Guesthouse vacation rentals in St. Augustine

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Top-rated guesthouse rentals in St. Augustine

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Palm Coast

4.91 out of 5 average rating, 134 reviews

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. Two rusty bikes available as well. 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

Aug 24 – 31

G$20,458 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.93 out of 5 average rating, 296 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!

Dec 15 – 22

G$16,177 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.94 out of 5 average rating, 302 reviews

The Rohde House, The Rohde Guest House

Our place is close to nightlife, public transport, the airport, the city square, and parks. It's good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). Five minute walk to the "Nights of Lights", two minute walk to Francis Field event field, where many festivals, concerts and activities are held. Five minute drive to the ocean beach at Vilano. Many Restaurants and bars in walking distance, including sports bar, martini bar, Irish pub and more.

Jan 11 – 18

G$31,886 GYD per night

Guest favorite

Guesthouse in Palm Coast

4.99 out of 5 average rating, 269 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.

Jun 16 – 23

G$26,516 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.95 out of 5 average rating, 295 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.

Sep 23 – 30

G$29,103 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.88 out of 5 average rating, 101 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.

Jan 30 – Feb 6

G$27,635 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.86 out of 5 average rating, 251 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!

Nov 6 – 13

G$20,211 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.98 out of 5 average rating, 211 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!

Oct 4 – 11

G$34,910 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.97 out of 5 average rating, 316 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). We have 2 complimentary bikes for you to get around downtown! Up in the trees with great natural light, hardwood floors, and high vaulted ceilings. Come and see St. Augustine, Florida!

Aug 21 – 28

G$19,975 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.99 out of 5 average rating, 316 reviews

Pelican Guesthouse-Spacious/Quiet/Comfortable

Quiet, spacious guesthouse with light filled interiors. Very comfortable beds and immaculately kept. 10 min from gorgeous beaches and the old world charm of St Augustine historic downtown. Friendly neighborhood and accessible to beautiful walks along the Matanza River. Self check in, private entrance, two flat screened TV's, full kitchen (stove, large refrigerator and microwave) Full laundry room and off street parking.

Aug 25 – Sep 1

G$23,218 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.91 out of 5 average rating, 530 reviews

Captain's Quarters Tiny House

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).

Feb 12 – 19

G$17,877 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.94 out of 5 average rating, 227 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.

Oct 3 – 10

G$20,384 GYD per night