Discover the allure of St. Augustine, Florida! This enchanting destination boasts a wealth of history, culture, and natural splendor. Explore towering lighthouses, a maritime museum, and the iconic Castillo de San Marcos National Monument to immerse yourself in centuries of rich history. Get up close and personal with exotic creatures at the St. Augustine Alligator Farm Zoological Park. Or, for a taste of local flavor, indulge in a free tour and spirit tasting at St. Augustine Distillery.
Relax on pristine beaches or wander the pedestrian-friendly St. George Street. Find spiritual solace at the stunning Cathedral Basilica of St. Augustine. And for the ultimate in luxury, book one of the best vacation rentals with private pool in St. Augustine, Florida, and unwind with loved ones in style.
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 April 12, 2024.
1. Roomy vacation rental with heated pool (from USD 441)
This is a roomy St. Augustine vacation rental perfect for families. The screened and heated pool is the property’s highlight and offers a refreshing experience. The pool comes with a thermostat for heating, and the temperature is between 78 - 85°F (25.56 - 28.44°C). The house is tastefully furnished with a cozy living room, a well-equipped kitchen, and outdoor spaces. Dogs weighing up to 50 lbs (22.68 kgs) are allowed for a non-refundable fee.
The property is located just a minute’s drive from the beach and downtown St. Augustine, known for its art galleries, chic boutiques, and fine restaurants.
2. Pet-friendly home in quiet neighborhood (from USD 298)
This charming vacation home is the perfect place to relax and soak up the Florida sun. With a private pool, crystal blue and ready to take a dip, and a spacious patio with a table and chairs, you will have a splendid time. The pool is fully fenced, so you don’t have to worry about your little ones accidentally falling into the water. And even if you don’t want to get into the water, you can sit on the patio furniture and work on your tan.
This renovated home located just a one-minute drive from the beach and five minutes from downtown offers the best location in St. Augustine. Dogs weighing less than 50 lbs (22.68 kg) are welcome to join you for a non-refundable fee.
3. Porpoise Point (from USD 251)
Discover Porpoise Point, your waterfront paradise! Enjoy the stunning Salt Run and Vilano Beach views from this Matanzas River rental. Relax on the pool deck while enjoying the serene water views. The private pool is perfect for a relaxing swim. Moreover, the rental includes kayaks, fishing poles, bikes, and paddleboards. The brand-new dock is perfect for fishing, kayaking, or tying up your boat.
Dogs are allowed with a pet fee and breed, weight, and number approval. The rental boasts new furnishings, a fully stocked kitchen, comfortable beds, and two living spaces with large TVs. Top attractions like Old Town Trolley Tours, St. Augustine Pirate & Treasure Museum, and Royal St Augustine Golf and Country Club are nearby, too.
Top guest reviews
Cleanliness:
the house is great and is cleanit was well cleaned upon our arrival and everything works great hereHost:
kinda a bummer but the management company was somewhat helpful although it was never fixed before we leftbeautiful property with owner not terribly engagedRead more reviewsLocation:
we loved this house the quietness and location was greatreally nice neighborhood that was very quiet and was close to everythingwe really enjoyed the location the dock was priceless to see the dolphinsthe location is fantastic great neighborhood and everyone is very friendlywe drive 3 miles to the beach for amazing walks and people watching
4. Modern pool house in tropical paradise (from USD 427)
Experience the ultimate tropical paradise at this modern pool house in the sought-after Davis Shores neighborhood. This cozy yet elegant vacation home is equipped with brand-new furnishings, a chef’s delight kitchen, and a plush living room. The open floor plan maximizes space. You can enjoy your favorite shows on a large Smart TV in the living room and primary bedroom.
Step outside and unwind by the heated pool surrounded by mature landscaping and a pergola for romantic candlelit dinners. The guest bedroom opens directly into the pool area while the living room overlooks the pool, so you can look out at the soothing waters even from your bed. Pool towels are provided to make cleaning up easier.
5. Historic cottage with heated pool (from USD 269)
Experience historic charm and modern convenience at this cottage in St. Augustine. Renovated for your comfort, this 1875 cottage boasts comfortable furnishings and original artwork. Relax by your private heated saline pool, which comes with a pool deck and seating. The pool is located by the door, and you and your family can enjoy it in peace.
Enjoy an open floor plan, two patios, and an equipped kitchen with a breakfast bar. Each bedroom has a queen-size bed and ensuite bathroom, too.
Top guest reviews
Amenities & Room:
excellent air conditioning and fansthis place has a private heated pool and a beautiful patiothe pool is not only private but heated perfectly which we floridians lovedmy children loved the pool and the charming swing outside the cottagewe are a family of 4 and we were very comfortable in this charming cottageCleanliness:
it was very clean and well maintainedthe cottage was clean and tastefully decoratedthe place is clean spacious and perfect if your looking for a place to relaxthe house was clean safe and homey and in a quiet neighborhoodwonderful host great location very clean and beds very comfortableHost:
pauline was an amazing hostpauline was a wonderful host and provided the perfect home for our family's vacationpauline was extremely helpful with giving suggestions on all the best places to gowe had excellent communications with pauline and she was so kind to allow us to check in earlythe host provides plenty of ideas to make your visit enjoyableRead more reviewsLocation:
super close/walking distance to everything in st augustinegreat location awesome poolgreat location and very comfortable cottagethis place is the perfect location for a stay in st augustinelocation was still peaceful relaxing and private
Superhost
6. Charming home with roofed porch (from USD 391)
This heated pool home in historic St. Augustine comes with a clear roof so that you can take in the sights while swimming a few laps. The lap pool comes with a roofed porch, where you can laze out. The pool waters are warm, but if you’d like to heat the pool further, it can be arranged for a surcharge.
Inside the home, a fully stocked kitchen makes meal prep easy, and the lap pool and backyard are perfect for relaxing. The house is near top-notch restaurants and stores. Three parking spaces are available, too.
The home is family-friendly with games and a television with streaming services provided. The bedrooms are well-appointed, and the bathrooms have basic toiletries.
Top guest reviews
Amenities & Room:
the pool and back yard were perfect for our needspool and yard were gorgeousmore amenities i’ve ever seen in our many rentals plus many great games toys for pool etcthe house just ‘flowed’ and was just a comfortable place to behomes was beautiful pool was so convenient for the 7 of us (girls trip)Cleanliness:
beautiful clean home full of comfortvery clean beautiful and spaciousthe entire house was very clean and felt spacious and welcomingthe house was sparkling clean & the pictures do not do the space justicethe house was very clean and very cuteHost:
the hosts were very communicative and welcomingthe host was extremely easy to communicate withevelyn was a fantastic host and quick to respond to any questionsthe owner is very responsive thoughtful and went 'the extra mileevelyn’s a great host and we had a wonderful stayRead more reviewsLocation:
gorgeous house walking distance to downtownla dolce vita is located in the ideal area to easily walk downtowngreat location to town and the best restaurants we ate at were walking distance from homeamazing location and hosteasy walk to local restaurants and attractions
7. Casa Costera (from USD 381)
Welcome to Casa Costera, your perfect home away from home. This stunning bungalow with a private fenced pool awaits you. With a spacious interior boasting original hardwood floors, a fully renovated kitchen and bath, and cozy bedrooms, Casa Costera is perfect for your holiday. Soak up the sun on the large sun deck by the pool or walk to the Conch House Restaurant.
The location of Casa Costera provides access to the best of St. Augustine, including the beaches and The St. Augustine Amphitheatre. Its pet-friendly policy makes it a perfect getaway for you and your furry friend.
8. Stunning home with pool and spa (from USD 295)
Discover the perfect place to stay in St. Augustine, Florida. This property in the Davis Shores neighborhood is ideal for families and friends. It’s a short walk to downtown and a five-minute drive from the beach. The fully furnished property includes beach towels, chairs, baby gear, books, and board games.
Enjoy the brand-new pool and spa, perfect for summer fun. The asymmetrical pool is close to the porch, so you can keep an eye on your kids while chatting in the shade.
Top guest reviews
Amenities & Room:
nice accommodations pillows and beds were extra comfyCleanliness:
the house was clean and well maintained as picturedthe space is decorated modern with clean linesthe house was spacious modern clean and very comfortableHost:
she is clearly a super-hostamy was a wonderful host and so easy to communicate withamy was very responsive whenever we had any questions or needed somethingbeautiful property very kid friendly spacious and comfortableRead more reviewsLocation:
we could easily walk to downtown stwe really like the location of the house as wellamy’s place is a great house in the perfect locationit’s close to all the nice beaches the historic quarter and many great restaurantswe had a wonderful vacation at amy’s place
9. Romantic downtown escape with heated pool (from USD 279)
Enjoy a romantic getaway at a charming downtown rental with a private entrance and heated pool. This saline pool is open all year, so you can take a dip whenever you want. Indoors, the spacious living area has a large television and a modern kitchen with island seating for three. It’s located in St. Augustine’s historic district, near popular tourist destinations, restaurants, and cafes. The beach is just four minutes away by car.
Top guest reviews
Amenities & Room:
the pool is heated and delightfulthe pool and fenced in yard was an excellent additionit's an oasis with the beautiful backyard that includes a poolheated pool was a nice added touchthe bed was super comfortable for a terrific night's sleepCleanliness:
so clean and beautiful inside and outit was clean bright and invitingpauline’s place was very clean which was very important to us during covid-19very beautiful and clean home and very close to all the attractionsHost:
pauline was the perfect hostpauline was extremely attentive to our questions and needs and made us feel extra welcomeeverywhere we went people were kind and friendlypauline was very responsive with our questions prior to and during our staypauline was a wonderful host with excellent communicationRead more reviewsLocation:
awesome house close to everythinglocated in a beautiful neighborhood with restaurants and attractions within walking distanceperfect location within walking distance of the all the downtown spotsbeautiful home very close to downtownthe location was quiet and beautiful while still being close to everything
10. Quaint home built in the 1930s (from USD 225)
Step into this attractive 1930s poolside cottage. Tucked away on a quiet, tree-lined street, this charming cottage offers the ideal retreat for those looking to escape the hustle and bustle of everyday life. Relax on the front porch with a cup of coffee, listen to the morning birds, or dip in the delightful saline pool. The pool does not have a lock, so be careful when your little ones are wandering outside the house. Since the home is in a quiet neighborhood, the hosts also request that the pool be used minimally late at night. A barbecue grill is also provided, so you can plan a cookout, too!
The cottage has an open living room and dining area, with medium-sized bedrooms and ample natural light filtering in.
Top guest reviews
Amenities & Room:
this 1930’s cottage is cozy and a delightno streaming device so be sure to bring your own but wifi was stablepool is nice to just chill shower has great water pressuredespite its size it was very comfortable for our family of fourCleanliness:
it is clean well-equipped and very comfortablethe old historic clean cozy house matches the historic beauty of st augustineamazing place clean comfy and exactly what our family neededwe also looooved the pool everything was clean and tidy and very welcomingclean peaceful and a variety of beautiful house accessories to enjoyHost:
aloe was an excellent hostaloe and renee are terrific hostshouse has everything you need and aloe and renee are great hostsaloe was very friendly and very accommodatingRead more reviewsLocation:
fun place close to everythingspot was good for a weekend away close to downtownit is a very unique house and a really neat neighbor hood very close to historic downtownsuch a cute place to stay in close proximity to night life sights and great places to eatgreat location for those looking to explore the area
Unwind in style on your St. Augustine getaway
Discover luxury and budget-friendly vacation rentals with private pools at St. Augustine, Florida. Relax on the beach or take a romantic carriage ride. St. Augustine offers unforgettable experiences! Rediscover yourself on a luxurious vacation by booking a stunning home with a pool.
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