Holiday rentals with a pool in St. Augustine Shores

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, 158 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.

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Guest suite in Butler Beach

A serene waterfront view is captured at sunset, showcasing a pool surrounded by lush grass and palm trees. A shaded seating area is positioned next to the pool, overlooking the water where boats can be seen in the distance.

4.93 out of 5 average rating, 693 reviews

Waterfront suite, Dogs are cool no pet fee

Newly remodeled, waterfront suite. See dolphins, Osprey, and more frolicking in our amazing backyard overlooking the Matanzas river, & did I mention the breathtaking sunsets. 6 minute drive to Crescent Beach, one of the most beautiful beaches in Florida. Close to downtown historic St Augustine 20 min, Amphitheater concert venue is 15 min. Private entrance, full on suite bath, fishing dock, kitchenette, pool, ample free parking & internet included. Professional pool cleaning is on Mondays.

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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, 448 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!

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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, 132 reviews

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

Escape to our Zen Spa Retreat! Enjoy the soothing heated pool and hot tub, unwind on the expansive patio, or find tranquility in the zen-inspired interiors. This spacious 3 bedroom 2 bathroom is located in a quiet neighborhood close to Old St. Augustine, beaches and restaurants. Blackout curtains and smart TVs in every bedroom! Our fully equipped kitchen, washer, dryer, dishwasher, workspace and garage ensure convenience during your stay. Unwind in our serene oasis for the perfect Zen getaway!

FamilyLocationIndoor spaces

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, 231 reviews

Downtown • Historic Whitney House • Luxury 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.

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4.92 out of 5 average rating, 170 reviews

2 King Beds - Walk to Beach

Experience the ultimate getaway at our charming beach retreat, just a short stroll to the beach. Perfect for families, friends, or couples looking to relax and unwind, the perfect blend of comfort and convenience Enjoy a restful night's sleep in two luxurious king-size beds, designed for comfort and relaxation Stay connected with fast, reliable Wi-Fi throughout the property, ensuring you never miss a beat Enjoy the convenience of instant hot water, you never have to worry about running out

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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, 177 reviews

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

ValueFamilyHospitality

4.98 out of 5 average rating, 343 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

Loins Bridge 0.5m away, 2 Bedroom, Private Hot Tub

Couples Retreat Near Downtown St. Augustine. 0.5 miles from the Bridge of Lions. Enjoy a secluded courtyard, relaxing water fountain, and new 4-person hot tub. Wine down and watch the sunset in a peaceful setting after a exploring. Off-street parking is included. Restaurants, bars, coffee shops, and local favorites are only steps away. Perfect for a romantic getaway, weekend escape, or special occasion. Special requests and accommodations are available to help make your stay unforgettable.

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Guesthouse in Butler Beach

A tranquil outdoor space features a well-maintained heated pool surrounded by lush greenery and colorful flowers. Seating areas with black Adirondack chairs are positioned around the pool, offering a peaceful setting. A covered patio stands in the background, complementing the inviting atmosphere.

4.95 out of 5 average rating, 213 reviews

Heated Pool Beach Bungalow Steps to the Ocean

Beautiful brand new in 2022 en-suite Bungalow beach side! Perfect for a romantic get a way or just one person, just 600 steps to the beach. Five minutes to the St Augustine pier and 10 minutes to the oldest city in the US, Historic Downtown St Augustine. Not only do you have the most comfortable bed to fall into, a 50" TV, recliners and an amazing heated pool. Beautiful beach sunrises, fishing, hiking, Concerts at the Amphitheater. For your safety you have an electronic keyless entry.

ValueFamilyCheckout

A serene sunset is captured over calm waters, reflecting warm hues of orange, pink, and purple. The horizon is lined with subtle clouds, enhancing the tranquil scene. The peaceful atmosphere invites relaxation and appreciation of nature's beauty.

5 out of 5 average rating, 129 reviews

Windjammer 208, Oceanfront and Riverview

Beautiful newly renovated condo in Crescent Beach, with spectacular views of the beach as well as the Matanzas river. Coffee while watching sunrise on your east balcony and wine while watching the sunset on the Windjammer fishing pier, while dolphins are entertaining you. 10 miles from historic St Augustine, a couple of miles from Marine land and a variety of restaurants close by. Flatscreen TV'S in all the rooms for your convenience when the weather does not allow you on the beach.

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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, 106 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.

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Superhost

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.

Apartment in St. Augustine

4.84 out of 5 average rating, 102 reviews

Luxury Retreat in St. Augustine

Escape to Isla Antiguas in St. Augustine, FL, and indulge in luxury at this stunning 2-bed, 2-bath Airbnb. Perfectly designed for comfort and style, this upscale retreat offers a fully equipped kitchen, elegant living spaces, and plush bedrooms. Enjoy top-tier amenities, including a sparkling pool, fitness center, and scenic surroundings. Just minutes from historic downtown and pristine beaches, this getaway is ideal for relaxation and adventure. Book now for an unforgettable stay!

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Popular amenities for St. Augustine Shores rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A living area is featured with a light yellow wall and large windows allowing natural light. A blue sofa and a recliner are arranged around a circular coffee table. A television is mounted on a white console, with framed artwork adorning the walls.

4.83 out of 5 average rating, 113 reviews

Ocean Village Club-First Floor Access.

ValueFamilyQuiet

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, 124 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

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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.

4.98 out of 5 average rating, 108 reviews

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

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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, 201 reviews

Beautiful Beach Home - Sleeps 12

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4.99 out of 5 average rating, 166 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

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach

ValueLocationWalkability

4.99 out of 5 average rating, 140 reviews

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

LocationFamilySleep quality

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, 99 reviews

Poolside Oasis ~ walking distance to Downtown

LocationFamilyLong stay

4.97 out of 5 average rating, 115 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

ValueFamilyHeating

Condo rentals with a pool

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, 112 reviews

Hideaway at Crescent Breach - St. Augustine

ValueFamilyCleanliness

5 out of 5 average rating, 115 reviews

2br condo in st Augustine across from Beach

LocationValueSleep quality

A spacious bedroom is equipped with a large bed adorned with plush, blue pillows. A sliding glass door opens to a private balcony offering a scenic view. A small seating area with two chairs is visible outside. A flat-screen TV is positioned on a dresser.

4.95 out of 5 average rating, 206 reviews

After Dune Delight, BEACH FRONT w/Fishing Pier

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Condo in St. Augustine Beach

A bright living area includes a comfortable sofa and two accent chairs arranged around a glass coffee table. Natural light enters through large windows, illuminating the space. A flat-screen television is mounted on the wall, and coastal-themed artwork adds a subtle decorative touch.

4.9 out of 5 average rating, 225 reviews

St Augustine Beach, no stairs, clean, 2 BR 2 Bath

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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, 157 reviews

Family Beach Condo - Steps To The Sand Or Pool

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Lush greenery frames a wooden pathway leading to a sandy beach, with palm trees and residential buildings visible in the background. The sky is illuminated by soft hues of sunset, creating a serene backdrop for the coastal environment.

5 out of 5 average rating, 134 reviews

Boutique Beachside condo with easy access to beach

ValueFamilyDecor

A wooden walkway leads towards the beach, framed by tall grasses and gentle waves. The sun sets on the horizon, casting warm hues of orange and pink across the sky and reflecting on the water's surface.

4.94 out of 5 average rating, 318 reviews

Gorgeous Sea Place Ocean View Condo

LocationFamilyPool

A view framed by lush tropical plants reveals the expansive waterway, with its calm, reflective surface. The image captures a serene outdoor space, featuring stone flooring leading towards the grassy area and water, emphasizing the natural surroundings.

4.97 out of 5 average rating, 114 reviews

Incredible Waterfront Townhome

ValueLocationBackyard

Other holiday rentals with a pool

Superhost

A private screened-in pool area features a heated saltwater pool surrounded by comfortable lounge chairs. A dining table is set for outdoor meals under a vibrant umbrella, with lush greenery visible beyond the enclosure.

4.99 out of 5 average rating, 82 reviews

Heated Saltwater POOL, Harry Potter, Firepit, BBQ

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4.91 out of 5 average rating, 35 reviews

2/2 Oceanview Condo/Beach Access/Pools

LocationFamilyPool

Apartment in St. Augustine

A serene pool area is surrounded by modern apartment buildings, with vibrant palm trees complementing the inviting atmosphere. Lounge chairs are positioned for relaxation beside the water, and a colorful sunset paints the sky in soft hues, creating a tranquil ambiance.

4.99 out of 5 average rating, 73 reviews

Resort Style 1B/1B APT, 10 min Beach/Downtown

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Apartment in St. Augustine

The pool area features a large rectangular swimming pool with lounge chairs lining the sides. Palms and landscaped greenery surround the pool, creating a relaxing atmosphere. A warm sunset casts a golden glow over the scene, enhancing the coastal oasis vibe.

4.94 out of 5 average rating, 67 reviews

Luxury Costal Oasis Close to Beach & Amphitheater

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4.94 out of 5 average rating, 53 reviews

Ping Pong• Pets• DT 10 mins• BBQ• King• Fast Wifi

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Apartment in Butler Beach

An aerial view showcases the Ocean Village Club community, highlighting two buildings surrounding landscaped green areas and a swimming pool. A sandy beach is visible in the background, with the ocean gently lapping at the shore, accessible via a boardwalk.

5 out of 5 average rating, 28 reviews

*Walk To Beach and Restaurants with Pools, Tennis*

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Condo in St. Augustine Shores

A serene view of the inner coastal water is captured through a framing of palm trees and other foliage. A sailboat is visible in the distance, set against a backdrop of clear blue sky and grassy shoreline.

5 out of 5 average rating, 33 reviews

St.Augustine Relaxing

ValueLocationLaundry

A spacious living area is presented with soft blue walls and wooden flooring. Comfortable seating includes a blue couch and patterned chair. A dining table with white chairs is set in the foreground, illuminated by natural light from window treatments, enhancing the inviting ambiance.