Holiday rentals with a pool in St. Simons Island

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Popular amenities for St. Simons Island rentals with a pool

House rentals with a pool

Top guest favourite
Home in St. Simons Island
4.96 out of 5 average rating, 157 reviews

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

AvaRating, 5 stars2 weeks ago
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!
Guest favourite
Home in St. Simons Island
5 out of 5 average rating, 12 reviews

Beautiful 4 bedroom home with a pool!

NicoleRating, 5 stars2 days ago
Beautiful home, perfect to host a small family reunion. House is well stocked with kitchen essentials, linens, towels, and room to accommodate multiple people. The pool was awesome and the perfect way to end each day.
Superhost
Home in St. Simons Island
5 out of 5 average rating, 3 reviews

May Joe Cottage-Walk to Village, Pier, and Beach

DelRating, 5 stars8 months ago
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.
Guest favourite
Home in St. Simons Island
4.96 out of 5 average rating, 55 reviews

The Mint Julep on beautiful Saint Simons Island

EmilyRating, 5 stars1 month ago
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.
Top guest favourite
Home in St. Simons Island
5 out of 5 average rating, 18 reviews

Seaside Serenity

BrookeRating, 5 stars1 week ago
Our group had a fantastic experience staying at Derek‘s home. Highly recommend! It’s within walking distance to all of the shops and restaurants, there is a golf cart on site that you can rent daily, fantastic pool, plenty of space for a large group of friends/family. Stay here, you won’t be disappointed!
Superhost
Home in St. Simons Island
4.77 out of 5 average rating, 13 reviews

The Grey Pearl - Swimming Pool, Premier Location!

BrianRating, 5 stars1 month ago
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!
Guest favourite
Home in Jekyll Island
4.93 out of 5 average rating, 15 reviews

Great Home 3 beds 2 Bath 3 min local Beach, Bikes

JamesRating, 5 stars4 months ago
We loved this home. These are hosts that genuinely put their heart and soul into providing a peaceful and beautifully furnished home. Thank you, Don and Marcia.
Guest favourite
Home in St. Simons Island
4.97 out of 5 average rating, 76 reviews

Fig, a Boutique Modern Home w/ Swimming Pool

JosephRating, 5 stars9 months ago
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.

Apartment rentals with a pool

Top guest favourite
Apartment in St. Simons Island
4.99 out of 5 average rating, 85 reviews

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

LoriRating, 5 stars3 days ago
We enjoyed our stay and will be back to visit again! Close to restaurants and plenty of things to do in the area. Very nice place to stay.
Guest favourite
Apartment in St. Simons Island
4.92 out of 5 average rating, 65 reviews

Lovely 2-BR/2-BA Condo w/balcony & 2 pools

Mary MargaretRating, 5 stars2 days ago
The location was perfect! Unit exactly as described. Loved that the unit was a few steps away from the playground! The pools are nice. I appreciated the laundry detergent and bath soap/shampoo/conditioner!! The AC will not go below 70°, but that wasn’t an issue for us. I would definitely stay there again!
Top guest favourite
Apartment in St. Simons Island
4.93 out of 5 average rating, 88 reviews

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

BradfordRating, 5 stars1 week ago
Responsive host and clean unit. Perfect location for a quiet stay to visit family in surrounding area. Convenient for all your needs.
Top guest favourite
Apartment in St. Simons Island
4.98 out of 5 average rating, 107 reviews

Ocean Vibes Retreat (dog friendly)

ChristyRating, 5 stars1 month ago
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.
Guest favourite
Apartment in St. Simons Island
4.88 out of 5 average rating, 74 reviews

Cheery 2 BD/2BA Near Village!

WendyRating, 5 stars5 days ago
We just finished a 3 week stay at Cynthia’s place and we were so sad to leave! The location and condo complex are perfect. The pools are clean, one is super quiet and one is appropriate for kids, both are great. It is an easy walk into town, also close to the beach. The unit is so comfortable, 2 great bedrooms and bathrooms, very comfortable couch and chairs for relaxing in the living room. I cooked dinners during the week and had everything I needed. We walked to restaurants on the weekends. This is a 5 star property for sure, thanks for a great stay!
Guest favourite
Apartment in St. Simons Island
4.93 out of 5 average rating, 56 reviews

Spacious Condo in the Heart of St. Simons

MelanieRating, 5 stars2 days ago
Cindy's place was exactly as described. Very comfortable and clean. She provided all of the information that was needed. I did not have to reach out for anything. Highly recommend her place.
Superhost
Apartment in St. Simons Island
4.92 out of 5 average rating, 38 reviews

Beach Club condo! Pool, Hot Tub and tennis

RobertRating, 5 stars6 months ago
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.
Superhost
Apartment in St. Simons Island
4.73 out of 5 average rating, 114 reviews

Ocean Walk Super Host Family and Pet Friendly

JenniferRating, 5 stars3 weeks ago
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!

Quick stats about holiday rentals with a pool in St. Simons Island

  • Total rentals

    920 properties

  • Nightly prices starting at

    £7 before taxes and fees

  • Total number of reviews

    20K reviews

  • Family-friendly rentals

    830 properties are a good fit for families

  • Pet-friendly rentals

    310 properties allow pets

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

Destinations to explore