Holiday rentals with a pool in St. Augustine Beach

4.99 out of 5 average rating, 148 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, 121 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

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, 221 reviews

Historic Designer Home • Luxury Baths • Steps2DWTN

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.

Home in St. Augustine Beach

A fenced backyard features a heated pool surrounded by tropical palm trees and lounge areas. Bright pool floats add color to the blue water. An orange umbrella provides shade over a seating area, while a hammock is visible in the background, nestled among the foliage.

4.77 out of 5 average rating, 251 reviews

Heated Pool, Mini Golf, Walk to Beach, Beach Gear

Add my home to your wishlist, click the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* >Heated Pool! (option to heat for $60/day or $350/wk) >Private beach walk in the neighborhood >Mini golf >Propane fire pit + BBQ >3 days of supplies (TP, trash bags, pods, etc) >Tons of private parking >2 smart TVs w Netflix (no cable) >Playstation 4 with games >Dogs OK (*nightly pet fee; 3 dogs max) >Washer + Dryer >Drip coffeemaker + Keurig >See picture captions about home layout.

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.

4.91 out of 5 average rating, 101 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

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, 155 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

A spacious outdoor pool area is surrounded by lounge chairs and palm trees, providing a serene environment for relaxation. An adjacent building features balconies, offering views of the pool. A pergola is visible nearby, complementing the inviting atmosphere of the gated community.

4.93 out of 5 average rating, 125 reviews

Sun & Sea - Beach & Heated Pool, Pet Friendly!

Indulge in the comfort and style of this spacious one-bedroom king bedroom couple's retreat. Situated on the ground floor, this end unit is conveniently located within walking distance of restaurants and shops. This oceanfront complex offers top notch amenities, including a beach walkover, two pools (one heated), tennis courts, shuffleboard, a well-equipped gym, and a grill area, all within a secure gated community. Enjoy coastal proximity, with downtown St. Augustine only 10 minutes away.

A light and airy living area features a comfortable gray sofa, a wooden coffee table, and a blue accent chair. A large flat-screen television is mounted on the wall opposite, while sliding glass doors provide access to a balcony area with outdoor seating.

4.97 out of 5 average rating, 202 reviews

St Augustine Beach Condo, Pools, Bikes, Beach Gear

Relax and unwind at our beautiful beach getaway. This one bedroom condo is located close to all St. Augustine has to offer. You can walk to the beach or take a quick drive to historic downtown. Ocean Village Club is a gated complex that has private beach access just a seven minute walk from your door, two swimming pools, tennis courts, grilling area, and free parking. This second floor unit is light and airy, immaculate, and beautifully decorated. We are family owned and operated.

4.89 out of 5 average rating, 208 reviews

Beachy Condo| Steps to Beach | Pools | Hot Tubs

Champagne Sunrise on Private Balcony Anyone? Unwind at our updated St. Augustine beach condo-just 150 steps to white sand beach. Dip into 1 of 5 hot tubs, cool off in 2 sparkling pools (one is heated for those cool winter days). Challenge friends to a tennis match, pickleball rally, or bocce ball showdown. Craving nightlife, history, and culinary delights? Walk to restaurants or take a trolley in historic Old Town St. A. Full kitchen/laundry in unit. Private beach access.

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, 183 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 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, 251 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 the condo immediately next door for rent, Ocean Front Escape: https://www.airbnb.com/h/saint-augustine-oceanfrontescape. Our checkin process is contact free. We use a Nest lock on the front door.

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, 283 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!

Popular amenities for St. Augustine Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House 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.

4.95 out of 5 average rating, 38 reviews

Luxury Home with Pool, Pickle Ball and Hot Tub

4.97 out of 5 average rating, 130 reviews

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

4.95 out of 5 average rating, 37 reviews

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

Home in St. Augustine Beach

A private backyard oasis features a heated pool surrounded by paved stone flooring. Multiple seating options are provided, including four loungers and a dining table with chairs. Soft lighting is strung across the patio, and a privacy fence encloses the area, enhancing the relaxation space.

5 out of 5 average rating, 46 reviews

Heated Pool | 4 King En-Suites | Walk to the Beach

4.97 out of 5 average rating, 106 reviews

An inviting outdoor area features a stone fire pit surrounded by white adirondack chairs. A vibrant sunset casts warm colors over the scene, while a solar heated pool glistens nearby. Lounge chairs, umbrellas, and tropical landscaping enhance the charming ambiance.

Home in Butler Beach

Island Retreat: Pool/Hot Tub/Tiki Bar/Close2Beach

4.93 out of 5 average rating, 15 reviews

Private Pool/Spa! Walk to Beach & Two Kitchens

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, 53 reviews

17 Palms Beach House

A spacious backyard is highlighted by a private round pool, surrounded by lush greenery and palm trees. An outdoor cabana features a bar area, while a well-maintained lawn adds to the inviting atmosphere. The charming pink structure complements the serene setting.

5 out of 5 average rating, 132 reviews

Pink Palms *Pool* Party ~ Walk to Downtown

Apartment rentals with a pool

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, 137 reviews

Oceanfront Retreat!

The living area is furnished with a comfortable sofa and armchair, providing a relaxed seating space. A media console holds a television, and large sliding doors lead to a private balcony. Natural light fills the room, highlighting a neutral color palette.

4.91 out of 5 average rating, 372 reviews

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool

Apartment in Crescent 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, 109 reviews

Hideaway at Crescent Breach - St. Augustine

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, 447 reviews

4Ocean Front Condo With Pool unit 4

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, 147 reviews

Family Beach Condo - Steps To The Sand Or Pool

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, 314 reviews

Gorgeous Sea Place Ocean View Condo

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, 127 reviews

Boutique Beachside condo with easy access to beach

Apartment in Crescent Beach

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, 103 reviews

Incredible Waterfront Townhome

Other holiday rentals with a pool

Apartment in St. Augustine

A spacious swimming pool is framed by palm trees and modern apartment buildings. Lounge chairs are arranged beside the water, inviting relaxation. The sky is painted with warm hues at sunset, creating a tranquil atmosphere around the serene pool area.

4.92 out of 5 average rating, 83 reviews

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

5 out of 5 average rating, 31 reviews

Coastal Chic Condo!

4.99 out of 5 average rating, 78 reviews

The May House - Heated Pool - Historic Downtown

4.93 out of 5 average rating, 58 reviews

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.

Flat in St. Augustine

Luxury Costal Oasis Close to Beach & Amphitheater

4.88 out of 5 average rating, 32 reviews

Flat in St. Augustine

Luxury Resort Style w/ Pool & Gym close to Beach

A dining area is presented with a wooden table set for six, complemented by upholstered chairs. Light fixtures hang elegantly above, and a cozy living space is visible beyond, featuring a gray sectional sofa and large windows allowing natural light.

5 out of 5 average rating, 24 reviews

St.Augustine Beach,Seaside at Anastasia,Condo

Cottage in St. Augustine Beach

4.9 out of 5 average rating, 61 reviews

Sea Turtle Beach Cottage 2/2 with bikes and pool