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 August 19, 2024.
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1. Saint Sylvan (from USD 94)
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.
2. Monarch Gardens (from USD 175)
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.
3. Cute cottage with elegant decor (from USD 125)
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.
4. Stylish loft with great amenities (from USD 119)
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.
5. Weeden Cottage
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.
St. Augustine, Florida, United StatesSuperhost
Accommodates: 4
6. Luxury condo with a pool (from USD 128)
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.
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
8. Well-equipped home with a fire pit (from USD 158)
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.
9. Luxury house built in early 1900s (from USD 145)
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.
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.
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.
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