Vacation rentals with a pool in Historic District, St. Augustine

A serene outdoor space is featured, highlighting a heated pool surrounded by lounge chairs and a firepit. An outdoor bar with seating is present, along with palm trees adding a tropical touch. A comfortable gathering area is available, ideal for relaxation.

4.92 out of 5 average rating, 105 reviews

Beach paradise w/pool, firepit, hot tub, mini golf

Less than two blocks from the beach and just 7 minutes to historic downtown Saint Augustine. Heated pool, hot tub, firepit, putting greens, outdoor bar featuring TV, gas grill & fridge. Separate guest suite that includes its own kitchen and bathroom. Tennis courts/basketball court/pickle ball court/baseball field and dog park just steps away directly across the street. House & guest suite completely renovated in 2021, including addition of backyard paradise. This is like your own private resort!

5 out of 5 average rating, 140 reviews

Southern Charmer w/Pool - Walk to Everything!

Stellar location...easily park and walk to historic sites! Spacious and modern inside but a classic Southern home on the outside. Lots of room to grill out or lounge around the heated saline pool. Beautiful views of the famed Mission from the upper/lower porches. And you'll appreciate how well stocked this home is too...if we don't provide it you probably don't need it! If you need another rental we have a 4 bedroom w/pool right next door. It's called Walk to Everything plus pool and Cottage.

4.96 out of 5 average rating, 187 reviews

A screened lanai features a private heated pool surrounded by paver stones. Comfortable seating options are provided, including two chairs and a wooden bench. Large windows allow natural light to fill the space, while a view of a spacious backyard is visible beyond the screen.

Home in Lincolnville

Walk downtown, pool beach min to everything pet ok

HEATED pool home in the heart of historic St Augustine, Walk to the NIGHT OF LIGHTS; just a few miles from spectacular beaches! Weddings/Family time. 4 large bedrooms with 3 full baths. 1 bedroom downstairs and 3 upstairs. Relax in the screened in lanai with beautiful lap pool! Large back yard. Enjoy cooking in our huge kitchen while your family relaxes in the living room, or have enjoy playing foosball after a day at the beach or touring our beautiful city! Walk to everything! Pet friendly

Guesthouse in St. Augustine

A pool area is showcased with a clear blue pool surrounded by a stone patio. Two lounge chairs are positioned on one side, complemented by a thatched umbrella. A covered seating area can be seen in the background, adding to the inviting ambiance of the outdoor space.

4.98 out of 5 average rating, 139 reviews

Historic St. Augustine 2/1 Cottage & Pool

About this space: Welcome to this poolside cottage located in Historic St. Augustine. This cottage is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This cottage has 2 bedrooms and 1 full bathroom, living room, kitchen and direct access to the pool. This space: This is a detached cottage located behind the main house Guest access: Keyless code entry Other things to note: Please keep in mind that the pool is a shared space :)

4.94 out of 5 average rating, 113 reviews

CLUB MED•Paradise • Privacy • PETS Ok•BIG PooL•

This beautiful home (2000sqft) is just a few blocks from the ocean which has easy beach access,including a play ground for children. Then a street over is the river which has boat ramp! You can also enjoy a local neighborhood restaurant just down the street with a water front view where the sunsets are mesmerizing! The home has been completely remodeled and has a gated back yard with a big pool for you and your family to enjoy. It is also a short drive to the historical down town St.Augustine.

The outdoor living area features a heated pool surrounded by a patio. Several white seating chairs are positioned beside the pool, with a dining table visible in the background. Lush greenery and wooden fencing create a private, serene setting.

4.96 out of 5 average rating, 104 reviews

New luxury heated pool home steps from the beach!

Welcome to the Coral Door House! Tranquil retreat at the beach. Newly built spacious and modern luxury home. A private entrance to a very special and secluded beach is just 6 houses down. An easy short walk with the stocked provided beach cart. Outdoor living space has a 10 X 20 heated pool and plenty of seating. A perfect place to relax after a day at the beach. We’d love to host you and your family so let us know when you want to come stay, and we can discuss more details from there!

Guesthouse in St. Augustine

A tranquil outdoor space features a well-maintained heated pool surrounded by lush greenery and colorful flowers. Seating areas with black Adirondack chairs are positioned around the pool, offering a peaceful setting. A covered patio stands in the background, complementing the inviting atmosphere.

4.93 out of 5 average rating, 141 reviews

Heated Pool Beach Bungalow Steps to the Ocean

Beautiful brand new in 2022 en-suite Bungalow beach side! Perfect for a romantic get a way or just one person, just 600 steps to the beach. Five minutes to the St Augustine pier and 10 minutes to the oldest city in the US, Historic Downtown St Augustine. Not only do you have the most comfortable bed to fall into, a 50" TV, recliners and an amazing heated pool. Beautiful beach sunrises, fishing, hiking, Concerts at the Amphitheater. For your safety you have an electronic keyless entry.

4.97 out of 5 average rating, 129 reviews

The backyard features a sparkling heated pool surrounded by a spacious sundeck. Lounge chairs are positioned around the pool, providing ample seating for relaxation. String lights overhead create a warm ambiance, enhancing the outdoor space.

Home in Lincolnville

Southern Comfort - Downtown|Hot Tub|Heated Pool

The Southern Comfort is a 4BR/3.5BA home located right in the heart of Downtown St. Augustine on the famous King Street. High-end, designer touches will be found in all features of the home with respect to the 110+ year old character preserved in the 2020 renovation. Centrally located with a blend of privacy, convenience and a modern luxury design. Private, sparkling heated pool and hot tub with lounges perfect for lazy days by the water. #1 Vacation Rental in Downtown St. Augustine.

Superhost

A sparkling pool is framed by palm trees, with lounge chairs arranged along the deck. Bright blue skies with scattered clouds reflect off the water's surface, creating a serene atmosphere. A shaded pergola is visible in the background.

Condo in St. Augustine

4.78 out of 5 average rating, 230 reviews

Great 1 bedroom 1 bath condo with heated pool

Great condo in an Oceanside community You cannot see the ocean from this condo 5-10 minute walk to the beach Private boardwalk to the beach Condo is in 3rd floor must climb stairs no elevator **** Tennis courts 2 pools 1 heated Shuffle Board Gym Restaurants and bars you can walk to Pet Friendly with a $100 pet fee Only 1 dog is allowed and we must register the dog before you check in The security will not let you on the premises if the dog has not been registered Pull out couch

Superhost

A clear swimming pool is surrounded by palm trees and lounge chairs. The bright blue water reflects the sun, while nearby buildings feature balconies that offer views of the pool area. The scene conveys a relaxing atmosphere in a coastal setting.

Condo in St. Augustine Beach

4.85 out of 5 average rating, 161 reviews

Ocean Side Complex with Heated pool B-24

Ocean Side Condo Complex. Just to be clear Ocean Side does not mean Ocean Front. You will not see the ocean from the balcony 1 Bedroom 1 Bath. There is a queen air mattress that 2 people can sleep on and can be put in the living room Must be 21 years old to rent IMPORTANT! This unit is DOG friendly. No other pets of any type are allowed. There is a $100 Pet Fee due when you book a reservation. I have to register them before you arrive No trailers or boats allowed or campers

A large pool is showcased, featuring a gradual entry with stone steps and a raised spa. Surrounding the pool, multiple lounge chairs are positioned, offering ample space for relaxation. Lush greenery provides privacy, complemented by a shaded umbrella nearby.

4.96 out of 5 average rating, 276 reviews

"The Pink House" Uptown St Augustine Charmer

Visit Historic St. Augustine & truly "Have It All!!" Walk to downtown sights, trolley, fort from your expansive secluded oasis. Our lovingly decorated and well stocked home features a wraparound porch. Spacious outdoors, shared amongst just 4 rental properties, with resort-quality pool+cabana, multiple seating areas, argentine grill, hammocks. Book our co-listings upstairs - "The Attic" or guest cottage "The Little Pink House" to add another bed + bath for your group!