The town of Seaside lies along the shores of northwest Florida. It is characterized by its New Urbanist design, picturesque walking paths, and a long stretch of pristine beaches. Home to beautiful pastel-colored houses surrounded by curated lawns and white picket fences, this Florida town is the filming location for the popular film “The Truman Show”. This community takes pride in its Instagram-worthy pavilions which serve as beach entrance markers and protection for the dunes in the area. After a day of exploring this dreamy destination, return to your holiday homes and enjoy water activities away from the crowd of beachgoers. If this piques your interest, read on for the best vacation rentals with private pool in Seaside, Florida.
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 August 31, 2025.
1. Feelin' Tip'Sea (from USD 2432)
This coastal home is ideally located in Park District, a few steps from a long stretch of beautiful beach. If you wish to easily explore the quiet neighborhood, four adult bicycles are available for use.
Here, guests will have access to multiple screened porches, an outdoor shower, and a chef’s kitchen. Meanwhile, the private resort-style pool comes with a sun shelf so guests can enjoy the cold water while laying out under the sun. On the other hand, for those who’d like to stay in the shade, they can do so under the built-in umbrella in the pool.
Santa Rosa Beach, Florida, United States
19.08 km (11.9 mi) from The Village of Baytowne WharfSuperhost
Accommodates: 12
Top guest reviews
Host:
the home and host definitely exceeded our expectationsthe host made everything so nice for usthe property management team was very responsive - literally answering our questions within minutesthe host was incredibly responsive and check-in/check-out was a breezeLocation:
great location - within walking distance of the beach shops and clubgreat location our group will definitely be backthe house was amazing perfect location walking distance to the beach and seaside squareyou couldn’t ask for a better locationi absolutely recommend staying at this house great location and beautiful homeCleanliness:
the cleanliness of the house was top notch and we had truly everything we neededthe house was spotless and was perfect for our large multigenerational groupeverything was so clean and laid out nicely for us when we got therewhat can i say? this was the best mother’s day the house was so beautiful and cleanRead more reviewsAmenities & Room:
walked everywhere beach watercolor pools restaurants little shops all super closethe kitchen is updated and had everything we needed for a fabulous week
2. Into the Mystic (from USD 1079)
Into the Mystic can accommodate a total of 12 people. Its large front porch welcomes guests into the main living area, featuring distinct architectural characteristics such as a vaulted ceiling, beadboard walls, and antique pine floorings.
Location-wise, the beach is only 300 steps from the property. From here, the sea is easily accessible. After a long day out, relax in your fenced pool which comes with a private seating area for resting after long laps. Right beside the pool area is ample parking for those bringing vehicles. The property also comes with a six-seater GEM cart exclusive for guests’ use.
Santa Rosa Beach, Florida, United States
18.98 km (11.8 mi) from The Village of Baytowne Wharf
Top guest reviews
Host:
the owner patrick was accommodating and responsive with any concernsdefinitely would recommend this home and ownerthe manager was great to deal with and super helpfulthe owner was amazing to work with and very responsivehe was extremely responsiveLocation:
beautiful and close to everythingawesome location with a 2 minute walk to everythingawesome property close to everythinglove the location so close to beachlocation was great short walking distance to watercolor and seasideCleanliness:
this house is beautiful it is decorated so nice and is very cleanlots of room comfortable beds super cleanthe house is perfect clean and has great amenitiesthe rooms are beautiful and the bathrooms are very spaciousRead more reviewsAmenities & Room:
the resort amenities including all the pools are perfect and beautifulwifi and tv worked greatwe loved having a private pool as well as camp watercolor with all the resort amenitiesthe house was beautiful and comfortable and fit our needs perfectlythis home had comfortable beds beautiful linens spacious rooms an incredibly well-stocked kitchen--everything we could have asked for
3. Western Lake Drive (from USD 3972)
This luxurious home in WaterColor offers stunning Western Lake views. You can enjoy the said views right from the open-plan first floor, laden with windows and plenty of comfortable seating. You can also spend your downtime here as the space is equipped with a cable TV.
Outside, one of the property’s highlights is the private pool with loungers for sunbathing and post-dip meals. Additionally, guests can enjoy eating in the elegant dining room overlooking the backyard. Cap off the night with a cozy movie marathon in the home theater.
Santa Rosa Beach, Florida, United States
18.73 km (11.7 mi) from The Village of Baytowne Wharf
Top guest reviews
Host:
thank you for hosting our group highly recommendRead more reviewsLocation:
we loved the location and this home was absolutely beautiful
4. Western Lake Drive (from USD 1829)
This bright and airy 3-story accommodation can sleep up to 16 guests. Inside, the main house features a fully equipped gourmet kitchen, five sizeable king and queen bedrooms, and a bunk room for kids. The property also has a separate carriage house with its own king bedroom, bathroom, kitchen, and living area, should someone need the private space.
The highlight of the outdoor area is the private pool where you can swim as much as you’d like. Beside this is a roofed patio with plenty of seating space, perfect for morning coffee and wine nights with views of the lavish pool.
Santa Rosa Beach, Florida, United States
18.97 km (11.8 mi) from The Village of Baytowne Wharf
Top guest reviews
Host:
nada the property manager was very responsiveLocation:
location was also idealthe house was amazing and the location is perfectwe couldn’t have asked for a better location i can’t wait to book another trip at this housegreat location and absolutely gorgeous homeconvenient to seaside watercolor inn shops and eating this was the perfect locationCleanliness:
the house is clean and decor is nicewe had 15 people the rooms and bathrooms were spacious the house was cleanRead more reviewsAmenities & Room:
the interior decorating was stunning and the furnishings were very comfortable including all of the bedsthe pool was the perfect size and the back deck was great for entertainingthe kids loved the heated pool/outdoor spacethey had a great outdoor setup with a pool which our family utilized to the maxpool felt great after a few hours at the beach kids lived in it
5. Lucky Enough (from USD 1749)
Suitable for 10 guests, this charming beach cottage offers close proximity to the beach and town center. Additionally, credit to acquire beach gear rentals and services at Vacayzen is also provided, so guests can have a worry-free beach adventure.
The fun doesn’t stop on-site. Children will be delighted to swim and splash around the private pool in the backyard. The spacious screened porch is also a great spot to meditate and unwind with pool and nature views. Additionally, you can have your meals by the poolside, on a screened patio so you won’t have to worry about insects.
Santa Rosa Beach, Florida, United States
19.93 km (12.4 mi) from The Village of Baytowne WharfAccommodates: 8
Top guest reviews
Location:
this is a cute place and close to the beach accessgreat stay within walking distance to seaside multiple public beach access points nearby and well maintained propertyan easy walk to most everything you’ll needlocation condition and price were perfectawesome stay location was great to go into town and to go to the beachRead more reviewsAmenities & Room:
once house construction is complete on street behind the backyard pool will be great
6. Happy Place
True to its name, Happy Place guarantees a delightful stay for gatherings of up to 18 people. The accommodation peacefully lies in Beach District, providing convenient access to WaterColor and Seaside. Meanwhile, its interior is tastefully decorated with stylish designer furniture, white walls, and large windows.
Happy Place also features one of the biggest private pools in WaterColor. The poolside area is fitted with sun loungers, beach umbrellas, and pool toys to keep swimming time fun. You can also plug in the wireless music system and have an outdoor pool party with your company. Additionally, the deck overlooks the pool and allows for a nice spot to lounge around in peace.
18.93 km (11.8 mi) from The Village of Baytowne WharfAccommodates: 18
Minimum Nights: 3
Refund Policy :
Top guest reviews
Host:
owners are very responsivethe owners are wonderful and the property manager is very quick to answer any questionsresponsive property manager whenever i had a needthe owners of the property are attentive and available and maintain the home to the perfect leveleveryone associated with happy place was friendly and helpfulLocation:
the location is perfectgreat house in a perfect locationbest location in watercolorwonderful house and a great locationit’s the best location in watercolorCleanliness:
the whole house was very clean and beautifully decorated -- better than the picturesit was clean and the kitchen was well equipped for small meals and large family mealsthis house was perfect for our large family the house was clean and well equipped with everything we neededgreat location a spotlessly clean propertyRead more reviewsAmenities & Room:
the kitchen is well equipped and the indoor furniture is warm and invitingbeautiful views and accommodations plenty of space stocked kitchen pool and beach toysthe heated pool is always a huge hitlots of extras such as bikes and heated pool made our stay easy and funthe pool was lovely and there were lots of outdoor gathering spaces
Enjoy a Seaside vacation with your own pool
Wherever your feet take you around this quaint town, you’ll be met with natural beauty and picture-perfect sights. While you’re here, upgrade your stay by booking one of the best vacation rentals with a private pool in Seaside, Florida.
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