Holiday rentals with outdoor seating in Historic District, St. Augustine

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.

4.97 out of 5 average rating, 772 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

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, 174 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”)

Guesthouse 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, 406 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.

A spacious bedroom features a large bed with white bedding. Natural light enters through multiple windows, complemented by white shutters. A comfortable armchair is situated near the window, enhancing the cozy atmosphere of the room.

4.96 out of 5 average rating, 381 reviews

Updated Victorian apt in heart of downtown +VIEWS!

21 Orange Street is a bright and airy second story apartment with unparalleled views of historic downtown Saint Augustine and the bay front. Enjoy old world charm in our newly renovated circa 1860's home- furnished with modern and comfortable amenities! We are steps away from Saint George Street shopping, world class dining and lively bars. If you choose to spend your time here in a more relaxing way, you’ll love the spacious bedroom and our comfortable porch to take a break from it all.

5 out of 5 average rating, 230 reviews

A charming two-story cottage is seen behind an ornate wrought-iron gate, framed by vibrant green grass and well-maintained landscaping. Large windows allow natural light to fill the exterior, and a cheerful yellow door adds a welcoming touch.

Cottage in Lincolnville

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fenced yard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant and LaNuvelle * 10 minute walk to central downtown St Augustine

A dining area features a round table surrounded by four elegant chairs, adorned with light fabric. A large chandelier hangs above the table, illuminating the space. A bookcase and television are visible in the background, with decorative artwork showcasing local scenes on the walls.

5 out of 5 average rating, 101 reviews

132C Luxurious Relaxing Elegance at Casa de Flora🚭

This is such a beautiful and relaxing apartment for adults and children age 12 and up . There are lots of windows that flood the rooms with natural light. Much of the art work represents St Augustine. The furniture is comfortable and beautiful. The beds have freshly pressed linens for a wonderful night’s rest. The kitchen is set up so that coffee can be easily accessed even if someone is cooking or using the sink. It’s stocked with beautiful bar glasses and bar ware. You’ll LOVE it !

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, 216 reviews

Downtown • Historic Luxury • DesignerKitchen&Baths

Off Street Parking 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.

Guest favourite

The charming exterior of Casa Tranquila features a bright yellow facade with inviting screened-in porches. An American flag is proudly displayed, and colorful sunflowers add a natural touch to the lush landscaping, creating a welcoming entrance on a quiet street.

4.9 out of 5 average rating, 366 reviews

Casa Tranquila Comfy*Stylish*Walk Everywhere*Homey

Casa Tranquila is located on a quiet street only a blocks away from all the action in the heart of the nation's oldest city. Built in 1917 w/ 11 ft. ceilings, renovated in 2021 & is tastefully decorated & equipped with everything needed to make your stay in Historic St. Augustine a remarkable experience. Indoor dining area, updated kitchen, & an outdoor dinning on the screened in porch. Café & scones in the AM or cocktails & Tapas in the evening al fresco. See you soon.

A light-filled living area features a soft blue sofa adorned with decorative pillows. A wooden coffee table provides a functional centerpiece, and a flat-screen television is positioned on a white console with storage baskets. The space is complemented by natural light from the nearby windows.

4.86 out of 5 average rating, 555 reviews

Catch Some Rays on your Deck -walk everywhere

Welcome to The Grove! This one bedroom unit is nestled in the heart of Historic St. Augustine- less than a mile from the City Gates and all tourist amenities! One of the highlights of this unit is the private deck patio, providing a delightful outdoor space to unwind and enjoy your morning coffee or an evening glass of wine. Feel the historic vibes as you take in the views of the surrounding architecture and immerse yourself in the unique character of the neighborhood.

A well-lit living area features a plush dark recliner and a light-colored sofa, arranged around a small coffee table. A decorative lamp adds warmth beside a window. A TV is positioned on a black stand, while framed artwork and a plant enhance the welcoming space.

4.97 out of 5 average rating, 238 reviews

Dog-friendly, Walk Everywhere apt with FREE BIKES

Come stay in this completely renovated, beautiful second floor, pet-friendly one bedroom apartment with a large fully-equipped eat-in kitchen. A spacious balcony with rocking chairs. Shared use of the fabulous back yard with picnic tables, BBQ grills, and bicycles! One parking space guaranteed. Best part: The location! About a five-minute walk to historic downtown and Flagler. Super comfy queen size 4-post bed. Pet fee is $40 per dog per stay (max of 2 dogs).

A cozy living area features a comfortable sofa paired with a light-colored armchair and a round coffee table. Natural light flows through multiple windows, illuminating the space. The full kitchen is visible, showcasing modern appliances and blue cabinetry, complemented by woven wall decor.

4.96 out of 5 average rating, 208 reviews

Charming 1 Bedroom apt, Historic St Augustine

You will love this newly remodeled one bedroom apartment in Historic St. Augustine. Originally built in 1910 and completely updated in 2023. Just two blocks from St. George St, walking distance to Flagler and all of downtown St Augustine. This apartment offers one bedroom with king size bed, full kitchen and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

An open-concept living area features a comfortable gray sofa, a coffee table, and a TV on a stand. Natural light fills the space through the windows, and a dining table with chairs is visible in the background. A patterned rug adds warmth to the wooden floor.

4.95 out of 5 average rating, 333 reviews

Downton Abbottry 2/2 - 5 Min Walk To City Gates

Enjoy this charming 1910 Sears & Roe Buck catalog home that has been meticulously maintained home just a 5 minute walk to the City Gates and downtown. You have a private back patio space to enjoy coffee in the morning or a glass of wine in the evening. Or just take a leisurely stroll to many fine restaurants that St Augustine has to offer.

Popular amenities for Historic District, St. Augustine outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

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, 196 reviews

Newly built w/garage In The Heart of 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.

4.94 out of 5 average rating, 144 reviews

Charming 3 bedroom cottage, feed the peacocks!

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, 105 reviews

Luxury Modern Home in Prime Location 2BDR-3BTH

A charming Victorian home is showcased with a bright yellow exterior, framed by lush greenery. The two-story structure features a spacious porch with white railings and decorative trim. A welcoming sign is positioned at the entrance, indicating the property's name.

4.92 out of 5 average rating, 247 reviews

DOWNTOWN ~ Victorian Home ~ ABOVE CUPCAKE SHOP!

Guest favourite

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, 140 reviews

Carriage Manor- Next to Fountain of Youth & Beach

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, 114 reviews

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

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

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

Apartment rentals with outdoor seating

Superhost

A bright and airy room is showcased, featuring a spacious queen bed and a Murphy bed for flexible use. The area includes a comfortable blue chair next to a small table, with natural light flooding in from windows and a private entrance visible.

4.84 out of 5 average rating, 302 reviews

100 Steps to Beach, Deck w Ocean View, Beach Gear

A bright sleeping area features a spacious bed with a light-colored coverlet. Flanking the bed are two bedside tables, each with a lamp providing soft illumination. The room is accented with light blue walls and a piece of serene artwork, enhancing the relaxed atmosphere.

4.98 out of 5 average rating, 243 reviews

Seahorse Studio (Very Walkable + Free Parking)

A bright and airy bedroom features a spacious bed with a light blue blanket, flanked by matching bedside tables with lamps. A comfortable chair sits in the corner, and decorative art in shades of turquoise adorns the walls. Natural light filters through the window, enhancing the serene ambiance.

4.96 out of 5 average rating, 385 reviews

SeaGlass on Vilano Beach~St. Augustine, FL

A charming two-story apartment stands above a pool area framed by lush greenery. The balcony offers a view of the pool, while the surrounding landscape features vibrant foliage and mature oak trees. The pool is bordered by textured paving stones and a patio set in the background.

4.99 out of 5 average rating, 588 reviews

Villa Tizoc

A cozy sleeping area features a spacious bed adorned with a patterned bedspread and accented by a decorative pillow. A bedside table holds a small lamp, while a dark cabinet provides additional storage. Light filters in through a window dressed with textured blinds.

4.97 out of 5 average rating, 191 reviews

Traveler’s Nest of uptown St. Augustine with pool!

Two white rocking chairs are positioned on a concrete patio, accompanied by a small table featuring a potted floral arrangement. The entrance to the studio, framed by double doors, is visible in the background, enhancing the inviting outdoor space.

4.99 out of 5 average rating, 202 reviews

Beachside Studio

The exterior of a two-story building showcases a contemporary design with a vibrant turquoise front door and matching chairs on the balcony. White wooden siding contrasts with dark railings, while lush greenery and landscaping enhance the entrance.

4.98 out of 5 average rating, 468 reviews

*2BR* Luxe Loft Close to Everything | Balcony

A serene beach scene captures a golden cloud formation reflecting on the wet sand. Soft waves gently roll in, harmonizing with the distant silhouette of a pier. A solitary bird stands at the water's edge, adding to the tranquil atmosphere.

4.96 out of 5 average rating, 138 reviews

Beautiful 2 story apt 1 block to beach 1 queen bed

Condo rentals with outdoor seating

Guest favourite

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.

Condo in St. Augustine Beach

4.85 out of 5 average rating, 260 reviews

Ocean Side Complex w/ Heated Pool B-15

A light-filled living room features a cozy sectional sofa adorned with decorative cushions. A stylish coffee table sits atop a patterned rug, and a modern TV is positioned on a sleek white media console. Natural elements are introduced through plants and woven wall decor.

4.95 out of 5 average rating, 155 reviews

The Bohemian Rhapsody! In the middle of it ALL!

Condo 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, 234 reviews

Ocean Front Gem: Top Floor Corner Unit

4.97 out of 5 average rating, 124 reviews

A brightly lit living area features a comfortable brown sofa and two accent chairs with blue cushions. A coffee table is positioned centrally, complementing the light rug beneath. The dining area is visible, showcasing a dark table set for six, with wall art enhancing the space.

Condo in Lincolnville

Middle of Historic District + Quiet at Night

The living room features a comfortable gray sofa facing a wall-mounted television. A round coffee table sits on a light area rug, complemented by decorative plants. Bright natural light fills the space through sliding glass doors, leading to a balcony.

4.98 out of 5 average rating, 159 reviews

Pretty walk to Old Town, Anastasia Island 2 bdrm

A bright living area features large floor-to-ceiling windows that provide sweeping ocean views. Comfortable seating is arranged around a central coffee table adorned with decorative items. A Smart TV is positioned for easy viewing, while a ceiling fan adds a cooling breeze.

4.98 out of 5 average rating, 108 reviews

Family Beach Condo - Steps To The Sand Or Pool

5 out of 5 average rating, 112 reviews

Lush greenery frames a wooden pathway leading to a sandy beach, with palm trees and residential buildings visible in the background. The sky is illuminated by soft hues of sunset, creating a serene backdrop for the coastal environment.

Condo in Treasure Beach

Boutique Beachside condo with easy access to beach

A light and airy living area features a comfortable gray sofa, a wooden coffee table, and a blue accent chair. A large flat-screen television is mounted on the wall opposite, while sliding glass doors provide access to a balcony area with outdoor seating.