If you live in the US and fancy a long, refreshing holiday in a charming old town by the beach, you really don’t need to go that far to the Caribbean or Latin America. St. Augustine in northeastern Florida combines centuries-old buildings of colonial design, wonderful beaches, and a warm ambiance, typical of Caribbean towns. Must-visit attractions here include the St. Augustine Lighthouse & Maritime Museum, which houses a lighthouse dating back to 1875 which you can climb and enjoy exceptional views of the ocean from. Kids will enjoy the St. Augustine Pirate & Treasure Museum, while a fun family picnic is possible at St. Augustine Beach. With great attractions, a friendly ambiance, and the classic vibes of a historic old town, St. Augustine is perfectly suited for long, relaxing holidays. Scroll down for the best long-term rentals in St. Augustine, Florida, for appropriate accommodations.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 13, 2024.
1. Saint Sylvan (from USD 108)
Chic, colorful, and super trendy, this cute little bungalow named Saint Sylvan was built in the 1920s! Its bright blue exterior and unique design make it seems like it was built by a creative, contemporary designer. But the interiors will remind you of old times, with comfy wooden floors, vintage rattan furniture, and beautiful rugs ornamenting the house. As a pleasant addition, the owners provide two adult bikes and a small kid’s bike free of charge, which makes it much easier and more fun to explore the area.
Another nice bonus of staying in Saint Sylvan is the 30% discount on rent for a monthly stay.
Top guest reviews
Cleanliness:
super clean and amazingly roomy and comfyHost:
arielle is a wonderful host very caring for details and super easy to communicate withRead more reviewsLocation:
we really enjoyed our stay at the bungalow the house is charming and is in a great locationwe loved her place and we look forward to be back any time we are in the aerea
Superhost
2. Monarch Gardens (from USD 160)
This lovely cottage is named Monarch Gardens, which seems to be an appropriate name as its garden is just so beautiful it feels fit for a king. The vast green garden on which the house stand comes with plenty of large trees, home to a number of chirping birds and even butterflies. For a cozy afternoon with your family, have a nice barbecue lunch in the garden, which has a grill beside a nice patio with plenty of chairs and a table. There is also a large hammock where you can unwind and take a good nap while listening to the sound of rustling leaves and singing birds.
Have the most relaxing vacation in this delightful cottage and enjoy an additional 10% discount for a stay of 28 days or more.
Top guest reviews
Amenities & Room:
we were very pleased with the well appointed kitchenCleanliness:
the cottage was clean and welcomingit’ (website hidden by airbnb) clean well maintained perfectly landscaped and well stocked for an airbnbthis home is immaculately clean all the way down to the outdoor grillthe cottage was spotless and beautifully furnishedclean and liz is the perfect hostHost:
the host was very friendlyliz is an amazing hostshe was very communicative and sweetand liz was an amazing hostlis is the perfect host she pays attention to all the detailsRead more reviewsLocation:
the location was absolutely perfecta cute cottage so close to downtown and many eateries within walking distancethe location was perfect for stgreat location right on the island easy walk to castle and old townthe location is perfect for a daily walk into town
3. Cute cottage with elegant decor (from USD 110)
Situated on a vast grass yard surrounded by large trees, this cute cottage offers maximum comfort and privacy. Located in a historic neighborhood just next to the downtown area, the cottage guarantees a quiet environment while still offering easy access to everything you need. The cottage itself is super comfy with a nice countryside vibe to it, with a wooden porch, wooden floors, and tasteful decorations ornamenting the house.
The cottage offers a 16% discount for weekly stays and an even bigger discount of 30% for monthly stays.
Top guest reviews
Amenities & Room:
beds were comfortable and the cottage is very homeyCleanliness:
very clean and adorable little cottagesuper clean and tidy placevery warm welcoming feeling and clean environmentnice and clean cottagea clean and cozy cottage 6 minutes from downtownHost:
marybeth was a great host she was quick to respond and answer any questions i hadRead more reviewsLocation:
such a cute little place to staythis place is amazing close to all the attractionsthe neighborhood was nice and quiet and the location convenient for get aroundexcellent place to stay and close to the historic districtloved the house close to downtown and very quiet
4. Stylish loft with great amenities (from USD 120)
With an almost-perfect 4.98 score on the Airbnb website, this stylish loft is a definite fan favorite! With necessary appliances such as a washer, dryer, and a fully fitted kitchen, and fun entertainment amenities such as a TV, books, and board games, everything is provided in this gorgeously designed loft. The decorations are well thought out, with funky art pieces and wall paintings further adding to its overall aesthetics.
Another great highlight of this loft is the 33% discount that it offers for stays of more than 28 days.
Top guest reviews
Amenities & Room:
so many amenities comfortable beds ac works great and so nicely decoratedthis space is just as pictured – adorably decorated with comfortable furnishings vibrant colors and lush texturesi just love how they decorated the space is very comfortable incredibly well stockedCleanliness:
the space was very clean and just as pictured in the listingsuper clean to boot too the best parts are the personal touches thoughthe home is clean and relaxing; our kiddo loved the games that were thereHost:
stephanie was a generous host who quickly responded to our communicationsstephanie was very responsive too - a superb hostthank you so much for the amazing gift basket as well great place and great hostsuch a unique space with thoughtful hosts we enjoyed the small surprisesamazing so kind and welcomingRead more reviewsLocation:
beautiful place close to everything would definitely stay againwe enjoyed the location and the back 40 restaurant right down the streetgreat location private and feels safestephanie’s place was fantastic the location is in the middle of everything; downtown isn’t far nor is the beachit was an easy ~1 mile walk to many restaurants and activities
5. Weeden Cottage (from USD 244)
This custom-designed cottage combines an ideal location with a truly magnificent interior design and amenities. Downtown St. Augustine is within walking distance, but if you’re feeling adventurous and want to explore the city further, the cottage management provides some bikes for you to use too.
The cottage itself is just so sleek and gorgeously decorated. Most of its interior is styled in immaculate white, including the walls and most of its furniture. The natural wooden floor and colorful carpets add a nice balance to the spotless white vibe. On the outside, green is the highlight, with plenty of lush green shrubs and trees in the yard. A 15% discount for weekly stays is generous enough, but it gets even better with a 25% discount for monthly stays.
Top guest reviews
Amenities & Room:
cottage has all the amenities and was beautifully kept and cozyexactly as described very comfortablegreat kitchen fully stockedthe kitchen is amazing - perfectly updated and equippedCleanliness:
nicely updated very clean and comfortablesuper clean and decorated with true sti loved this place the beds were comfortable and was very cleanit was so stylish and cleaneverything was very clean and beautifully decorated it felt like homeHost:
the host was absolutely amazingawesome area the hosts are greatbeautiful house and the owners were informative and attentivetodd and kristi were great hosts and the house was perfect for our party of two couplescommunication with the owners was quick and easy and their restaurant recommendations were greatRead more reviewsLocation:
short easy walking distance from downtown stlocated within walking distance to the best of stlocation is fantastic walk to dinner and explore styou can walk to numerous restaurants and attractionsdon't think twice about booking this location; you will not be disappointed
6. Luxury condo with a pool (from USD 166)
If you’re looking for a nice rental with a pool in downtown St. Augustine, this condo is the perfect choice for you. A walk through downtown St. Augustine is a great way to spend the day, but if you’re feeling lazy, simply take a dip in its uniquely shaped pool, which can be heated from April to November. In case of unpleasant weather, the large 52-in HDTV within its cozy living room comes with full Netflix and Hulu to stave off boredom. A warm bath in its lovely tub seems like a great idea as well.
Enjoy all the best things that this condo offer with an additional 25% discount for monthly stays.
Top guest reviews
Amenities & Room:
the heated pool was the bestbeautiful space loved the pool and patio spaceno separate dining area but you can easily eat at kitchen counter or at the table outsideCleanliness:
she keeps it immaculately cleanvery clean and beautiful placeour unit was clean and well stockedit was very very cleanthere were no beach towels however bathroom towels and linens were fluffy and clean and comfortableHost:
the pool is inviting and the hosts communicativekirsten was very responsive and a wonderful her hostkristen was amazing we couldn't have asked for a better hostkirsten's place is just as pictured and she is such a welcoming hosthost was very responsive in answer to our questions and apartment was sparkling clean with everything we neededRead more reviewsLocation:
great location - it is an easy walk to everythingthe location was great- definitely walkable to the main downtown areathe location was great; within walking distance of the main strip and lots of restaurantslocation was great walking distance from all the shops and restaurantslocation to town was amazing
7. Beautiful bungalow with a small garden
Located in Lincolnville, a historic part of downtown St. Augustine, is this cozy bungalow. With plenty of great museums and historic sites within walking distance, history buffs will delight in the bungalow’s ideal location. The vibrant St. George Street with all its authentic bars, coffee shops, and boutique stores is also reachable on foot in five minutes.
If you don’t want to head out, the bungalow is comfy enough for you to just unwind inside the house all day. Wooden floors, plush couches, and a large HDTV in the living room make for cozy movie nights. There is also a cute garden with trees and plenty of chairs, offering the perfect place to have coffee in the morning. Book for an extended stay of at least 28 days for a massive 40% discount on rent.
St. Augustine, Florida, United StatesAccommodates: 4
Top guest reviews
Cleanliness:
the house was very clean location was great good communication with host as wellperfect little outsid seating area home was so clean and the bed was extremely comfortablegreat location clean spacious and stylish can't wait to be backvery clean and a short walk to everythinggabby was easy to communicate with and the house was spotlessRead more reviewsLocation:
cute house great location had everything we neededbeautiful and cozy very close to the main attractions and restaurantsgabby’s bnb was cute and clean and in a pretty good locationit is also right around the corner from one of the best breakfast places the blue hen cafelocation was great and super clean
8. Well-equipped home with a fire pit (from USD 154)
Located in Uptown St. Augustine, this lovely house has all the best sites within walking distance. Although near the tourist areas, this house is located in a quiet neighborhood with comfy surroundings. The rental has a nice wooden porch and a fire pit under large trees.
Make use of the home’s massive 45% discount on rent for stays of 28 days or more.
Top guest reviews
Amenities & Room:
the wifi worked perfectlylaundry detergent plenty of coffee snacks and little things that made everything easierthere is a nice covered porch with plenty of room to sit and enjoy the outdoors as wellthe pillows weren’t comfortable and seemed old and the bedroom could benefit from some blackout curtainsthe fridge also had water bottles and condiments the shower had great water pressure and clean towelsCleanliness:
very clean and quietsuper clean and smelled amazinggreat communication and the house was very nice and cleanit is so clean and awesomethe place was so clean and invitingHost:
lorie is a great hostshe was super responsive and made us feel at homeeveryone was so nice and friendlythe owner lori is great and very thoughtfulthe hostess was very responsive to our questionsRead more reviewsLocation:
the location was an easy walk to old town and other stuff even closerlocation is perfect can easily walk to everythingla casita is in a perfect location within walking distance to everythingperfect location and just overall great little houseit’s an easy walk to many restaurants shopping and activities
9. Luxury house built in early 1900s (from USD 151)
If you travel to a historic old town like St. Augustine, why not stay in a historic old house such as this one? Just blocks away from the Castillo de San Marcos fortress, this elegant house was built in the early 1900s, Although just recently renovated, the house still maintains its vintage vibe, particularly its rustic exterior. Meanwhile, the sleek interior features all the modern amenities, such as a 42-in HDTV, WiFi, and a fully fitted kitchen.
A monthly stay in this luxurious vintage house comes with a generous 43% discount.
Top guest reviews
Amenities & Room:
the space was extremely comfortable and had everything we neededkitchen has necessary items for cooking a easy mealthe queen bed is very comfortableCleanliness:
the location is wonderful and the place is clean comfortable and charmingHost:
valerie was a very friendly and helpful hostvalerie was helpful with the couple of hiccups we had along the waythe owner was very nice and quick with communicationval was a great host and was quick to respond the couple of times we texted heraugustine- host includes a guide of best local restaurants which was also super helpfulRead more reviewsLocation:
great location and super cute placegreat location about a 15-minute walk to historic stsuch a cute placegreat house in a great locationgreat place and great location
10. The Anastasia House (from USD 194)
Prime location, gorgeous interiors, and complete amenities, everything you need for a wonderful holiday in St. Augustine is here in The Anastasia House. The historic areas of downtown St. Augustine, the majestic St. Augustine Amphitheatre, and Anastasia State Park beach are all less than a mile (1.6 km) away from the property.
To allow you to explore all those attractions with maximum freedom and comfort, the owner provides four bikes, and beach towels and beach toys are provided for the kids. The sleek and fabulous interiors also come with a washer and dryer, a fully equipped kitchen, fast WiFi, and a huge HDTV.
A nice 31% discount awaits if you book for a stay of 28 days or more.
Top guest reviews
Amenities & Room:
very comfortable furnishings and quiet locationthere was even hand sanitizer in every roomthese are the most comfortable beds we’ve slept on in agesbeds were super comfortable & the living area space was very cozythe beds were very comfortableCleanliness:
and spotlessly clean thanks againvery clean and cozy homethe house was very clean and enjoyablehome was very clean and comfortablehouse very comfy and clean host very friendlyHost:
lovely people and awesome hoststhe host are so thoughtful and have thought of everythingamanda and wes were great hosts we would definitely recommendamazing location we had a lovely time and they owners were very tentative about responding to questions we hadRead more reviewsLocation:
very close to beach old city attractions shopping etcthe location is wonderfulgreat location and close to almost everythingin a super convenient location and close to everything while still being homeycute baby-friendly spot in a great location we really enjoyed being able to walk and bike everywhere
A relaxing holiday in St. Augustine
A charming historic city, St. Augustine is the perfect destination for a nice, long, relaxing holiday in the South. Guaranteed to make your mind even lighter is the huge additional discount that these properties offer for extended stays! So what are you waiting for? Book one of these properties and have a fabulous getaway in St. Augustine.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to