Vacation rentals with a pool in St. Augustine Beach

4.99 out of 5 average rating, 155 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.

4.98 out of 5 average rating, 132 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

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.

4.87 out of 5 average rating, 122 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!

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, 225 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.

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, 107 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

4.98 out of 5 average rating, 338 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

Perfect location 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.

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, 163 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

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, 190 reviews

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!

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.

4.94 out of 5 average rating, 179 reviews

Bel oc'ean, 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**

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, 155 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!

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, 255 reviews

Ocean Front Gem: Top Floor Corner Unit

Top floor, direct ocean front, 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.

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, 377 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.

Popular amenities for St. Augustine Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 140 reviews

Tide Pool | 4/3 Eclectic Escape | Pool & Rooftop

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, 447 reviews

Your Home Away From Home

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, 102 reviews

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

Superhost

Home in St. Augustine Beach

4.72 out of 5 average rating, 36 reviews

Ocean Vista Beach House, Pool, Spa, Steps To Sand

Home in St. Augustine Beach

A vibrant outdoor space features a well-manicured lawn surrounding a rectangular pool and lounge chairs. A wooden deck rises above, while colorful pool floats rest in the water. Shades from an umbrella provide a relaxing area, complemented by a clear blue sky.

4.88 out of 5 average rating, 49 reviews

Silver Palms - Summer in Style: Beach + Pool!

5 out of 5 average rating, 6 reviews

Home in Butler Beach

Beach Oasis with Heated Pool and Hot Tub

A private saltwater pool is surrounded by a spacious deck and lush greenery. Palm trees frame the area, offering a shielded retreat. A patio space is visible, providing comfortable seating options and direct access to the home.

4.92 out of 5 average rating, 162 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

4.97 out of 5 average rating, 100 reviews

A heated pool is illuminated in bright blue under the night sky, surrounded by lounge chairs positioned on a tiled patio. Lush greenery and palm trees are visible in the background, contributing to a relaxed outdoor ambiance.

Home in Butler Beach

Beach Getaway | Pool | Sleeps 16

Condo rentals with a pool

4.85 out of 5 average rating, 108 reviews

Oceanfront Condo! Located at Pier Park!

Superhost

A spacious balcony offers a wide view of the beach and ocean, framed by an elegant arched opening. Green dunes and distant waves are visible, while a flock of birds gracefully moves across the sky, adding to the serene coastal atmosphere.

4.88 out of 5 average rating, 139 reviews

Oceanfront Retreat!

4.89 out of 5 average rating, 210 reviews

Beachy Condo| Steps to Beach | Pools | Hot Tubs

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, 111 reviews

Hideaway at Crescent Breach - St. Augustine

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, 119 reviews

Seaglass Villa, a Sunny Beachside Retreat

4.92 out of 5 average rating, 146 reviews

Quiet, Updated Condo - Pool, Bikes & Pickleball!

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, 137 reviews

361 Fun in the Sun | Direct Oceanfront Ground Floor

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.

4.95 out of 5 average rating, 161 reviews

Summerhouse - Direct Oceanfront Corner Unit

Other vacation rentals with a pool

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.

4.93 out of 5 average rating, 43 reviews

Luxury Home with Pool, Pickle Ball and Hot Tub

5 out of 5 average rating, 28 reviews

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

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, 69 reviews

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

4.99 out of 5 average rating, 70 reviews

Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo

5 out of 5 average rating, 11 reviews

Home in Lincolnville

Rare Downtown Oasis | Private Pool + Parking

4.96 out of 5 average rating, 24 reviews

Beacher's Lodge Oceanfront Balcony Suite #328

A private backyard area features a heated pool amidst a paved patio. A tiki bar with seating and a TV is situated nearby. Sun loungers line the poolside, along with tropical landscaping. Soft evening light enhances the ambiance of the space.

4.98 out of 5 average rating, 58 reviews

17 Palms Beach House