Vacation rentals with a pool in St. Augustine Shores

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.

4.98 out of 5 average rating, 120 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.

Guest suite in Treasure Beach

A serene waterfront view is captured at sunset, showcasing a pool surrounded by lush grass and palm trees. A shaded seating area is positioned next to the pool, overlooking the water where boats can be seen in the distance.

4.92 out of 5 average rating, 624 reviews

Waterfront suite, Dogs are cool no pet fee

Newly remodeled, waterfront suite. See dolphins, Osprey, and more frolicking in our amazing backyard overlooking the Matanzas river, & did I mention the breathtaking sunsets. 6 minute drive to Crescent Beach, one of the most beautiful beaches in Florida. Close to downtown historic St Augustine 20 min, Amphitheater concert venue is 15 min. Private entrance, full on suite bath, fishing dock, kitchenette, pool, ample free parking & internet included. Professional pool cleaning is on Mondays.

The exterior of a single-story house is displayed, featuring a sloped roof and an inviting entryway. Green grass surrounds the home, complemented by mature trees and landscaped bushes. A concrete driveway leads up to the entrance, providing accessible access.

4.99 out of 5 average rating, 425 reviews

Your Home Away From Home

1,800 SF, 2 bedrooms, 2 1/2 bathrooms, on a secluded 5 acre lot just minutes from Historic Downtown and St. Augustine Beach. The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms (1 with TWINKLE mattress) ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small upcharge for 5 or more. Motorcycle friendly! We also do live on the property!

An open living area features a light-toned laminate floor and a spacious dark sofa facing a wall-mounted TV. A white coffee table sits in front of the sofa, while two wooden stools are positioned nearby. The kitchen is visible in the background, with natural light coming through the window.

4.86 out of 5 average rating, 273 reviews

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool

1 Bedroom interior Condo in Oceanfront Complex (no view of the ocean) King Bed, Queen Sleeper Sofa, TV's in Living Room and Bedroom, 1st Floor unit with screened patio, Fully Equipped Kitchen, Dishwasher, Washer/Dryer, WiFi, Cable TV, Clubhouse, Fitness Room, Tennis Courts, 2 Swimming Pools (1 heated) Shuffleboard Courts, Picnic Area & Private Beach Walkway. Dog Friendly (1 DOG ONLY) with a $100 pet fee due on Check In. Restricted Breeds: Rottweiler, Pit bull, Doberman, Chow, German Shepherd.

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.

4.94 out of 5 average rating, 180 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.

A large swimming pool is surrounded by lounge chairs under a clear blue sky, with palm trees swaying gently nearby. The pool's serene water reflects the adjacent condominium buildings, creating a tranquil atmosphere for guests.

4.91 out of 5 average rating, 230 reviews

The Salty Suite Resort style condo

This modern 1 bed/1 bath rental unit has access to a private walk way to 2 pools, beach (5 min walk from door to sand) & tennis courts all in a gated community right on famous A1A in the Oldest City in the Nation. Perfectly situated by the beach or a quick Uber ride to Downtown to check out the history of the Oldest City in the Nation & try some other great local restaurants. We provide an in room guidebook telling you all the must do's in the town & helpful hints too! See you soon!

A screened-in balcony offers views of the lush greenery and marshlands beyond. Colorful cushions adorn a comfortable seating area, while a small wooden table sits centrally. Natural light fills the space, creating a peaceful atmosphere for relaxation.

4.99 out of 5 average rating, 116 reviews

Riverfront direct views-Get it ALL in St Augustine

Do not compromise-Just get it all! This is the hidden gem you were waiting to find. Only a few minutes from historic downtown and the area's best beaches, The Conquistador offers 3 swimming pools, tennis, tennis/pickleball courts, trails, a fishing pier, playgrounds, BBQ area, pavilion and plenty of space to roam and relax under the amazing Oak canopy. The beach or Downtown a mere 12 minute drive. Stay in your very private condo and enjoy the gorgeous views of the Manatee River.

A light and airy living area features a comfortable gray sofa, a wooden coffee table, and a blue accent chair. A large flat-screen television is mounted on the wall opposite, while sliding glass doors provide access to a balcony area with outdoor seating.

4.98 out of 5 average rating, 173 reviews

Beach Condo, Pools, Bikes, Short Walk to Beach

Relax and unwind at our beautiful beach getaway. This one bedroom condo is located close to all St. Augustine has to offer. You can walk to the beach or take a quick drive to historic downtown. Ocean Village Club is a gated complex that has private beach access just a seven minute walk from your door, two swimming pools, tennis courts, grilling area, and free parking. This second floor unit is light and airy, immaculate, and beautifully decorated. We are family owned and operated.

A bright and airy living area is depicted, featuring a round dining table surrounded by four white chairs. A sectional sofa with light grey upholstery is positioned nearby, complemented by decorative pillows. A well-equipped kitchen area is visible, with modern appliances and cabinetry, providing a functional space.

4.93 out of 5 average rating, 181 reviews

Beach Life in Oceanview Condo

The balcony faces one of Florida's most beautiful beaches - Crescent Beach. Just 3 minutes walk from the beach, enjoy incredible sunrises and sunsets every day, heated pool, outdoor barbecue, free parking available. 15 minutes from downtown St. Augustine, surrounded by all the amenities, start your holiday on this beautiful, ancient beach. We offer short term and long term rentals hoping to provide you and your family with a relaxing, comfortable and quiet holiday resort.

A comfortable living area is showcased with a light-colored sofa and armchair. Natural light flows in through sliding glass doors. A flat-screen TV is mounted on the wall, and a coffee table rests on a wooden floor, surrounded by decorative items.

4.94 out of 5 average rating, 132 reviews

Bel oc'ean, St Augustine beach

Close to shopping and restaurants. 15 min drive to historic downtown. Perfect for families, couples, friends, or solo travelers. Enjoy having no stairs to climb! Family friendly vacation. New king bed. Fully equipped kitchen, free WiFi, 2 pools (one heated), full size washer/dryer in unit, Smart TV, pet friendly 1 Dog Only, requires $50 (cash) registration fee upon check in. There is also a flat $15 Pet Fee for guests bringing a dog. **Strictly NON-SMOKING unit**

5 out of 5 average rating, 112 reviews

Lush greenery frames a wooden pathway leading to a sandy beach, with palm trees and residential buildings visible in the background. The sky is illuminated by soft hues of sunset, creating a serene backdrop for the coastal environment.

Condo in Treasure Beach

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.

A serene pool area is framed by modern apartment buildings, with palm trees lining the perimeter. Stylish lounge chairs are placed around the water, and vibrant sunset colors fill the sky, creating a calming ambiance.

4.97 out of 5 average rating, 102 reviews

>•< Resort Style Retreat >•<

Welcome to our cozy and stylish 1-bedroom, 1-bathroom apartment situated in the serene and picturesque coastal town of Saint Augustine Beach. This thoughtfully designed space offers a blend of comfort and relaxation—ideal for individuals or couples looking for a peaceful getaway. Nestled by the intercoastal waterway, the apartment boasts one of the most stunning views from the balcony where you can unwind and soak in the beauty of your surroundings.

Popular amenities for St. Augustine Shores rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 51 reviews

A comfortable living area features a sectional sofa and an accent chair, arranged around a coffee table. A flat-screen TV is mounted on the wall. Large windows allow natural light to illuminate the space, revealing views of greenery outside.

Home in Treasure Beach

Serenity by the Sea - Steps to the Ocean Condo

The modern exterior of the Palma Beach House is highlighted by a spacious driveway leading to a stylish garage with large glass doors. Lush landscaping, including palm trees and vibrant plants, complements the clean lines of the home under a dusky sky.

5 out of 5 average rating, 56 reviews

Palma Beach House

The exterior of the home features a two-story structure with a welcoming porch. Potted plants hang from the posts, and a decorative sign is positioned near the entrance. Lush greenery and various plants are arranged along the pathway leading to the front steps.

4.98 out of 5 average rating, 197 reviews

Historic St. Augustine 2/2 Duplex & Pool

A private pool is featured on a covered porch, showcasing clear blue water. Wooden deck surrounds the pool, with railings providing safety. Lush greenery and nearby homes are visible in the background, enhancing the outdoor space.

4.89 out of 5 average rating, 177 reviews

Beautiful Beach Home - Sleeps 12

An inviting pool area features lounge chairs and a vibrant mural, while an outdoor dining space with a large table is prepared for gatherings. Inside, a serene bedroom showcases soft colors and modern furnishings. A playful bunk room is also designed for fun and relaxation.

5 out of 5 average rating, 114 reviews

Walk 2 Beach | Game Room | Firepit |Heat/Salt Pool

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.

4.99 out of 5 average rating, 128 reviews

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

An outdoor cabana area is presented, featuring a pool table and bar seating alongside a private heated pool. Surrounding lush turf and palm trees create a serene environment. The space is illuminated by recessed lighting, enhancing the inviting vibe for relaxing and entertaining.

5 out of 5 average rating, 105 reviews

Welcome to Pink Palms - Heated Pool - Walk to DT

4.96 out of 5 average rating, 171 reviews

Pool home oasis steps to ocean

Condo rentals with a pool

The spacious living room features large windows offering panoramic views of the ocean. An extra-large sectional couch provides ample seating, complemented by a central coffee table. A flat-screen TV is mounted on the wall, while a dining area is visible through the glass doors leading to the balcony.

4.95 out of 5 average rating, 101 reviews

Bella Coastal View with Ocean Views sleeps 6

A bright, enclosed balcony is depicted with a comfortable chair, a small table, and a decorative area rug. Large glass windows showcase expansive ocean views, while light wood paneling complements the aqua-tiled feature wall. Ocean breezes are welcomed through the open layout.

4.93 out of 5 average rating, 105 reviews

Newly Remodeled Ocean View Condo-Upgrades Galore!!

Superhost

An unobstructed view of the ocean is captured, showcasing gentle waves rolling onto the sandy shore. A lush, grassy dune line is visible in the foreground, contrasting with the deep blue water under a clear sky.

4.79 out of 5 average rating, 264 reviews

Black Friday! $79/night Nov. & Dec-Oceanfront Pool

Superhost

A sandy beach stretches into the distance, meeting calm ocean waters under a clear blue sky. Gentle waves can be seen lapping at the shore. A wooden boardwalk winds through the grassy area, leading down to the beach, where a few umbrellas and people can be spotted.

4.85 out of 5 average rating, 344 reviews

Oceanfront 1st Floor-Crescent Beach

A spacious balcony overlooks a sandy beach and the ocean, where gentle waves meet the shore. Palm trees are visible in the foreground, providing a tropical backdrop. Beachgoers can be seen enjoying the sun and surf under clear blue skies.

4.94 out of 5 average rating, 137 reviews

Summerhouse - Direct Oceanfront Corner Unit

A view from the balcony showcases a wooden walkway leading to the ocean, bordered by lush greenery. The expansive sea is visible, with gentle waves and a clear sky dotted with clouds. Two cups are placed on a table in the foreground, inviting relaxation.

4.92 out of 5 average rating, 106 reviews

Seagrass Condo - ocean front, 1 bedroom/1bath

A sunset scene is depicted with two people walking along the beach, silhouetted against the vibrant orange and yellow hues of the sky. The sun is setting on the horizon, reflecting shimmering light on the water, while a figure is seen swimming in the background.

4.95 out of 5 average rating, 124 reviews

St Augustine Beach 2 Bed Condo

A well-appointed bedroom features a spacious bed adorned with a variety of decorative pillows. Soft light illuminates the room, highlighting a coastal-themed artwork of an umbrella in the background. A bedside lamp can be seen, adding a cozy touch to the ambiance.

4.94 out of 5 average rating, 106 reviews

Sun & Sea | 2 pools - 1 heated!

Other vacation rentals with a pool

Townhouse in St. Augustine

A view from the patio features a wooden boardwalk leading to the beach, surrounded by lush greenery and palm trees. The sky is bright with scattered clouds, reflecting a sunny beach scene. The well-kept grass area invites outdoor leisure.

4.97 out of 5 average rating, 35 reviews

Nights of Lights Deals- Oceanfront Luxury Home!

The exterior image captures a multi-story building surrounded by lush palms and vibrant landscaping. A serene pool is centrally located, featuring lounge chairs arranged around its perimeter, with gentle sunset hues illuminating the scene.

4.95 out of 5 average rating, 21 reviews

River Front | Condo with Amenities

A serene pool area is surrounded by modern apartment buildings, with vibrant palm trees complementing the inviting atmosphere. Lounge chairs are positioned for relaxation beside the water, and a colorful sunset paints the sky in soft hues, creating a tranquil ambiance.

5 out of 5 average rating, 29 reviews

Resort Style 1B/1B APT, 10 min Beach/Downtown

4.98 out of 5 average rating, 189 reviews

A spacious deck overlooks a clear blue saltwater pool surrounded by lounge chairs and umbrellas. Lush greenery and palm trees frame the view of the water and dock area in the distance, creating a serene outdoor space for relaxation.

Cottage in St. Augustine

Fun Waterfront Retreat, Heated Pool, Rooftop Deck

A contemporary resort-style swimming pool is surrounded by lounge chairs and umbrellas. The building in the background features a modern design with multiple levels, and palm trees are placed throughout the area. The sky displays vibrant hues as the sun sets.

4.98 out of 5 average rating, 43 reviews

St Augustine Luxury Resort Living on the Island!

5 out of 5 average rating, 93 reviews

2 BR Condo in St Augustine across from Beach

A calming sleeping area features three decorative wall panels with palm leaf designs. A spacious bed is adorned with soft pillows and a cozy blanket. A blue accent chair and a natural fiber rug complete the inviting atmosphere, with subtle lighting enhancing the overall comfort.

4.96 out of 5 average rating, 52 reviews

Beach condo, sleeps 6, heated pool, surf board

The spacious pool area features lounge chairs lining the water's edge, with palm trees providing shade. A water feature gently flows into the pool, and the surrounding apartment complex is visible in the background, basking in warm sunset light.