House holiday rentals 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.

4.98 out of 5 average rating, 119 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.

The historic home features a grand façade with elegant columns and a decorative balcony. A wrought iron gate opens to a brick pathway leading to the entrance. Large windows allow for ample natural light, framed by soft garden landscaping against a vibrant sunset backdrop.

4.97 out of 5 average rating, 421 reviews

Genovar Mansion Rose Garden Suite Private Entrance

The direct view of a gorgeous live oak canopy on Magnoila Avenue and incredible architecture make this historic home a memorable place to stay. This romantic ground floor suite is perfect for couples with a private entrance, queen poster bed, living room, spacious bathroom, individual climate control, heirloom antiques and reserved driveway parking spot. The home is located within the historic district, close to trolley stops and within easy walking distance to downtown. 6 minutes to the beach.

A modern kitchen features sleek gray cabinetry and a striking wood-accented range hood. An island with seating for four complements a large dining table with additional seating for six. Stylish decor and ample lighting create a functional and inviting cooking space.

4.99 out of 5 average rating, 150 reviews

Unmatched Luxury + Just Renovated + Dream Getaway!

💰No nickel & diming—AirBnb & cleaning fees in nightly rate! 🏡Luxurious modern design w/ historic charm 🔥Cozy outdoor fire pit for relaxing evenings 🛏️Best Sleep Guarantee-Mattresses are Westin Heavenly beds 👩‍💻Dedicated workspace & reliable top-speed internet for top productivity ✔️Luxury toiletries,plush linens & household supplies 🐕Bring your whole family, pet-friendly space! 🏖️Complimentary beach gear for fun in the sun 🚴5-minute bike ride to downtown 🍳Fully stocked gourmet kitchen!

A cozy living area is highlighted by a neutral-toned sofa and a wooden coffee table, all set on a textured area rug. A large mirror adds depth while soft natural light filters through the windows. A small plant and decorative items enhance the inviting feel.

4.97 out of 5 average rating, 237 reviews

Uptown Attic - Your Secret Escape

Located in the desirable Uptown District in Historical Downtown St. Augustine, this charming early 1900’s home is the perfect local experience. Featuring alley access to a private driveway with a designated one car parking spot, this newly renovated apartment is steps from all of the city’s hot spots. Guests can easily walk or bike to all of the famous tourist attractions, fantastic dining, and even the area’s famous beaches. This cozy space is also the perfect escape to just stay in and relax.

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, 105 reviews

Welcome to Pink Palms - Heated Pool - Walk to DT

🏝️ 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

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, 108 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

The contemporary two-story home features a modern exterior with a mix of horizontal and vertical siding. A balcony is visible on the second floor, accompanied by a small table and chairs. A fully fenced yard surrounds the property, with palm trees adding to the landscaping.

4.97 out of 5 average rating, 164 reviews

LUX Riberia – 311 | 12-min walk to Historic DTN

LUX RIBERIA COLLECTION - Contemporary, architectural magnificence located in the heart of the eclectic Lincolnville neighborhood in Downtown St. Augustine. Effortlessly explore the Oldest City with a quick 12-min walk into the Historical Downtown for all the top sights, hottest bars & restaurants. Two-story, minimalist style home with double heighted ceilings, fits 6 guests spaciously across the 2 BD, 2.5 BA layout with fully fenced backyard. Views of San Sebastian River perfect for Sunsets.

A spacious waterfront deck offers lounge seating with blue cushions, set against a vibrant sunset sky filled with pink and orange hues. A hammock is positioned nearby, with palm trees framing the stunning view of the water and docks in the background.

5 out of 5 average rating, 131 reviews

Waterfront - Lion’s Bridge & Old Town View

Walk across the Bridge of Lions to downtown St. Augustine with amazing restaurants and attractions. Half a mile to historic downtown! Less than 1 mile to the Castillo de San Marcos fort. Anastasia State Park Beach, the world famous Alligator Farm and Zipline, and the lighthouse are less than two miles away. Several restaurants and bars only a few blocks away. Whether going to the old fort, lighthouse or Flagler College, our home provides a great base for exploring an amazing part of Florida!

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, 125 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

A modern home with a distinctive triangular roof stands among lush greenery. A manicured lawn extends in front, bordered by palm trees. The building features a combination of light-colored siding and wooden accents, with a small balcony that adds to its architectural charm.

5 out of 5 average rating, 104 reviews

Luxury Modern Home in Prime Location 2BDR-3BTH

Book your Fall vacation with us! Our contemporary home offers comfort, elegance, and curated amenities. Explore the historic downtown, climb the lighthouse, enjoy live performances, indulge in local cuisine, and relax on the nearby beach. The Lighthouse Beacon is the perfect retreat for families and friends, catering to all preferences. Experience the magic of Saint Augustine and create cherished memories. Book your stay now and let us be your guiding light in this captivating city.

4.96 out of 5 average rating, 171 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.

A hot tub is positioned on the deck, offering a view of the ocean and white sandy beach in the distance. Two houses flank the view, while lounge chairs are visible in the shared yard, contributing to the inviting outdoor space.

4.96 out of 5 average rating, 191 reviews

Luxurious Oceanfront Home

Beautiful, oceanfront home professionally designed with luxurious finishes and incredible ocean views. Relax on the sprawling back deck overlooking the water after a game of bocce ball. Stroll down the private sidewalk, just steps to the beautiful, white-sand beach. Cook a gourmet meal in the state-of-the-art kitchen, or grill out on the deck using the gas grill. Sit around the fire pit under the stars and roast marsh mellows while listening to the ocean waves.

Popular amenities for house rentals in St. Augustine

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.

5 out of 5 average rating, 13 reviews

Luxury Home with Pool, Pickle Ball and Hot Tub

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

Heated Pool/Hot Tub 1 mile to dwntn/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

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, 105 reviews

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

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, 52 reviews

The May House - Heated Pool - Historic Downtown

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, 133 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

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!

Weekly house rentals

A charming white cottage showcases a welcoming porch adorned with hanging planters. An American flag flutters by the entrance, while a gravel pathway leads up to the home, surrounded by manicured greenery and shaded by large trees, creating a serene exterior setting.

5 out of 5 average rating, 89 reviews

Palo Haus 1918 Cottage in Downtown St. Augustine

5 out of 5 average rating, 10 reviews

New! Hot Tub! Walk to Historic District! Fire Pit!

A charming two-story house features a pale pink exterior with white trim and a spacious balcony. Lush palm trees surround the property, and a driveway leads to a garage beneath the home. The serene setting is complemented by a clear blue sky in the background.

5 out of 5 average rating, 24 reviews

Lighthouse View/Amp/Beach/Town

The exterior of a modern two-story home is displayed, featuring a mix of light and dark gray materials. A welcoming entrance is accessed by a set of stairs, with landscaped areas visible on both sides, including palm trees and shrubs.

4.96 out of 5 average rating, 72 reviews

192 Riberia Downtown Luxury Home

The exterior of the house showcases a charming pink facade framed by wooden shutters on the windows. A decorative front door with dual handles is situated centrally, while a paved walkway leads to the entrance, surrounded by greenery.

4.98 out of 5 average rating, 53 reviews

Historic Home in Downtown St. Augustine

The exterior of the tiny house is shown, featuring a light green facade with white trim. A wooden front door with a decorative wreath is centered beneath a small overhang. Natural sunlight casts shadows from nearby trees, and a fenced yard is visible alongside well-maintained shrubs.

4.95 out of 5 average rating, 38 reviews

Saint Augustine Pecan House

A bright living area features a green couch adorned with colorful cushions, paired with a cozy coffee table and patterned seating. Large windows allow natural light to fill the space, while a ceiling fan enhances airflow. A decorative rug complements the earthy tones of the room.

4.93 out of 5 average rating, 59 reviews

Newly Renovated Whimsical Cottage, 2 Beds, Hot Tub

5 out of 5 average rating, 21 reviews

Walk Downtown •King Bed Cottage •Nights of Lights

Private house rentals

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, 53 reviews

Private Pool | 3 King Suites | Steps to the Beach

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, 53 reviews

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

A spacious living area features a comfortable brown leather sofa and two accent chairs. The room is enhanced by a decorative fireplace with a herringbone pattern and soft natural light streaming through large windows. Light wood flooring complements the overall airy aesthetic.

5 out of 5 average rating, 70 reviews

Luxury Retreat | St. Augustine | Beach + The Amp

A charming coastal house is depicted with a traditional exterior, featuring dark shingles and a welcoming porch. A staircase leads to the entrance. The background is graced with a colorful sunset, casting soft light over the surrounding greenery and homes.

4.91 out of 5 average rating, 76 reviews

Oceanfront Rustic Cottage by the Sea

4.9 out of 5 average rating, 21 reviews

Great house, excellent location!

The sitting room features a blend of warm green and golden hues. A brown leather sofa is adorned with colorful pillows, complemented by a green accent chair. Sunlight filters through the white window blinds, illuminating a vibrant area rug and a piece of art depicting a pelican.

5 out of 5 average rating, 95 reviews

La Rêverie | Downtown Boutique, Historical Chic

4.96 out of 5 average rating, 25 reviews

Adults Only Themed Kink BDSM Role Play Bondage

A wooden dock extends over calm water, leading towards a vibrant sunset. Tree silhouettes frame the scene, while soft, warm colors reflect off the water's surface, creating a serene atmosphere that enhances the natural beauty of the waterfront.