Holiday rentals with a pool in St. Augustine

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, 154 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.

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 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, 138 reviews

Pink Palms *Pool* Party ~ Walk to Downtown

🏝️ Luxurious Private Heated Pool Home In Historic Downtown and Family Friendly! - Private Heated Pool & large backyard with tons of gorgeous palms - Outdoor cabana with grill, fans, pool table, kid toys, bocce, corn hole and seating - Walking distance to the Castillo de San Marcos Fort, Fountain of Youth, Uptown shops, The Bayfront and St. George Street - Wild Peacocks in backyard 🦚 - Less than 10 mins to Vilano Beach 🌊 - Sleeps 6/ 2 King beds, 2 XL twin beds (daybed trundle) - Pet Friendly

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 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

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!

Treehouse in St. Augustine

4.92 out of 5 average rating, 659 reviews

courtyardtreehouseinthehistoricdistrict

You have found your cozy oasis tucked in a (Real) Treehouse lodged in Ancient Oak. Set in a lush tropical garden in the historic district. It’s a minimalist’s dream, exemplifying the appeal of tiny living: compact, clean, efficient and 2 1/2 blocks to the historic districts shopping and restaurants. Relax on the Sun Deck, Rain Deck or in the Courtyard’s Tropical Garden The day time peaceful beauty is only eclipsed by the the nighttime display of laser lights projected onto the oaks canopy.

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.

4.95 out of 5 average rating, 192 reviews

A comfortable living area is showcased with a gray sofa adorned with decorative pillows. A glass coffee table sits in front, accented by a floral arrangement. Two windows provide natural light, and stylish curtains frame the view. A small bookshelf stands against the wall.

Flat in Vilano Beach

Charming Vintage Intracoastal Apartment

This breathtaking property is located on a quiet neighborhood street in Vilano Beach area on the river, minutes from the beach and a few miles from Historic Downtown St. Augustine. Apartment is on the second floor facing picturesque streets of Vilano Beach area. Waterfront private outside dining area with a grill, dock, and boardwalk are available on the waterfront side of the property. Famous local restaurants Cap's on the Water and Aunt Kate's are within walking distance from the property.

Superhost

The Tiki Bar area features a long bar with high chairs surrounded by vibrant wall murals and greenery. Cozy seating is arranged with colorful cushions on a grass-like rug, creating a relaxed atmosphere for socializing and enjoying refreshments.

4.76 out of 5 average rating, 121 reviews

Heated Pool, Tiki Lounge, Steps to Beach, Games

Save my home by clicking the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* >Sparkling heated pool (pool heat - $60 day/$350 wk) >Steps from sand! (1 min walk) >NOW with a new Tiki Bar in garage! >Blocks to boat ramp, bring your boat + jet-ski! >Dogs OK! 2 dog max (w nightly fee) >Beach gear >Propane BBQ >DT St. Aug is a 10 min drive >Drip coffee pot >Washer + Dryer >2-3 parking spots >Cable in LR, other TV's are smart. >3 days of supplies (TP, trash bags, pods, etc.)

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, 162 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

Popular amenities for St. Augustine 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.

4.93 out of 5 average rating, 43 reviews

Luxury Home with Pool, Pickle Ball and Hot Tub

4.94 out of 5 average rating, 140 reviews

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

Home in St. Augustine Beach

4.86 out of 5 average rating, 235 reviews

St. Aug Oceanfront Home w/ Heated Pool & Firepit

5 out of 5 average rating, 154 reviews

Private oasis, heated pool, exceeds expectations

5 out of 5 average rating, 10 reviews

Sparking Pool, Steps to Beach, Game Room, TVs, BBQ

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

The exterior of a two-story vacation home is showcased, featuring a welcoming porch with wooden railings and steps leading up to the entrance. The surrounding landscape includes a spacious paved driveway, lush greenery, and various trees, creating a serene atmosphere.

4.93 out of 5 average rating, 103 reviews

Vilano Beach Home, 3 Bed, 2 Masters, Heated Pool

4.97 out of 5 average rating, 133 reviews

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

Apartment rentals with a pool

Apartment 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, 127 reviews

Riverfront direct views-Get it ALL in St Augustine

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, 255 reviews

Ocean Front Gem: Top Floor Corner Unit

Apartment in Butler Beach

5 out of 5 average rating, 101 reviews

"Drift Away" at The Ocean Gallery

Apartment in Lincolnville

Covered seating is arranged around a sleek coffee table on a patio with a view of a large heated pool, accented by palm trees and umbrellas. A dining area with a table and chairs is visible, offering ample space for relaxation and enjoyment.

4.92 out of 5 average rating, 181 reviews

F1, Downtown, POOL, beaches, porch, parking!

Apartment in Crescent Beach

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

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.

4.96 out of 5 average rating, 190 reviews

Newly renovated! Steps to BEACH & POOL!

Apartment in Butler Beach

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, 131 reviews

Boutique Beachside condo with easy access to beach

Apartment in Butler Beach

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, 153 reviews

Family Beach Condo - Steps To The Sand Or Pool

Other holiday rentals with a pool

Luxe

5 out of 5 average rating, 75 reviews

Palma Beach House

4.99 out of 5 average rating, 69 reviews

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.

Flat in St. Augustine

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

4.99 out of 5 average rating, 639 reviews

A charming two-story apartment stands above a pool area framed by lush greenery. The balcony offers a view of the pool, while the surrounding landscape features vibrant foliage and mature oak trees. The pool is bordered by textured paving stones and a patio set in the background.

Flat in St. Augustine

Villa Tizoc

5 out of 5 average rating, 6 reviews

Beach Oasis with Heated Pool and Hot Tub

4.99 out of 5 average rating, 70 reviews

Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo

4.96 out of 5 average rating, 85 reviews

The May House - Heated Pool - Historic Downtown

4.95 out of 5 average rating, 43 reviews

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

An open-concept living area showcases high cedar wood ceilings and large sliding doors that lead to the pool area. A spacious sectional sofa is adorned with decorative pillows, complemented by a vibrant area rug. The neighboring dining area features a stylish table, enhancing the inviting atmosphere.