Holiday rentals with a pool in St. Augustine Beach

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, 129 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.

A swimming pool is surrounded by lounge chairs, with palm trees providing shade in the background. Blue skies and scattered clouds create a bright atmosphere. The pool area features a smooth surface and a safety railing on one side.

4.84 out of 5 average rating, 267 reviews

Ocean Side Complex w/ Heated Pool B-15

Great Condo in a Beach Side Community But just to be clear Beach Side does not mean Ocean Front you will not be able to see the Ocean from the Patio The Condo is located next to Shopping Restaurants, and Historic Downtown, Great Beaches for a relaxing stay and 2 pools 1 heated Year Round 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

An expansive view of a serene beach is captured, featuring soft sand and gently lapping waves. Sparse vehicles are seen along the shoreline, with stretches of greenery and dunes adding texture to the landscape. The horizon showcases a clear blue sky, merging with the ocean.

4.91 out of 5 average rating, 229 reviews

St Augustine Beach, comfy condo

Relax on the beach or unwind at the pools. Close to shopping and restaurants. 15 min drive to historic downtown. Perfect for families, couples, friends, solo travelers. You're an 8 minute walk on property to beach with beach chairs, umbrella, and a beach mat. Fully equipped kitchen, free WiFi, 2 pools (one heated), fitness room, full size washer/dryer in unit, Smart TV, pet friendly 1 Dog Only, $50 cash reg fee plus a flat $15 Pet Fee for those bringing a dog **Strictly NON-SMOKING**

4.91 out of 5 average rating, 151 reviews

2 King Beds - Walk to Beach

Experience the ultimate getaway at our charming beach retreat, just a short stroll to the beach. Perfect for families, friends, or couples looking to relax and unwind, the perfect blend of comfort and convenience Enjoy a restful night's sleep in two luxurious king-size beds, designed for comfort and relaxation Stay connected with fast, reliable Wi-Fi throughout the property, ensuring you never miss a beat Enjoy the convenience of instant hot water, you never have to worry about running out

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.

4.95 out of 5 average rating, 114 reviews

Sun & Sea | 2 pools - 1 heated!

Indulge in the comfort and style of this spacious one-bedroom king bedroom couple's retreat. Situated on the ground floor, this end unit is conveniently located within walking distance of restaurants and shops. This oceanfront complex offers top notch amenities, including a beach walkover, two pools (one heated), tennis courts, shuffleboard, a well-equipped gym, and a grill area, all within a secure gated community. Enjoy coastal proximity, with downtown St. Augustine only 10 minutes away.

4.93 out of 5 average rating, 100 reviews

A welcoming living room features a comfortable couch and accent chairs with geometric patterns. A wooden coffee table sits in the center, surrounded by light-colored walls and wood flooring. Natural light enters from sliding glass doors that lead to a private balcony, enhancing the spacious feel.

Flat in St. Augustine

SEA & SALT|2-min walk Beach|2x Sparkling Pools

Welcome to the Sea & Salt Retreat of St. Augustine Beach! Fit 4 people in this spacious 2BR/2.5BA condo that is a 2-min walk to our beautiful white sand beach and a 1-min walk to the pool with cabana and chaise lounges. Effortlessly enjoy relaxation at the beach, lounge all day in the sun at the sparkling clean pool, or drive 12-mins to the Historic Downtown St. Augustine. Phenomenal amenities: Two sparkling clean pools, clubhouse, tennis courts, pickleball, racquetball, and basketball!!

Guest house 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.

4.95 out of 5 average rating, 190 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 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.

4.97 out of 5 average rating, 183 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.

The living area features comfortable seating, including a soft blue sofa and an armchair, arranged around a white coffee table. Light-colored décor and subtle greenery create a relaxed ambiance. The space is illuminated by a contemporary chandelier, with a view of the kitchen and dining area in the background.

4.95 out of 5 average rating, 166 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!

4.91 out of 5 average rating, 199 reviews

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.

Flat in St. Augustine

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.

Apartment in Treasure Beach

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.

5 out of 5 average rating, 115 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.

Guest suite in St. Augustine

A screened-in pool area features a crystal-clear water pool with a shallow entry. Two chairs, one green and one yellow, are positioned beside the pool, surrounded by natural greenery and a wooden fence. Sunlight brightens the space, creating a relaxing outdoor ambiance.

4.94 out of 5 average rating, 359 reviews

Ground floor--just 365 steps to beach!

Beautiful ground floor of a two-story house only 365 steps from one of the most beautiful beaches in the United States. Close to the Ancient City, with all its amenities and attractions. Within walking distance of great restaurants and bars. Private entrance, pool, fully furnished kitchenette with Keurig type coffeemaker, Internet, Cable TV. Two bedrooms, one with a queen bed, and the other a double Murphy bed. On-site parking for one car provided.

Popular amenities for St. Augustine Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 433 reviews

Your Home Away From Home

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.

4.99 out of 5 average rating, 212 reviews

Historic St. Augustine 2/2 Duplex & Pool

A private saltwater pool is surrounded by a spacious deck and lush greenery. Palm trees frame the area, offering a shielded retreat. A patio space is visible, providing comfortable seating options and direct access to the home.

4.94 out of 5 average rating, 143 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

The exterior of the coastal home is adorned with blue siding under a clear sky. Palm trees flank the driveway, adding a tropical touch. A spacious front yard features lush greenery and an inviting walk path leading to the entrance.

4.93 out of 5 average rating, 101 reviews

2 Masters-Heated Pool & Spa+1 min Walk to Beach

The home features a modern design set against a serene backdrop of trees and greenery. A spacious driveway leads to the entrance, framed by well-maintained lawns and landscaped shrubs. The exterior showcases large windows and a combination of muted colors, contributing to a harmonious appearance.

4.84 out of 5 average rating, 253 reviews

Spacious St. Augustine Home "The Gold Knocker"

An inviting outdoor area features a stone fire pit surrounded by white adirondack chairs. A vibrant sunset casts warm colors over the scene, while a solar heated pool glistens nearby. Lounge chairs, umbrellas, and tropical landscaping enhance the charming ambiance.

4.97 out of 5 average rating, 104 reviews

Island Retreat: Pool/Hot Tub/Tiki Bar/Close2Beach

A spacious backyard is highlighted by a private round pool, surrounded by lush greenery and palm trees. An outdoor cabana features a bar area, while a well-maintained lawn adds to the inviting atmosphere. The charming pink structure complements the serene setting.

5 out of 5 average rating, 114 reviews

Pink Palms *Heated Pool* Walk to Downtown

A modern white house is depicted with a covered entrance and a spacious patio area. A heated saltwater pool sits in the foreground, surrounded by a fenced yard. Two lounge chairs are positioned nearby, with a charcoal grill visible at the edge of the pool area.

4.97 out of 5 average rating, 101 reviews

Walk to Beach! Heated Pool•Boat Parking•EV Charger

Apartment rentals with a pool

A vibrant sunset casts warm hues across the sky, with wispy clouds highlighted by the fading light. A palm tree stands prominently in the foreground, while a wooden boardwalk leads toward the beach and the ocean, framed by patches of greenery.

5 out of 5 average rating, 139 reviews

BEAUTIFUL OCEAN VIEW 2 BEDROOM CONDO WITH POOL

A view overlooking the ocean reveals gentle waves and a clear blue sky. Green palm fronds are positioned in the foreground, while a red-roofed gazebo is visible on the beach, blending with the natural coastal landscape.

4.92 out of 5 average rating, 240 reviews

What a View! Sand & Sea!

Superhost

A spacious balcony offers a wide view of the beach and ocean, framed by an elegant arched opening. Green dunes and distant waves are visible, while a flock of birds gracefully moves across the sky, adding to the serene coastal atmosphere.

4.88 out of 5 average rating, 134 reviews

Oceanfront Retreat!

Apartment in Treasure Beach

A bright living area features soft pastel walls and wooden flooring. Cozy, floral-patterned seating is arranged around a light-colored coffee table. Large glass sliding doors lead to an outdoor space, while natural light enhances the room's warmth. A television is mounted on the wall.

4.94 out of 5 average rating, 117 reviews

++Perfect Romantic Getaway - Walk to the Sea

A private balcony features two light-colored chairs and a round table, providing views of the ocean and a nearby pool. The scenery includes lush greenery and a clear sky, while birds can be seen flying in the distance.

4.84 out of 5 average rating, 292 reviews

Direct Oceanfront ~ Fantastic Views!

5 out of 5 average rating, 104 reviews

2 BR Condo in St Augustine across from Beach

A view of the inviting swimming pool area is captured, featuring a large pool and a smaller hot tub surrounded by lounge chairs. The beach stretches out beyond, meeting the calm Atlantic Ocean under a clear blue sky, with palm trees framing the scene.

4.93 out of 5 average rating, 100 reviews

B207 Entire Oceanfront Condo Steps From Pool & Bch

A private balcony features two black chairs and a wicker table, overlooking sandy dunes leading to the ocean. The expansive view includes the calm blue water and a partly cloudy sky, creating a serene coastal atmosphere.

4.74 out of 5 average rating, 222 reviews

Long Time No Sea?-Oceanfront End Unit-Heated Pool!

Other holiday rentals with a pool

A spacious swimming pool is framed by palm trees and modern apartment buildings. Lounge chairs are arranged beside the water, inviting relaxation. The sky is painted with warm hues at sunset, creating a tranquil atmosphere around the serene pool area.

4.89 out of 5 average rating, 63 reviews

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

Townhouse in St. Augustine

A spacious master bedroom features a large bed with crisp linens and decorative pillows. A comfortable seating area includes a blue armchair with a striped accent cushion. Floor-to-ceiling sliding glass doors lead to a balcony, providing scenic views of the surrounding landscape.

4.98 out of 5 average rating, 43 reviews

Oceanfront Fully Updated Luxury Townhome w/ Pools!

5 out of 5 average rating, 11 reviews

Oceanfront, Pool, Tennis, BBQ, Patio, Free Parking

5 out of 5 average rating, 45 reviews

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.

Flat in St. Augustine

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

5 out of 5 average rating, 13 reviews

Coastal Chic Condo!

A stylish dining area features a modern table set with dark blue plates and gold accents. A contemporary chandelier hangs above, and a living space with a television is visible in the background, accompanied by natural light from sliding glass doors leading to a balcony.

4.88 out of 5 average rating, 41 reviews

Private Beach Access - NEW Reno, Pool & Jacuzzi

A private balcony features a table and two chairs, overlooking the beach and ocean. The expansive view showcases gentle waves and a clear blue sky, providing a serene setting for relaxation.

4.97 out of 5 average rating, 66 reviews

Oceanfront, Patio, Pool, Tennis, BBQ, Free Parking

A spacious living area is presented with soft blue walls and wooden flooring. Comfortable seating includes a blue couch and patterned chair. A dining table with white chairs is set in the foreground, illuminated by natural light from window treatments, enhancing the inviting ambiance.