Holiday houses in Historic District, St. Augustine

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

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Top Guest favourite

Apartment in St. Augustine

4.97 out of 5 average rating, 756 reviews

Balcony apt on USA’s oldest Street (St. George St)

"The Heart of St. Augustine" Voted #1 Airbnb in St Augustine by Trip 101, # 5 Top 10 Airbnb's in St. Augustine" by Territory Supply and in the "Top 15 Best Airbnb's in Florida" by Road Affair. Live music, scrumptious food, craft drinks, and the hustle and bustle of people walking the historic St. George St, all surround you. Relax and people watch from your balcony. Sightseeing, restaurants, trolley stop and nightlife are steps away. This apt is in the center of it all. NYE is a 3 night min

Top Guest favourite

Cottage in St. Augustine

4.99 out of 5 average rating, 189 reviews

Little Sister's Carriage House w/ Parking

Welcome to Little Sister's Carriage House, a bright and delightful historic cottage located only steps from all St. Augustine has to offer. Beautifully furnished and full of vintage touches, this home is the perfect blend of modern comfort and historic charm. With a personal garden, full vintage kitchen and tons of character, it's a one of a kind stay. Sip coffee on your porch, or take a short stroll into town. Park your car and walk everywhere! Locally operated by lifelong St. Augustinians

Top Guest favourite

Apartment in St. Augustine

4.95 out of 5 average rating, 274 reviews

Treetop Cottage - 3 blocks from Historic District

Located right in the heart of the leafy historic district is this charming treetop cottage with its own eclectic style and modern design. The cottage features bright sun-filled living with a fully equipped kitchen, a generous king bedroom, a sparkling bathroom and Smart TVs with Netflix in each room. Enjoy a complimentary coffee at the cafe then leave the car parked and explore everything this beautiful area has to offer on foot with restaurants & attractions all just a short stroll away.

Top Guest favourite

Cottage in St. Augustine

5 out of 5 average rating, 103 reviews

Historical Cottage in Heart of Town! Park & Walk

Welcome to Groveside Cottage on one of historic streets of St. Augustine! In 1920s Grove Avenue was the home of several families of cigar makers and two cigar manufacturing companies. This lovingly restored cottage offers modern comforts while maintaining the character and charm of a circa 1900 home. Our coziest porch and fenced courtyard are great for a cup of coffee or a glass of wine to enjoy outdoors. Park and walk to discover all the wonderful things this historic downtown has to offer!

Guest favourite

Apartment in St. Augustine

4.96 out of 5 average rating, 367 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.

Top Guest favourite

Holiday home in St. Augustine

5 out of 5 average rating, 143 reviews

Walk Historic Downtown! "Hope & Glory"

You'll be one block from Historic Uptown Saint Augustine's shops, eateries & attractions. Enjoy smart TVs, luxury bedding with blackout curtains in bedrooms, screened in porch, back deck, bathing cabana with outdoor shower/clawfoot tub, gas fire pit and Weber grill, game room with darts, fooseball, crafts & More. Cozy, clean & relaxing. Fabulous fully-equipped kitchen, full privacy fence, off-street parking, paved driveway close to downtown and excellent beaches. Prime location!

Top Guest favourite

Home in St. Augustine

4.94 out of 5 average rating, 194 reviews

HistoricLuxury•Designer Kitchen&Baths•Walk&Trolley

No Cleaning Fee! 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet! Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

Top Guest favourite

Guesthouse in St. Augustine

4.96 out of 5 average rating, 340 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!

Top Guest favourite

Apartment in St. Augustine

4.95 out of 5 average rating, 197 reviews

Charming 1 Bedroom apt, Historic St Augustine

You will love this newly remodeled one bedroom apartment in Historic 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 with king size bed, 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 favourite

Bungalow in St. Augustine

4.93 out of 5 average rating, 216 reviews

Historic Full House 2min walk to Historic Downtown

I'm a lovely old home called La Casita in historic St. Augustine. Nice to meet ya! Flagler had me built to house his crew. I’m certified historic and charming too. I'm right downtown where you need to be so close to everything you'll want to see— The fort, the lighthouse, and all the rest. I’d be delighted if you were my guest. Comfort and peace is a phone call away. Please say yes. I want you to stay.

Top Guest favourite

Apartment in St. Augustine

4.95 out of 5 average rating, 200 reviews

Lemon Street Studio (Very Walkable + Free Parking)

Located just a few blocks from all that downtown has to offer, the Lemon Street Studio is the perfect way to enjoy your trip to St Augustine. Less than a 10 minute walk to St George Street, the Castillo de San Marcos, the Bayfront, and Flagler College. The one bedroom apartment welcomes you with free off-street parking, a private entrance, and a stylish space to relax after hitting the town.

Guest favourite

Apartment in St. Augustine

4.95 out of 5 average rating, 358 reviews

Apt A - Comfort of Home in Historic St Augustine

Charming old world apartment in the historic district (AND a short 3-4 miles from multiple beaches) with a completely updated bathroom and kitchen. The kitchen has all new appliances, cupboards and quartz countertop. My favorite part of this apartment is the porch where you can relax, enjoy your morning and evening beverages, watch horse drawn carriages and mingle with our neighbors...