Historic District, St. Augustine vacation rentals

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Top-rated vacation rentals in Historic District, St. Augustine

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Guest favorite

Apartment in St. Augustine

4.97 out of 5 average rating, 176 reviews

Tree Top View 2

This spacious tree-top apt overlooks a seldom used and quiet street. The private balcony has a view to majestic live oaks, a home to many squirrels and birds. A perfect place to sip a steaming mug of coffee in the morning or a glass of wine as the sun goes down. This apartment offers a king bed with a separate living area and an equipped kitchen. An easy walk into historic downtown St. Augustine, with it's many delicious eateries and tourist sites. We also rent the adjacent apt Tree Top View 1.

Guest favorite

Guesthouse in St. Augustine

4.99 out of 5 average rating, 328 reviews

Winery, Distillery, Chocolate, & Pizza

Winery, Distillery, Chocolate Factory, Pizza and historic downtown St Augustine all in walking distance. San Sebastian Winery .2 miles 4 minute walk Carmelo's Pizza .2 miles 4 minute walk Whetstone Chocolates .3 miles 5 minute walk St Aug Distillery .4 miles 9 minute walk Historic St George Street .5 miles 10 minute walk Fountain of Youth 1.4 miles 8 minute bike Beach - Anastasia State Park 3 miles 16 minute bike *****This private cottage is for 2 people only and no pets***** Enjoy your stay

Guest favorite

Home in St. Augustine

4.97 out of 5 average rating, 164 reviews

Uptown Attic - Your Secret Escape

Located in the desirable Uptown District in Historical Downtown St. Augustine, this charming early 1900’s home is the perfect local experience. Featuring alley access to a private driveway with a designated one car parking spot, this newly renovated apartment is steps from all of the city’s hot spots. Guests can easily walk or bike to all of the famous tourist attractions, fantastic dining, and even the area’s famous beaches. This cozy space is also the perfect escape to just stay in and relax.

Guest favorite

Guesthouse in St. Augustine

4.95 out of 5 average rating, 301 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

Apartment in St. Augustine

4.96 out of 5 average rating, 293 reviews

Updated Victorian apt in heart of downtown +VIEWS!

21 Orange Street is a bright and airy second story apartment with unparalleled views of historic downtown Saint Augustine and the bay front. Enjoy old world charm in our newly renovated circa 1860's home- furnished with modern and comfortable amenities! We are steps away from Saint George Street shopping, world class dining and lively bars. If you choose to spend your time here in a more relaxing way, you’ll love the spacious bedroom and our comfortable porch to take a break from it all.

Guest favorite

Loft in St. Augustine

4.95 out of 5 average rating, 101 reviews

The Sweet Spot Suite - Heart of Historic District

This newly remodeled space is in a class all by itself. Seated in the heart of St. Aug where you are right on(with a balcony hanging over) St. George Street, the pedestrian-only “strip” of the city (judged best in the country for walking). Located above the sweet spot ice cream shop and close to dining, nightlife, family-friendly activities, live music, the beach, and much more that our city offers. Please note: there is some noise related to this busy area. Check out my other listings.

Guest favorite

Home in St. Augustine

4.97 out of 5 average rating, 305 reviews

Genovar Mansion Rose Garden Suite Private Entrance

The direct view of a gorgeous live oak canopy on Magnoila Avenue and incredible architecture make this historic home a memorable place to stay. This romantic ground floor suite is perfect for couples with a private entrance, queen poster bed, living room, spacious bathroom, individual climate control, heirloom antiques and reserved parking spot. The home is located within the historic district, close to trolley stops and within easy walking distance to downtown. 6 minutes to the beach.

Guest favorite

Home in St. Augustine

4.87 out of 5 average rating, 112 reviews

Historic Old Fl. Walk Everywhere! East of US 1!

Lemondrop Cottage: an adorable 1920's downtown bungalow on a quiet street EAST of US1 and close to everything. 10 minute walk to Flagler, the Fort, St. George Street, etc. 1 bed/1bath, trundle bed, W/D, kitchen, bath, outdoor hot/cold shower, deck, TV & WiFi. Off street parking. The bedroom has a queen sized bed. The living room has a daybed with trundle bed for sitting & sleep. Pets require approval. Check when people say “downtown/uptown/walk to town”. I’m 0.4 miles away!

Guest favorite

Guest suite in St. Augustine

4.98 out of 5 average rating, 304 reviews

St. Augustine Studio*Private Entrance & Bath*Bikes

A private studio designed from a garage conversion. Separate key-less entry allows for self check-in and welcomes you to this comfortable, clean space with a queen size bed, your own bathroom, kitchenette, and 2 available parking spaces in the driveway. Mini-split AC cools and heats the studio comfortably. High speed internet, flatscreen television with Netflix for relaxing after a day of sightseeing. 2 bicycles for exploring our historic downtown less than 2 miles away.

Guest favorite

Apartment in St. Augustine

4.94 out of 5 average rating, 112 reviews

1-Bdrm Apt Historic St Augustine

Come enjoy this lovely carriage house apartment located in the heart of Historic Downtown St Augustine. Originally built in 1910 and completely updated in 2023. Just two blocks from St. George St, walking distance to Flagler and all of downtown St Augustine. This apartment offers one bedroom, full kitchen and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

Guest favorite

Home in St. Augustine

4.95 out of 5 average rating, 147 reviews

“La Casita” A Charming Uptown St Augustine Cottage

La Casita is located in the Uptown Shopping District. We have darling coffee shops just at the end of the block. Shopping and a convenience store too. We are just 2 blocks from the trolley shop snd visitors center..and, just a 10 min walk to downtown and the fort! We are just a 2 min walk to Francis Field, where many festivals are held. A 7 minute drive to Vilano beach! We are in a quiet and charming neighborhood.

Guest favorite

Apartment in St. Augustine

4.95 out of 5 average rating, 311 reviews

Comfort of Home in St Augustine

Charming apartment in the historic district with a completely updated bathroom with a deep soaking tub and a separate shower, double vanity, Carrera marble tile. The kitchen is new as well with all new appliances, cupboards and quartz countertop. My favorite part of this apartment is the large front porch where you can relax, enjoy your morning and evening beverages, people watch and mingle with the neighbors...