Guesthouse 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, 592 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, 386 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, 169 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, 335 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, 118 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, 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 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, 180 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.

Guesthouse in Lincolnville

The exterior of the two-story cottage showcases a combination of stone and stucco walls, framed by wooden shutters. A large tree provides shade in the foreground, and a welcoming pathway leads to the entrance, enhancing the home's charming architectural features.

4.94 out of 5 average rating, 462 reviews

Storybook Cottage-Historic Downtown St. Augustine

Welcome to Storybook Cottage on Lake Maria Sanchez in Historic Lincolnville, a scenic 8-10 minute walk from the heart of Downtown St. Augustine. Enjoy this beautiful two story, 2 BR/ 1.5 BA newly renovated cottage complete w a spacious family room and kitchen. Relax and enjoy your morning coffee or evening cocktails from the comfort of the balcony or the property's cozy courtyard. Perfect for a family trip or a romantic getaway to enjoy all that the Nation's oldest city has to offer.

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!

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, 477 reviews

Designer Island Studio • Walk and Bike to Downtown

Off Street Parking 4 Min Drive/ 15 Min Beautiful Walk to Historic Downtown 3 Min Drive to the Beach Guest Passes Fitness Club/Pool/Suana-Steam Rm/Yoga Looking to get away from the hustle & bustle of the city? This cottage surrounded by lush tropical garden is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a short drive away. With spacious living & modern amenities, the cottage offers maximum comfort & convenience.

4.94 out of 5 average rating, 105 reviews

Downtown Bungalow

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!

Popular amenities for St. Augustine guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guesthouse 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

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

Guesthouse in Jacksonville

A cozy workspace is highlighted by large windows offering natural light. A desk with a computer chair is positioned alongside two comfortable armchairs. A circular area rug and wooden ceiling add warmth to the space, while bookshelves and artwork adorn the surroundings.

5 out of 5 average rating, 9 reviews

Private Guesthouse

A cozy seating area features a gray sofa with patterned throw pillows, positioned in front of a glass coffee table. A small desk with a chair is visible in the background, alongside a decorative wall with geometric paneling. Natural light filters through the dark curtains.

Guesthouse in Fleming Island

4.67 out of 5 average rating, 3 reviews

Attached Updated In-Law-Suite

Guesthouses with a patio

4.95 out of 5 average rating, 38 reviews

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.

Guesthouse in Palm Coast

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, 9 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.

4.88 out of 5 average rating, 160 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, 18 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.

Guesthouse in Palatka

Palatka Golf Cottage

Guesthouse 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.

4.9 out of 5 average rating, 48 reviews

World Golf Village Casita

Guest house rentals with a washing machine and dryer

The exterior of the two-story cottage is surrounded by lush greenery, featuring tall banana plants and other foliage. A wooden porch leads to a dark green front door, enhancing the inviting entrance. Soft lighting fixtures are mounted on either side of the door.

5 out of 5 average rating, 18 reviews

La Casita in Historic District

4.97 out of 5 average rating, 135 reviews

The living area features a grey couch with decorative pillows, complemented by a coffee table made of rattan. A vibrant area rug adds texture, while tropical-themed artwork adorns the wall. Natural light enters through a door leading to the outside.

Guesthouse in Palm Coast

Palm Coast Guesthouse

Guesthouse 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, 101 reviews

Pet-friendly guest house near St George w/ balcony

Guesthouse 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, 116 reviews

Blues It Up - Beachside Studio Apartment

Guesthouse 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

4.97 out of 5 average rating, 29 reviews

Vilano Beach GUEST house/pet/BBQ/RV&Boat prkng

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.