St. Simon is a seaside town situated southeast of Georgia, offering tourists the experience of fun coastal living. History buffs can enjoy riding the Island Trolley and exploring Fort Frederica National Monument to learn about the illustrious history of the town. Visit the famous lighthouse to get Instagram-worthy shots of the neighboring Jekyll Island and Brunswick. With a long stretch of shoreline and several shops, spending a day at the beach is possible almost all year round. Feeling lazy about hitting the beach? Summer or not, here are the best vacation rentals with private pool in St Simons, Georgia, perfect for your stay on a trip to the island.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on January 18, 2025.
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1. Sassy Peach Cottage (from USD 486)
Situated just 0.1 mi (0.16 km) from the St. Simons Lighthouse Museum, this five-bedroom house is ready to accommodate a group of 14 travelers. Have a fun time in the huge pool that can be heated in colder months for a small fee. The swimming pool area also features beach chairs for sun bathing, tables with comfy seating, and a parasol for some shade. Aside from the cool breeze, huge oak trees act as a canopy for the patio and the yard, perfect when the scorching heat of the sun is too much to bear.
After exploring the nearby attractions and the beach, relax your tired muscles inside the house, which has an open layout with a fully functional kitchen and a comfortable living area.
Top guest reviews
Host:
great owners very helpful and easy to reachdefinitely recommend this property and the ownersthe island itself is very walker friendly so if you bring your pooch(es) you won't be disappointedthe owners were very responsive anytime we had a question about the houseRead more reviewsLocation:
walking distance to the adorable downtownthe location is ideal being within walking distance of the water as well as downtown restaurants and shopsgreat location and lots of bedsthe location is walking distance to downtown its spacious beautiful and had everything we neededthis was a beautiful house in such a convenient location
2. Kahlua's Cottage (from USD 350)
Conveniently located next to Beach Drive, this bungalow features a modern kitchen, a comfy lounge area, and bedrooms fitted with either queen or twin beds. A family of eight will each have their favorite spot on any of the three patios with bed swings, plush cushions, and rocking chairs. The well-maintained gunite pool guarantees a refreshing time while staying in this part of the neighborhood. After enjoying the beach, relax your tense muscles in the hot tub while sipping a glass of wine.
Stay connected with dependable Wi-Fi so you can continue to finish your remote job. The parking space can fit up to three cars, and it is perfect if you wish to explore more of the St. Simons attractions.
Top guest reviews
Host:
great stay and very responsive managerswould recommend to others and i would stay here again because the owners were so greatLocation:
great location to beach and villagethis location is super convenient to restaurants shopping and the beachgreat location - close to everything and easy to get towe love this house and the locationvery comfortable home and in a good location near the beach and village stores and restaurantsCleanliness:
the house is very clean and comfortableit was clean and comfortable plenty of room for 6 of us and a very well stocked kitchenthere was plenty of room for us cozy and clean cottageRead more reviewsAmenities & Room:
plenty of room for fun or just to chill outwifi had great download speed so i could do my work there without an issue
3. Mermaid Cottage (from USD 479)
Located in a quiet neighborhood, this four-bedroom house is suitable for a large group of travelers or a family of ten. The courtyard area features a large heated pool, perfect if you’re too lazy to go to the beach. Enjoy sunbathing on the various beach chairs surrounding the pool to get that golden tan skin you’ve always wanted.
Make use of the outdoor shower to get rid of the sand after enjoying the beach, which is just two blocks away from the property. Guests can rent a golf cart that will take them anywhere, including Neptune Park, St. Simons Lighthouse Museum, and the island pier.
Top guest reviews
Host:
martha is a trusting generous hostthis cottage is just wonderful and the owner is very easy to communicate withLocation:
nice quiet location but easily accessible to everythingeverything you could ever need in a house great location to town and beachperfect location super cute and clean accomodationsCleanliness:
very spacious and clean and quietcomfortable beds and very clean the pool was a perfect temperature our family loved itRead more reviewsAmenities & Room:
the heated pool is perfectloved the heated poolpool and patio were great relaxing spaces thanksthe two living rooms are great for families to spread out and relaxthe heated pool is also a wonderful addition
4. Floataway Cottage (from USD 1199)
Spend your well-deserved break in this ocean-view house located just a three-minute walk from Olive Way Beach. Enjoy bonding moments with the entire family in the gated courtyard, featuring a private plunge pool. The grilling area is an expansive space with enough seating, perfect for a barbeque party while swimming. An additional fee is required to heat the plunge pool, but towels and beach chairs are free to use.
This is a four-story house with an elevator serving each floor for a convenient stay. Take advantage of the rooftop patio for a picturesque view of the neighborhood or just to chill out under the night sky.
Top guest reviews
Host:
host was accessible and very responsive to questions and issuesthe host was super nice and quick to respond to any questions we hadthe host was immediately responsive to all our communicationsthe owners were very accommodating and made sure we had everything we needed for the long weekendthe owner was so amazing during the pandemic planning and re-planning of this vacationLocation:
the house is nicely located near the village and a short walk to the beachgreat location to the beach and other island activitiesCleanliness:
the house is beautiful very clean the beds and pillows are super comfortablethis was perfect spacious clean large kitchen and dining areaspacious extremely well-equipped clean an easy walk to the beachRead more reviewsAmenities & Room:
it was perfect and the heated pool is not to be missedthe house had everything for everyone - plenty of beautiful bedrooms and bathrooms living space and rec spacewe enjoyed the ping pong table the heated pool and the bikes - something for everyone
5. Beautiful home in a quiet neighborhood (from USD 321)
This modern house located just two and a half blocks from the beach is an ideal spot for a family of eight planning to explore the beauty of St. Simons. The property is tucked away in a quiet area yet close enough to reach the downtown shops and marina. Guests have access to the entire house, which is complete with three bedrooms, a fully functional kitchen, and a glass-enclosed sunroom. The patio and the expansive outdoor space are perfect for hanging out, flying kites, and playing with your pets.
Spend the day at the beach and dip in the private swimming pool in the evening. The pool is not too deep, so kids who are learning to swim will surely enjoy it.
Top guest reviews
Host:
the owner was great to work with as wellcontact persons for inquiries were very helpful and went above and beyondproperty manual was helpfulLocation:
location was good as wellclose to many attractions although a car or bike is desirablewe loved the pool and it was close to everythingwe all enjoyed the pool the location and just being able to relax and get away from it allshort walk to the beach and the house was perfect for usRead more reviewsAmenities & Room:
the house was perfect with the pool attached
6. Upscale two-bedroom guesthouse (from USD 166)
Perfect for a small family or traveling couples, this two-bedroom house provides a tranquil dwelling place on the south end of St. Simons Island. Have your morning coffee on the outdoor deck or relax in the living room with a comfy sectional, a large flat-screen TV, and a dining set.
The pool area is suitable for warmer months, and it is complete with plush seating, beach chairs, and outdoor lights. Note that the pool cannot be heated and it is not allowed to be used after 9 pm.
Top guest reviews
Location:
great location and very spaciousperfect location for enjoying island life and the surrounding areanice neighborhood for walking convenient to everythingperfect place to stay in st simons great locationhaving a private garage bay to park in was a nice feature as wellCleanliness:
we loved this place great location very clean and very modern and newRead more reviewsAmenities & Room:
beds were so comfortable kids even said the bunk beds were comfortable too
7. Sunshine Daydreams (from USD 425)
This classic beach house located about 0.5 mi (0.8 km) from East Beach combines vintage charm with modern facilities for a guaranteed delightful stay. The saltwater swimming pool is big enough for a poolside party. There are a barbeque grill, a table with a parasol, and various pool floats.
After soaking up the sun, unwind in the living room with contemporary furniture or prepare a sumptuous meal for the whole family in the well-equipped kitchen.
Top guest reviews
Host:
we would stay here again the owners were very easy to work withLocation:
very spacious and location is greatwe absolutely loved the location of this beach housegreat location tucked away and in a perfect spoteasy walking distance to the beach with public access on 6th and 8th streetsthis place was amazing and perfectly locatedCleanliness:
a+ to how clean the house was thanksthe linens and most of the counters were cleanit was clean and convenient to the beach and restaurantshowever the home is in need of a good deep cleanRead more reviewsAmenities & Room:
very comfortable house with plenty of space and amenities
8. Historic house with oceanfront pool (from USD 1698)
Make your vacation extra special while staying in this historic oceanfront house built in 1935. The house boasts a minimalist interior with trendy furniture and modern amenities, promising a delightful stay. Enjoy the ocean view while in the pool, which has a safe depth of 3.5 ft. (1.1 m) and 6 ft. (1.8 m) for the shallow end and deep end, respectively. During the colder months, the pool can be heated for a minimum charge of 50 USD per night.
If you need to leave the house, take a short 10-minute walk to reach the pier and the town center, where you will find restaurants and local shops.
Top guest reviews
Host:
ryan is an amazing hostthe beach is lovely and very family friendlythe house is lovely and the host called to check on us and had everything we neededLocation:
the location was greatgreat location close to everythinggreat house in convenient locationhouse is located in great area- easy walk to the lighthouse and village shopping/ dining areaperfect location to enjoy the islandCleanliness:
the decor is simple but clean and classythe kitchen was very spacious which made cooking and clean up super easythe house was clean neutrally decorated and had just about everything we neededvery comfortable the house was very nice and clean but a had a cozy relaxed feellots of spacious rooms and super comfy bedsRead more reviewsAmenities & Room:
the pool is an excellent addition and the sunsets are stunning—prompt response times on questions regarding the housethe kitchen space is perfect for cooking playing games and congregatingwe used the pool quite a bit as wellthe beds and linens were comfortable toothe house was perfect with an amazing kitchen and ample space for guests to gather downstairs
9. The Fig House (from USD 395)
Find solitude as you stay in this clean house with a modern ranch style, located less than 2 mi. (3.2 km) from the town center. The mossy oak trees around the yard complement the dreamy feel of the property, ideal when hanging out after a strenuous day. Spend time soaking in the heated pool, which goes almost 6 ft. (1.8 m) deep. The backyard has walls of bamboo plantings and yucca trees, assuring ultimate privacy when sunbathing around the pool area.
When not swimming, the entire family can relax inside the house, which has several comfy spots to lounge, including in the sunroom and living room, which are both filled with natural light.
Top guest reviews
Host:
bryce is very quick at responses and is a great hostbryce was such a great hostthe owner was even kind enough to leave us some fresh eggs which was a sweet touchbryce was a great host and i look forward to booking her beautiful home again when i returnLocation:
the location was greatamazing place great location so close to the beach and downtown arealocation was perfect no more than a 5-7 minute driveme and my girlfriends could not have loved this house more- great location and beautiful neighborhoodgreat place for a getaway pool is awesome great locationCleanliness:
house was sparkling cleanevery part of the house is modern and cleanwe came with a toddler and really appreciated the (clean) booster seat and (clean) toy basketsthis home is perfect it was very clean and decorated so wellthe fig house is a very nice vacation rental very clean and stylishly decoratedRead more reviewsAmenities & Room:
i am a huge fan of mid century modern architecture and this house encompasses itthe pool was absolutely perfectthe house was absolutely perfect for our two families we played with the kids in the pool all daythe pool is even bette then pictures and the perfect way to relax
10. Lazy Oaks
This lovely, four-bedroom house is ready to accommodate up to 10 guests, with rooms fitted with either a king or queen-sized bed. The interior is brightened by a high ceiling, polished floors, and huge windows.
Outside, the sprawling swimming pool is a perfect place to chat and hang out, with shallow sections for kids to join the fun. Take advantage of the barbecue grill on the patio, perfect when planning a small poolside party with your loved ones. The pool can be heated for a price of 40 USD per day so make sure to inform the owner two days in advance before check-in.
St. Simons Island, Georgia, United StatesAccommodates: 10
Top guest reviews
Location:
it was in a great locationit is in the perfect spot and within walking distance to the beach and all restaurants and shopsCleanliness:
it is brand new with plenty of room and is very clean and brightso much that we have already booked our next trip it was beautiful clean and everything you needwonderful house very maintained and clean pool is fantastic and an easy walk to the beachRead more reviewsAmenities & Room:
it also has a beautiful private pool with a very shallow section perfect for small childrenthe pool was nice however it was to cool to enjoy it
Seek relaxation in St. Simons
A favorite beach town among locals and tourists alike, this island is not to be missed when exploring neighboring cities such as Savannah and Jacksonville. Retreat to a thrilling haven as you discover the best vacation rentals with a private pool in St. Simons, Georgia, perfect for your upcoming holiday break.
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