Holiday rentals with a pool in Vilano Beach

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, 127 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.

4.99 out of 5 average rating, 113 reviews

Backyard Oasis w/Heated Pool, Game Room, Fire-pit

Welcome to your dream vacation home - a perfect retreat designed for families & friends seeking to escape & relax in style. This stunning home is a blend of modern luxury & family-friendly amenities that make it ideal for both relaxation & fun. Soak up the sun by a heated pool, challenge each other in the game room, or find your zen with a yoga session - there’s truly something for everyone! The proximity to the beach, St. Augustine, & boat ramp makes it super convenient for exploring the area.

An outdoor cabana area is presented, featuring a pool table and bar seating alongside a private heated pool. Surrounding lush turf and palm trees create a serene environment. The space is illuminated by recessed lighting, enhancing the inviting vibe for relaxing and entertaining.

5 out of 5 average rating, 113 reviews

Pink Palms *Heated Pool* 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, recessed lights and seating - Walking distance to the Castillo de San Marcos Fort, Fountain of Youth, Uptown shops, The Bayfront and St. George Street - Less than 10 mins to Vilano Beach 🌊 - Sleeps 6/ 2 King beds, 2 XL twin beds (daybed trundle) - Pet Friendly - Event Venue

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.

4.95 out of 5 average rating, 206 reviews

Downtown HistoricLuxury • Designer Kitchen & 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.

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, 417 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.

4.94 out of 5 average rating, 166 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 St. Augustine

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.

An inviting outdoor pool area features a heated pool surrounded by lounge chairs and a large umbrella. Soft lighting illuminates the space, highlighting the wooden fencing and lush greenery in the background.

4.98 out of 5 average rating, 176 reviews

"Once Upon A Tide" Beach House *Heated Pool* King

Welcome to Once Upon a Tide Beach House in Vilano Beach (Salted Heated Pool) This brand new luxury beach house is in a perfect location. 3 blocks to the beach , 1 block to the intracoastal . A short drive to Historic Downtown St. Augustine. Very spacious and well pointed home with 2 living rooms, the main living room is on the first floor and a second living room is upstairs in the loft area. Private back yard oasis with a salted heated pool, cabana. I promise you will not want to leave!

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, 135 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 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, 164 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!* No Cleaning Fee! No Surprise Fees! >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.)

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, 132 reviews

Tide Pool - Heated Pool/Hot Tub/Golf Cart

Welcome to Tide Pool! Built in 2020 and decorated with an eclectic beach flair using art and decor from the original owner's world travels. It has 4 bedrooms: Master on 2nd floor with king bed - Master on 3rd floor with king bed - Bedroom on 3rd floor with queen bed - Bedroom on 3rd floor with 2 queen beds. The outside of the home features a heated pool, hot tub, outdoor seating, fire pit, corn hole, and a rooftop deck with panoramic views of the ocean and historic St. Augustine.

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, 169 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.

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, 175 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.

Popular amenities for Vilano Beach rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 59 reviews

Private Pool | 3 King Suites | Steps to the Beach

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, 121 reviews

Luxury heated pool steps from the beach -pool bar!

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, 433 reviews

Your Home Away From Home

The outdoor area features a private pool surrounded by palm trees and greenery. Lounge chairs with blue cushions are arranged by the poolside, complemented by striped umbrellas. Potted plants with vibrant flowers add color to the space, creating a tranquil setting for relaxation.

5 out of 5 average rating, 144 reviews

Private oasis, heated pool, exceeds expectations

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, 141 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

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.

4.97 out of 5 average rating, 101 reviews

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

The outdoor pool area features a sparkling pool surrounded by paver stones. Comfortable loungers, including a sectional and two egg chairs, create inviting relaxation spots, with greenery providing a natural backdrop. String lights are hung above, enhancing the cozy ambiance of the space.

5 out of 5 average rating, 46 reviews

Beachside CasaAzul! Heated Pool Spa Oasis!

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, 123 reviews

The Salty Seashell, Coastal Pool Home, Sleeps 8

Apartment rentals with a pool

Apartment in St. Augustine Beach

A swimming pool is surrounded by lounge chairs, with palm trees providing shade in the background. Blue skies and scattered clouds create a bright atmosphere. The pool area features a smooth surface and a safety railing on one side.

4.84 out of 5 average rating, 267 reviews

Ocean Side Complex w/ Heated Pool B-15

An open living area features a light-toned laminate floor and a spacious dark sofa facing a wall-mounted TV. A white coffee table sits in front of the sofa, while two wooden stools are positioned nearby. The kitchen is visible in the background, with natural light coming through the window.

4.86 out of 5 average rating, 282 reviews

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool

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.

4.97 out of 5 average rating, 238 reviews

Ocean Front Gem: Top Floor Corner Unit

4.79 out of 5 average rating, 269 reviews

Sand & Surf! Nights of Light Deals-Oceanfront Pool

An expansive view of a serene beach is captured, featuring soft sand and gently lapping waves. Sparse vehicles are seen along the shoreline, with stretches of greenery and dunes adding texture to the landscape. The horizon showcases a clear blue sky, merging with the ocean.

4.91 out of 5 average rating, 227 reviews

St Augustine Beach, comfy condo

Superhost

A sandy beach stretches into the distance, meeting calm ocean waters under a clear blue sky. Gentle waves can be seen lapping at the shore. A wooden boardwalk winds through the grassy area, leading down to the beach, where a few umbrellas and people can be spotted.

4.86 out of 5 average rating, 347 reviews

Oceanfront 1st Floor-Crescent Beach

Apartment in Treasure Beach

4.95 out of 5 average rating, 144 reviews

Beachfront! Creston by the Sea, 11D!

5 out of 5 average rating, 103 reviews

2 BR Condo in St Augustine across from Beach

Other holiday rentals with a pool

Home in Ponte Vedra Beach

4.8 out of 5 average rating, 44 reviews

3 Bed 3 Bath Oceanfront Home Ponte Vedra Florida

A modern coastal retreat features a welcoming front facade with a light-colored exterior and dark-shingled roof. A decorative ship's wheel is mounted above the garage, complemented by a paved driveway and a lush green lawn. Two inviting porch chairs are set on the covered entryway.

5 out of 5 average rating, 29 reviews

4BR Heated Pool, Walk to Beach, Double Master BR!

An outdoor pool area is framed by a spacious patio featuring lounge chairs and an outdoor dining set. The large heated pool reflects the clear blue sky, and shaded areas are created by an umbrella. The surrounding landscape includes trees and fencing for added privacy.

4.98 out of 5 average rating, 61 reviews

1 Block to Beach! Heated Pool, Near Historic Dist.

A private backyard features a sparkling blue pool surrounded by a tiled deck. Lounge chairs are positioned on one side, while vibrant red chairs sit nearby. Sunlight filters through the trees, creating a serene atmosphere in the outdoor space.

4.95 out of 5 average rating, 73 reviews

Beach House, Pool, Golf Cart, Game Room, BBQ,

5 out of 5 average rating, 61 reviews

The May House - Heated Pool - Historic Downtown

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.

4.95 out of 5 average rating, 91 reviews

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

5 out of 5 average rating, 25 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