Holiday rentals with a pool in St. Augustine

4.97 out of 5 average rating, 127 reviews

Home in Flagler Beach

Walk to Beach | Pool, Spa & Private Dock

This isn’t just a beach house — it’s your private coastal escape. Start your morning with coffee and a short walk to the beach. Spend the day poolside or out on the water, then unwind in the spa as the sun sets over the intracoastal. 👉 A perfect mix of beach days and relaxing waterfront evenings. 📍 Location • Walk to beach • Short drive to Flagler Beach restaurants & shops • Quiet, private neighborhood Centrally located between St. Augustine and Daytona Beach -35 minutes LBTR #37009

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, 216 reviews

Downtown Luxury • Gourmet Kitchen • STEPS 2 DTWN !

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.

Guest house in St. Augustine

The exterior of the casita features a gabled roof with large glass windows, allowing natural light to enter. Two double doors provide access, surrounded by lush green plants and palms. A covered entryway leads to the main entrance, enhancing the inviting appearance.

4.94 out of 5 average rating, 437 reviews

The Garden Casita in St. Augustine Florida

Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

4.98 out of 5 average rating, 111 reviews

Htd Pool/Arcade, FirePit& PuttingGreen 1.2 mi DT

ISLE BE BACK 🌴— a brand NEW modern home! Dates fill quickly for spring & summer — save your stay now! 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 ✔ Easy self check-in & free parking

4.98 out of 5 average rating, 191 reviews

A spacious deck overlooks a clear blue saltwater pool surrounded by lounge chairs and umbrellas. Lush greenery and palm trees frame the view of the water and dock area in the distance, creating a serene outdoor space for relaxation.

Cottage in St. Augustine

Perfect Waterfront Retreat w/Pool & Rooftop Deck

You've found your waterfront oasis tucked under the White Birds of Paradise! This spacious retreat was formerly a commercial art gallery. Two queen beds, one full bathroom & full kitchen make for comfortable living! You have a fenced path leading you down to the beautiful waters of Salt Run where a rooftop deck & salt water in-ground pool invites you to relax and slow down. Less than a mile to downtown St. Augustine, a little over a mile to the Amphitheater and about 3 miles to the beach.

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, 146 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

Home in St. Augustine South

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.

4.98 out of 5 average rating, 125 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 :-)

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, 122 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.

A tranquil backyard area is featured, showcasing a heated pool surrounded by lush greenery. Two black chairs are positioned on the stone patio, offering a comfortable spot for relaxation. The space is enclosed by vibrant tropical plants, enhancing the private atmosphere.

4.96 out of 5 average rating, 180 reviews

Pool home oasis steps to ocean

Cottage style home with comfortable porches to enjoy sound of ocean waves breaking on the front and back porches. Pool in the back yard (heated by request for $50 per day) cookshed, fenced with lush trees and woods to the east. The inside looks large with high wood ceilings and multiple windows and glass doors to the beautiful pool area. Located on a dead end street in a family neighborhood with 5 star restaurants nearby. Fifteen minute drive to downtown St. Augustine.

4.93 out of 5 average rating, 135 reviews

The backyard is illuminated by soft lighting, showcasing a private heated pool surrounded by a screened enclosure. Lush palm trees and well-maintained landscaping enhance the tranquil atmosphere. The two-story home is visible in the background, adding to the serene nighttime setting.

Home in Butler Beach

Hawaiian Island Escape ~ Heated Pool/Spa/Beach

This getaway is nestled on the "island" in a quiet residential neighborhood, with small touches of Hawaiian decor. ~ Just a 2min drive to the closest beach entrance, or a 12min walk. ~ Private heated pool (up to 85) + hot tub ~ Large backyard with marsh front view ~ 15 -20min drive to historic downtown ~ 11min drive to the St Augustine Pier ~ 13min drive to Marineland ~ 17min drive to Washington Oaks Gardens State Park ~ 7min drive to Publix or Winn Dixie

A spacious screened-in pool area features a large blue swimming pool surrounded by patio tiles. Comfortable seating arrangements with multiple chairs and a table are visible nearby, providing a relaxed space for leisure. Natural light streams in through the screened enclosure.

4.93 out of 5 average rating, 177 reviews

Heated Pool, Beach, Patio Lounge, Near Downtown

Add my home to your wishlist, click the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* >HUGE screened in pool! Heat pool for $60/day or $350/wk. >500 steps to beach >3 TV's with streaming apps (not cable) >Lots of parking! >.5 miles to Publix grocery store >Short drive to marina, restaurants, boat rentals >Walk to intracoastal >Short drive to DT St. Aug >Washer + Dryer >BBQ Grill >3 days of supplies (TP, trash bags, etc.)

Apartment 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, 216 reviews

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

Lovely beach life awaits you at this home away from home in the heart of St Augustine beach. Enjoy the excellent location just steps away from the no driving beach, St Johns County fishing pier and local restaurants. Pool on site. YMCA across the street. St Augustine Amphitheater with its great concert program 1.7 miles away. Two bedroom two bathrooms , private entrance, tastefully decorated inviting you to enjoy Beach Life at its fullest.

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.

4.94 out of 5 average rating, 32 reviews

Luxury Home with Pool, Pickle Ball and Hot Tub

Home in Ponte Vedra Beach

4.81 out of 5 average rating, 53 reviews

Oceanfront | Pool, Pet Friendly, Large Deck!

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, 437 reviews

Your Home Away From Home

Luxe

Home in Butler Beach

5 out of 5 average rating, 65 reviews

Palma Beach House

The exterior of the home features a two-story structure with a welcoming porch. Potted plants hang from the posts, and a decorative sign is positioned near the entrance. Lush greenery and various plants are arranged along the pathway leading to the front steps.

4.99 out of 5 average rating, 221 reviews

Historic St. Augustine 2/2 Duplex & Pool

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.

4.95 out of 5 average rating, 149 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

An open concept living space is featured, showcasing a mix of comfortable seating options including a leather sofa and a spacious sectional sofa. Natural light floods the area, enhancing the wooden flooring. Decor includes stylish wall art and plants, adding a relaxed, beach-inspired vibe.

4.95 out of 5 average rating, 110 reviews

Heated pool home with interactive gaming system

Home in St. Augustine South

5 out of 5 average rating, 26 reviews

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

Apartment rentals with a pool

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, 176 reviews

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

A scenic view reveals a sandy beach framed by rolling dunes and lush greenery. A wooden boardwalk leads to a shaded gazebo overlooking the ocean. The sky is clear with scattered clouds, creating a peaceful atmosphere by the water.

4.83 out of 5 average rating, 337 reviews

Shell Shack - Resort Beachside Condo

Apartment in Crescent Beach

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, 197 reviews

After Dune Delight, BEACH FRONT w/Fishing Pier

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.

4.95 out of 5 average rating, 175 reviews

Newly renovated! Steps to BEACH & POOL!

Apartment in St. Augustine Beach

A person is seen in a casual pose near a life-size alligator statue on a wooden deck. The surrounding area features lush greenery, enhancing the natural setting. The alligator's mouth is open, and the wooden railing adds a rustic touch to the scene.

4.93 out of 5 average rating, 392 reviews

~Heated Pool~Hot Tub~Steps to the Beach~King Bed

A private balcony is presented, offering panoramic ocean views. The space includes a textured table and four chairs, with one set featuring floral upholstery. Green grass and sandy shorelines blend into the sea under a clear blue sky, enhancing the sense of tranquility.

4.98 out of 5 average rating, 102 reviews

Wade n Sea Ocean Front Condo

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, 134 reviews

Family Beach Condo - Steps To The Sand Or Pool

A cozy living area features a blue sofa accompanied by a decorative chair and a wooden coffee table. A ceiling fan provides airflow in the space. The open layout offers a view of the kitchen, where modern appliances and a breakfast bar create a welcoming atmosphere.

4.85 out of 5 average rating, 173 reviews

Ocean Side Complex with Heated pool B-24

Other holiday rentals with a pool

4.86 out of 5 average rating, 7 reviews

Flat in St. Augustine

Marina Cove Coastal Haven|Pool, Games, Near Beach

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, 95 reviews

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

A modern kitchen features white cabinetry and stainless steel appliances, including a refrigerator and microwave. A granite countertop provides ample workspace, while a dining table with dark wooden chairs offers seating for six. Natural light is filtered through nearby windows.

4.96 out of 5 average rating, 57 reviews

Ground floor newly remodeled 1 BR beachside condo

4.9 out of 5 average rating, 10 reviews

Home in Palm Coast

Coastal Luxe Retreat | Team Joseph Ellen

4.93 out of 5 average rating, 82 reviews

A resort-style pool is surrounded by lounge chairs, palm trees, and blue umbrellas. The water sparkles under a clear sky. Modern buildings are positioned on either side, enhancing the spacious and inviting pool area.

Flat in St. Augustine

St. Augustine Escape w/Pool, Gym, Games MORE!

4.91 out of 5 average rating, 47 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

5 out of 5 average rating, 27 reviews

A spacious living area is highlighted by a light-toned sectional couch with soft pillows. Modern decor includes a wall-mounted TV displaying a beach scene. Nearby, a small table and chairs invite relaxation with views of the exterior landscape through large glass doors.

Flat in Vilano Beach

Modern Coastal Retreat