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, 162 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.

LocationFamilyQuiet

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, 133 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!

ValueLocationOutdoor spaces

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

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!

ValueLocationIndoor spaces

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, 179 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

LocationValueCleanliness

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

LocationFamilyPool

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

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 :-)

ValueFamilyAccuracy

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.

ValueLocationPets

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.

4.85 out of 5 average rating, 106 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!

FamilyLocationQuiet

Condo in St. Augustine Shores

A screened-in balcony offers views of the lush greenery and marshlands beyond. Colorful cushions adorn a comfortable seating area, while a small wooden table sits centrally. Natural light fills the space, creating a peaceful atmosphere for relaxation.

4.99 out of 5 average rating, 133 reviews

Riverfront direct views-Get it ALL in St Augustine

Do not compromise-Just get it all! This is the hidden gem you were waiting to find. Only a few minutes from historic downtown and the area's best beaches, The Conquistador offers 3 swimming pools, tennis, tennis/pickleball courts, trails, a fishing pier, playgrounds, BBQ area, pavilion and plenty of space to roam and relax under the amazing Oak canopy. The beach or Downtown a mere 12 minute drive. Stay in your very private condo and enjoy the gorgeous views of the Manatee River.

FamilyValueAir conditioning

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, 195 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**

LocationFamilyLong stay

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, 159 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!

FamilyLocationLaundry

Guest suite in St. Augustine Beach

A screened-in pool area features a crystal-clear water pool with a shallow entry. Two chairs, one green and one yellow, are positioned beside the pool, surrounded by natural greenery and a wooden fence. Sunlight brightens the space, creating a relaxing outdoor ambiance.

4.94 out of 5 average rating, 382 reviews

Ground floor--just 365 steps to beach!

Beautiful ground floor of a two-story house only 365 steps from one of the most beautiful beaches in the United States. Close to the Ancient City, with all its amenities and attractions. Within walking distance of great restaurants and bars. Private entrance, pool, fully furnished kitchenette with Keurig type coffeemaker, Internet, Cable TV. Two bedrooms, one with a queen bed, and the other a double Murphy bed. On-site parking for one car provided.

FamilyValueAccess

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 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, 109 reviews

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

ValueLocationBackyard

4.84 out of 5 average rating, 102 reviews

Tiki Time-Pool & Heated Spa, Amazing Backyard

FamilyValueAmenities

A secluded poolside area is showcased, featuring a structured cabana adorned with soft seating. Nearby, comfortable lounge chairs are positioned around a tranquil swimming pool, surrounded by a clean, landscaped space with tropical plants and a shaded umbrella, inviting relaxation.

4.8 out of 5 average rating, 107 reviews

Beautiful Ocean View Pool Home ~ Heated Pool

LocationValueAmenities

4.99 out of 5 average rating, 146 reviews

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

ValueLocationComfort

4.99 out of 5 average rating, 161 reviews

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.

Home in Vilano Beach

Floridian Bungalow•2 Min Walk to Beach•Heated Pool

ValueFamilyTV

4.99 out of 5 average rating, 168 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

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

ValueLocationAccess

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, 111 reviews

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

ValueLocationParking

4.97 out of 5 average rating, 117 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

FamilyValueCleanliness

Condo rentals with a pool

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.

5.0 out of 5 average rating, 138 reviews

Boutique Beachside condo with easy access to beach

LocationFamilyAmenities

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.

4.77 out of 5 average rating, 282 reviews

Great 1 bedroom 1 bath condo with heated pool

ValueFamilyHospitality

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, 129 reviews

Heated Pool, Ocean Views, Beach, Playground, BBQ

FamilyValueWi-Fi

4.92 out of 5 average rating, 255 reviews

The Salty Suite Resort style condo

ValueLocationBarbecue

A bright living room features an open layout illuminated by natural light. Neutral-toned furniture is paired with colorful accent pillows. A natural jute rug lies beneath a low coffee table, while a ceiling fan enhances airflow. Large glass doors open to an outdoor area.

4.99 out of 5 average rating, 130 reviews

Seaglass Villa, a Sunny Beachside Retreat

ValueFamilyLayout

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.

4.98 out of 5 average rating, 261 reviews

Ocean Front Gem: Top Floor Corner Unit

LocationFamilyAir conditioning

A bright living area is furnished with two dark leather sofas and a wooden coffee table. Natural light enters through large sliding glass doors, which lead to a patio. A decorative painting and a flat-screen TV complete the space, accented by neutral tones and coastal decor.

4.96 out of 5 average rating, 215 reviews

Ocean Front Condo only Steps to the Beach.

FamilyLocationComfort

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.

4.96 out of 5 average rating, 200 reviews

Newly renovated! Steps to BEACH & POOL!

ValueLocationTV

Other holiday rentals with a pool

4.92 out of 5 average rating, 300 reviews

The exterior of a one-story unit is displayed with a red metal roof and a welcoming porch. A colorful umbrella provides shade over outdoor seating. A grill is positioned nearby, and landscaped areas with flowers enhance the entrance.

Cottage in Butler Beach

Livin’ the Dream at St. Augustine Beach

LocationValueAir conditioning

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, 218 reviews

Heated Pool Beach Bungalow Steps to the Ocean

LocationFamilyAccess

Condo in St. Augustine Shores

A screened-in balcony offers a view of lush greenery and the waterway, with comfortable seating arranged around a glass-topped table. Colorful cushions provide a relaxed seating area, inviting quiet moments outdoors while enjoying the natural surroundings.

5.0 out of 5 average rating, 56 reviews

Sunrise Paradise on Intracoastal Front

FamilyValueSleep quality

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.

5.0 out of 5 average rating, 33 reviews

St.Augustine Relaxing

ValueLocationKitchen

An aerial view captures the beachfront property, highlighting lush green lawns, palm trees, and a clear view of the ocean. The marked building is set against a backdrop of the beach and walking path, with two pools visible in the communal area.

4.98 out of 5 average rating, 90 reviews

St. Augustine Beach Condo 2 bed/2 bath Heated Pool

FamilyValueCleanliness

Luxe

The modern exterior of the Palma Beach House is highlighted by a spacious driveway leading to a stylish garage with large glass doors. Lush landscaping, including palm trees and vibrant plants, complements the clean lines of the home under a dusky sky.

5.0 out of 5 average rating, 80 reviews

Palma Beach House

FamilyValueCheckout

Apartment in St. Augustine

4.93 out of 5 average rating, 68 reviews

Luxury Costal Oasis Close to Beach & Amphitheater

LocationFamilyComfort