Holiday rentals with a pool in St. Augustine Beach

Home in St. Augustine Beach

A serene pool area is surrounded by palm trees and lush greenery, featuring a clear, inviting pool. Two green lounge chairs are placed beside the water, while a sun umbrella provides shade. The house stands in the background, illuminated by the afternoon sun.

Steps to Beach | Heated Pool, Patio Bar | Fire Pit

Discover your perfect St. Augustine Beach getaway! Beachside living - just steps to the beach (2-minute walk) with no road crossings! Enjoy walking to nearby restaurants and shops or take a quick 11-minute drive to downtown St. Augustine! Inside, enjoy an open floor plan and a recently updated kitchen. Outside, enjoy the fire pit, outdoor bar, pool with a sun shelf that's perfect for kids and a soothing waterfall, creating a tropical paradise where you can unwind after a day of beach adventures!

4.94 out of 5 average rating, 115 reviews

4.99 out of 5 average rating, 163 reviews

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 Butler Beach

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 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

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

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

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, 114 reviews

4.9 out of 5 average rating, 180 reviews

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.

Home in Butler Beach

Beach & Serenity; The Perfect Location in St. Aug

Forget your worries in this spacious and serene space. Beautiful beach house 6 blocks to beach, 2 blocks to intercoastal Drive on to the beach at one end of the street, Easy walk to the best sunsets at the marsh Restaurants at each end of the street Upstairs and downstairs screened porches *PLEASE NOTE, AND THIS IS IMPORTNAT * We cannot split weekends. Friday and Saturday nights booked together *ONE PET PER STAY W/ APPROVAL *no washer/dryer available, hang dry only *STRICT CHECK IN/OUT TIMES

4.94 out of 5 average rating, 120 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 Butler Beach

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!!

A living area features a cooling ceiling fan and large windows with light-filtering curtains. A wall-mounted TV displays an aquatic scene. A light-colored coffee table sits on wooden flooring, complemented by decorative plants and a woven tray.

4.78 out of 5 average rating, 285 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

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.

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 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

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**

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!

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 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, 170 reviews

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

4.99 out of 5 average rating, 149 reviews

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

A spacious screened-in pool area features a large blue swimming pool surrounded by patio tiles. Comfortable seating arrangements with multiple chairs and a table are visible nearby, providing a relaxed space for leisure. Natural light streams in through the screened enclosure.

4.93 out of 5 average rating, 201 reviews

Heated Pool, Beach, Patio Lounge, Near Downtown

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.

4.99 out of 5 average rating, 162 reviews

Floridian Bungalow•2 Min Walk to Beach•Heated Pool

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

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

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

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.

5.0 out of 5 average rating, 203 reviews

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

Apartment rentals with a pool

4.86 out of 5 average rating, 117 reviews

Oceanfront Condo! Located at Pier Park!

4.9 out of 5 average rating, 164 reviews

Sunrise Special | Steps to Beach | Ocean Front

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!

4.92 out of 5 average rating, 174 reviews

2 King Beds - Walk to Beach

5.0 out of 5 average rating, 217 reviews

The Flirty Flamingo St Augustine Beach 3 BR Condo

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

Apartment in Crescent Beach

The living room features sliding glass doors that open to a private balcony overlooking the ocean. A comfortable blue armchair by the window is complemented by light blue curtains, while natural light fills the space, creating a serene ambiance.

Hideaway at Crescent Breach - St. Augustine

4.93 out of 5 average rating, 115 reviews

A sunlit indoor pool area features large glass doors that open to an outdoor pool surrounded by palm trees. Comfortable lounge chairs are positioned around the poolside, creating a relaxing space for guests. A hot tub is visible in the foreground, enhancing the inviting atmosphere.

5.0 out of 5 average rating, 296 reviews

Ocean Gallery 1/1, 2 pools

Other holiday rentals with a pool

Flat in St. Augustine Beach

Beachfront St. Augustine Getaway-Pool & Ocean View

4.92 out of 5 average rating, 212 reviews

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, 187 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

A dining area is presented with a wooden table set for six, complemented by upholstered chairs. Light fixtures hang elegantly above, and a cozy living space is visible beyond, featuring a gray sectional sofa and large windows allowing natural light.

5.0 out of 5 average rating, 35 reviews

St.Augustine Beach,Seaside at Anastasia,Condo

Flat in St. Augustine Beach

A wooden boardwalk stretches across sandy dunes, leading directly to the ocean. Gentle waves can be seen meeting the shoreline under a bright blue sky dotted with fluffy white clouds. Chairs and umbrellas are scattered along the beach in the distance.

2 BR ocean view gem: minutes to St Augustine

4.9 out of 5 average rating, 89 reviews

Superhost

4.67 out of 5 average rating, 3 reviews

Ocean Front St. Augustine Beach Unit | Pool View

5.0 out of 5 average rating, 64 reviews

St. Augustine Beach, Seaside at Anastasia, Condo

A bright, open dining area is seen featuring a round table surrounded by upholstered chairs. Natural light floods the space through large windows, showcasing ocean views. A stylish chandelier hangs above the table, and a modern kitchen countertop is visible in the foreground.