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

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Top-rated Holiday Houses with Outdoor Seating in Historic District, St. Augustine

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in St. Augustine

4.98 out of 5 average rating, 178 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.

31 Oct – 7 Nov

$243 NZD per night

Guest favourite

Home in St. Augustine

4.94 out of 5 average rating, 281 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.

26 Sep – 3 Oct

$259 NZD per night

Guest favourite

Apartment in St. Augustine

4.99 out of 5 average rating, 187 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.

14–21 Sep

$257 NZD per night

Guest favourite

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.

23–30 Sep

$272 NZD per night

Guest favourite

Apartment in St. Augustine

4.96 out of 5 average rating, 245 reviews

StA Hideaway - Upper Unit Apt Minutes From Beach

This tastefully remodeled second floor residence is located in a quiet historic neighborhood. It offers tons of natural light with modern amenities while preserving the historic character of the of the home. With comfortable furnishings, and a stylish, fully equipped kitchen, you'll feel right at home the while you enjoy your morning coffee or evening wine from the balcony. Whether you're seeking a weekend getaway or an extended stay, this property is designed to cater to your every need.

14–21 Nov

$262 NZD per night

Guest favourite

Loft in St. Augustine

4.95 out of 5 average rating, 98 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.

17–24 Aug

$275 NZD per night

Guest favourite

Apartment in St. Augustine

4.98 out of 5 average rating, 147 reviews

C5 Flagler location, city center, patio, beaches

Relax in this cozy and comfortable downstairs apartment with patio. Don't worry about the struggle of downtown parking, PARKING IS FREE on site (1 designated spot for your apartment). So many nearby attractions just steps (or a trolley ride) from the door including shopping on St. George St, restaurants and sandy beaches where you can rent paddle boards, kayaks, small sailboats and more. Netflix, Hulu, Roku, CNN, FOX, E, Bravo, HGTV, TLC, History, A&E, USA, Travel, and much more.

26 Jun – 3 Jul

$298 NZD per night

Guest favourite

Apartment in St. Augustine

4.98 out of 5 average rating, 348 reviews

*2BR* Luxe Loft Close to Everything | Balcony

This newly renovated 2 bedroom apartment is nestled above STA Flawless Beauty Lounge and sits in an area being re-juvenated in St. Augustine. Walk to Back 40 Urban Cafe, a favorite with the locals. The interior is professionally designed (designmd.co) and is ideal for guests who appreciate fun, funky, eclectic touches. Getting married? Stay at the same property where you can get your hair / makeup / photo shoot done with your bridesmaids! Check out STA FLAwless Beauty Lounge!

9–16 Jan

$270 NZD per night

Guest favourite

Guest suite in St. Augustine

4.98 out of 5 average rating, 301 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.

13–20 Jul

$225 NZD per night

Guest favourite

Cottage in St. Augustine

4.96 out of 5 average rating, 160 reviews

Masters Manor A Gothic Themed Cottage

This 1900 gothic style charmer is a unique place to call home while visiting our city. From the dark aesthetic, custom woodwork and warm lighting ..you'll find this home has a very comforting feel to it. The eclectic decor offers a whimsical, inviting atmosphere! It's located in West Augustine under 2 mi from downtown and less than 6 mi from both beaches. A local Brewery, Bakery and Breakfast joint are .5 away Photo shoots, cinematography/music videos welcomed🦇

16–23 Jun

$225 NZD per night

Guest favourite

Bungalow in St. Augustine

4.92 out of 5 average rating, 322 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.

26 Oct – 2 Nov

$298 NZD per night

Guest favourite

Home in St. Augustine

4.94 out of 5 average rating, 145 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.

5–12 Apr

$275 NZD per night