Guesthouse holiday rentals in Anastasia Island

4.9 out of 5 average rating, 367 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!

LocationValueHospitality

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, 186 reviews

Island’s Edge Guest Cottage on Anastasia Island.

Professionally cleaned marsh front private cottage with amazing views. Nestled between the state park, our famous AMP, great beaches & downtown. Your deck is perfect for a bbq, bird watching & sunset cocktails. ☹️Sorry no marsh access.☹️ Please Note: this is a space where the main house is visible from the cottage. We do have a small dog that will be contained for the entirety of stay. Park trails and beach are close by. Stroll over to the Saturday morning market at “the Amp”. You’ll love it.

LocationFamilyCheckout

A cozy sleeping area features a spacious bed layered with a woven throw and decorative pillows. Soft lighting highlights the wooden accents. A comfortable chair is visible beside a small round table, creating a welcoming atmosphere.

4.97 out of 5 average rating, 273 reviews

BambooLane Hideaway near Beach, Amphitheater-DWTN

Sophisticated, tropical hideaway. Your retreat, quiet, respectful & peaceful. All are welcome here with love and respect. Perfect for singles, couples, looking to rest and relax or to explore this historic Florida shore, the ‘Bamboo lane hideaway’ offers unique accommodations complete with a custom-designed interior and laid-back beach vibe. One thing to consider before booking is that our place is tiny but mighty. Complementary bikes to Explore the Lighthouse, Zoo, Beaches, AMP, & Downtown.

FamilyValueCleanliness

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, 333 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!

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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, 173 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.

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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, 458 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.

LocationFamilyOutdoor spaces

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, 215 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.

ValueFamilyIndoor spaces

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, 508 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.

ValueLocationCheckout

4.88 out of 5 average rating, 513 reviews

Designer studio · walk/bike downtown

Off Street Parking with Private Entrance 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.

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Superhost

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.

Guesthouse in Butler Beach

4.87 out of 5 average rating, 129 reviews

Blues It Up - Beachside Studio Apartment

Located in Butler Beach this beautiful, modern, coastal efficiency apartment will accomodate 2 guests. Enjoy a short walk to the beach or drive on beach access just down the street. Close to restaurants and shopping. Butler Beach is located on Anastasia Island between Crescent Beach and St. Augustine Beach. Tones of Blue is a 2 bedroom 2 bath cottage on the property next door that is a seperate vacation rental. The garage is not included in the rental. Sorry, no pets or smoking

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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, 153 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.

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