Holiday rentals with outdoor seating in St. Augustine South

Guest suite in St. Augustine

A living space features a white sofa adorned with a patterned throw, complemented by a rustic wooden coffee table. A large round mirror and star decorations hang on the walls, while a ceiling fan adds functionality. Doorways lead to adjacent rooms, including a bathroom.

4.98 out of 5 average rating, 525 reviews

Winter Hawk Hideout

15 minutes from ol' St Augui. Located in the heart of this typical Florida woods and nested by oaks that saw the Seminole War as we are walking distance from Ft Peyton and 2 miles away from where Osceola was captured. The house sits on half acre of gardens and the decor is ranch, asian and whimsical .The goal is for you to feel transported away for a while. I do have 2 very small, well behaved and quiet dogs and one never seen cat. They do not have access to your quarters or are allowed in.

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, 435 reviews

Your Home Away From Home

1,800 SF, 2 bedrooms, 2 1/2 bathrooms, on a secluded 5 acre lot just minutes from Historic Downtown and St. Augustine Beach. The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms (1 with TWINKLE mattress) ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small upcharge for 5 or more. Motorcycle friendly! We also do live on the property!

A welcoming living room features a comfortable couch and accent chairs with geometric patterns. A wooden coffee table sits in the center, surrounded by light-colored walls and wood flooring. Natural light enters from sliding glass doors that lead to a private balcony, enhancing the spacious feel.

4.93 out of 5 average rating, 101 reviews

SEA & SALT|2-min walk Beach|2x Sparkling Pools

Welcome to the Sea & Salt Retreat of St. Augustine Beach! Fit 4 people in this spacious 2BR/2.5BA condo that is a 2-min walk to our beautiful white sand beach and a 1-min walk to the pool with cabana and chaise lounges. Effortlessly enjoy relaxation at the beach, lounge all day in the sun at the sparkling clean pool, or drive 12-mins to the Historic Downtown St. Augustine. Phenomenal amenities: Two sparkling clean pools, clubhouse, tennis courts, pickleball, racquetball, and basketball!!

Place to stay in St. Augustine

A stone fountain stands at the center of a lush courtyard, surrounded by vibrant green ferns and tropical plants. A wooden bench is positioned nearby, offering a tranquil space for relaxation amid the serene sounds of cascading water.

4.91 out of 5 average rating, 984 reviews

Moon Over the Courtyard in the Historic District

You have found your cozy oasis tucked under an ancient Oak tree in a private, lush tropical Courtyard in the Historic District of St Augustine. Sit by the fountain, feed the roaming tortoises day or enjoy the fire and the 1000's of tiny lights reflected on the tree canopy by night. This small studio and exemplifies the appeal of tiny living: compact, clean, efficient, and convenient. The Courtyard is a short walk from all of the Historic Districts Shops, Restaurants and Attractions.

Bungalow in St. Augustine

A screened-in porch showcases a relaxing atmosphere with wooden ceilings and large windows. A colorful hammock hangs beside a sofa and a blue coffee table, while natural light fills the space. Outdoor seating complements the inviting decor, surrounded by lush greenery.

5 out of 5 average rating, 107 reviews

Tropical Bungalow Near Beaches Downtown &

Sea-Glass Bungalow Tropical Peaceful Retreat. All are welcome here! Feel your worries melt away as the tropical breeze rustles the private garden, enjoy unique features such as hanging hammocks & screened-in porch. This unique space has a style all its own. Artistic accents highlight this converted garage into a modern studio.. When you’re not relaxing in this tropical oasis, explore the Lighthouse, Alligator Farm & Bird Watching, White-Sand BCHs, The AMP & DWTN all this< 1mi away.

4.98 out of 5 average rating, 107 reviews

A cozy bedroom features warm wood paneling and a large window allowing natural light to fill the space. A spacious bed is dressed in a patterned quilt, with two pillows placed at the headboard. A ceiling fan hangs above, and an air conditioning unit is mounted on the wall.

Cottage in St. Augustine

The Castle Cottage

Tucked away in the trees of Vilano Beach is a little known magical hideaway, the Castle Cottage. This cottage was hand-crafted by a master carpenter in the 80s and displays beautiful woodwork throughout. This perfect getaway location allows you to be free from the crowds but still within five miles of downtown St. Augustine. It is located within a half mile of three popular local restaurants and only steps to the beach! It also features a magnificent view of the nearby Castle Otttis.

Guest suite in St. Augustine

A light-filled living area is depicted, featuring a spacious couch positioned against a vibrant artwork of a clownfish. Sliding glass doors lead to a serene outdoor space, while colorful paintings adorn the walls, adding artistic charm to the room.

4.99 out of 5 average rating, 488 reviews

Art Studio Space – Quiet – Walk to Beach

This very private studio apartment is on Anastasia Island, with its own entrance across the street to Anastasia State Park, which includes the St. Augustine Amphitheater in a quiet, friendly beach neighborhood. This ideal location is quite literally "a walk in the park" to a beautiful undeveloped Florida beach; or a 10 minute drive across the famous Bridge of Lions to historic downtown St. Augustine – with quick access to the many local attractions and great restaurants in the area.

Guest suite in St. Augustine

A spacious studio features a king bed with a patterned blanket, complemented by a cozy sofa and armchair. A kitchenette is visible in the background, along with a modern ceiling fan overhead. Large windows allow natural light to fill the room.

4.98 out of 5 average rating, 390 reviews

Cozy studio 15 mins to beaches & historic downtown

Outstanding location and amenities, 15 minutes to beaches and historic downtown (Nights of Lights!) Minutes walk to the intercostal w/ piers, boat ramps, perfect for pleasant walks. Close to lots of shopping and dining. Quiet, friendly neighborhood, ample parking-trailers & boats welcome. Kid friendly w/ toys, pack & play + more. Laundry, walk-in shower, private entrance. Private deck w/ cheerful seating. Well equipped kitchenette. Easy drive to theme parks, Daytona + more.

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, 401 reviews

SeaGlass on Vilano Beach~St. Augustine, FL

Beach & Ocean lovers retreat- Steps to quiet beach, close to historic area, short scenic walk to grocery/waterfront dining/roof top cocktails Gem w/lots of outdoor living. Bright, spacious cottage-style apartment w/kitchenette (No oven/stove). Fenced/gated large property. Easy 1 min walk to quiet beach! Convenient walkable beach neighborhood. Short Uber ride to historic district. Perfect for couple (baby up to 2yrs welcome) solo traveler, Flagler College parents.

Flat in St. Augustine Beach

The exterior of a tropical retreat is captured, showcasing a wooden deck with colorful surfboard decorations on the walls. Bright green foliage and plants frame the entrance, while sunlight creates playful shadows on the stucco surface.

4.99 out of 5 average rating, 145 reviews

Beach Break! Walk to the beach! 1BRw/Private Patio

Beach Break! Enjoy your beach vacation and all St. Augustine Beach has to offer from the perfect tropical retreat! This luxury 1 Bedroom / 1 Bath accommodation is centrally located within short walking distance to the beach, coffee shops, the taco shop, surf shops, restaurants, parks, and shopping! After your day at the beach, come back to relax in the hammock under the palms in your private tropical patio. You'll fall in love with BEACH BREAK!

An outdoor space features a wooden pergola adorned with warm string lights, creating a cozy ambiance. Seating areas include wicker chairs and a small table, surrounded by potted plants and vibrant flowers. The fully fenced backyard provides a private setting for relaxation.

4.95 out of 5 average rating, 159 reviews

Historic Downtown - firepit/pet friendly/fenced-in

Our home offers the ideal combination of comfort, convenience, and style. Experience the vacation of a lifetime at our 3bd/2ba luxury home which offers a fully fenced in private backyard for pets, BBQ grill, firepit, and playground for the littles. Minutes from the best St. Augustine has to offer: • Beaches -12 mins • Castillo de San Marcos -9 mins • Alligator Farm -10 mins • Fountain of Youth -10 mins Pet fee: $20/pet/day

The kitchen and dining area feature modern gray cabinetry and stainless steel appliances. A round dining table with black chairs is positioned on a patterned area rug. Natural light enters through two windows, illuminating the space and offering a view of the neighboring buildings.

4.98 out of 5 average rating, 384 reviews

Short Scenic walk into Historic St Augustine

Stay in Style on Anastasia Island Step into timeless elegance at this fully renovated 1920s apartment. Nestled in the heart of historic Davis Shores, this beautiful retreat blends old Florida charm with modern comfort. 🌴 Perfect Location Walk across the Bridge of Lions to the cobblestone streets, shops, and restaurants of historic St. Augustine. Surrounded by local cafés, parks, and coastal scenery.

Popular amenities for outdoor seating rentals in St. Augustine South

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A spacious living area features a brown sofa paired with two green chairs, complemented by a wooden coffee table on a patterned rug. Sunlight filters through large windows, illuminating a dining area with a wooden table and decorative shelving. A ceiling fan adds comfort to the room.

4.99 out of 5 average rating, 134 reviews

The Emerald~Pet Friendly~Downtown~Beach~Boho Chíc

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.

4.97 out of 5 average rating, 203 reviews

Luxurious Oceanfront Home

A spacious living area features a large 75-inch television mounted on the wall. A stylish leather couch and wooden coffee table provide seating, while a modern kitchen with bar stools offers additional space for dining. Warm lighting from pendant fixtures enhances the inviting atmosphere.

4.96 out of 5 average rating, 200 reviews

Close to downtown, 3BR,6Beds,Movies, Ping Pong,Fun

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.

4.99 out of 5 average rating, 119 reviews

Luxury Modern Home in Prime Location 2BDR-3BTH

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.

4.95 out of 5 average rating, 146 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

A modern kitchen showcases a central island with a wooden countertop and a contemporary sink. A stylish backsplash in soft pink tiles complements stainless steel appliances. Natural light is admitted through a skylight, while a welcoming living area is visible to the side, featuring a cozy orange sofa.

4.96 out of 5 average rating, 138 reviews

Hen House Saint Augustine

The historic home features a grand façade with white siding and tall columns supporting a covered balcony. Decorative lights and a festive wreath adorn the front entrance. A beautifully detailed wrought-iron gate opens to a landscaped pathway leading to the door.

4.95 out of 5 average rating, 458 reviews

Genovar Mansion Master Suite Private Entrance

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.

4.96 out of 5 average rating, 195 reviews

“La Casita” A Charming Uptown St Augustine Cottage

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.

4.82 out of 5 average rating, 311 reviews

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

Flat in St. Augustine Beach

A shaded outdoor area features a hammock with striped fabric, inviting relaxation. Stone pavers lead to a landscaped garden area with green foliage and seating. A patio setting is visible in the background, complete with table and chairs for outdoor dining.

4.88 out of 5 average rating, 283 reviews

Low Tide - Beach Bungalow

An open living area is illuminated by natural light from multiple windows, featuring light-colored walls and warm wood flooring. A gray sofa with a striped throw sits beside a round coffee table. The kitchen area contains white cabinetry and modern appliances, with a dining table set for four.

4.91 out of 5 average rating, 490 reviews

Downtown Bungalow- Walk to Downtown, Mins to Beach

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.

4.96 out of 5 average rating, 202 reviews

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

4.99 out of 5 average rating, 211 reviews

Beachside Studio

A well-lit bedroom features a spacious bed adorned with decorative linens. A mirror and wooden table add functional charm. Natural light filters through the window, which leads to a small deck area. A painting on the wall complements the room’s calming atmosphere.

4.88 out of 5 average rating, 211 reviews

Old Town "Gem"

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, 486 reviews

*2BR* Luxe Loft Close to Everything | Balcony

A modern bathroom features a walk-in shower enclosed by clear glass, with tile work in earthy tones. A stylish vanity with a solid surface sink is complemented by a large mirror. Natural light filters through a window, providing a fresh and bright ambiance.

4.97 out of 5 average rating, 120 reviews

Clean simple and cozy home in St. Augustine

Apartment rentals with outdoor seating

Apartment in St. Augustine Beach

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.

4.84 out of 5 average rating, 267 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, 167 reviews

The Bohemian Rhapsody! In the middle of it ALL!

Apartment 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.

4.98 out of 5 average rating, 243 reviews

Ocean Front Gem: Top Floor Corner Unit

Apartment in Lincolnville

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.

4.97 out of 5 average rating, 144 reviews

Middle of Historic District + Quiet at Night

5 out of 5 average rating, 105 reviews

St Augustine coastal chic 2br across from Beach

Apartment in St. Augustine Beach

A cozy living area features soft beige furnishings and decorative blue pillows. A wooden coffee table occupies the center, while a stone fireplace adds warmth. Large sliding doors provide natural light and reveal views of the outdoors, framed by sheer curtains.

4.93 out of 5 average rating, 136 reviews

Cozy Beach Townhome - Bikes, Garage & Pickle Ball!

A large swimming pool is surrounded by lounge chairs under a clear blue sky, with palm trees swaying gently nearby. The pool's serene water reflects the adjacent condominium buildings, creating a tranquil atmosphere for guests.

4.92 out of 5 average rating, 240 reviews

The Salty Suite Resort style condo

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.