Vacation rentals with a pool in St. Augustine

Guesthouse in St. Augustine

A pool area is showcased with a clear blue pool surrounded by a stone patio. Two lounge chairs are positioned on one side, complemented by a thatched umbrella. A covered seating area can be seen in the background, adding to the inviting ambiance of the outdoor space.

4.98 out of 5 average rating, 193 reviews

Historic St. Augustine 2/1 Cottage & Heated Pool

About this space: Welcome to this poolside cottage located in Historic St. Augustine. This cottage is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This cottage has 2 bedrooms and 1 full bathroom, living room, kitchen and direct access to the pool. This space: This is a detached cottage located behind the main house Guest access: Keyless code entry Other things to note: Please keep in mind that the pool is a shared space :)

A well-maintained pool is surrounded by lush greenery and potted plants. Two adults and a child are enjoying the water, while a dog swims nearby. A blue kayak floats on the surface, contributing to a relaxed, family-friendly atmosphere.

4.94 out of 5 average rating, 124 reviews

CLUB MED•Family Paradise Retreat-Bring the Dogs

This beautiful home (2000sqft) is just a few blocks from the ocean which has easy beach access,including a play ground for children. Then a street over is the river which has boat ramp! You can also enjoy a local neighborhood restaurant just down the street with a water front view where the sunsets are mesmerizing! The home has been completely remodeled and has a gated back yard with a big pool for you and your family to enjoy. It is also a short drive to the historical down town St.Augustine.

A serene outdoor space features a clear, in-ground heated pool surrounded by natural landscaping. Comfortable lounge chairs and a shaded dining area under an umbrella offer inviting spots for relaxation. A tree provides added greenery nearby, creating a tranquil, private environment.

4.86 out of 5 average rating, 116 reviews

Brand NEW Beach House with HEATED pool!

Brand NEW vacation rental in St. Augustine! Gorgeous open floor plan that was designed and built specifically as a vacation rental. This home features 3 bedrooms, 2 full baths, huge 16ft ceilings and an amazing in-ground, heated pool! Enjoy your morning coffee on the front porch with natural privacy from the beautiful oak trees or lounge by the pool and entertain on the patio. 3 blocks from the beach, a block away from the intercoastal and a quick 10 min drive to historic downtown St. Augustine!

A spacious living room features a light-colored sofa adorned with decorative pillows and a glass coffee table. Two elegant armchairs with floral patterns are placed beside the sofa, and natural light streams through large windows adorned with wooden shutters. A cozy area rug anchors the seating area.

4.94 out of 5 average rating, 216 reviews

Downtown Luxury • Gourmet Kitchen • STEPS 2 DTWN !

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

4.98 out of 5 average rating, 109 reviews

Htd Pool/Arcade, FirePit& PuttingGreen 1.2 mi DT

ISLE BE BACK 🌴— a brand NEW modern home! Dates fill quickly for spring & summer — save your stay now! Welcome to your ultimate St. Augustine getaway! Just 5 mins from downtown, this fun-filled retreat is perfect for families, friends, or anyone looking to relax and play. Swim in the pool, compete on the putting green, roast s'mores by the fire pit, or challenge your crew on the retro Pac-Man machine—all without leaving the house! ✔ Sleeps 8 comfortably ✔ Easy self check-in & free parking

Superhost

The Tiki Bar area features a long bar with high chairs surrounded by vibrant wall murals and greenery. Cozy seating is arranged with colorful cushions on a grass-like rug, creating a relaxed atmosphere for socializing and enjoying refreshments.

4.76 out of 5 average rating, 112 reviews

Heated Pool, Tiki Lounge, Steps to Beach, Games

Save my home by clicking the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* >Sparkling heated pool (pool heat - $60 day/$350 wk) >Steps from sand! (1 min walk) >NOW with a new Tiki Bar in garage! >Blocks to boat ramp, bring your boat + jet-ski! >Dogs OK! 2 dog max (w nightly fee) >Beach gear >Propane BBQ >DT St. Aug is a 10 min drive >Drip coffee pot >Washer + Dryer >2-3 parking spots >Cable in LR, other TV's are smart. >3 days of supplies (TP, trash bags, pods, etc.)

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, 145 reviews

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

Home in St. Augustine Beach

An aerial view captures the vibrant pink A-Frame home against a backdrop of serene ocean waves and a clear sky. The surrounding palm trees and nearby beach create an inviting coastal atmosphere. The beach is easily accessible, with well-defined paths leading to the sandy shoreline.

4.88 out of 5 average rating, 219 reviews

Ocean Front Private Getaway in St. Augustine Beach

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!

Guest suite in St. Augustine

A spacious bedroom is furnished with a king bed, complemented by decorative pillows and a throw blanket. A large area rug with colorful patterns covers the tiled floor. Natural light enters through two windows, framed by light curtains, while a bedside lamp adds soft illumination.

4.95 out of 5 average rating, 760 reviews

Sheepdog Hideway - on Anastasia Island near Amp!

Awesome, private guest suite located on Anastasia Island near the St Augustine Amphitheater! Walking distance to Anastasia State Park! Enjoy staying on the island without all the hustle of a hotel. We have beach cruiser bikes available for use! We are 1.5 miles from the closest public beach access and a 3 mile bike ride to downtown St Augustine! Update for COVID-19 pandemic: We will be spraying all hard surfaces with EPA-approved sanitizer to do our best to make sure surfaces are safe.

4.94 out of 5 average rating, 101 reviews

Beach Bums Paradise|Private Pool|8-min walk to BCH

Welcome to Beach Bums Paradise, where sun-kissed days and relaxation await you. Nestled in only an 8-min walk from the sandy shores, this idyllic property seamlessly blends the best of both worlds: an exquisite private pool, private hot tub, fire pit and the enchanting allure of the beach, just three short blocks away. If you dream of a vacation filled with sun-soaked days, gentle ocean waves, and blissful poolside lounging, then look no further! New private fully fenced backyard!

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.

4.99 out of 5 average rating, 178 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.

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.

4.96 out of 5 average rating, 179 reviews

Pool home oasis steps to ocean

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.

Popular amenities for St. Augustine 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, 437 reviews

Your Home Away From Home

4.96 out of 5 average rating, 49 reviews

Island Oasis - Between Downtown & the 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, 138 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

A spacious entryway leads into an open concept living area with natural light highlighting the wood flooring. The inviting space includes a modern kitchen visible in the background, a comfortable seating arrangement, and access to a staircase.

5 out of 5 average rating, 159 reviews

Southern Charmer w/Pool - Walk to Everything!

Superhost

The outdoor area features a large pool alongside a spa, surrounded by a paved deck. The two-story home showcases a spacious upper deck, illuminated by string lights, with ample seating and a television visible. Lush greenery completes the inviting outdoor space.

4.8 out of 5 average rating, 101 reviews

5BR Group Friendly Home w/ Pool & Fire Pit

An open concept living space is featured, showcasing a mix of comfortable seating options including a leather sofa and a spacious sectional sofa. Natural light floods the area, enhancing the wooden flooring. Decor includes stylish wall art and plants, adding a relaxed, beach-inspired vibe.

4.94 out of 5 average rating, 109 reviews

Heated pool home with interactive gaming system

5 out of 5 average rating, 50 reviews

Private Heated Pool • Walk to Amp • Game Room

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, 176 reviews

Heated Pool, Beach, Patio Lounge, Near Downtown

Condo 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, 142 reviews

BEAUTIFUL OCEAN VIEW 2 BEDROOM CONDO WITH POOL

Condo in St. Augustine Beach

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, 269 reviews

Ocean Side Complex w/ Heated Pool B-15

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!!

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, 238 reviews

St Augustine Beach, comfy condo

4.94 out of 5 average rating, 153 reviews

A sandy beach extends towards the horizon, meeting rolling waves under a clear blue sky. Dune grass sways gently in the foreground, with a wooden boardwalk leading to the shore. Beach chairs and umbrellas are visible in the distance, indicating a welcoming recreational area.

Condo in Crescent Beach

Pelican Inlet 2 Bedroom Condo Steps from the Beach

Condo in St. Augustine Beach

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, 175 reviews

Newly renovated! Steps to BEACH & POOL!

4.9 out of 5 average rating, 157 reviews

A spacious living area is furnished with a large blue sectional sofa and a wooden coffee table. A ceiling fan circulates air. Natural light enters through a balcony door, offering a view of the beach and surrounding coastal decor.

Condo in Vilano Beach

Ocean Views! 4 decks Beachside of A1A. Pool!

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.

4.97 out of 5 average rating, 132 reviews

Family Beach Condo - Steps To The Sand Or Pool

Other vacation rentals with a pool

4.86 out of 5 average rating, 37 reviews

Sunshine Dip | Sleeps 8, Relaxing, Pool, WIFI

The exterior view of the house features a light blue three-level structure with multiple windows. A fenced backyard is displayed, showcasing a pool surrounded by lounge chairs and a paved patio area. Lush green grass enhances the outdoor space.

4.97 out of 5 average rating, 29 reviews

OceanView Home! Optional PoolHeater and Elevator!

Superhost

Condo in Crescent Beach

4.75 out of 5 average rating, 8 reviews

Beacher's Lodge Balcony Suite #312

5 out of 5 average rating, 15 reviews

Condo in Crescent Beach

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

A screened-in patio features a sectional seating arrangement with dark cushions. A decorative pillow with the text 'stay awhile' is placed on one of the seats. Natural light filters through the surrounding trees, creating a relaxed ambiance for outdoor enjoyment.

4.94 out of 5 average rating, 94 reviews

Hot tub, pool, beach! A Million Memories

5 out of 5 average rating, 18 reviews

St. Augustine Dream Beach Condo!

Apartment in Vilano Beach

A spacious living area is highlighted by a light-toned sectional couch with soft pillows. Modern decor includes a wall-mounted TV displaying a beach scene. Nearby, a small table and chairs invite relaxation with views of the exterior landscape through large glass doors.

5 out of 5 average rating, 27 reviews

Modern Coastal Retreat