Vacation rentals with a pool in St. Augustine

4.99 out of 5 average rating, 146 reviews

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

ISLE BE BACK 🌴— brand NEW modern home! **Golf Cart Access for an additional fee Please inquire if interested!** 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 ✔Self check-in & free parking

4.99 out of 5 average rating, 162 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.

5.0 out of 5 average rating, 156 reviews

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

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, 168 reviews

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

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, 114 reviews

Sunset Cove 2 - Pool - Sea Views - Walkable

Stunning new luxury 2br/2.5ba pool home with peeks of Salt Run and Anastasia State Park: * Pool Heat Available for $30 per day - Contact us after booking for details * Private pool + backyard * Parking for 3 cars * 2 king bedrooms w/ en-suite bathrooms & smart TVs w/ Netflix * 2 min drive (or 20 minute walk) to historic downtown St. Augustine * 2 min drive to the beach (Anastasia State Park) * 5 min walk to lighthouse, Alligator farm, restaurants & bars * Fully stocked and equipped kitchen

4.94 out of 5 average rating, 233 reviews

Downtown • Parking for 2 + Wraparound Porch

Historic Whitney House • Newly renovated 1,700 sq ft designer home Private driveway parking for 2 • Steps to trolley & St. George Street Gourmet kitchen, 2 en-suite bedrooms, 3 luxury baths, Starlink WiFi, wrap-around porch + sunny deck. Fitness club & pool passes included. Modern luxury in the heart of historic downtown St. Augustine. Perfect for couples or small groups seeking modern luxury, easy parking, and a walkable base right in the heart of historic downtown St. Augustine.

A private saltwater pool is centrally located within a spacious patio area, surrounded by well-maintained grassy lawns. Lounge chairs are positioned alongside the pool, while tables and chairs can be seen in the background. The home features sliding glass doors providing access to the pool area.

4.97 out of 5 average rating, 110 reviews

Music on Marilyn- Steps from the Amp! •Jacuzzi•

Nights of Lights & mere seconds from the St. Augustine Amphitheater— a short bike ride to the beach and downtown, this modern escape is 3 beds and 2 baths. Welcome to Music on Marilyn! This is the quintessential St. Augustine experience. Nestled on a quiet street that dead ends to the intracoastal, walking distance to the St. Augustine Amphitheater, Lighthouse, Anastasia Park, Alligator Farm and much more! St. Augustine Beach and historic downtown are just a short bike ride away.

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, 201 reviews

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

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.

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.

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!

4.96 out of 5 average rating, 200 reviews

Condo in St. Augustine Beach

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.

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.

4.98 out of 5 average rating, 262 reviews

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.

4.92 out of 5 average rating, 199 reviews

Heated Pool, Beach, Patio Lounge, Near Downtown

Add my home to your wishlist, click the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* >HUGE screened in pool! Heat pool for $60/day or $350/wk. >500 steps to beach >3 TV's with streaming apps (not cable) >Lots of parking! >.5 miles to Publix grocery store >Short drive to marina, restaurants, boat rentals >Walk to intracoastal >Short drive to DT St. Aug >Washer + Dryer >BBQ Grill >3 days of supplies (TP, trash bags, etc.)

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, 161 reviews

Floridian Bungalow•2 Min Walk to Beach•Heated Pool

Discover Catch 33, a cheerful Floridian cottage with artful details, creature comforts and a private heated pool. Just steps from Vilano Beach, you’ll find shell-filled mornings, sunny shorelines, seafood restaurants, a fishing pier, and glowing sunsets. In under 10 minutes, explore St. Augustine’s 450 years of history, lively music, and vibrant dining.

Popular amenities for St. Augustine rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private swimming pool is framed by stone patio tiles, with lounge chairs positioned on one side. Tall trees provide shade in the background, while a two-story house can be seen, featuring large windows and outdoor living areas.

4.93 out of 5 average rating, 115 reviews

Steps to the beach, heated pool with guest house

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.

5.0 out of 5 average rating, 170 reviews

Southern Charmer w/Pool - Walk to Everything!

A private pool area is showcased, featuring a large, clear swimming pool surrounded by a spacious patio. Lush greenery and palm trees create a serene atmosphere. Sliding glass doors provide access to the home, while a shaded pergola adds an inviting touch to the outdoor space.

4.95 out of 5 average rating, 104 reviews

Poolside Oasis ~ walking distance to Downtown

A large heated saltwater pool presents a curved design with a spa area seamlessly integrated. The pool area is surrounded by pavers and features vibrant turquoise lounge chairs. Lush greenery and decorative planters enhance the tranquil outdoor setting, enclosed by a white privacy fence.

4.99 out of 5 average rating, 125 reviews

Heated Pool/hot tub! 1 mile to dwntn/beach

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.

4.77 out of 5 average rating, 126 reviews

Heated Pool, Tiki Lounge, Steps to Beach, Games

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, 451 reviews

Your Home Away From Home

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, 138 reviews

The Salty Seashell, Coastal Pool Home, Sleeps 8

A private heated pool is surrounded by a spacious patio designed for relaxation. Comfortable lounge chairs are positioned nearby, alongside a well-maintained yard with decorative plants. The pool house features a playful mermaid mural on its exterior, adding a touch of charm to the outdoor space.

4.93 out of 5 average rating, 163 reviews

Splash & Explore

Condo rentals with a pool

4.92 out of 5 average rating, 190 reviews

Covered seating is arranged around a sleek coffee table on a patio with a view of a large heated pool, accented by palm trees and umbrellas. A dining area with a table and chairs is visible, offering ample space for relaxation and enjoyment.

Condo in Lincolnville

F1, Downtown, POOL, beaches, porch, parking!

Condo in St. Augustine Beach

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.

Peerless on the Pier

4.89 out of 5 average rating, 215 reviews

4.98 out of 5 average rating, 160 reviews

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.

Condo in Butler Beach

Family Beach Condo - Steps To The Sand Or Pool

5.0 out of 5 average rating, 120 reviews

2br condo in st Augustine across from Beach

The living room features a sliding glass door that provides a direct view of the beach. A comfortable sofa is positioned near a coffee table, while a side table and chair complement the seating arrangement. Natural light brightens the space, enhancing coastal decor.

4.99 out of 5 average rating, 144 reviews

361 Fun in the Sun | Direct Oceanfront Ground Floor

4.92 out of 5 average rating, 172 reviews

Condo in Butler Beach

2 King Beds - Walk to 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.

4.93 out of 5 average rating, 114 reviews

Hideaway at Crescent Breach - St. Augustine

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.

4.92 out of 5 average rating, 181 reviews

Pelican Inlet 2 Bedroom Condo Steps from the Beach

Other vacation rentals with a pool

Apartment in St. Augustine

A serene outdoor area features a suspended basket chair, surrounded by lush greenery and sun loungers beside a sparkling pool. Umbrella-shaded tables provide shade, while the building's modern architecture stands in the background, enhancing the inviting atmosphere of the space.

Luxury Retreat in St. Augustine

4.85 out of 5 average rating, 107 reviews

Cottage in St. Augustine Beach

The kitchen features modern appliances, including a refrigerator, microwave, and dishwasher. White cabinetry provides ample storage. A dining table with four chairs is positioned near the door, and a light fixture illuminates the space. A decorative rug adds a touch of warmth.

Beautiful Beach Cottage

4.95 out of 5 average rating, 508 reviews

4.98 out of 5 average rating, 350 reviews

A private hot tub is set in a serene outdoor area surrounded by greenery and wood paneling. The tub is equipped with a cover and nearby is a container holding spa towels, providing a relaxing space for guests.

Villa in St. Augustine

2 Bedroom, Private Hot Tub, walk to Loins Bridge

4.86 out of 5 average rating, 57 reviews

Home in Butler Beach

Beach Walk · Pool · Pickleball · Arcade · Golf

An outdoor area is depicted, featuring a salt-water pool surrounded by lounge chairs and shaded by a red umbrella. Permanent string lights provide soft illumination. Tropical landscaping and a covered space in the background suggest an inviting environment for relaxation and leisure.

4.9 out of 5 average rating, 52 reviews

Luxury Home with Pool, Pickle Ball and Hot Tub

Superhost

5.0 out of 5 average rating, 4 reviews

Island Home • Pool • Putting Green • Walk to Amp

Home in St. Augustine Beach

Luxury Beach Retreat, Pool Spa Sauna Yoga Studio

5.0 out of 5 average rating, 5 reviews