Holiday rentals with a pool in St. Augustine

The front entrance features a pastel green exterior with a light purple door partially open. Two large lanterns flank the door, while lush greenery frames the pathway. A small mailbox is attached to the wall beside the door.

4.98 out of 5 average rating, 106 reviews

Walk to Everything plus Pool and bonus Cottage!

Our charming 4/3.5 home with heated saline pool is a quiet retreat from a day spent exploring beautiful St. Augustine! We are Downtown just blocks from the famed Fort. So close to the action you can park the car and forget about it! And best of all you really get 2 houses in 1 (double Kitchens and Livingrooms)! Perfect for extended families or friends catching up. If you need another rental we have a 4 bedroom with pool right next door. It's called Southern Charmer w/Pool - Walk to Everything.

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, 435 reviews

Your Home Away From Home

1,800 SF, 2 bedrooms, 2 1/2 bathrooms, on a secluded 5 acre lot just minutes from Historic Downtown and St. Augustine Beach. The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms (1 with TWINKLE mattress) ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small upcharge for 5 or more. Motorcycle friendly! We also do live on the property!

The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.

4.94 out of 5 average rating, 215 reviews

Downtown HistoricLuxury • Designer Kitchen & Baths

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.

Guest house in St. Augustine

The exterior of the casita features a gabled roof with large glass windows, allowing natural light to enter. Two double doors provide access, surrounded by lush green plants and palms. A covered entryway leads to the main entrance, enhancing the inviting appearance.

4.94 out of 5 average rating, 428 reviews

The Garden Casita in St. Augustine Florida

Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

4.98 out of 5 average rating, 104 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

An inviting outdoor pool area features a heated pool surrounded by lounge chairs and a large umbrella. Soft lighting illuminates the space, highlighting the wooden fencing and lush greenery in the background.

4.98 out of 5 average rating, 183 reviews

"Once Upon A Tide" Beach House *Heated Pool* King

Welcome to Once Upon a Tide Beach House in Vilano Beach (Salted Heated Pool) This brand new luxury beach house is in a perfect location. 3 blocks to the beach , 1 block to the intracoastal . A short drive to Historic Downtown St. Augustine. Very spacious and well pointed home with 2 living rooms, the main living room is on the first floor and a second living room is upstairs in the loft area. Private back yard oasis with a salted heated pool, cabana. I promise you will not want to leave!

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, 142 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

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.

4.98 out of 5 average rating, 125 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 :-)

A well-maintained outdoor pool area is framed by palm trees and lush green landscaping. The sparkling blue pool features a central fountain and is surrounded by loungers, creating a serene environment for relaxation.

4.87 out of 5 average rating, 314 reviews

Full Condo in St. Augustine’s World Golf Village

Escape to St. Augustine and enjoy a one bedroom condo with new brand new renovations and upgrades! Explore the resort amenities including free unlimited access to three pools, a hot tub, lighted tennis and pickleball courts, playground, and fitness center. Located within the private gates of the World Golf Village, home of the King and Bear Golf Course. Minutes away from restaurants, shopping and the Golf Hall of Fame. Travel to Historic St. Augustine and beaches in less than 30 minutes!

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, 178 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.

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 out of 5 average rating, 275 reviews

Ocean Gallery 1/1, 2 pools

Bright, airy and beachy, this condo at Ocean Gallery pairs resort-style amenities with an exceptionally clean, stylish and comfortable condo. Perfect for a couple or one family, it sleeps up to 4 in beds (primary bed sleeps 2; pullout sofa in living area sleeps 2 additional guests - perfect for kids). You’ll be a few steps from 1 of the 2 pools, and a 5 minute leisurely stroll through the complex will take you to the beach!

4.97 out of 5 average rating, 127 reviews

The exterior of the house is showcased, featuring a blue facade with a well-maintained driveway. A private dock extends into the water, with views of the lush surroundings, including palm trees and a serene pond, adding to the peaceful ambiance.

Home in Flagler Beach

Resort-Style Living: Beach Home w/Salt Pool, Spa

Imagine your perfect day: waking up to stunning intracoastal views, fishing from your private backyard dock, then strolling along the cinnamon coquina shell beach via your own walkover. This private retreat offers the best of both worlds—seclusion on a large lot with a pond, plus easy access to everything you need. You can launch your jet skis or canoe from the complimentary floating dock. LBTR #37009

Popular amenities for St. Augustine rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 125 reviews

Luxury pool & spa home steps to beach & 2 masters!

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.

5 out of 5 average rating, 106 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

4.93 out of 5 average rating, 57 reviews

A comfortable living area features a sectional sofa and an accent chair, arranged around a coffee table. A flat-screen TV is mounted on the wall. Large windows allow natural light to illuminate the space, revealing views of greenery outside.

Home in Treasure Beach

Serenity by the Sea - Steps to the Ocean Condo

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, 92 reviews

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

A private heated pool is encased in a screened enclosure, featuring clear blue water. Adjacent to the pool, a hot tub is visible, offering a relaxing retreat. Access to the pool area is framed by glass doors leading from the main house.

4.88 out of 5 average rating, 112 reviews

Zen Oasis | Heated Pool | Hot Tub | Beach 12-Min!

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, 219 reviews

Historic St. Augustine 2/2 Duplex & Pool

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, 136 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

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, 136 reviews

Splash & Explore

Apartment rentals with a pool

Apartment 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.

4.98 out of 5 average rating, 243 reviews

Ocean Front Gem: Top Floor Corner Unit

Superhost

A sandy beach stretches into the distance, meeting calm ocean waters under a clear blue sky. Gentle waves can be seen lapping at the shore. A wooden boardwalk winds through the grassy area, leading down to the beach, where a few umbrellas and people can be spotted.

4.86 out of 5 average rating, 351 reviews

Oceanfront 1st Floor-Crescent Beach

Apartment in Treasure Beach

4.95 out of 5 average rating, 144 reviews

Beachfront! Creston by the Sea, 11D!

5 out of 5 average rating, 105 reviews

St Augustine coastal chic 2br across from Beach

Apartment 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, 172 reviews

Newly renovated! Steps to BEACH & POOL!

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.

4.94 out of 5 average rating, 144 reviews

Summerhouse - Direct Oceanfront Corner Unit

A living area features a light-colored sofa and a glass coffee table, with a large wall-mounted television. Expansive sliding glass doors provide a view of the ocean. Two lamps illuminate the space, complemented by a blue and white patterned area rug.

4.91 out of 5 average rating, 442 reviews

4Ocean Front Condo With Pool unit 4

The bedroom features a king-size bed with a quilted bedspread and decorative pillows. A bedside lamp sits on a dark wooden nightstand. Large windows with drapes allow natural light into the space, creating a serene environment. A comfortable chair is positioned near the window.

4.97 out of 5 average rating, 102 reviews

Luxury Golf & Spa condo in Beautiful St. Augustine

Other holiday rentals with a pool

5 out of 5 average rating, 13 reviews

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

5 out of 5 average rating, 24 reviews

A spacious outdoor area features a swimming pool surrounded by lounge chairs and palm trees. The Atlantic Ocean is visible in the background, with sandy beach leading to the water's edge. A grassy area is present, contributing to the inviting landscape.

Flat in St. Augustine

Tradewinds at Crescent Beach #113 (monthly Jan-Mar

Superhost

New place to stay

St. Augustine Cottage With Private Heated Pool

A living area features a grey sofa with decorative pillows, a light wood coffee table, and a dining space with a round table and wooden chairs. Mirrored walls reflect natural lighting, while a ceiling fan circulates air. A sliding door opens to a private balcony with ocean views.

4.8 out of 5 average rating, 15 reviews

Beacher's Lodge Balcony Suite #419

4.97 out of 5 average rating, 76 reviews

A resort-style pool is surrounded by lounge chairs, palm trees, and blue umbrellas. The water sparkles under a clear sky. Modern buildings are positioned on either side, enhancing the spacious and inviting pool area.

Flat in St. Augustine

St. Augustine Escape w/Pool, Gym, Games MORE!

4.99 out of 5 average rating, 67 reviews

The May House - Heated Pool - Historic Downtown

4.94 out of 5 average rating, 35 reviews

Walk 2 Beach | Salt/Heat Pool | Game Room | EV