Vacation rentals with a pool in St. Augustine Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in St. Augustine Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

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 St. Augustine

4.98 out of 5 average rating, 108 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.

Top guest favorite

A clear pool is surrounded by lounge chairs and colorful seating options. A vibrant beach ball floats on the water's surface. Lush greenery is visible beyond a white fenced area, and the sky is partly cloudy, enhancing the outdoor setting.

Home in St. Augustine

5 out of 5 average rating, 146 reviews

Short Walk to the Beach with Heated Pool

Our 4 bedroom, 2.5 bath house has 8 beds and a futon which can sleep 10 adults or 6 adults and 5 children. The spacious kitchen with a gas range is completely stocked with cooking utensils, pots, pans and spices to make delicious meals. Enjoy grilling on the back deck while watching beautiful sunsets. Ping pong matches can be enjoyed downstairs. Beach chairs, towels, boogie boards, umbrellas, beach wagon and toys are provided. Parking on premises. The pool deck has lounge chairs and a fire pit.

Top guest favorite

A large swimming pool is positioned within landscaped grass areas, surrounded by palm trees and lounge chairs. The ocean is visible in the distance, with accommodations flanking either side of the pool, creating a family-friendly environment.

Condo in St. Augustine

4.98 out of 5 average rating, 114 reviews

361 Fun in the Sun | Direct Oceanfront Ground Floor

Direct Oceanfront, ground floor flat unit, no stairs. Located in Crescent Beach at Summerhouse. Family oriented complex located on over 25 acres with four pools and large grass areas. Highly desired 2 bedroom unit. This property is ground level and directly oceanfront. Flat style layout not a townhouse, there are two steps to the front door but otherwise no stairs. Sliding door opens directly to covered back porch. Please see our our other property 461 More Fun in the Sun, 3 Bedroom

Top guest favorite

A view from the rooftop deck features a bright blue sky with fluffy clouds above. The inviting saltwater pool is visible below within a stone patio area, surrounded by lush greenery. Bar-height chairs and tables line the deck, offering a scenic spot for relaxation.

Cottage in St. Augustine

4.98 out of 5 average rating, 182 reviews

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.

Top guest favorite

The private saltwater pool and spa are surrounded by lush tropical landscaping, featuring a covered cabana and chaise lounge seating. The water glows softly in the evening light, with the spa situated adjacent to the pool, creating a serene atmosphere for relaxation.

Home in St. Augustine

4.99 out of 5 average rating, 107 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

Top guest favorite

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.

Condo in St. Augustine Beach

4.97 out of 5 average rating, 221 reviews

Ocean Front Gem: Top Floor Corner Unit

Top floor, direct ocean front, corner unit with elevator and beautiful unobstructed views of the beach from both bedrooms, living room, dining room, kitchen and private balcony. We have upgraded the condo and believe it to be the best condo in 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.

Top guest favorite

A spacious pool area is highlighted by a clear blue water surface, featuring a gentle sloping entrance. Lounge chairs are arranged around the pool, with palm trees providing shade in the background. Surrounding buildings display a warm architectural style, completing the inviting setting.

Condo in St. Augustine

4.96 out of 5 average rating, 190 reviews

Ocean Front Condo only Steps to the Beach.

Self-Check-In, Covid-19 Protocol Cleaning Utilized, Ground level, oceanfront unit w/ 2 bedrooms/2 baths at Sea Place, a quaint seaside community. Has updated kitchen & walk-in shower, washer/dryer, wifi, cable & covered patio. Amenities: 2 pools (not heated), tennis, racquetball, & beach access; 4 beach chairs & umbrella provided. Located near shops, restaurants & historic St. Augustine. 2 nights min stay. Max: 4 guests. No pets (per HOA), smoking or parties please. No BBQ grill per HOA.

Guest favorite

A spacious bedroom is furnished with a king bed, complemented by decorative pillows and a throw blanket. A large area rug with colorful patterns covers the tiled floor. Natural light enters through two windows, framed by light curtains, while a bedside lamp adds soft illumination.

Guest suite in St. Augustine

4.95 out of 5 average rating, 691 reviews

Sheepdog Hideway - on Anastasia Island near Amp!

Awesome, private guest suite located on Anastasia Island near the St Augustine Amphitheater! Walking distance to Anastasia State Park! Enjoy staying on the island without all the hustle of a hotel. We have beach cruiser bikes available for use! We are 1.5 miles from the closest public beach access and a 3 mile bike ride to downtown St Augustine! Update for COVID-19 pandemic: We will be spraying all hard surfaces with EPA-approved sanitizer to do our best to make sure surfaces are safe.

Top guest favorite

The exterior of the house features a wrap-around porch with white railings, complemented by shaded areas and lush landscaping. A brick pathway leads up to the entrance, framed by palm trees and greenery, showcasing a welcoming facade against a clear blue sky.

Home in St. Augustine

4.99 out of 5 average rating, 202 reviews

HistoricLuxury•Designer Kitchen&Baths•Walk&Trolley

No Cleaning Fee! 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 3-BR Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury bath. 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 favorite

A cozy living area features soft beige furnishings and decorative blue pillows. A wooden coffee table occupies the center, while a stone fireplace adds warmth. Large sliding doors provide natural light and reveal views of the outdoors, framed by sheer curtains.

Condo in St. Augustine Beach

4.95 out of 5 average rating, 110 reviews

Steps to Beach, Bikes & Beach Equipment Included!

Discover your perfect getaway at our beautifully updated condo in St. Augustine Beach, FL. With pristine oceanfront views and convenient beach access, our 2-bed, 2-bath retreat is a relaxing haven. Enjoy a fully equipped kitchen, comfortable living area, and private balconies. Exclusive community amenities include a private beach boardwalk, pool, and hot tub. Beach essentials, bicycles, and the proximity to shops, restaurants, and downtown make this the ideal beach retreat.

Top guest favorite

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.

Home in St. Augustine

4.96 out of 5 average rating, 158 reviews

Dune Bungalow

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.

Guest favorite

A circular pool is surrounded by a stone patio, with several lounge chairs positioned around the perimeter. Palm trees stand nearby, and a multi-story building is visible in the background, completing the tranquil resort atmosphere.

Condo in St. Augustine

4.9 out of 5 average rating, 121 reviews

Oceanfront Retreat!

Welcome to our Oceanfront Retreat! Close to everything St. Augustine has to offer. Beautiful beach, outstanding restaurants, museums, magnificent architecture, and a strong history dating back to 1565. Everyone wants to feel relaxed and refreshed on vacation. We have created a space that is comfortable and inviting to accomplish just that. Equipped with new finishes to anticipate your needs for a luxurious vacation. We hope you enjoy our little piece of paradise!