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.

4.99 out of 5 average rating, 163 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.

5.0 out of 5 average rating, 108 reviews

St.Augustine Beach,Seaside at Anastasia,Condo

Seaside at Anastasia is directly across the street from the ocean, St. Johns pier, weekly farmers market, walk to great restaurants. Just minutes away from historical downtown Saint Augustine. Enjoy our heated pool and exercise room. This condo is a 3 bedroom, 2 bath, laundry room, full upgraded kitchen and patio with access to pool. No stairs to worry about. 1st floor Condo with parking directly in front of the unit. Handicapped parking and access to the unit is also in front of this condo.

A vibrant swimming pool reflects the evening sky, surrounded by well-maintained landscaping. Poolside seating includes colorful lounge chairs and a dining set, while a floating flamingo adds a playful touch. Soft lighting from string lights enhances the serene atmosphere as dusk approaches.

4.99 out of 5 average rating, 141 reviews

HGTV-Style Home + Pool + Walk/Bike to Attractions

Off Street Parking 3 Min Drive/ 15 Min Walk to Historic Downtown 2 Min Drive to the St Augustine Amphitheater 2 Min Drive to Anastasia State Park Beach 1 Min Drive to Anastasia Fitness Club/Suana-Steam Rm/Pool Looking to get away from the hustle & bustle of the city? This designer home with an amazing pool is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a minutes away. With spacious living & modern amenities, the Home offers maximum comfort

Home in St. Augustine Beach

The exterior of the house features a two-story structure with a spacious upper deck, which is shaded by two large blue umbrellas. Brightly colored plants line the base of the home, complementing the fresh coastal aesthetic.

Beachside, Pool, Super Clean, steps 2 beach, 5star

"Our stay was perfect! The home was spotless and well appointed with everything we needed. Dominick was a great host" * Less than 500 steps to St Augustine Beach! ⛱️ * Super comfortable and meticulously clean. ✨️ * 75 steps to beautiful community pool 🏊‍♂️ * towels + beach chairs + beach cart ⛱️ * 100% cotton sheets and towels ☁️ * comfy beds and pillows, extra pillows + blankets, living room + den * Upper and lower decks. * Fully stocked kitchen * On the Golden Mile

4.98 out of 5 average rating, 113 reviews

4.99 out of 5 average rating, 170 reviews

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 Vilano Beach

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

🌴 Featured in Good Housekeeping & Designed by HGTV-featured Builders ✨ 🏡 New 2023 Luxury Coastal Home 🛏️ 2 King Suites + 2 Queen Bedrooms 🛁 3.5 Bathrooms 💦 Private Saltwater Pool + Heated Spa/Hot Tub 🍹 Poolside Cabana & Outdoor Kitchen 🚲 Bikes, Beach chairs, Cooler & Toys included 🌿 Tropical Backyard Oasis w/ Mature Palms, Lounge Chairs, Outdoor Shower & Turf 👣 Walk 0.2 miles to the beach 🌅 Stroll 0.2 miles to Cap’s for Waterfront Sunset Dinner 🏰 10 min to Historic St. Augustine

An enclosed lanai features a heated saltwater pool surrounded by a sleek concrete deck. Colorful lounge chairs are positioned nearby, and greenery is visible outside the mesh screens. The walls exhibit a calming light hue, contributing to a serene poolside atmosphere.

4.97 out of 5 average rating, 140 reviews

The Salty Seashell, Coastal Pool Home, Sleeps 8

Relaxing heated pool home in a quiet and safe neighborhood. Our home is clean and spacious located a few steps from the Intracoastal Waterway equipped with a boat launch. We are 10-mins from Old Town or the beach and less than 5 mins from restaurants, grocery stores, and shopping. Experience our lovely saltwater pool enclosed in a lanai. Our home has 3 bedrooms and two bathrooms, full kitchen, and a open family room. Each bedroom has brand new beds. Fast WIFI. Boat/Trailer/RV Friendly :-)

Home in St. Augustine Beach

St. Aug Oceanfront Home w/ Heated Pool & Firepit

Just steps from the ocean and a 10-minute drive to historic downtown St. Augustine, this one-of-a-kind 1970s pink three-story A-frame is the perfect backdrop for your next vacation, bachelorette party, or relaxing getaway. Inside, you’ll find a bright, cheerful space—ideal for popping mimosas in the morning or unwinding after a sun-soaked day with private beach access. Whether you're staying for the weekend or the season, you're sure to make lasting memories. I can’t wait to host you!

4.87 out of 5 average rating, 246 reviews

A light-filled living area showcases a comfortable seating arrangement, featuring two red armchairs facing a coffee table. Large sliding glass doors provide a view of the ocean and lead to a private balcony. A flat-screen TV is mounted on the wall, enhancing the relaxed decor.

4.89 out of 5 average rating, 217 reviews

Peerless on the Pier

Newly renovated ocean front condo 2 bed/2.5 bath townhouse (2 story) Enjoy the views from the balcony offering a great place to enjoy your coffee in the morning, and watch the sunrise and the sound of the waves. The condo is walking distance to local restaurants and the St.Augustine beach pier. This is the closest condo on St. Augustine Beach to the downtown historic district. NO SMOKING 🚭 NO PETS. The unit is located on the second floor of the building. There is no elevator.

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.

4.92 out of 5 average rating, 154 reviews

Quiet, Updated Condo - Pool, Bikes & Pickleball!

Relax at our beautifully updated 2BR/2.5BA condo in a quiet, family-friendly St. Augustine Beach community! Newly renovated guest (not yet pictured) and powder bathrooms completed for summer 2026. Enjoy easy beach access via a private boardwalk, pool, hot tub, tennis & pickleball courts, beach gear, bicycles, private balconies, and a fully stocked kitchen. Conveniently located near restaurants, shops, and historic downtown St. Augustine—perfect for your next coastal getaway!

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.

4.96 out of 5 average rating, 202 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!

A bright living area features large floor-to-ceiling windows that provide sweeping ocean views. Comfortable seating is arranged around a central coffee table adorned with decorative items. A Smart TV is positioned for easy viewing, while a ceiling fan adds a cooling breeze.

4.98 out of 5 average rating, 162 reviews

Family Beach Condo - Steps To The Sand Or Pool

Our beach condo on Crescent Beach has been our family’s haven for years, and we’re excited to share it with you! The breathtaking ocean views from our living room and balcony are just the start—enjoy a renovated kitchen, comfy bedrooms, and family-friendly touches that make this place truly special. Whether you’re here to relax, explore historic St. Augustine, or enjoy the natural beauty of Anastasia State Park, we hope you’ll create lasting memories like we have!

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.

4.98 out of 5 average rating, 262 reviews

Ocean Front Gem: Top Floor Corner Unit

Top floor, direct oceanfront, 2 bedroom, 2 bathroom corner end unit condo with elevator and unobstructed beach views from both bedrooms, living room, dining room, kitchen and private balcony in beautiful St Augustine Ocean and Racquet Resort. We also offer for rent the condo immediately next door, Ocean Front Escape: https://www.airbnb.com/h/saint-augustine-oceanfrontescape. Our checkin process is contact free. We use a smart lock on the front door.

Popular amenities for St. Augustine Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 162 reviews

A private heated pool is surrounded by a spacious patio featuring paver stones and tropical landscaping. A wooden pergola provides shade, complemented by lounge chairs and vibrant orange seating. The cottage's white exterior is visible in the background, framed by swaying palm trees under a clear blue sky.

Home in Vilano Beach

Floridian Bungalow•2 Min Walk to Beach•Heated Pool

4.99 out of 5 average rating, 148 reviews

HtdPool w/Arcade, Fire, GolfCart Access, 1.2 mi DT

4.97 out of 5 average rating, 118 reviews

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.

Home in Crescent Beach

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

5.0 out of 5 average rating, 201 reviews

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 Vilano Beach

Don’t You Wanna? Heated Pool & SPA 4Bed & 3Bath

The two-story beach house is framed by a lush green lawn and palm trees, featuring a spacious front porch with white chairs. Large windows and a gabled roof enhance the inviting appearance. A clear blue sky serves as the backdrop.

4.9 out of 5 average rating, 180 reviews

Beach & Serenity; The Perfect Location in St. Aug

A modern home is surrounded by a well-kept backyard featuring a private pool and spacious patio. Comfortably arranged lounge chairs provide a relaxing spot. The exterior showcases light-colored siding and elevated balconies, with palm trees dotting the landscape for a tropical feel.

4.89 out of 5 average rating, 116 reviews

Sunset Cove 2 - Pool - Sea Views - Walkable

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.

4.9 out of 5 average rating, 204 reviews

Beautiful Beach Home - Sleeps 12

A secluded poolside area is showcased, featuring a structured cabana adorned with soft seating. Nearby, comfortable lounge chairs are positioned around a tranquil swimming pool, surrounded by a clean, landscaped space with tropical plants and a shaded umbrella, inviting relaxation.

4.81 out of 5 average rating, 111 reviews

Beautiful Ocean View Pool Home ~ Heated Pool

Apartment rentals with a pool

4.89 out of 5 average rating, 213 reviews

Beachy Condo| Steps to Beach | Pools | Hot Tubs

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.

4.95 out of 5 average rating, 199 reviews

Beautiful ocean, St Augustine beach

A vibrant view shows lush green lawns and palm trees leading to the outdoor pool area, with the ocean visible in the background. Two white buildings frame the scene under a clear blue sky, emphasizing the serene coastal atmosphere.

4.87 out of 5 average rating, 130 reviews

Heated Pool, Ocean Views, Beach, Playground, BBQ

A private balcony is presented, offering panoramic ocean views. The space includes a textured table and four chairs, with one set featuring floral upholstery. Green grass and sandy shorelines blend into the sea under a clear blue sky, enhancing the sense of tranquility.

4.98 out of 5 average rating, 112 reviews

Wade n Sea Ocean Front Condo

5.0 out of 5 average rating, 217 reviews

The Flirty Flamingo St Augustine Beach 3 BR Condo

Apartment in Crescent Beach

2br condo in st Augustine across from Beach

5.0 out of 5 average rating, 120 reviews

Apartment in 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.

Summerhouse - Direct Oceanfront Corner Unit

4.95 out of 5 average rating, 173 reviews

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.

4.85 out of 5 average rating, 290 reviews

Ocean Side Complex w/ Heated Pool B-15

Other holiday rentals with a pool

4.83 out of 5 average rating, 111 reviews

Flat in Butler Beach

*Newly Remodeled 3/2 Oceanfront ~ 3 King Beds!*

Townhouse in St. Augustine Beach

The living area features a combination of a leather sectional and a futon, providing comfortable seating. A flat-screen TV is positioned within the space, and a ceiling fan is mounted above. Large sliding glass doors open to a balcony, allowing natural light and views.

Beach Front Condo in Saint Augustine Beach

4.91 out of 5 average rating, 186 reviews

Flat in St. Augustine Beach

The image features a wide sandy beach with gentle waves lapping at the shore. The shoreline extends along the coast, showcasing a mixture of sand and beach vegetation. A clear blue sky complements the tranquil scenery, providing a serene backdrop for relaxation.

Island Blue|3min walk to Beach|Pool|Hot Tub

5.0 out of 5 average rating, 61 reviews

A serene beach landscape is depicted at sunrise, with gentle waves rolling onto the shore. A solitary figure can be seen walking along the water's edge, as the sky is filled with soft orange and golden hues. The scene captures the peaceful ambiance of the beachfront.

4.92 out of 5 average rating, 88 reviews

Ocean Front Ground Floor End Unit, Steps To Beach

4.87 out of 5 average rating, 60 reviews

Beach Walk · Pool · Pickleball · Arcade · Golf

Flat in St. Augustine Beach

Beach Condo Private Beach Access 2 Pools Tennis

4.97 out of 5 average rating, 30 reviews

Flat in St. Augustine Beach

A private balcony features two chairs and a tall table, offering a stunning view of the ocean and sandy beach. Lush greenery frames the scene, while the horizon showcases an expansive blue sky and gentle waves in the distance.

luxurious oceanfront condo amazing views! King bed

4.96 out of 5 average rating, 90 reviews