House vacation 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, 420 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 welcoming porch is highlighted by an orange umbrella providing shade. Lush greenery and potted plants surround the entrance to the cottage, which features a decorative front door. Comfortable seating is visible, creating a cozy outdoor space for relaxation.

4.91 out of 5 average rating, 173 reviews

Historic St. Augustine Cottage - Walk everywhere!

*OLD FLORIDA: A charming 1920s bungalow in a peaceful neighborhood. *WALKABLE to everything old town *PRIVATE PARKING. (BEWARE: “Street parking” means first come/first served). *FIRE PIT (wood provided) *BIKES *HAMMOCK *OUTDOOR SHOWER: hot/cold *BBQ grill: charcoal provided This cozy 1 bed/1 bath has a queen bed, a living room with daybed/trundle, fully stocked kitchen, W/D, TV, WiFi, Dogs allowed: $100 fee. Located only 0.4 miles from downtown—(check distance when others say “walkable”)

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, 236 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.

The kitchen is equipped with modern stainless steel appliances, including a refrigerator and dishwasher. Black cabinetry complements the white countertops. Natural light streams in from a window above the sink, adorned with a small plant, enhancing the functional layout.

4.85 out of 5 average rating, 346 reviews

Cozy, Pet-friendly Private House near downtown

Cozy, pet-friendly house with full kitchen and laundry facilities 1.5 miles from the center of historic downtown St Augustine. 6 miles from beaches. Down to earth vibe. Fenced yard. Good quality mattresses on both beds (Tempurpedic in master and Sealy pillow-top in the other). Driveway parks up to two cars. Walking distance to several bakeries and restaurants and a convenience store. Large dog crate provided. Happy to provide local recommendations - we love it here and want you to love it, too!

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.

4.98 out of 5 average rating, 194 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 :)

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.

4.99 out of 5 average rating, 214 reviews

Downtown • Historic Luxury • DesignerKitchen&Baths

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.

A spacious master bedroom features a king bed with white bedding and a gray upholstered bed frame. Natural light enters through large windows with blinds. A small side table and lamp are present, along with a bench at the foot of the bed, creating a welcoming environment.

4.93 out of 5 average rating, 111 reviews

Orange St Gem | 8-min walk to St. George St & Fort

Welcome to our charming 3BR/1.5BA home in the heart of historic downtown St. Augustine. With its central location just an 8-min walk (.5 mile) from St. George Street, Castillo de San Marcos, and the hottest bars and restaurants in the city - Perfect home base when exploring St. Augustine, the home struts a fully fenced, private backyard and 2x balconies that allow for enjoying the Florida sun! 8-min drive to Vilano Beach, 14-min drive to St. Augustine Beach.

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, 308 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 charming exterior of the house is framed by lush greenery, with a well-maintained front yard and a white picket fence featuring decorative accents. Soft lighting highlights the inviting entrance, enhancing the serene atmosphere of the property.

4.99 out of 5 average rating, 186 reviews

Fun & Artsy 3BR/2BACottage in Downtown St. Aug

Discover serenity in this charming, hidden gem nestled in a quaint downtown neighborhood. A short stroll will lead you to vibrant festivals at Francis Field and St. Augustine's finest dining, bars, tours, and more. Art, music, and local culture are woven into the very fabric of this locale. Whether you're unwinding with a movie, savoring morning coffee in the backyard, or lounging on the front patio, we've curated the perfect escape.

A dining area is featured with a blue table at its center, surrounded by four wooden chairs with woven seats. Natural light filters through bamboo shades on the windows, highlighting a wooden sideboard displaying beach-themed decor.

4.98 out of 5 average rating, 116 reviews

Perfect One Bedroom Cottage in Lighthouse Park

One bedroom one bath cozy cottage vibe! Perfect couples retreat. This is one half of a duplex. The second half is currently vacant. Excellent location. 5 blocks to the lighthouse. 1 mile to historic downtown. 1.3 miles to the Amphitheater. 0.8 miles to Anastasia State park. 3 miles to the St. Augustine Beach Pier. Walking distance to many great restaurants and bars, mini golf, and boutique shops! Walk or bike to downtown!

The exterior of La Casita features a welcoming porch with seating for two, surrounded by greenery and flowering plants. The entrance is marked by a decorative clock, while the landscape includes gravel areas and a fire pit, creating an inviting outdoor atmosphere.

4.95 out of 5 average rating, 177 reviews

“La Casita” A Charming Uptown St Augustine Cottage

La Casita is located in the Uptown Shopping District. We have darling coffee shops just at the end of the block. Shopping and a convenience store too. We are just 2 blocks from the trolley shop snd visitors center..and, just a 10 min walk to downtown and the fort! We are just a 2 min walk to Francis Field, where many festivals are held. A 7 minute drive to Vilano beach! We are in a quiet and charming neighborhood.

Superhost

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, 138 reviews

Charming Historic Cottage with Movie Loft & Patio

- 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 Historic District, St. Augustine house rentals

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

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!

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, 422 reviews

Your Home Away From Home

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

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, 117 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, 124 reviews

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach

Superhost

A modern home features a welcoming front porch with seating and large windows, surrounded by lush green landscaping. A palm tree and decorative plants accent the well-maintained lawn, contributing to the inviting exterior. The driveway provides ample space for parking.

4.91 out of 5 average rating, 114 reviews

new 4 bedroom home, 2 master-suites and pool

The front exterior of the Dolphin house presents a mid-century modern design, framed by two palm trees. A stone pathway leads to the entrance, surrounded by lush green grass and planted flowers. Two turquoise chairs are positioned on the porch, inviting relaxation.

4.88 out of 5 average rating, 137 reviews

Best of Both Worlds- Family Oasis

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, 87 reviews

Palo Haus 1918 Cottage in Downtown St. Augustine

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

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

The exterior of the home is showcased, featuring wooden stairs leading to the upper deck. Lush green grass surrounds the property, accented by decorative landscaping and palm trees. A paved driveway provides access to a garage, with a wooden fence offering privacy.

4.88 out of 5 average rating, 138 reviews

Carriage Manor- Next to Fountain of Youth & Beach

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

4.91 out of 5 average rating, 65 reviews

The Secret Garden On Locust!

4.98 out of 5 average rating, 89 reviews

LaidBack Escape w/ Pool~Golf~PacMan*Near Downtown

A serene screened-in porch features a comfortable loveseat and a pillowed chair, surrounded by large windows with natural light. Decorative curtains and a ceiling fan enhance the tranquil atmosphere, while lush greenery is visible in the outdoor area beyond.

4.96 out of 5 average rating, 54 reviews

Villa 1928 “Pumpkin” Luxe Home- Hidden Gem

Private house rentals

A charming, single-story home with a brick pathway leading to the front door. The white exterior is complemented by green plants and landscaping. Shuttered windows and a decorative railing enhance the welcoming appearance. A subtle gabled roof and chimney complete the traditional look.

5 out of 5 average rating, 45 reviews

Cottage on Magnolia Ave-Walk to Uptown Shops

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, 28 reviews

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

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, 99 reviews

Luxe Lemon Lower in Historic Downtown St Aug.

A private backyard retreat features a heated pool surrounded by lush greenery and vibrant plants. Loungers are positioned on the pool deck, and a shaded dining area is included. A hot tub is integrated into the pool area, offering a relaxing escape amidst nature.

5 out of 5 average rating, 5 reviews

Downtown, Pool, Hot Tub, $300 in Free Tickets!

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 charming cottage exterior is framed by lush greenery, featuring a sloped metal roof and inviting porch steps. The front door is painted in a soft gray, while vibrant plants add pops of color beside the entrance, creating an inviting look for guests.

5 out of 5 average rating, 10 reviews

October discounts | Walk downtown |dog-friendly

5 out of 5 average rating, 18 reviews

Walk Downtown •King Bed Cottage •Nights of Lights

The charming exterior of Casa Del Sol features pastel blue siding adorned with vibrant teal accents. Lush greenery and colorful potted plants create an inviting entrance, while a sun motif adds character. The well-maintained pathway leads to a welcoming front door, enhancing the cottage's curb appeal.