Guest house holiday rentals in Anastasia Island

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.

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!

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 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.

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.

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!

Island’s Edge Guest Cottage on Anastasia Island.

Fresh and clean, 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 & cocktail sunsets. ☹️Sorry no marsh access.☹️ Park trails are close as is the beach. Enjoy a stroll over to the Saturday morning market at “the Amp”. You’re gonna just love it here.

Unique stay in the Hammock filled with local art

Come hang in the shade in one of the last pieces of 'Old Florida' in the Hammock! A studio apartment filled with local art and awesome thrift finds :) Our tree lined neighborhood is perfect for a quiet get away that is close to the beach and walking distance to the river. We are minutes away from many different beach access, and 2 miles from Bings (boat ramp) and Malacompra trails. St. Augustine is 25 minutes away, Daytona is 30 minutes, Orlando 1.5 hours away

Romantic Island Studio • Walk & Bike to Downtown!

No Cleaning Fee! 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.

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 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.

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.