
Holiday rentals with a pool in Saint Simons Island
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Top-rated rentals with a pool in Saint Simons Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Saint Simons Island rentals with a pool
House rentals with a pool

Great Island Location!
We felt comfortable and enjoyed our stay!

Ocean Views with Swimming Pool.
Excellent stay. My sons and I stayed for a week to play some golf at some of the wonderful courses nearby. The location of the unit matches the pictures shown. The unit is near the water, is spacious and updated without being cluttered. Everything (TV, frig, air conditioner, etc) worked well and the property has beautiful views of the ocean. The property manager was very proactive and regular about communication on all things related to our stay. A great place to stay for a quiet and peaceful break.

Tabby Shack SSI - heated POOL, 3b/2ba, allows dogs
Great stay at TabbyShack. It was clean and tidy but has all the basic supplies you need. The family loves the backyard and pool and outdoor shower. The couch was also a great spot to get out of the heat and relax. Great hosts who were easy to communicate with and offered up a ton of local suggestions we used.

Rivera Retreat - Private Pool in SSI
We enjoyed our stay at Nicole’s home on St Simons! It was close to everything was nice and clean. We appreciated her quick replies and her kindness. Many thanks!

Newly Renovated Home with Golf Course Views
We’ve come to SSI for many years for annual golfing event. This was our first stay at this property. Absolutely no regrets and we will return. Interior renovations give clean, modern, and so comfortable feel. Everything was better than described, everything worked wonderfully. Our host was super responsive and accommodating. Don’t hesitate, we loved being there.

The Big Peach on the Beach (3 min. Walk)
We had a wonderful time, and the place was such a quaint, comfortable atmosphere. Restaurants within walking distance when parking is somewhat limited. The beach is literally two seconds away and easy access. Host was very hospitable and accessible the entire time. Will definitely return in the future.

SSI Beach House + Private Pool & Hot Tub w/Bikes!
We had a great experience at 411 Oak St. The location can’t be beat; short walk to excellent restaurants, shops and the public beach access points. Our teens loved the independence this gave them to go explore and do what they wanted without needing us to drive them. The house was clean and well thought out. Plenty of room for our family of 5. The hosts are generous with the little things like dishwasher detergent, coffee pods, and tissues. It makes arrival feel so much more welcoming and low stress when you don’t have to immediately take inventory and run to the store. The beds were very comfortable. Our favorite part was the backyard. The tree canopy, pool, and hot tub made for a private-feeling peaceful environment. This was our first visit to SSI so we had a lot of questions. Alyson and team were very helpful with recommendations for fishing, eco tours and golf. Thanks for making our first trip to SSI absolutely perfect!

Renovated Beach House Rental on St. Simons Island
We thoroughly enjoyed our stay at Maria’s place. It was very clean and welcoming. Felt like home from the get go. Madia was a great host. She always responded quickly and communicated clear instructions for check in and out. You can tell the details of the Airbnb were really thought out. Everything went so well together. It was a very clean and comfortable space. All the amenities listed were there. We hope to stay again one day!
Apartment rentals with a pool

Driftwood paradise, ocean view!
Beautiful lodging and setting. The place is very well stocked and very clean. There were many small touches that meant a lot (a Keurig and a full-size coffee pot; a personal fan in the bedroom along with the ceiling fan). Small things that are helpful. There is a great view of the ocean and easy access to the beach. The island is small so it is very easy to get around to see things and to great restaurants. We enjoyed the historic district and the Georgia sea turtle center. We loved lunch at the restaurant by the Holiday Inn and dinner at the Jekyll and Hyde restaurant (pricey, but absolutely delicious). We also enjoyed lunch at the Wharf. We did have noisy neighbors above us the last night. I almost went upstairs to ask them to be quiet (but decided it wasn't worth it). They were heavy walkers, not partyers. There's not much a host can do about that. If we return to Jekyll Island we will stay here again.

Seascape Serenity in the Beach Club Resort
Great place! So convenient to everything! I will say that the lent trap for the dryer needs to be thoroughly cleaned as soon as possible! We had the best time!

Pickleball on site & walk Mallery Park PB courts
We’ve been coming here for three years and it never disappoints. It is always clean and the host is always super nice and responsive. It’s very close to the beach and restaurants. We love walking to get breakfast, shop, and to go eat dinner in the evenings.

Turtle Cottage: Great location and Turtles too!
We were here for the graduation of our granddaughter. What a wonderful experience. Home was just right and host is above expectations and so kind. You will have an amazing trip on Saint Simon island. Lots to do and great restaurants. Close to shops, and the beach. Don’t miss the World War II museum and lighthouse. Top of lighthouse you can see forever.

Oceanfront. SSI, Ga Beach Club
Most items met or exceeded our expectations. My wife and grown son were super-thrilled. The host's response was very late, and I didn't get help in time at all. Everything else is good.

Spacious Condo in the Heart of St. Simons
Cindy’s place was just what we needed for our vacation! It was the perfect little space - especially the sun room! We will definitely stay again!

St Simons Townhouse Close to Beach and Village
I definitely WILL return!! I felt so at home in Ryan's place!! Clean and fully stocked! we had an issue with the upstairs cable access, but it didn't take away from the great, comfortable stay we had!!!

Great ocean views from living room and the master
Beautiful condo, exceptionally clean, exactly as advertised. On a very quiet street, close to the beach and lovely view of the ocean! We walked to town, which included shopping, the lighthouse, pier and lots of great places to eat. This was our first visit to St Simon’s and we will definitely be back. Check in process was super easy and when I went into the office to return the keys, staff was very friendly. The only thing I didn’t love was the bed in the main bedroom, it was very hard. Other than that, amazing trip!
Home rentals with a private pool

Great Dunes Cottage
It was a great place. Great location, beds were comfortable, pool fantastic. We will be back.

Newmans Beachview
Nice home with great location.

Turtle Dunes

Kisses Cottage

Austin Mermaid

Sweetpeas Cottage

A Lifelong Dream
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