
Vacation 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

Live like a local on SSI! Bike to BEACH! Pool/Spa
Cj and Zach were super kind and always responded fast when something was needed. This house was clean and a great spot to come to for the weekend!

Beautiful 4 bedroom home with a pool!
We loved our stay in this beautiful SSI home! It was the perfect location for our family getaway. The space was great with comfortable accommodations for our party of 8. The home was spotless, the kitchen was nicely appointed & organized, and the outdoor patio/pool area was a favorite hangout spot. This home is conveniently located in the heart of SSI with restaurants and shopping within walking distance. The kids safely biked and walked all over this amazing island. Highly recommend: 5⭐️s!

May Joe Cottage-Walk to Village, Pier, and Beach
We had to decide to chance the trip due to TS Debby. We checked in with realtor the morning after TS Debby hit. He responded immediately to our query and was on his way out to check the property. He managed to find someone to clean the pool, he indicated that services were up and running. We checked with a few local supermarkets and they were still stocked and opened. Had a small hiccup with one of the doors right after check-in and the maintenance man came right over. We were quite impressed at the level of service. The pool offered hours of fun for my three grandchildren 11 and under. It was great to have that option after spending time on the beach. It was a perfect 75th birthday with my family.

Three little birds oasis
A beautiful weekend on St. Simon. Went to celebrate our daughter and her fiancé. Great location, plenty of room for our family and friends. Beautiful screened in porch where we ate breakfast and were able to visit with everyone. Thank you for a great Easter weekend!

The Mint Julep on beautiful Saint Simons Island
Our family of four stayed at the Mint Julep for our spring break week in mid-March and it exceeded every expectation. The house was perfectly furnished and the layout worked great for our pre-teen kids to be on one side in the bunk room with their own bathroom, and for us parents to be on the other side of the house with an en suite. We enjoyed the screened porch for morning coffee and the kids used the pool every day (we were glad we requested it be heated, definitely a must for March as it was still in the 60s some days). We also enjoyed the firepit and outdoor TV. You can’t beat the location. We walked to dinner and breakfast daily, and my husband ran the trail right outside the front door every day too. We hope to be back again next year.

Seaside Serenity
The home is beautiful and very comfortable for a large group. We had senior members of our family with us, so it was nice to have bedroom options on the main level. We would LOVE to stay here again! You are only a block or two (level easy walk) from the pier, shops, restaurants and a park—just lovely! The property managers are great and super responsive, can’t ask for better.

The Grey Pearl - Swimming Pool, Premier Location!
Terrific home! Great location near the pier and the lighthouse. It was a perfect house for our golf trip. Everyone had their privacy and big kitchen and TV areas made it great to watch college basketball. The outdoor space is AMAZING with the pool, fireplace and sitting area. You can walk down the street for a great view of the water and also stroll through the shops and nearby restaurants. Very pleased with our trip!

Fig, a Boutique Modern Home w/ Swimming Pool
Sixth or seventh time staying at The Park. It’s a relaxing slice of heaven and perfect for those with 1-2 little kids. A home away from home for us.
Condo rentals with a pool

Oceanfront Condo w/view! | Free Bikes! | Updated!
Very nice and well described. Host had great communication. Would definitely stay again.

Lovely 2-BR/2-BA Condo w/balcony & 2 pools
We had a great stay! The location is convenient to beaches and the pier. Condo was comfortable and clean. It has beach chairs and towels which was very helpful.

Location! WALK to BEACH, Village & PIER! 2 POOLS*
Responsive host and clean unit. Perfect location for a quiet stay to visit family in surrounding area. Convenient for all your needs.

Ocean Vibes Retreat (dog friendly)
Mary made us feel right at home! Her place was incredible, it had everything we needed to enjoy a long weekend on the island for my son’s wedding. We appreciate the welcome note and the bottle of wine and doggie treats. She really went above and beyond to make us feel welcomed.

Cheery 2 BD/2BA Near Village!
4th time staying at Ocean Walk and my favorite by far!

Spacious Condo in the Heart of St. Simons
Great stay! I think the photos may be a bit outdated because the place was even better looking / updated than the photos! Affordable, clean, and a nice location - only a short drive from the beach and pier 🥰 Thanks Cindy.

Beach Club condo! Pool, Hot Tub and tennis
Carols place was great. It was extremely clean. The bathrooms were a little older but the paint was fresh. The facility was great. A nice pool and multiple jacuzzis. Very easy drive to many resturants.

Ocean Walk Super Host Family and Pet Friendly
We had a great time at a beautiful place for our very first rental! Lots to do just within the little community for different age ranges. Short distance to multiple things to do. Great host and would stay again!
Home rentals with a private pool
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- St. Catherines Beach
- East Beach
- Boneyard Beach
- Sea Island Beach
- Ocean Forest Golf Club
- Amelia Island Lugar Lindo
- St. Marys Aquatic Center
- Amelia Island State Park
- The Golf Club at North Hampton
- Dungeness Beach
- Stafford Beach
- St. Simons Public Beach
- Nanny Goat Beach
- Groot's Beach
- Fernandina Beach Golf Club
- St Simons Surf Sailors