  • What are some things to do near Saint Simons Island?

    Explore historic landmarks like the St. Simons Lighthouse Museum, stroll through oak-lined parks, or discover local shops and art galleries. Outdoor activities such as cycling, birdwatching, and kayaking around marshes are also often recommended.

  • How is the weather near Saint Simons Island?

    Saint Simons Island has mild winters around 43–65°F (6–18°C) and warm, humid summers reaching 89°F (32°C), with higher rainfall in late spring and summer. Expect comfortable evenings much of the year, with the possibility of coastal breezes.

Destinations to explore