House holiday rentals in Historic District, St. Augustine

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, 439 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 two-story house is presented with a classic design, featuring large windows with green trim. Two small chairs are positioned on the porch, which is adorned with soft white curtains. Lush greenery surrounds the exterior, creating a welcoming entryway.

4.85 out of 5 average rating, 220 reviews

Uptown Classic 2 | Effortless Exploration of STA

Uptown Classic #2 is a 2BD/1BA home (1st floor) that sleeps 6 and is located in the heart of St. Augustine. Effortlessly explore the Oldest City with the ease of a 5-min walk to St. George Street - Top sights, local award-winning bars & restaurants surround the home in all directions. Each space features a true mark of distinction with casual, elegant living from the double height living room to the outdoor patio. 5-min drive to the beach.Pet-Friendly: Must send message 4 approval- Pet fee $98.

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, 249 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.

A spacious backyard is highlighted by a private round pool, surrounded by lush greenery and palm trees. An outdoor cabana features a bar area, while a well-maintained lawn adds to the inviting atmosphere. The charming pink structure complements the serene setting.

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

A spacious living room features a light-colored sofa adorned with decorative pillows and a glass coffee table. Two elegant armchairs with floral patterns are placed beside the sofa, and natural light streams through large windows adorned with wooden shutters. A cozy area rug anchors the seating area.

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.

The home’s exterior is characterized by a modern architectural style with a covered front porch featuring four rocking chairs. A wide concrete path leads to the entrance, flanked by well-maintained green landscaping under a clear blue sky.

4.98 out of 5 average rating, 205 reviews

Newly built w/garage In The Heart of St.Augustine

Click [♡ Save] button to easily find this listing again before your dates are booked. Great walkable location on a safe quiet street; Spacious and nice for entertaining and relaxing. Bikes and beach chairs included. Very comfortable beds. The porches have rocking chairs too. The home is on one level which is also nice for elderly with mobility challenges. Guests say this is a convenient stay for local weddings, special events¸ and an enjoyable vacation. Send us a message to plan your stay.

A modern kitchen is presented with sleek white cabinetry and a striking granite countertop. Stainless steel appliances are neatly arranged, and a large sink is installed in the island. A textured black backsplash complements the overall design, creating a functional cooking space.

4.93 out of 5 average rating, 162 reviews

Historic 10 Dupont Lane

In St Augustine's historic neighborhood. Completely modernized, but we kept the old charm. New everything. Included amenities bikes, BBQ, Fire pit, outdoor lounge furniture, private patio, laundry inside, Nespresso maker, coffee included, soaps and shampoos, beach essentials. Everything you need is here. Just bring your suit case. 5-10 minute walk to the center of town. Catch the trolly at the end of the street. Buy your tickets here and receive a discount. Welcome to a fun memorable stay.

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, 211 reviews

Historic St. Augustine 2/2 Duplex & Pool

About this space: Welcome to this 2 unit home located in Historic St. Augustine. This home is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This home has 2 bedrooms and 2 full bathrooms, a living room, kitchen, den and direct pool access. This space: This home is a 2 unit house Guest access: There is a lockbox on the door with a key inside Other things to note: Please keep in mind that the pool is a shared space :)

A serene outdoor space is surrounded by lush green palm trees and various potted plants. Soft gravel covers the ground, with pathways leading to a green door, enhancing the natural ambiance of the area.

4.96 out of 5 average rating, 108 reviews

Luxe Lemon Lower in Historic Downtown St Aug.

Stay in the heart of Historic Downtown St Augustine in this 100yr old 2BR/1B completely renovated in 2023! Only a 7 min walk to Downtown a 12 min drive to the beach, you'll love this charming home! Guests should be adults or older children. 1 parking space available. Note: The loft atop this unit is also rentable, w/ connected or disconnected private entrance, & sleeps 2. Ask us or search "AirBNB Lemon LOFT" or "AirBNB Lemon WHOLE" to rent loft or the whole house.

A spacious bedroom features a king size bed adorned with soft linens and decorative pillows. Two bedside lamps provide gentle lighting. A comfortable bench sits at the foot of the bed. Large glass doors lead to a serene patio area, while sheer curtains allow natural light to enter.

4.96 out of 5 average rating, 327 reviews

Calm cozy couples cottage close to Downtown & Bch

Enjoy St. Augustine – the nation’s oldest city – and everything it has to offer from this cozy, beach themed 1 bed / 1 bath getaway. Located near the heart of the city, it is close enough to walk to the historic St. George Street while also maintaining privacy and quiet comfort. With new, modern amenities, a back porch, a yard, and ample dedicated parking, this home is everything you could want on your trip to beautiful St. Augustine, Florida.

The compact kitchen features modern appliances, including a coffee maker, kettle, and stovetop. A stainless steel sink is situated on a wooden countertop, while a window offers a view of the serene outdoor space. The overall design blends functionality with a clean aesthetic.

4.8 out of 5 average rating, 166 reviews

Safe Haven, Unique two story carriage

Our romantic "Safe Haven" is compact upscale living in a two-story carriage house located 3 blocks from St George St and steps from shopping and dining! Private garden in the back and a shared garden and patio out front. Also Safe Haven House offers a private balcony! Queen bed & shower upstairs in bedroom, basic kitchen essentials (no spices) , laundry, sitting area & TV downstairs. FREE Private and Street parking.

A charming blue cottage is surrounded by lush greenery. The front porch features decorative railings and shutters, while the vibrant yellow front door stands out. The brick pathway leads to an inviting entryway, with large windows allowing natural light to fill the space.

4.88 out of 5 average rating, 146 reviews

Historic St. Augustine Cottage, Movie Loft & BBQ

- Discover the charm of Blue Bell Cottage in the heart of St. Augustine's Historic District. - Cozy movie loft with reclining sofas and a projector for a home theater experience. - Beautiful private patio featuring a BBQ grill, fountain, and tranquil outdoor seating. - A short walk to Ripley’s, the fort, and downtown’s best shops and restaurants. - Book your stay today and enjoy a peaceful retreat in a prime location.

Popular amenities for house rentals in Historic District, St. Augustine

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, 105 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

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

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!

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

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, 150 reviews

Charming Downtown Cottage with Private Pool!

A private heated pool is surrounded by a spacious patio designed for relaxation. Comfortable lounge chairs are positioned nearby, alongside a well-maintained yard with decorative plants. The pool house features a playful mermaid mural on its exterior, adding a touch of charm to the outdoor space.

4.93 out of 5 average rating, 134 reviews

Splash & Explore

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

A modern white house is depicted with a covered entrance and a spacious patio area. A heated saltwater pool sits in the foreground, surrounded by a fenced yard. Two lounge chairs are positioned nearby, with a charcoal grill visible at the edge of the pool area.

4.97 out of 5 average rating, 101 reviews

Walk to Beach! Heated Pool•Boat Parking•EV Charger

Weekly house rentals

The exterior of a cozy home is showcased, featuring a gravel driveway leading to a welcoming porch. Lush greenery surrounds the property, with wooden fencing providing privacy. Subtle outdoor lighting hangs above the porch, enhancing the inviting atmosphere.

5 out of 5 average rating, 46 reviews

2BR/2B Home-Walk to St. Aug

A stone pathway bordered by lush grass leads toward the ocean, where the sun sets on the horizon. The scene is framed by palm trees and greenery. A seating area with dark chairs is located on the right, providing a serene view of the beach.

4.99 out of 5 average rating, 114 reviews

The Coral Sea Casa- Oceanfront! Tiki bar!

4.97 out of 5 average rating, 30 reviews

Cozy 2BR • Walk to Dntn • 7 mins to beach

5 out of 5 average rating, 12 reviews

Eclectic•Colorful• Fun designer 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, 59 reviews

Historic Home in Downtown St. Augustine

A charming mid-century home features a welcoming front porch with seating. Lush greenery and Spanish moss surround the property, enhancing its tranquil setting. The entrance is marked by a slate stone walkway and a decorative sign, contributing to the home's inviting appearance.

4.95 out of 5 average rating, 159 reviews

Charming 3 bedroom cottage, feed the peacocks!

The living area features a spacious sectional couch with assorted cushions, facing a large television. Natural light streams through multiple windows. The dining area, visible in the background, includes a table for six and high-backed chairs, complementing the modern kitchen with bar seating.

4.92 out of 5 average rating, 102 reviews

Downtown St. Augustine Bungalow | Walk Everywhere

4.92 out of 5 average rating, 76 reviews

The Secret Garden On Locust!

Private house rentals

4.91 out of 5 average rating, 44 reviews

Historic St Augustine | Dog Friendly CourtyardArea

A modern home is showcased in a spacious backyard, highlighted by a fire pit and cozy outdoor seating. Lush palm trees surround the area, while warm evening light enhances the inviting exterior of the house.

5 out of 5 average rating, 58 reviews

Coastal Retreat | 2 Kings | Fire Pit | 1m Downtown

4.95 out of 5 average rating, 83 reviews

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.

Home in Lincolnville

192 Riberia Downtown Luxury Home

A serene bedroom features a spacious bed with a textured white coverlet, complemented by decorative star motifs on the wall. A small bedside table holds a floral arrangement, while natural light filters through sheer curtains, contributing to a calming ambiance.

5 out of 5 average rating, 18 reviews

I bed-1bath on 2nd fl in Uptown - Free parking

5 out of 5 average rating, 39 reviews

Private Cottage • Walk to Downtown • King Bed

The living room features a plush deep blue velvet sectional sofa with bright yellow pillows, positioned around a rustic wooden coffee table. A large television is mounted on the wall, while a vibrant abstract mural adds a colorful backdrop to the room. Natural light flows in from a nearby door.

4.99 out of 5 average rating, 85 reviews

Cozy Romantic Luxury Retreat • Sauna • Fire pit

5 out of 5 average rating, 24 reviews

New! La Cabanita | Historic 1882 Cottage Downtown