Holiday rentals with outdoor seating in Historic District, St. Augustine

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Top-rated rentals with outdoor seating in Historic District, St. Augustine

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Guest favourite

Guest house in St. Augustine

4.99 out of 5 average rating, 327 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

2–9 Jun

$194 SGD per night

Guest favourite

Cottage in St. Augustine

4.98 out of 5 average rating, 180 reviews

Bamboo Lane Hideaway near AMP, Downtown & Beaches

Sophisticated, tropical hideaway. Your retreat… quiet, respectful & peaceful. All are welcome here with love and respect. Perfect for singles, couples, looking to rest and relax or to explore this historic Florida shore, the ‘Bamboo lane hideaway’ offers unique accommodations complete with a custom-designed interior, laid-back beach vibe, and complimentary parking pass for downtown. Explore the nearby Lighthouse, Zoo, white-sand Beaches, Amphitheater & Downtown all less than 1.6 miles away.

29 Oct – 5 Nov

$159 SGD per night

Guest favourite

Home in St. Augustine

4.93 out of 5 average rating, 104 reviews

Genovar Mansion Master Suite Private Entrance

The direct view of the gorgeous live oak canopy on Magnolia Avenue and incredible architecture make this historic home a memorable place to stay. This romantic master suite is perfect for couples with a private entrance, queen poster bed, spacious bathroom with two shower heads and body jets, private balcony, individual climate control and 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.

14–21 Jul

$193 SGD per night

Guest favourite

Serviced apartment in St. Augustine

5.0 out of 5 average rating, 68 reviews

Tree Top View 1

Our spacious apartment overlooks a quiet & seldom used street. The private balcony has a beautiful 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 at sunset. This apartment offers a king bed with separate living area and an equipped kitchen. We're an easy walk into historic downtown St. Augustine, and it's many delicious eateries and tourist sites. We also rent the adjacent apt, Tree Top View 2.

24–31 Jul

$152 SGD per night

Guest favourite

Guest house in St. Augustine

4.95 out of 5 average rating, 296 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.

6–13 Sep

$189 SGD per night

Guest favourite

Flat in St. Augustine

4.99 out of 5 average rating, 112 reviews

2-Bdrm Apt in Downtown St Aug

Come enjoy this spacious, two bedroom 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. Large dining table, a den that offers a quiet space to work and sofa bed, and large kitchen make this space perfect for your stay! Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

22–29 Oct

$221 SGD per night

Guest favourite

Flat 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.

23–30 Oct

$204 SGD per night

Guest favourite

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.

24 Apr – 1 May

$192 SGD per night

Guest favourite

Home in St. Augustine

4.86 out of 5 average rating, 110 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!

27 Oct – 3 Nov

$189 SGD per night

Guest favourite

Guest suite in St. Augustine

4.97 out of 5 average rating, 111 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.

6–13 Aug

$143 SGD per night

Guest favourite

Bungalow in St. Augustine

4.92 out of 5 average rating, 325 reviews

Uptown Classic Bungalow Comfy Walk Everywhere

The Uptown Bungalow is located on a quiet street only a block away from all the action in the heart of the nation's oldest city. Built in 1910 the unit has been renovated, is tastefully decorated ,and is equipped with everything you will need to make your stay in St. Augustine a great experience. Dine in the kitchen or an outdoor patio set on the screened in porch where the guests can enjoy a café & scones in the AM or in the evenings cocktail & Hors d'oeuvres.

29 Mar – 5 Apr

$202 SGD per night

Guest favourite

Home in St. Augustine

4.95 out of 5 average rating, 146 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.

28 Feb – 7 Mar

$193 SGD per night