Vacation rentals with a pool in St. Augustine Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in St. Augustine Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

An expansive backyard features a refreshing saltwater pool and a hot tub, surrounded by lush turf landscaping. A two-story building with a wooden staircase overlooks the serene outdoor space, framed by palm trees and vibrant plants. Lounge chairs are positioned nearby for relaxation.

Home in St. Augustine

4.98 out of 5 average rating, 112 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

Experience the ultimate beachside getaway at our fully renovated Airbnb, just steps away from the sun-kissed sands. This luxurious retreat offers modern comfort with a private pool and inviting hot tub, allowing you to unwind in style. The recently upgraded interior boasts premium amenities, ensuring a relaxing stay. Outside, lush turf landscaping surrounds the pool, creating an oasis of comfort. Whether you're lounging by the pool, or enjoying the beach a stone's throw away, Driftmark delivers.

Top guest favorite

The outdoor area features a private saltwater pool with a custom spa, surrounded by lush tropical landscaping. A spacious cabana is included, with comfortable seating beneath flowing white drapes. A shaded umbrella is positioned beside the pool, enhancing the relaxation space.

Home in St. Augustine

4.99 out of 5 average rating, 114 reviews

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach

* Built in 2023- luxe coastal furnishings & linens * Featured in 2024 Good Housekeeping Mag🌟 * 2 King Suites (1 on each floor) | 2 Queen Bedrooms | 3.5 Baths * Private Saltwater Pool & Spa/Hot Tub * Poolside Cabana | Outdoor Kitchen | Front Porch * Bikes, Beach Toys, Beach Chairs * Lush Tropical Landscaping * 0.2 miles - gorgeous quiet beach * 5.5 miles- historic downtown St Augustine- The oldest city in the United States! * 0.2 miles - Cap's Restaurant for sunset dinner on the water

Top guest favorite

Home in St. Augustine

4.99 out of 5 average rating, 112 reviews

Floridian Bungalow•2 Min Walk to Beach•Heated Pool

Have fun with the whole family at this playful Floridian cottage full of artful amusements and creature comforts. Catch 33 features a private heated pool and is only steps from the sands of Vilano Beach. Here, you will enjoy solitary mornings collecting shells, a roomy shore for sunbathing, local seafood restaurants, a pier for fishing and a glowing sunset. In under 10 minutes, you can immerse yourself in 450 years of colonial history, a lively music scene and vibrant culinary experiences.

Top guest favorite

A balcony table is set for two, featuring white plates and cups, with expansive ocean views. Lush greenery and sandy beach can be seen in the distance under a clear blue sky, creating a serene and inviting outdoor space.

Condo in St. Augustine Beach

4.97 out of 5 average rating, 225 reviews

Ocean Front Gem: Top Floor Corner Unit

Top floor, direct ocean front, corner unit with elevator and beautiful unobstructed views of the beach from both bedrooms, living room, dining room, kitchen and private balcony. We have upgraded the condo and believe it to be the best condo in St Augustine Ocean and Racquet Resort. We also offer the condo immediately next door for rent, Ocean Front Escape: https://www.airbnb.com/h/saint-augustine-oceanfrontescape. Our checkin process is contact free. We use a Nest lock on the front door.

Guest favorite

A spacious backyard is shown, featuring a private heated saltwater pool surrounded by lush green grass. Tall trees and natural greenery create a secluded atmosphere. The patio adjacent to the house is visible, offering a serene view of the outdoors.

Home in St. Augustine

4.94 out of 5 average rating, 124 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

Welcome to your peaceful Oasis. This home is beautiful, secluded, and fenced in 3/4-acre with nature at your back door. It's going to WOW you! There is plenty of room for everyone to spread out with an open floor plan. Includes: Pool Table, Dart Board, Board games, Hammock, Saltwater heated pool, & peaceful pond with waterfall. Come relax and have fun. Just minutes to Historic Downtown, Beaches, Restaurants & I-95. 30 min from Jax 40 mins from Daytona $100 pet fee & $50 a pet up to 3.

Guest favorite

A spacious outdoor pool area is surrounded by well-maintained lounge chairs, with vibrant umbrellas providing shade. The condominium building features multiple levels and has a warm color scheme, highlighted by palm trees. Clear blue skies add to the inviting atmosphere.

Apartment in St. Augustine Beach

4.94 out of 5 average rating, 189 reviews

Modern & Comfy Beach Gem: Pool ~ Ocean Views ~ Pkg

Welcome to Turtle Trace St. Augustine, Anastasia Island - Oceanfront Steps to the Beach!! Right out the patio door is the spectacular pool and the amazing ocean! Updated unit is in beautifully maintained gated community. Come stay here and get that feeling of being at home, people come back year after year because they love it! You can see why so many people make this their home away from home. If you have any questions please email us and we will try our best to accommodate you!!

Top guest favorite

The image displays a sparkling swimming pool surrounded by palm trees and sun chairs. A set of tables and an umbrella are positioned near the poolside, while a multi-story building with balconies is visible in the background against a clear blue sky.

Condo in St. Augustine

5 out of 5 average rating, 118 reviews

Windjammer 208, Oceanfront and Riverview

Beautiful newly renovated condo in Crescent Beach, with spectacular views of the beach as well as the Matanzas river. Coffee while watching sunrise on your east balcony and wine while watching the sunset on the Windjammer fishing pier, while dolphins are entertaining you. 10 miles from historic St Augustine, a couple of miles from Marine land and a variety of restaurants close by. Flatscreen TV'S in all the rooms for your convenience when the weather does not allow you on the beach.

Top guest favorite

The outdoor area features a heated pool surrounded by comfortable lounge chairs and shaded umbrellas. A spacious patio includes additional seating and a tranquil atmosphere, enhanced by palm trees and bright blue skies.

Home in St. Augustine

4.99 out of 5 average rating, 152 reviews

4Bed, 3Bath-Heated Pool & SPA-Don't You Wanna?

Don't You Wanna...4 Bedroom, 3 Bath with HEATED POOL, SPA, and Outdoor Shower located in the heart of Vilano Beach of historic St. Augustine, FL. Our conveniently located home allows you to bring family and friends to share memories with a nice sunset or sunrise just down the street at the third street beach access point. Want to have a nice dinner at one of the most popular restaurants in all of St. Augustine? Walk around the corner to Cap's On The Water for great dining.

Guest favorite

A cozy living area features soft beige furnishings and decorative blue pillows. A wooden coffee table occupies the center, while a stone fireplace adds warmth. Large sliding doors provide natural light and reveal views of the outdoors, framed by sheer curtains.

Condo in St. Augustine Beach

4.96 out of 5 average rating, 112 reviews

Steps to Beach, Bikes & Beach Equipment Included!

Discover your perfect getaway at our beautifully updated condo in St. Augustine Beach, FL. With pristine oceanfront views and convenient beach access, our 2-bed, 2-bath retreat is a relaxing haven. Enjoy a fully equipped kitchen, comfortable living area, and private balconies. Exclusive community amenities include a private beach boardwalk, pool, and hot tub. Beach essentials, bicycles, and the proximity to shops, restaurants, and downtown make this the ideal beach retreat.

Top guest favorite

A spacious outdoor pool is surrounded by lounge chairs, providing ample seating for guests. The clear blue water invites relaxation, while palm trees and landscaped areas offer a tropical ambiance. Nearby buildings are visible in the background, enhancing the resort atmosphere.

Condo in St. Augustine Beach

4.95 out of 5 average rating, 145 reviews

Newly renovated! Steps to BEACH & POOL!

Our little slice of paradise is situated in the heart of St. Augustine Beach right on A1A Beach Blvd. Our unit, recently renovated, is just steps from the beach and closest building to the pool! 2 outdoor pools (1 heated in winter), 5 hot tubs & tennis courts. Perfect location to enjoy our beautiful beaches & all that Anastasia Island has to offer! Historic St. Augustine is less than 7 miles away. Unit is equipped with everything you need for a perfect beach vacation!

Top guest favorite

A tranquil backyard area is featured, showcasing a heated pool surrounded by lush greenery. Two black chairs are positioned on the stone patio, offering a comfortable spot for relaxation. The space is enclosed by vibrant tropical plants, enhancing the private atmosphere.

Home in St. Augustine

4.96 out of 5 average rating, 163 reviews

Dune Bungalow

Cottage style home with comfortable porches to enjoy sound of ocean waves breaking on the front and back porches. Pool in the back yard (heated by request for $50 per day) cookshed, fenced with lush trees and woods to the east. The inside looks large with high wood ceilings and multiple windows and glass doors to the beautiful pool area. Located on a dead end street in a family neighborhood with 5 star restaurants nearby. Fifteen minute drive to downtown St. Augustine.

Top guest favorite

A serene swimming pool is surrounded by a white fence and dotted with lounge chairs. Lush tropical foliage frames the area, adding to the tranquil setting. A sign warns to watch your step, and a glimpse of the beach is visible in the background.

Condo in St. Augustine

5 out of 5 average rating, 103 reviews

Boutique Beachside condo with easy access to beach

Skipper’s Hideaway is a charming beachside retreat that sleeps up to six, with a king bed, queen sofa pull-out, and twin daybed with trundle. Located on the ground floor for easy access, the condo offers a partial Atlantic Ocean view from the living room window. Just steps from Crescent Beach, this peaceful spot is perfect for relaxing. For more excitement, the shops, restaurants, and nightlife of downtown St. Augustine are only a 15-minute drive away.