Holiday rentals with a pool in St. Simons

The spacious studio features a queen bed dressed in light linens, complemented by a decorative throw. Large glass doors open to a private balcony surrounded by greenery. A seating area with a chair by the window invites relaxation, while a sleek entertainment console holds a large TV.

5 out of 5 average rating, 113 reviews

Salt Air Villas - Walk to Beach Pier Restaurants

Studio close to beach, village, restaurants, shopping. Gated condo community, covered parking. Perfect couples getaway, business trip or extended stay. One bedroom, 1-queen bed, one bath, large shower, jetted tub & private balcony. Fully stocked kitchen, 2-burner cooktop, fridge w/freezer, sink, microwave, toaster oven. Keurig coffee maker. Decorative touches throughout. Large Screen Samsung Smart TV+ROKU Guest Mode. Comfy furnishings, washer/dryer. Not suitable for children No Smoking No Pets

A walkable path of stepping stones is bordered by various plants and shrubs, leading to the entrance of a well-maintained home. Lush greenery, including tall grasses and a large succulent, adds a natural element, while soft sunlight filters through trees in the background.

4.96 out of 5 average rating, 99 reviews

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!

4.89 out of 5 average rating, 133 reviews

Location! WALK to BEACH, Village & PIER! 2 POOLS*

After a relaxing nights sleep, walk out to the balcony and enjoy the amazing lake views & the sounds & smells of the salty ocean breeze, which is just down the street. Enjoy a workout in the gym, a game of pingpong/corn hole next to the lake, or a dip in one of the luxurious pools. Sit back & relax after a day at the beach & watch a movie on one of the smart TVs. This condo is nestled in the heart of SSI, a short walk to shopping, golfing, restaurants, historic sites, parks, the pier, & more.

A wooden sign marks the entrance to Gascoigne Condominiums, displaying the name prominently. Surrounding landscaping features lush green bushes and a bed of colorful flowers, including shades of purple and white, contributing to the welcoming atmosphere of the community.

4.93 out of 5 average rating, 113 reviews

A Super Host Best Favorite on St. Simon's Island

Completely Renovated! This newly furnished condo is a great place to come back to after exploring all St. Simons Island has to offer. Just a short 3 miles from the beach and village area, it's perfect for a small family or couple. The condo has private parking and a great community pool. Enjoy a cocktail on the private deck while you make dinner on the grill! A Smart Home with Alexa in every room. You can have music in any room or the whole house, turn lights on and off by voice and more.

The living area features comfortable seating, including a light-colored armchair and a dark couch, placed around a circular table. A dining area is visible, showcasing a blue and white color scheme with upholstered chairs. Natural light fills the room through large windows adorned with blinds.

4.96 out of 5 average rating, 119 reviews

Large Open 2 Bed 2 bath Condo Overlooks Pool

You have found one of the best vacation rental condos on St. Simons Island. Comfortable and spacious, 1,100 sq ft, 2 bedroom, 2 bathroom in South Island gated complex, just two miles from the beach and Pier area. Upstairs. Perfect for as little as 1 guest or as many as 6. This condo is kept immaculately clean and fresh. Along with king in the master, the 2nd bedroom has a new queen full memory foam mattress. Pool, fitness room, fast Wifi, free gated parking, laundry. Lots of natural light!

A clear view of the swimming pool is presented, featuring a spacious area with surrounding palm trees and lounging chairs. The water appears inviting in the sunlight, with a gentle curve along the edge. Nearby buildings provide a backdrop to the outdoor scene.

4.91 out of 5 average rating, 442 reviews

Beach Walk -optional BIKES-Pool-Walk 2 PierVillage

This cozy 1 bedroom condo has many upgrades. U will enjoy the south-island location close 2 many shops & restaurants. U can walk 2 Pier Village & other entertainment. King in Master & living room has queen sleeper sofa. Comes w/ new furnishings & BUSINESS CLASS WIFI. 2 tennis courts, 2 pools (1 heated), laundry facilities (coin operated), ping pong, fitness center, playground, private stocked lake, & includes USAGE OF 2 BIKES for an additional charge. NO PETS or ANIMALS ALLOWED. SEE RULES

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.

4.96 out of 5 average rating, 341 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.

4.91 out of 5 average rating, 103 reviews

A bright living room is presented with a large flat-screen television mounted on the wall. Two comfortable armchairs are positioned around a textured area rug, with a coffee table at the center. Natural light filters through sheer curtains, revealing an outdoor patio area.

Townhouse in St. Simons

Lovely OceanWalk Condo, Pools, Golf Cart Available

Escape to The Marsh Mellow, a renovated 3-bedroom townhome on St. Simons Island! Perfect for families, it's just a short distance to the beach and vibrant Pier Village. Enjoy a private patio, dedicated workspace, and fantastic community amenities including two heated pools, pickleball and tennis courts, and a gym. Your ideal island getaway awaits! A golf cart is available to rent separately, is exclusively for our guests, and is about half the cost that carts rent for on the Island.

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.

4.98 out of 5 average rating, 236 reviews

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!

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.

4.98 out of 5 average rating, 137 reviews

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!

A bright living area features a comfortable seating arrangement with soft cushions. A glass coffee table sits at the center, showcasing decorative items. Large sliding doors provide access to a balcony with an ocean view, while light-colored curtains frame the windows.

4.93 out of 5 average rating, 120 reviews

OCEAN VIEW-St. Simons says Relax at The Beach Club

Check out this gorgeous and updated condo in The Beach Club! There is a pool and private beach access for guests.It has a beautiful ocean view and a private balcony. The first bedroom features a King size bed, balcony access, and a private bathroom with a large walk in shower. The second bedroom has a Queen size bed and access to the shared hall bath. Please send a message with any questions!

4.84 out of 5 average rating, 146 reviews

Turtle Cottage: Lagoon Views & Convenient Location

Welcome to our cozy St. Simons townhouse! Enjoy coffee on the deck while watching turtles in the lagoon, then head out—beaches, shops, and restaurants are just 2.5 miles away. With 3 comfy bedrooms, a spacious living area, and a fully equipped kitchen, you'll have everything you need for a relaxing stay.

Popular amenities for St. Simons rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A living room area features a comfortable sectional sofa and a wooden coffee table. A television is positioned in front, with a light grey area rug grounding the space. The open layout connects to a dining area and a well-equipped kitchen, illuminated by natural light.

5 out of 5 average rating, 94 reviews

Great Island Location!

5 out of 5 average rating, 9 reviews

Coastal Comfort Stroll to Village, Pool & Tennis

An inviting pool area is illuminated at night, featuring a spacious swimming pool alongside a hot tub. Lounge chairs are positioned around the pool, with a shaded umbrella providing space for relaxation. The house in the background showcases warm lights spilling from large windows.

4.96 out of 5 average rating, 177 reviews

Live like a local on SSI! Bike to BEACH! Pool/Spa

The outdoor space features a well-maintained pool surrounded by lush greenery. Comfortable lounge chairs are positioned nearby, and a small seating area offers a place to relax. The space is bordered by a wooden fence, providing privacy and a tranquil atmosphere.

5 out of 5 average rating, 60 reviews

Tabby Shack SSI - heated POOL, 3b/2ba, allows dogs

Superhost

4.88 out of 5 average rating, 16 reviews

Luxury St. Simons Home: Pool, Beach & Pet Friendly

5 out of 5 average rating, 13 reviews

Relax and Unwind I Private Pool + Outdoor Oasis!

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.

4.97 out of 5 average rating, 58 reviews

The Peachy Palm

A cozy living area is provided with two comfortable armchairs and a round ottoman on a patterned rug. A large television is mounted on the wall above a wooden console table. Natural light enters through sliding glass doors leading to a private outdoor space.

4.98 out of 5 average rating, 40 reviews

Relaxing Lakeview Stay – Near Beach + Pool

Apartment rentals with a pool

4.99 out of 5 average rating, 111 reviews

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

Apartment in Jekyll Island

Two blue Adirondack chairs are positioned on a cement patio, offering a view of the ocean and coastal grass. The backdrop features a tranquil shoreline, with gentle waves and a clear sky, creating an inviting outdoor space for relaxation.

4.87 out of 5 average rating, 115 reviews

Driftwood paradise, ocean view!

A collage showcases the welcoming living area with plush seating and large windows, a private balcony with ocean views, a serene saltwater pool surrounded by palm trees, and the beautifully landscaped community featuring multiple buildings and inviting amenities.

5 out of 5 average rating, 54 reviews

Beach Please! Top Floor*Balcony Ocean View*Pool

A cozy bedroom is visible, featuring a wooden headboard with decorative pillows arranged on a spacious bed. Light-colored curtains frame the windows, while soft lamps sit on bedside tables. Four art pieces depicting coastal themes are displayed above the bed.

5 out of 5 average rating, 48 reviews

Cozy, End-Unit Condo-Pool!

A swimming pool area is surrounded by a white fence, featuring a central pool and a smaller hot tub. Lounge chairs are arranged around the decking, and a gazebo can be seen nearby. Lush greenery and trees provide a natural backdrop.

4.75 out of 5 average rating, 123 reviews

Ocean Walk Super Host Family and Pet Friendly

A comfortable living area is furnished with a beige sofa and a recliner, accompanied by a wooden coffee table. Natural light enters through glass sliding doors, leading to a private deck surrounded by greenery. A ceiling fan provides a sense of airiness.

4.92 out of 5 average rating, 113 reviews

Saint Simons Island T 10 Ocean Walk 1 Bedroom

4.94 out of 5 average rating, 18 reviews

Ocean Walk Beautiful Ground Floor Lake View Condo!

A cozy living area features a light-colored sofa adorned with a multicolored striped pillow. Two bedside lamps provide soft illumination beside a round, fish-themed mirror. A wooden coffee table sits on a striped area rug, with a console table visible in the background.

4.97 out of 5 average rating, 148 reviews

Beach Hideaway~great location~pool~ground floor

Other holiday rentals with a pool

The townhome exterior is framed by lush greenery, with manicured shrubs and trees providing a natural, serene environment. A paved driveway leads to a single-car garage for each unit, showcasing a blend of architectural styles in a peaceful neighborhood setting.

5 out of 5 average rating, 5 reviews

Salty Paws

Superhost

Townhouse in St. Simons

4.84 out of 5 average rating, 38 reviews

Golf Cart | Pool | Bikes | Beach Gear | Porch

A wooden deck is furnished with two blue Adirondack chairs, inviting relaxation. Lush greenery frames the space, while expansive marsh views stretch toward the horizon under a partly cloudy sky.

5 out of 5 average rating, 11 reviews

Marsh to the Beach, 2 Bedroom Island Rental

5 out of 5 average rating, 15 reviews

Tranquility Place

A gated swimming pool area is surrounded by lush palm trees and oak trees adorned with Spanish moss. Lounge chairs are placed around the pool, complemented by striped umbrellas providing shaded spots. Soft sunlight reflects off the water, creating a serene environment.

4.89 out of 5 average rating, 101 reviews

Mandevilla, Modern Home w/ Pool Near Pier Village

A private pool is surrounded by a spacious deck, featuring two floating pool toys. The area is shaded by a large, centuries-old oak tree. A cozy seating area is visible in the background, bordered by greenery and privacy fencing.

4.98 out of 5 average rating, 85 reviews

Close to Beach Heated Pool and Spa-Rent Golf Cart!

A beautifully landscaped yard features lush greenery, including palm trees and shrubs. The house, with its inviting architecture, is partially visible, showcasing a large porch and shaded areas. A wind chime stands prominently in the foreground, adding to the serene outdoor environment.

Flat in Brunswick

4.84 out of 5 average rating, 166 reviews

Beautiful private 1 bedroom. Heated pool & jacuzzi

A refreshing swimming pool is surrounded by lounge chairs and tropical landscaping. The pool area is framed by well-maintained buildings, creating a serene atmosphere. Tall trees provide shade, and a clear blue sky complements the inviting setting.