Guesthouse holiday rentals in St. Augustine

4.91 out of 5 average rating, 583 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).

4.99 out of 5 average rating, 377 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.

4.97 out of 5 average rating, 322 reviews

Guesthouse in Palm Coast

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.

5 out of 5 average rating, 102 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.

4.95 out of 5 average rating, 388 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.

4.94 out of 5 average rating, 158 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

4.93 out of 5 average rating, 445 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, 298 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!

4.92 out of 5 average rating, 170 reviews

Guesthouse in Palm Coast

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

Superhost

4.88 out of 5 average rating, 468 reviews

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.

4.96 out of 5 average rating, 338 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!