Guest house holiday rentals in St. Augustine

An outdoor seating area features multiple blue Adirondack chairs arranged around a circular stone patio, complemented by a small green table. A lamp post stands nearby, and a flag flutters gently in the breeze, surrounded by lush greenery and tall palm trees.

4.91 out of 5 average rating, 591 reviews

Captain's Quarters Tiny House

Welcome to our newly spacious and private renovated bathroom with our outdoor shower. See photos! This Tiny House has all you need for a cozy, private stay while visiting St. Augustine. The Tiny House sits on 3/4 acres. You will feel the tranquility of this magical property and only 10 minutes to Vilano Beach or the Historic Downtown. The studio is equipped with a sink, toilet, kitchenette, coffee/tea. Commune with nature in your Private Exotic Outdoor Shower, hottub (closed July & August).

A spacious living area features a light-colored sofa, complemented by a wooden coffee table with books. A cozy bed is visible in the background, alongside a modern fan and decorative wall art. Soft gray tones create a relaxing ambiance throughout the room.

4.99 out of 5 average rating, 383 reviews

Pelican Guesthouse-Spacious/Quiet/Comfortable

Quiet, spacious guesthouse. Comfortable beds and immaculately kept. Read our reviews :) A few miles from gorgeous beaches, historic downtown and St Augustine Amphitheater. Friendly neighborhood, accessible to beautiful walks along the Matanza River. Public park and playground at the end of the street. Self check in, private entrance, flat screened TV's, full kitchen. Thoughtful decor and local artwork to enjoy. Full laundry room and off street parking for two car. Strictly a pet-free listing.

A pool area is showcased with a clear blue pool surrounded by a stone patio. Two lounge chairs are positioned on one side, complemented by a thatched umbrella. A covered seating area can be seen in the background, adding to the inviting ambiance of the outdoor space.

4.98 out of 5 average rating, 166 reviews

Historic St. Augustine 2/1 Cottage & Pool

About this space: Welcome to this poolside cottage located in Historic St. Augustine. This cottage is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This cottage has 2 bedrooms and 1 full bathroom, living room, kitchen and direct access to the pool. This space: This is a detached cottage located behind the main house Guest access: Keyless code entry Other things to note: Please keep in mind that the pool is a shared space :)

A comfortable seating area is highlighted by a gray sofa and two woven chairs. A colorful area rug anchors the space, with a coffee table placed in the center. Natural light streams through large windows, enhancing the room's relaxed ambiance.

4.91 out of 5 average rating, 334 reviews

10 Minutes to EVERYTHING!! Modern Serene Studio

Serene Studio is just that- a quiet, peaceful, private space to lay your head after exploring St. Augustine. Our 500 sq. foot studio cottage is detached from the main house, where we live. It's set in a residential neighborhood that runs along the Intracoastal Waterway (which makes for gorgeous morning or evening strolls). We're a 10 minute car ride (without traffic!!) to the historic downtown or St. Augustine Beach. Serene Studio is the best of both worlds without the noise, hustle and bustle!

A spacious studio features a king-sized bed with a soft green coverlet and a cozy dark sectional sofa. Natural light enters through windows, highlighting the modern kitchen area and dining space in the background. A bathroom door is visible on the right side.

4.95 out of 5 average rating, 116 reviews

Historic Downtown Studio

Experience the charm and elegance of historic St. Augustine, Fl in our quaint carriage house. Located with in walking distance of many iconic landmarks, such as Flagler College, and the San Sebastián winery. Immerse yourself in the city culture, unique shops and dining scene. Whether you're seeking a romantic getaway or a cozy solo retreat, our carriage house offers a blend of comfort and convenience. Book your stay with us and experience the charm of this historic destination like a local.

A bright living area features a black leather sofa paired with textured cushions, complemented by a low coffee table. A television is positioned on a console, and windows allow natural light to fill the space. Artwork adorns the walls, adding character to the room.

4.99 out of 5 average rating, 110 reviews

Comfortable and Gently Disney.

Take it easy at this unique and tranquil getaway. Whether you're here for a short stay or here to explore.... There's something for the princess at heart and for the adventurer. There's a comfortable hybrid mattress for two plus an extra memory foam mattress for two and a tent with a crib size memory foam pillow. Kitchenette is nicely equipped. A fireplace for ambiance under the TV. The bathroom has all the necessities with a walk-in shower. Relax on the patio under the sun and stars.

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, 401 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 tranquil outdoor space features a well-maintained heated pool surrounded by lush greenery and colorful flowers. Seating areas with black Adirondack chairs are positioned around the pool, offering a peaceful setting. A covered patio stands in the background, complementing the inviting atmosphere.

4.94 out of 5 average rating, 175 reviews

Heated Pool Beach Bungalow Steps to the Ocean

Beautiful brand new in 2022 en-suite Bungalow beach side! Perfect for a romantic get a way or just one person, just 600 steps to the beach. Five minutes to the St Augustine pier and 10 minutes to the oldest city in the US, Historic Downtown St Augustine. Not only do you have the most comfortable bed to fall into, a 50" TV, recliners and an amazing heated pool. Beautiful beach sunrises, fishing, hiking, Concerts at the Amphitheater. For your safety you have an electronic keyless entry.

A compact kitchen area features wooden shelving displaying various ceramic bowls, pots, and decorative items. The full-size stove is positioned under a light fixture, with a dark sink and wooden countertop enhancing functionality. Artwork and plants add touches of decor above the counter.

4.88 out of 5 average rating, 302 reviews

Tiny House three blocks from beach!

The tiny house at the Crescent Beach house is a one bedroom one bath detached guesthouse ! The bedroom includes a queen bed and closet. There is a great kitchen with a full size stove/oven, keurig, and microwave. Wifi and a large TV with Netflix only, no cable. Beach chairs, towels, and umbrella included! Soak in the great Florida beach lifestyle. There’s a board walk beach access at the end of the street ! This tiny house is adjacent to a two story home which is a separate Airbnb!

The welcoming entrance features a vibrant green door framed by two stylish black chairs on a wooden porch. Natural wood columns support the overhang, adding a charming touch to the inviting space.

4.94 out of 5 average rating, 103 reviews

Downtown Bungalow *Newly Listed*

This charming bungalow is the perfect escape from the hustle and bustle of daily life. With a cozy living area, a comfortable bedroom, and access to laundry on-site, you'll have everything you need for a relaxing vacation. Located just minutes from popular attractions and restaurants in the area, you'll have the best of both worlds - a peaceful retreat and convenient access to all the excitement. Book your stay today and experience the ultimate retreat!

The exterior of the studio features a welcoming entryway with a wooden deck bordered by tropical plants. Light green shutters frame the door, while a shaded pathway leads to the entrance, invoking a serene atmosphere enhanced by natural greenery.

4.96 out of 5 average rating, 503 reviews

Newly Renovated, Clean, Private, Studio

Aunt Suzie's Hideaway. Experience St. Augustine like a local. Fun, relaxing, tropical, historic, magical. Bring your bike, board, boat, or kayak. Safe, quiet neighborhood, walk, bike, fish or picnic along the intracoastal waterway and marsh. 1 mile to Shands Flagler Hospital, 4 miles to downtown historic district and 5 miles to the beach and Amphitheater. Small fully equipped kitchen, queen bed, large bathroom, sitting area, dining or worktable.

The interior features an open living area with a light-colored sofa and a decorative cushion. A wall mural depicting a natural landscape is complemented by wooden beams overhead. A television is mounted on the wall across from a kitchenette with modern amenities.

4.95 out of 5 average rating, 124 reviews

The Boathouse Studio on Anastasia Island

Welcome to The Boathouse, a stylish studio space surrounded by a tropical garden on Anastasia Island. The studio is a raised detached guest house with private parking, outdoor lanai space and alley entrance. Newly renovated space as of September 2023. The interior is perfect for couples or singles wanting a quiet and stylish stay close to everything St. Augustine has to offer.

Popular amenities for guest house rentals in St. Augustine

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guest house in Jacksonville

A modern living area is furnished with a gray sofa and two light-colored armchairs. A textured rug covers the floor, while large windows allow natural light to illuminate the space. The kitchen can be partially seen in the background, featuring contemporary appliances.

4.89 out of 5 average rating, 27 reviews

Luxury Cottage with River Access

Guest house in Lincolnville

The exterior of a charming house features a welcoming porch with rocking chairs and an American flag. A spacious bedroom is visible, showcasing a neatly made bed adorned with decorative pillows and a textured blanket. Large windows allow natural light to fill the room.

At Journey's End Lewis & Clark

A serene dock house is positioned on stilts over calm waters, with a wooden walkway leading to its entrance. Soft colors of the evening sky are visible above, while clouds drift past, creating a tranquil atmosphere surrounding the retreat.

Guest house in Middleburg

4.78 out of 5 average rating, 37 reviews

Dock House

Guest house in Treasure Beach

A vibrant pool area is depicted in the foreground, featuring clear blue water. A stylish guesthouse stands in the background, characterized by large windows and a balcony. An umbrella shades a seating area next to the pool, creating a relaxing outdoor space.

5 out of 5 average rating, 44 reviews

Casita by the Sea - Second Floor

A wooden pier extends into calm waters, framed by a sprawling tree above. The horizon is painted with soft hues of orange and purple as the sun sets, creating a serene backdrop for the gently rippling water.

4.76 out of 5 average rating, 115 reviews

The Coral Shell

The view captures the tranquil St. John's River at sunset, with boats docked along the wooden pier. Silhouetted trees frame the scene, enhancing the peaceful ambiance of the water reflecting golden hues from the horizon.

Private room in Welaka

4.78 out of 5 average rating, 41 reviews

Waterfront Guesthouse on the St John's River

A quaint guest house features a wooden facade with a welcoming porch. Two white chairs are situated on the porch, inviting relaxation. The entrance is framed by a set of steps leading to a sturdy door, surrounded by trees and greenery.

Private room in Palatka

5 out of 5 average rating, 4 reviews

The Boom Boom Room

5 out of 5 average rating, 3 reviews

Madeira Suite St. Augustine near the Amphitheater

Guest house rentals with a patio

Guest house in Palm Coast

A charming cottage is framed by lush greenery and tropical plants. A wooden pathway leads to the entrance, which features a small porch with an inviting Adirondack chair. The exterior is painted in soft green, reflecting a serene outdoor setting.

4.94 out of 5 average rating, 36 reviews

Paradise Cottage Ideal location

The image features a charming guest house surrounded by lush greenery and palm trees. A stone bench with light-colored seating circles the base of a palm tree, while steps lead to a welcoming entrance adorned with arching windows and decorative elements. Bright blue sky complements the vibrant setting.

5 out of 5 average rating, 8 reviews

LaCasita, a quick walk downtown

A private cottage exterior features a deck with outdoor seating under an umbrella. Adjacent lounge chairs provide a place to relax. The structure is surrounded by grass and mature trees, with a small grill visible nearby.

4.87 out of 5 average rating, 158 reviews

Island’s Edge Guest Cottage on Anastasia Island.

A charming cottage is surrounded by lush greenery and a variety of trees. A pathway of pavers leads to the entrance, with a covered porch inviting guests to explore. Natural light filters through the leaves, creating a peaceful outdoor setting.

4.72 out of 5 average rating, 61 reviews

Vilano Beach Cottage

5 out of 5 average rating, 17 reviews

The exterior of the guest house features a pale green facade accented by a white door with a decorative glass panel. A small garden area with gravel and potted plants is present, surrounded by a wooden fence and lush greenery, creating an inviting entrance.

Guest house in Palatka

Palatka Golf Cottage

Guest house in Lincolnville

The exterior of a two-story home is showcased, featuring a covered porch with rocking chairs and a prominent American flag. An inset image highlights a cozy interior with a large bed, a television, and a kitchenette, complemented by light wooden floors and warm wall tones.

At Journey's End Key West

A well-lit bedroom features a spacious bed dressed in floral-patterned linens. A comfortable chair and desk are positioned beside a large window that opens to an outdoor seating area. A mirrored dresser reflects the bright light, while a small television sits on a cabinet within the room.

5 out of 5 average rating, 3 reviews

Fully equipped studio apartment.

The spacious studio features a kitchenette with light-colored cabinetry, a dining area with a round table and blue chairs, a cozy seating area, and a queen bed adorned with a teal quilt. Ample natural light fills the room through multiple windows.

4.89 out of 5 average rating, 46 reviews

World Golf Village Casita

Guest house rentals with a washing machine and dryer

Guest house in East Palatka

A wooden dock extends over calm waters, leading toward a covered structure. The sky is painted with vibrant hues of orange and purple as the sun sets, creating a serene backdrop. Two hanging lights are mounted on a post, illuminating the scene.

Waterfront 1br guest house, close to everything

A private balcony features wooden decking and a small round table with two chairs, surrounded by lush greenery. A red door leads into the apartment, providing a bright focal point against the natural backdrop.

4.72 out of 5 average rating, 100 reviews

Amazing Location! Balcony Bikes Free Parking Dntwn

Guest house in Butler Beach

The modern coastal apartment presents a bright exterior featuring blue and maroon accents. Lush greenery surrounds the pathway leading to the entrance, with a driveway providing ample parking space. The inviting atmosphere is enhanced by clear blue skies overhead.

4.89 out of 5 average rating, 115 reviews

Blues It Up - Beachside Studio Apartment

Vibrant greenery is showcased in the garden surrounding the exterior of the cottage. Open pink shutters frame large windows, allowing natural light to filter in. A variety of tropical plants and colorful flowers create a lush and inviting atmosphere.

4.88 out of 5 average rating, 473 reviews

Designer Island Studio • Walk and Bike to Downtown

Guest house in East Palatka

A vibrant sunset paints the sky in hues of pink and orange over the St. John's River, with a dock extending into the water. Inset images show a comfortable living area with a reclining couch and television, alongside an exterior view of the charming yellow guest house surrounded by greenery.

5 out of 5 average rating, 58 reviews

Riverfront Fishing and Sunsets Over the St John's

4.96 out of 5 average rating, 27 reviews

Vilano Beach GUEST house/small pet/RV&Boat prk/BBQ

A charming single-story home is featured, surrounded by lush greenery. A welcoming front porch with steps leads to double doors, while a concrete driveway extends towards manicured shrubs. Sunlight filters through the trees, enhancing the inviting exterior.

4.98 out of 5 average rating, 45 reviews

Irie-Inn

A modern kitchen features white cabinetry with sleek handles and granite countertops. Stainless steel appliances, including an oven and fridge, are present. A ceiling fan offers ventilation, while a red and white patterned rug adds a pop of color. Natural light filters through the window accented by wooden walls.