Guesthouse vacation rentals in St. Augustine

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, 199 reviews

Historic St. Augustine 2/1 Cottage & Heated 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 :)

4.91 out of 5 average rating, 363 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 charming guest house is depicted, featuring a blue exterior and white trim. Stairs lead to the entrance, adorned with potted plants. A white fence surrounds the property, while a cactus sits in the foreground. Light filtering through trees highlights the inviting atmosphere.

4.96 out of 5 average rating, 111 reviews

Downtown cottage in perfect spot

An easy stroll to historic downtown St. Augustine’s shops, restaurants, trolleys, pubs, tourist hot spots and the country’s oldest fort. Only a 6-minute drive to the beach. Fully furnished, bright with ample windows & quaint. This guest house is on the same property - separated by an awesome courtyard - as an historic 1800s Victorian house. But you’ll have this entire cottage to yourself and it’s very private. Two bedrooms, each with a full-size bed & a large, comfortable couch in living room.

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.

4.89 out of 5 average rating, 323 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 large smart tv for own subscriptions, 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!

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, 181 reviews

Island’s Edge Guest Cottage on Anastasia Island.

Fresh and professionally cleaned marsh front private cottage with amazing views. Walk or pedal from this adorable cottage to any of the local attractions. Nestled between the state park, our famous AMP, great beaches & downtown. Everything is close by. Your deck is perfect for a bbq, bird watching & sunset cocktails. ☹️Sorry no marsh access.☹️ Park trails and beach are close by. Stroll over to the Saturday morning market at “the Amp”. Ask me about our “Concert Package” You’ll love it here.

A spacious king-sized bed is dressed in a soft comforter, accented by decorative pillows. Natural light streams in through two windows, revealing a glimpse of the greenery outside. Nightstands with lamps flank the bed, and an air conditioning unit is mounted on the wall.

4.95 out of 5 average rating, 164 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.

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.

4.94 out of 5 average rating, 446 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.

4.95 out of 5 average rating, 203 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.

4.93 out of 5 average rating, 497 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.

4.88 out of 5 average rating, 509 reviews

Coral Cottage Designer Studio•Walk/Bike 2 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.

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, 149 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.

The front entrance of a duplex is visible, featuring a light pink facade with decorative brick accents. A welcoming front door is framed by two potted plants with vibrant yellow flowers. A well-maintained lawn and a paved walkway enhance the inviting appearance of the home.

4.94 out of 5 average rating, 293 reviews

Sunset Casita

This is a duplex located off A1A in beautiful St. Augustine Beach. There is an oceanfront boardwalk to the beach nearby. Beach access by car is 2 blocks away. Publix, Winn Dixie and Starbucks are within walking distance as are many wonderful restaurants and shops. We are located five minutes from St. Augustine Amphitheater and 10 minutes to historic St. Augustine.

Popular amenities for St. Augustine guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guesthouses

4.89 out of 5 average rating, 45 reviews

Secluded Cottage-walk to amphitheater and more

Guesthouse 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.

4.97 out of 5 average rating, 75 reviews

Casita by the Sea - Second Floor - Heated Pool

4.72 out of 5 average rating, 124 reviews

The Coral Shell

Private room in St. Augustine

New place to stay

Private Room • Cozy Stay • St. Augustine

Guesthouse in Jacksonville

5 out of 5 average rating, 16 reviews

Private Guesthouse

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

Guesthouses with a patio

5 out of 5 average rating, 17 reviews

Coral Cottage

4.94 out of 5 average rating, 66 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.

4.9 out of 5 average rating, 31 reviews

LaCasita, a quick walk downtown

New place to stay

View of the Rio Studio Retreat

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.

4.68 out of 5 average rating, 74 reviews

Vilano Beach Cottage

4.95 out of 5 average rating, 43 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

4.92 out of 5 average rating, 66 reviews

R & R Loft - WGV - Studio Apt with Kitchenette

4.98 out of 5 average rating, 50 reviews

An open living space is visible, featuring a light-colored sofa with decorative cushions positioned near a dark leather chair. A round coffee table sits atop a patterned area rug. Large windows allow natural light, providing views of greenery outside, while a television stands on a low console.

Guesthouse in Palm Coast

Hammock Treehouse

Guesthouse rentals with a washer and dryer

Guesthouse in Fleming Island

5 out of 5 average rating, 3 reviews

Honey’s-An Adults only peaceful couples retreat

A wrought-iron gate framed by a wooden archway is positioned at the entrance of a quaint courtyard. A path of bricks leads through lush greenery, providing a welcoming approach. The surrounding fence and nearby homes contribute to the private and peaceful ambiance of the area.

4.95 out of 5 average rating, 22 reviews

La Casita in Historic District

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.

4.8 out of 5 average rating, 5 reviews

Waterfront 1BR/1.5BA relaxing private guest house

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, 119 reviews

Park & Walk Dntwn Cozy Romantic Couples Getaway

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.

4.86 out of 5 average rating, 125 reviews

Blues It Up - Beachside Studio Apartment

Guesthouse in East Palatka

5 out of 5 average rating, 68 reviews

Riverfront Fishing and Sunsets Over the St John's

4.8 out of 5 average rating, 40 reviews

Madeira Suite-walkable to amphitheater and more