10 Best Vacation Rentals With Private Pool In St. Augustine, Florida - Updated 2024

| 5 min read

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.

Stayed at this property?
St. Augustine, Florida, United States
PRIVATE VACATION HOME 12 Guests 6 Bedrooms 2 Bathrooms

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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.

Stayed at this property?
St Augustine, Florida, United States
PRIVATE VACATION HOME 10 Guests 4 Bedrooms 2 Bathrooms

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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.

Stayed at this property?
St. Augustine, Florida, United States
PRIVATE VACATION HOME 8 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
the house is great and is clean
it was well cleaned upon our arrival and everything works great here
kinda a bummer but the management company was somewhat helpful although it was never fixed before we left
beautiful property with owner not terribly engaged
we loved this house the quietness and location was great
really nice neighborhood that was very quiet and was close to everything
we really enjoyed the location the dock was priceless to see the dolphins
the location is fantastic great neighborhood and everyone is very friendly
we drive 3 miles to the beach for amazing walks and people watching
Read more reviews
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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.

Stayed at this property?
Saint Augustine, Florida, United States
PRIVATE VACATION HOME 4 Guests 2 Bedrooms 2 Bathrooms

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

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.

Stayed at this property?
St. Augustine, Florida, United States
147 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
excellent air conditioning and fans
this place has a private heated pool and a beautiful patio
the pool is not only private but heated perfectly which we floridians loved
my children loved the pool and the charming swing outside the cottage
we are a family of 4 and we were very comfortable in this charming cottage
it was very clean and well maintained
the cottage was clean and tastefully decorated
the place is clean spacious and perfect if your looking for a place to relax
the house was clean safe and homey and in a quiet neighborhood
wonderful host great location very clean and beds very comfortable
pauline was an amazing host
pauline was a wonderful host and provided the perfect home for our family's vacation
pauline was extremely helpful with giving suggestions on all the best places to go
we had excellent communications with pauline and she was so kind to allow us to check in early
the host provides plenty of ideas to make your visit enjoyable
super close/walking distance to everything in st augustine
great location awesome pool
great location and very comfortable cottage
this place is the perfect location for a stay in st augustine
location was still peaceful relaxing and private
Read more reviews

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.

Stayed at this property?
St. Augustine, Florida, United States
158 reviews   Superhost Wifi Available
ENTIRE HOME 6 Beds 10 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
the pool and back yard were perfect for our needs
pool and yard were gorgeous
more amenities i’ve ever seen in our many rentals plus many great games toys for pool etc
the house just ‘flowed’ and was just a comfortable place to be
homes was beautiful pool was so convenient for the 7 of us (girls trip)
beautiful clean home full of comfort
very clean beautiful and spacious
the entire house was very clean and felt spacious and welcoming
the house was sparkling clean & the pictures do not do the space justice
the house was very clean and very cute
the hosts were very communicative and welcoming
the host was extremely easy to communicate with
evelyn was a fantastic host and quick to respond to any questions
the owner is very responsive thoughtful and went 'the extra mile
evelyn’s a great host and we had a wonderful stay
gorgeous house walking distance to downtown
la dolce vita is located in the ideal area to easily walk downtown
great location to town and the best restaurants we ate at were walking distance from home
amazing location and host
easy walk to local restaurants and attractions
Read more reviews

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.

Stayed at this property?
St. Augustine, Florida, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

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.

Stayed at this property?
St. Augustine, Florida, United States
99 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 9 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 9

Top guest reviews
Amenities & Room:
nice accommodations pillows and beds were extra comfy
the house was clean and well maintained as pictured
the space is decorated modern with clean lines
the house was spacious modern clean and very comfortable
she is clearly a super-host
amy was a wonderful host and so easy to communicate with
amy was very responsive whenever we had any questions or needed something
beautiful property very kid friendly spacious and comfortable
we could easily walk to downtown st
we really like the location of the house as well
amy’s place is a great house in the perfect location
it’s close to all the nice beaches the historic quarter and many great restaurants
we had a wonderful vacation at amy’s place
Read more reviews

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.

Stayed at this property?
St. Augustine, Florida, United States
59 reviews   Superhost Wifi Available
ENTIRE HOME 1 Bed 4 Guests 1 Bedroom 1 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
the pool is heated and delightful
the pool and fenced in yard was an excellent addition
it's an oasis with the beautiful backyard that includes a pool
heated pool was a nice added touch
the bed was super comfortable for a terrific night's sleep
so clean and beautiful inside and out
it was clean bright and inviting
pauline’s place was very clean which was very important to us during covid-19
very beautiful and clean home and very close to all the attractions
pauline was the perfect host
pauline was extremely attentive to our questions and needs and made us feel extra welcome
everywhere we went people were kind and friendly
pauline was very responsive with our questions prior to and during our stay
pauline was a wonderful host with excellent communication
awesome house close to everything
located in a beautiful neighborhood with restaurants and attractions within walking distance
perfect location within walking distance of the all the downtown spots
beautiful home very close to downtown
the location was quiet and beautiful while still being close to everything
Read more reviews

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.

Stayed at this property?
Saint Augustine, Florida, United States
192 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
this 1930’s cottage is cozy and a delight
no streaming device so be sure to bring your own but wifi was stable
pool is nice to just chill shower has great water pressure
despite its size it was very comfortable for our family of four
it is clean well-equipped and very comfortable
the old historic clean cozy house matches the historic beauty of st augustine
amazing place clean comfy and exactly what our family needed
we also looooved the pool everything was clean and tidy and very welcoming
clean peaceful and a variety of beautiful house accessories to enjoy
aloe was an excellent host
aloe and renee are terrific hosts
house has everything you need and aloe and renee are great hosts
aloe was very friendly and very accommodating
fun place close to everything
spot was good for a weekend away close to downtown
it is a very unique house and a really neat neighbor hood very close to historic downtown
such a cute place to stay in close proximity to night life sights and great places to eat
great location for those looking to explore the area
Read more reviews

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.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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