Vacation rentals with a pool in Saint Simons Island

A large swimming pool is framed by a spacious deck and surrounded by greenery. Several lounge chairs are positioned nearby. Sunny skies with few clouds enhance the outdoor setting, providing a calm and open area for relaxation.

4.93 out of 5 average rating, 27 reviews

Rivera Retreat - Private Pool in SSI

The perfect family vacation house at the heart of Saint Simons Island! Just 2 minutes from Redfern Village and 5 minutes from the beach, this home is at the center of great food, shopping and beaches. When you're not out exploring the ocean or shops, stay home and enjoy a big, beautiful pool with a large deck, grill, indoor/outdoor dining patio and fireplace. The kitchen is fully stocked with everything from a Keurig to a crockpot. For beverages, enjoy both glass and plastic poolside drinkware.

4.97 out of 5 average rating, 77 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!

A covered balcony features a seating area overlooking a large swimming pool and landscaped grounds. Lush greenery surrounds the pool area, enhancing the view. The bright blue sky is visible above, contributing to a relaxed outdoor atmosphere.

4.91 out of 5 average rating, 322 reviews

Pool View - optional BIKES - Walk 2 Pier Village

Newly renovated 1 bedroom condo has the best balcony view. U will enjoy the south-island location close 2 many shops & restaurants. U can easily walk 2 the pier, shops, & restaurants. Walk to live music! Master has a King size bed & the living room has sleeper sofa. Unit comes w/ furnishings & BUSINESS CLASS WIFI. Access to tennis courts, 2 pools (1 heated) laundry facilities (coin operated). 2 bikes to use for additional fee. NO PETS or ANIMALS ALLOWED. CONTACT ME for a link to ALL listings.

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.

5 out of 5 average rating, 15 reviews

Savannah Cottage SSI- *Golf Cart Add-On Available!

Welcome to Savannah Cottage, located in the exclusive Coast Cottages neighborhood. Just one block from the beach, this spacious cottage is perfect for families looking to relax and enjoy the charm of island life. A quick bike or golf cart ride to the island’s favorite spots, the village pier, shops, and restaurants. Enjoy the island breeze on 3 spacious porches, perfect for coffee or sunset cocktails. Guests have access to two community pools, a pavilion, and a private boardwalk to the beach.

A private outdoor pool area features white chaise lounges adorned with soft cushions, shaded by large umbrellas. A small table holds refreshments beside the pool, with lush greenery and lighting enhancing the serene environment.

4.97 out of 5 average rating, 63 reviews

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.

A clear blue pool is framed by lush greenery and palm trees. The surrounding area features two levels of covered balconies from the building, creating a shaded atmosphere. Poolside lounge chairs are visible, inviting relaxation under the sunny sky.

4.97 out of 5 average rating, 305 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.

A large swimming pool is centrally located, surrounded by lounge chairs and umbrellas. Two multi-story buildings frame the pool area, featuring balconies overlooking the water. Lush palm trees enhance the tropical ambiance, creating an inviting outdoor space for relaxation.

4.98 out of 5 average rating, 206 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 saltwater 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 serene pool area is illuminated under a twilight sky, with a clear blue surface reflecting surrounding greenery. Lounge chairs and a nearby pool house are visible, along with floating pool noodles in the water, suggesting a welcoming space for relaxation and recreation.

4.92 out of 5 average rating, 103 reviews

Saint Simons Island T 10 Ocean Walk 1 Bedroom

One bedroom condo, located in Ocean Walk, is available for you to rent on Saint Simons Island. It has a fully equipped kitchen, king size bed, internet, and 2 TV’s with cable. Our condo is located on the second floor(no elevator) in the back of the complex. We have a private deck that is perfect for your morning cup of coffee. The complex has two pools (one seasonally heated), tennis courts and a pond. Ocean Walk is located less than a mile from the pier, beach, shopping and dining.

A clear blue swimming pool is surrounded by a spacious paved area featuring several lounge chairs. Lush greenery and shaded areas create a relaxing environment. A fence is visible in the background, adding to the sense of privacy.

4.98 out of 5 average rating, 124 reviews

Beach Hideaway~great location~pool~ground floor

GROUND FLOOR unit~GREAT LOCATION(mid/South Island)~walk to Redfern Village(many shops and restaurants), Southern Soul, Chickfila, Starbucks, etc~quick drive to the beach and pier~NEWLY REMODELED~GATED FAMILY ORIENTED COMMUNITY~ reliable WiFi~TV and sofa in living room~king bed & TV in master~queen bed & TV in spare~twin sleeper sofa in sunroom~pool & tennis court~NO PETS or ANIMALS ALLOWED, SEE RULES FOR HIGH PET FEE. **Parking -- My HOA does not allow work/business vehicles**

A spacious outdoor pool is surrounded by paved pathways and lounge chairs, set amidst lush greenery. The property includes a two-story building in the background, with large windows facing the pool area, creating an inviting scene for relaxation.

4.97 out of 5 average rating, 115 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!

4.92 out of 5 average rating, 104 reviews

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.

An outdoor area features a spacious pool alongside a spa, surrounded by brick flooring and well-maintained landscaping. Comfortable lounge chairs are positioned nearby, with an umbrella offering shade. Bike storage is visible in the background, complementing the serene environment.