Guesthouse vacation rentals in St. Augustine

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Top-rated guesthouse rentals in St. Augustine

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Guest favorite

Guesthouse in St. Augustine

4.91 out of 5 average rating, 545 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).

Guest favorite

Guesthouse in St. Augustine

4.99 out of 5 average rating, 339 reviews

Pelican Guesthouse-Spacious/Quiet/Comfortable

Quiet, spacious guesthouse. Comfortable beds and immaculately kept. Read our reviews:) A few miles from gorgeous beaches, the old world charm of St Augustine historic downtown and St Aug Amphitheatre. 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.

Guest favorite

Guesthouse in St. Augustine

4.98 out of 5 average rating, 120 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 :)

Guest favorite

Guesthouse in Palm Coast

4.99 out of 5 average rating, 286 reviews

Private beachside guest cottage

This private guest cottage is located just down the street from the beach in “The Hammock” area of Palm Coast. ( The beach and Hammock Beach Resort is just 1 mile away) If you love the outdoors, this cottage is for you! (Golf, fishing, beach, surfing, hiking, biking, boating) State and County Parks nearby. PLEASE read the entire listing descriptions below before booking, MOST IMPORTANT is the “Location / Neighborhood” description. This cottage can be reserved for a maximum of two guests only.

Guest favorite

Guesthouse in St. Augustine

4.95 out of 5 average rating, 330 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.

Guest favorite

Guesthouse in St. Augustine

4.92 out of 5 average rating, 117 reviews

Heated Pool Side 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.

Guest favorite

Guesthouse in St. Augustine

4.9 out of 5 average rating, 118 reviews

Island’s Edge Guest Cottage on Anastasia Island.

Fresh and clean, marsh front private cottage with bright new path lights and 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. You have to stroll over to the Saturday morning market at “the Amp”. You’re gonna love it here.

Guest favorite

Guesthouse in Lincolnville

4.94 out of 5 average rating, 375 reviews

Storybook Cottage-Downtown St. Augustine Preferred

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.

Guest favorite

Guesthouse in St. Augustine

4.87 out of 5 average rating, 274 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!

Guest favorite

Guesthouse in St. Augustine

4.97 out of 5 average rating, 270 reviews

“Little Pink House”-hidden gem in the 💗 of Uptown

Stay with us and you truly can "Have It All"!. Just steps from shopping and restaurants, yet nestled in a quiet neighborhood. Walk to St George Street, The Fort, Visitors Center, Trolley Station, Coffee Shops, The Bayfront. 7 minutes from the Beach. Relax after a day of sightseeing around the pool, and enjoy coffee or wine on the porch. Little Pink House is the guest cottage right behind Pink House Uptown Charmer. More space for your group!

Guest favorite

Guesthouse in Palm Coast

4.88 out of 5 average rating, 108 reviews

Cozy Studio PALM COAST /Flagler /Hammock Beach

Keep it simple at this peaceful place and come to relax with your family and friends in our beautiful jungle guesthouse. White sands, and lot of peace in the charm of the old Florida jungle. Our place is strategically located. Publix within 5 minutes walking, only 1 mile from the beach, live music, restaurants , rental bikes, fishing, kayak, horseback riding, golf, and much more...

Guest favorite

Guesthouse in St. Augustine

4.98 out of 5 average rating, 330 reviews

Loft in the trees

COMPLETELY PRIVATE ACCESS Loft guest suite above a detached garage in a great Historic North City neighborhood. Easy to get to the heart of downtown, Vilano Beach, and other attractions (less than 1 mile to ~2 miles depending on where you’re going). Up in the trees with great natural light, hardwood floors, and high vaulted ceilings. Come and see St. Augustine, Florida!