Holiday houses in Historic District, St. Augustine

4.97 out of 5 average rating, 745 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

4.97 out of 5 average rating, 229 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.

4.99 out of 5 average rating, 164 reviews

Apt C - Historic St Augustine Charm and Comfort

Nestled on a quiet residential street, this apartment in the trees is just a block from the start of restaurants, shops, bars and historic sites and just 3-4 miles from multiple beaches. We provide 2 beach chairs, cooler, umbrella and towels. A few amenities of this renovated apartment include a back deck, a massage chair, upscale appliances, designed to provide deep R&R after a day of sightseeing and beach play. Access to the apartment is via the staircase on the west side of the building.

Guesthouse in St. Augustine

4.95 out of 5 average rating, 381 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.

4.91 out of 5 average rating, 128 reviews

Charming Old-Florida Apartment

This darling Uptown apartment is in the thick of it! Next door to fabulous uptown shops and eateries -- including our own bodega and taproom. Walkable to bustling historic downtown, the fort, the Bridge of Lions, and the Matanzas River. Bikeable to Vilano Beach and Anastasia State Park. And a short drive to additional beaches on Anastasia Island or in Vilano. Enjoy a slice of Saint Augustine typically only enjoyed by the locals, and relax in the friendly historic Abbott Tract neighborhood.

4.95 out of 5 average rating, 187 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.

4.97 out of 5 average rating, 187 reviews

C5 Perfect location in 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. We have a drip coffee maker, coffee, decaf, creamers, and sugar. We offer Roku TV.

4.9 out of 5 average rating, 353 reviews

Casa Tranquila Comfy*Stylish*Walk Everywhere*Homey

Casa Tranquila is located on a quiet street only a blocks away from all the action in the heart of the nation's oldest city. Built in 1917 w/ 11 ft. ceilings, renovated in 2021 & is tastefully decorated & equipped with everything needed to make your stay in Historic St. Augustine a remarkable experience. Indoor dining area, updated kitchen, & an outdoor dinning on the screened in porch. Café & scones in the AM or cocktails & Tapas in the evening al fresco. See you soon.

4.97 out of 5 average rating, 118 reviews

Cute & Compact 1BR-Walk to town

This St. Augustine apt. is an 5-7 minute walk to St. Augustine's downtown hub and a 15 min. drive to the beach. This centrally located lower level apt. has an open concept kitchen and living room area. There is a small porch that allows guests to sit outside to enjoy their morning coffee. This apt. is a one BR (queen) with master bath and is perfect for 2 guests. ** One parking space provided on site and Free street parking for additional cars

Guesthouse in St. Augustine

4.97 out of 5 average rating, 331 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!

4.95 out of 5 average rating, 187 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.

Bungalow in St. Augustine

4.92 out of 5 average rating, 204 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.

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Popular amenities for Historic District, St. Augustine holiday rentals

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Pool

Free parking on premises

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Other great holiday rentals in Historic District, St. Augustine

5 out of 5 average rating, 79 reviews

Downtown Charmer with Pool - Perfect for Couples!

TammyRating, 5 stars4 weeks ago

We stayed at Pauline’s house for 1 week, and we had an amazing time! Her house is in an amazing neighborhood, and we didn’t have to take the car out of the driveway all week. The pool was wonderful, and our 2 pugs enjoyed exploring her fenced in backyard. The house was impressively clean, well-stocked and beautifully designed. I would highly recommend this property for a fun, relaxing time in gorgeous St. Augustine! Thank you Pauline!

5 out of 5 average rating, 66 reviews

Palo Haus | 1918 Cottage in Historic St. Augustine

ChrisRating, 5 stars4 days ago

House was perfect for the 4 of us. Very clean. The historic feel of the home fit right in with the area and the updates to the house were perfect. Would definitely stay here again.

Guesthouse in St. Augustine

4.9 out of 5 average rating, 252 reviews

SaraCasa - First Floor House 2Br/1.5Bath

CheriRating, 5 stars2 days ago

We just used it to sleep and bath really. But everything was nice and comfortable. There are people who rent the 2nd floor and you can definitely hear them but wasn't too bad for us. We also had a small issue with the keypad on the front door but Jason responded immediately and everything was good.

4.97 out of 5 average rating, 78 reviews

Uptown Loft - Bright - Modern - Walkable

VeronikaRating, 5 stars2 weeks ago

Andrea and Danny’s place was perfect. It was super clean, really well decorated and close to everything. I didn’t rent a car this time around so the fact that everything was walkable was super important to me. The hosts were very responsive and the unit had absolutely everything - hair dryer, iron, etc. 5 star stay - will definitely be returning here when I’m in St. Augustine again :)

4.94 out of 5 average rating, 34 reviews

Apartment - Above Mojo BBQ

NicoleRating, 5 stars1 month ago

A beautiful, clean and unique space. The beds were super comfortable and the linens were really nice. The master bedroom and bathroom were so much nicer than the description implies, it was a nice surprise. We loved the porches too. It is located in a perfect spot to enjoy what St Augustine has to offer. You could vaguely hear the restaurant below, but it wasn't bothersome. The street noise could be a little loud at times, but it did not take away from this amazing space, it is all part of the city's character. We absolutely recommend this space for anyone wanting to enjoy the downtown area.

Superhost

5 out of 5 average rating, 9 reviews

I bed-1bath on 2nd fl in Uptown - Free parking

JohnRating, 5 stars3 weeks ago

We celebrated my wife's birthday by coming to St. Augustine and Ann's place was PERFECT for what we were looking for. Nestled on a quiet side street just a couple blocks from historic downtown, this location is absolutely ideal - the perfect balance of proximity without hearing the crowds at some of the rowdier places in town. Ann offers a parking spot which is an absolute-must when staying near downtown - anywhere else is $20/day and street parking in town is virtually non-existent. When we arrived, we were greeted with a warm note and some fresh muffins! Our area was clean and prepared, and even featured a washer/dryer. Ann also lent us a pack-and-play for our toddler. I highly recommend this place as a former AirBnB owner myself - the attention to detail by the host is excellent, the house is perfectly situated, and the price is better than hotels or any of the other AirBnB locations we searched. If we come back, this is where we'll stay! (if you don't snatch it first!)

Superhost

Hotel room in Lincolnville

4.81 out of 5 average rating, 180 reviews

Downtown Romantic Boutique Bed & Bath, Unit 6

MarkRating, 5 stars1 day ago

Perfect place to stay if you're in town! The bed is ridiculously comfortable, and the room was super clean! Will definitely be staying again!