Holiday houses in Historic District, St. Augustine

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Top-rated holiday rentals in Historic District, St. Augustine

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Top Guest favourite
A charming view of the Italian restaurant Pizzalley's, featuring a decorative balcony adorned with hanging plants. The building’s colorful facade complements the vibrant street lined with trees and vintage-style street lamps, creating a lively atmosphere in the historic district.
Apartment in St. Augustine
4.97 out of 5 average rating, 767 reviews

Balcony apt on USA’s oldest Street (St. George St)

"The Heart of St. Augustine" Voted #1 Airbnb in St Augustine by Trip 101, # 5 Top 10 Airbnb's in St. Augustine" by Territory Supply and in the "Top 15 Best Airbnb's in Florida" by Road Affair. Live music, scrumptious food, craft drinks, and the hustle and bustle of people walking the historic St. George St, all surround you. Relax and people watch from your balcony. Sightseeing, restaurants, trolley stop and nightlife are steps away. This apt is in the center of it all. NYE is a 3 night min

Top Guest favourite
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.
Home in St. Augustine
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.

Top Guest favourite
A charming guest house is presented with a front porch featuring a decorative railing. Lush greenery and a small white picket fence frame the landscaped yard, while palm trees provide shade. The exterior showcases a light color palette, with contrasting trim and a welcoming entrance.
Apartment in St. Augustine
4.94 out of 5 average rating, 345 reviews

The Rohde House, The Rohde Guest House

Our place is close to nightlife, public transport, the airport, the city square, and parks. It's good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). Five minute walk to the "Nights of Lights", two minute walk to Francis Field event field, where many festivals, concerts and activities are held. Five minute drive to the ocean beach at Vilano. Many Restaurants and bars in walking distance, including sports bar, martini bar, Irish pub and more.

Top Guest favourite
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.
Guesthouse in St. Augustine
4.95 out of 5 average rating, 400 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.

Guest favourite
A dining area is showcased with a wooden table surrounded by six chairs, featuring vibrant floral upholstery. A woven pendant light hangs above, illuminating the space. An ocean-themed mural adorns the wall, complemented by potted plants positioned nearby.
Apartment in St. Augustine
4.92 out of 5 average rating, 135 reviews

Charming Old-Florida Apartment

This darling Uptown apartment is in the thick of it! Next door to fabulous uptown shops and eateries -- including our own bodega and taproom. Walkable to bustling historic downtown, the fort, the Bridge of Lions, and the Matanzas River. Bikeable to Vilano Beach and Anastasia State Park. And a short drive to additional beaches on Anastasia Island or in Vilano. Enjoy a slice of Saint Augustine typically only enjoyed by the locals, and relax in the friendly historic Abbott Tract neighborhood.

Top Guest favourite
The kitchen features a spacious layout with wooden cabinetry and modern appliances. A dining area is present with a round table and four chairs. Natural light enters through large windows, and a beige rug adds warmth to the hardwood floor.
Apartment in St. Augustine
4.94 out of 5 average rating, 288 reviews

Apt B - Historic District Home Away from Home

Key Lime Oasis is nestled on a tree lined residential street in historic Saint Augustine. There is lots to see and do starting a mere two block walk away, and multiple beaches within 3-4 miles. I provide 2 beach chairs, a cooler, umbrella and beach towels.. The apartment features all new appliances, a quiet back porch, French doors leading from the bedroom to a delightful bathroom with a large shower with a Bluetooth speaker. A complimentary parking pass to the city garage is provided.

Guest favourite
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, 214 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.

Top Guest favourite
The living and dining area features a light wood dining table set for six, complemented by a patterned area rug. A cozy seating arrangement includes a gray sofa and a comfortable armchair, with natural light flowing in from nearby spaces.
Apartment in St. Augustine
4.98 out of 5 average rating, 211 reviews

Inviting 2/2 BR - Walk to Town

This St. Augustine apartment is right in the heart of quaint & historic downtown! This lower level apartment is furnished with a king bed in the master bedroom with a bath and a queen bed in the second bedroom with bath and is perfect for 1-4 guests. A short 5-8 minute walk allows visitors to explore the many downtown historic sites, museums & restaurants. One parking spot is available on site. There is free parking on the surrounding streets for additional vehicles.

Top Guest favourite
A charming historic cottage features a welcoming front porch with seating. The entrance is framed by intricate light fixtures and is approached via a patterned brick pathway. Lush greenery offers a serene backdrop, contributing to the inviting atmosphere of the home.
Cottage in Lincolnville
5 out of 5 average rating, 144 reviews

~Romantic Historic 1888 Cottage~Walk to Downtown

Come live in history! This cottage traces its roots back to humble beginnings and it still stands today as one of Lincolnville's original historic treasures. Nestled in the heart of America's oldest city, this endearing circa 1888 cottage offers an intimate, refined escape with a boutique ambiance. This is the ideal retreat for travelers seeking a romantic getaway or guests who wish to be transported to a more graceful time. Discreet in scale but grand in experience.

Top Guest favourite
A private back deck features a round dining table surrounded by four green chairs, all positioned beneath a large red umbrella. A hot tub is visible in the background, complemented by potted plants along the edges. Sunlight illuminates the area, enhancing the inviting outdoor space.
Home in St. Augustine
4.98 out of 5 average rating, 219 reviews

Cordova House ,In the historic downtown .

The "Cordova House", built in 1900, is the Victorian Secret of the Ancient City District, featuring covered balconies in front and back, a private back deck, high ceilings, modern kitchen, a Kohler 10 head shower, two indoor spa tubs and more. Hot tub on the back deck.Located in the heart of downtown, yet also has off-street parking for up to two cars (very rare). Nothing compares.

Top Guest favourite
An open-concept kitchen showcases modern stainless steel appliances and quartz countertops. Pendant lights hang above the central island, complemented by bar stools. Natural light floods in from the windows, featuring white blinds, accentuating the warm wooden beams on the ceiling.
Cottage in St. Augustine
5 out of 5 average rating, 257 reviews

uptown blue cottage

The past is present in ancient Saint Augustine where you can stay steps away from everything you want to explore. The cottage overlooks the tranquil setting of the Mission Nombre de Dios as Uptown awaits exploration right around the corner with its boutique shops and restaurants. Just a few steps more lies the Castillo de San Marcos and all the action of downtown.

Top Guest favourite
A private balcony features wooden decking and a slatted roof, offering shade and protection. Two comfortable chairs and a small table sit on one side, while lush greenery and palm trees provide a natural backdrop, creating a peaceful outdoor retreat.
Apartment in St. Augustine
4.98 out of 5 average rating, 246 reviews

Tree Top View 1

Our 600 sq ft apartment offers a private balcony shaded by centuries-old live oaks, alive with birds and squirrels. The view also includes a touch of our neighbor’s eclectic backyard, adding local character. Inside, enjoy a king bed, separate living area, and kitchen. A short 1/2 mile walk brings you to historic downtown St. Augustine.

Popular amenities for Historic District, St. Augustine holiday rentals

Quick stats about holiday rentals in Historic District, St. Augustine

  • Total rentals

    310 properties

  • Nightly prices starting at

    $108 AUD before taxes and fees

  • Total number of reviews

    39K reviews

  • Family-friendly rentals

    190 properties are a good fit for families

  • Pet-friendly rentals

    140 properties allow pets

  • Rentals with a pool

    40 properties have a pool