Holiday rentals with a pool in St. Augustine

4.97 out of 5 average rating, 190 reviews

A cozy sleeping area features a spacious bed adorned with a patterned bedspread and accented by a decorative pillow. A bedside table holds a small lamp, while a dark cabinet provides additional storage. Light filters in through a window dressed with textured blinds.

Flat in St. Augustine

Traveler’s Nest of uptown St. Augustine with pool!

The Traveler's Nest is a unique and cozy studio apartment with a kitchenette, private backyard and access to a huge pool located in a quiet historic uptown St. Augustine neighborhood. It's just minutes to the Old City and Vilano Beach and Fort Mose National Park and Museum is 3min walk within the neighborhood! In addition, it's close to all your necessities (groceries, liquor store, restaurants, fast food....etc.) and there's a huge pool to relax and cool off when your not out seeing sites :)

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.

4.98 out of 5 average rating, 118 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.

A vibrant swimming pool reflects the evening sky, surrounded by well-maintained landscaping. Poolside seating includes colorful lounge chairs and a dining set, while a floating flamingo adds a playful touch. Soft lighting from string lights enhances the serene atmosphere as dusk approaches.

4.99 out of 5 average rating, 106 reviews

HGTV DesignerHome•HeatedPool•Walk/Bike 2 Downtown

Off Street Parking 3 Min Drive/ 15 Min Walk to Historic Downtown 2 Min Drive to the St Augustine Amphitheater 2 Min Drive to Anastasia State Park Beach 1 Min Drive to Anastasia Fitness Club/Suana-Steam Rm/Pool Looking to get away from the hustle & bustle of the city? This designer home with an amazing pool is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a minutes away. With spacious living & modern amenities, the Home offers maximum comfort

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.

4.95 out of 5 average rating, 402 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.

A well-lit outdoor living space features a heated pool surrounded by smooth pavers. Several adirondack chairs are positioned nearby for seating, and a dining table is set for outdoor meals. String lights illuminate the area, creating a cozy ambiance.

4.97 out of 5 average rating, 118 reviews

Luxury heated pool home steps from the beach!

Welcome to the Coral Door House! Tranquil retreat at the beach. Newly built spacious and modern luxury home. A private entrance to a very special and secluded beach is just 6 houses down. An easy short walk with the stocked provided beach cart. Outdoor living space has a 10 X 20 heated pool and plenty of seating. A perfect place to relax after a day at the beach. We’d love to host you and your family so let us know when you want to come stay, and we can discuss more details from there!

4.98 out of 5 average rating, 189 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

Fun Waterfront Retreat, Heated 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, 124 reviews

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+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

Guest house in St. Augustine

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.

4.94 out of 5 average rating, 177 reviews

Heated Pool Beach Bungalow Steps to the Ocean

Beautiful brand new in 2022 en-suite Bungalow beach side! Perfect for a romantic get a way or just one person, just 600 steps to the beach. Five minutes to the St Augustine pier and 10 minutes to the oldest city in the US, Historic Downtown St Augustine. Not only do you have the most comfortable bed to fall into, a 50" TV, recliners and an amazing heated pool. Beautiful beach sunrises, fishing, hiking, Concerts at the Amphitheater. For your safety you have an electronic keyless entry.

The outdoor area features a heated pool surrounded by comfortable lounge chairs and shaded umbrellas. A spacious patio includes additional seating and a tranquil atmosphere, enhanced by palm trees and bright blue skies.

4.99 out of 5 average rating, 160 reviews

4Bed, 3Bath-Heated Pool & SPA-Don't You Wanna?

Don't You Wanna...4 Bedroom, 3 Bath with HEATED POOL, SPA, and Outdoor Shower located in the heart of Vilano Beach of historic St. Augustine, FL. Our conveniently located home allows you to bring family and friends to share memories with a nice sunset or sunrise just down the street at the third street beach access point. Want to have a nice dinner at one of the most popular restaurants in all of St. Augustine? Walk around the corner to Cap's On The Water for great dining.

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, 154 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!

4.96 out of 5 average rating, 170 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.

Apartment in Treasure 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, 110 reviews

Boutique Beachside condo with easy access to beach

Skipper’s Hideaway is a charming beachside retreat that sleeps up to six, with a king bed, queen sofa pull-out, and twin daybed with trundle. Located on the ground floor for easy access, the condo offers a partial Atlantic Ocean view from the living room window. Just steps from Crescent Beach, this peaceful spot is perfect for relaxing. For more excitement, the shops, restaurants, and nightlife of downtown St. Augustine are only a 15-minute drive away.

Popular amenities for St. Augustine rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A large heated saltwater pool presents a curved design with a spa area seamlessly integrated. The pool area is surrounded by pavers and features vibrant turquoise lounge chairs. Lush greenery and decorative planters enhance the tranquil outdoor setting, enclosed by a white privacy fence.

5 out of 5 average rating, 101 reviews

Pool/Hot Tub Home 1 mile to downtown/beach

The exterior of a two-story beach house is showcased, featuring a blue balcony and a spacious driveway. Palm trees and landscaped greenery surround the property, creating a relaxed environment. A parked vehicle is visibly accommodated beneath the elevated house, enhancing accessibility.

4.95 out of 5 average rating, 127 reviews

Tide Pool - Heated Pool/Hot Tub/Golf Cart

4.99 out of 5 average rating, 121 reviews

An outdoor deck features a large dining table with a lantern at the center, surrounded by comfortable seating options. Lush greenery, including palms and large leaves, frames the view of the tranquil Lake Maria Sanchez, providing a peaceful setting for gatherings.

Home in Lincolnville

Lakeside Retreat |Private Pool| 8min walk Downtown

A fenced-in backyard features a heated pool, surrounded by a paved patio and shaded by mature bamboo. Two lounge chairs and two adirondack chairs are positioned nearby. A storage shed stands in the background, while an umbrella provides additional shade.

4.97 out of 5 average rating, 104 reviews

Oasis Pool House! Close to DT, Beach & Boat ramp

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.

4.94 out of 5 average rating, 132 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

An inviting pool area features lounge chairs and a vibrant mural, while an outdoor dining space with a large table is prepared for gatherings. Inside, a serene bedroom showcases soft colors and modern furnishings. A playful bunk room is also designed for fun and relaxation.

5 out of 5 average rating, 112 reviews

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

The home features a modern design set against a serene backdrop of trees and greenery. A spacious driveway leads to the entrance, framed by well-maintained lawns and landscaped shrubs. The exterior showcases large windows and a combination of muted colors, contributing to a harmonious appearance.

4.84 out of 5 average rating, 245 reviews

Spacious St. Augustine Home "The Gold Knocker"

A wooden gate opens to reveal a serene backyard with a heated saline pool surrounded by landscaped greenery. A shaded seating area and lounge chairs are visible near the pool, along with a dining space and umbrella, providing a relaxed outdoor ambiance.

4.97 out of 5 average rating, 151 reviews

Charming Downtown Cottage with Private Pool!

Apartment rentals with a pool

The spacious living room features large windows offering panoramic views of the ocean. An extra-large sectional couch provides ample seating, complemented by a central coffee table. A flat-screen TV is mounted on the wall, while a dining area is visible through the glass doors leading to the balcony.

4.95 out of 5 average rating, 101 reviews

Bella Coastal View with Ocean Views sleeps 6

A bright, enclosed balcony is depicted with a comfortable chair, a small table, and a decorative area rug. Large glass windows showcase expansive ocean views, while light wood paneling complements the aqua-tiled feature wall. Ocean breezes are welcomed through the open layout.

4.93 out of 5 average rating, 105 reviews

Newly Remodeled Ocean View Condo-Upgrades Galore!!

A view of the ocean and sandy beach is captured from the balcony. Lush green shrubs and grasses line the perimeter, enhancing the natural setting. The boardwalk is visible, leading to the beach, under a clear blue sky.

4.9 out of 5 average rating, 138 reviews

Sunrise Special | Steps to Beach | Ocean Front

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.

4.93 out of 5 average rating, 156 reviews

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

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.

4.94 out of 5 average rating, 135 reviews

Summerhouse - Direct Oceanfront Corner Unit

A view from the balcony showcases a wooden walkway leading to the ocean, bordered by lush greenery. The expansive sea is visible, with gentle waves and a clear sky dotted with clouds. Two cups are placed on a table in the foreground, inviting relaxation.

4.93 out of 5 average rating, 105 reviews

Seagrass Condo - ocean front, 1 bedroom/1bath

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.

4.98 out of 5 average rating, 107 reviews

Family Beach Condo - Steps To The Sand Or Pool

Apartment in St. Augustine Beach

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, 168 reviews

Ocean Side Complex with Heated pool B-24

Other holiday 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.

5 out of 5 average rating, 12 reviews

Luxury Home with Pool, Pickle Ball and Hot Tub

An aerial view of a modern beach house showcases a private heated pool surrounded by lounge chairs and lush landscaping. The ocean is visible in the background, along with neighboring homes. A spacious patio area features shaded seating and vibrant greenery.

5 out of 5 average rating, 50 reviews

Private Pool | 3 King Suites | Steps to the Beach

Townhouse in St. Augustine

A view from the patio features a wooden boardwalk leading to the beach, surrounded by lush greenery and palm trees. The sky is bright with scattered clouds, reflecting a sunny beach scene. The well-kept grass area invites outdoor leisure.

4.97 out of 5 average rating, 34 reviews

Nights of Lights Deals- Oceanfront Luxury Home!

Guest house in East Palatka

The rustic boathouse is positioned near a scenic wooden dock extending into the river. Sunlight reflects off the water while a peaceful horse stands nearby, surrounded by lush greenery. The weathered exterior of the boathouse complements the natural setting.

4.92 out of 5 average rating, 92 reviews

Charming Rustic Boathouse

Apartment in Treasure Beach

A bright living area features light wood flooring and soft beige walls. A comfortable sectional sofa and armchair are arranged around a wooden coffee table. Natural light filters through large windows dressed with light curtains, while a ceiling fan adds to the relaxing ambiance.

4.9 out of 5 average rating, 70 reviews

The Nest at Quail Hollow Oceanside 2br/2bth condo

A modern cottage exterior is highlighted, featuring a serene pool surrounded by stylish lounge chairs. A shaded patio area, framed by lush greenery, includes a pass-through window that opens to the kitchen. The warm tones of the roof contrast with the vibrant landscaping.

5 out of 5 average rating, 51 reviews

The May House - Heated Pool - Historic Downtown

5 out of 5 average rating, 24 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 St. Augustine

Modern Coastal Retreat