At iTrip St. Augustine, we take pride in offering exceptional vacation experiences in the nation’s oldest city. From charming historic homes to modern downtown retreats, our carefully curated collection of properties provides comfort, convenience, and style — all within easy reach of St. Augustine’s most beloved attractions. Our local team is dedicated to ensuring every guest feels right at home while enjoying everything this beautiful coastal town has to offer.
And there’s no better time to experience St. Augustine than during the Nights of Lights — when millions of tiny white lights illuminate the city, transforming its cobblestone streets, waterfront views, and historic landmarks into a winter wonderland.
If you’re planning to visit during this magical season, location is everything. Below are some of our favorite iTrip St. Augustine vacation rentals located near downtown, each offering its own charm and easy access to the sparkling festivities.
Where charm meets relaxation.
Just a 5–10 minute stroll to downtown, this cozy home blends modern comfort with old-Florida style. Families love the private backyard oasis — complete with a spa-pool, firepit, and deck — and the nostalgic game room for cozy nights in. Nestled in the quiet Lincolnville district, it’s just steps from St. Augustine Distillery, San Sebastian Winery, and the Lightner Museum.
Experience downtown from your private balcony.
You can’t get closer to the heart of the action than this! Perched above Hypolita Street, this spacious apartment lets you enjoy cobblestone views, walk to top restaurants and bars, and people-watch with a glass of wine in hand. With free parking and unbeatable walkability, you’ll be right in the center of the Nights of Lights festivities.
Historic grandeur in the heart of the Old City.
A true showstopper, this century-old Spanish Moorish home once belonged to sculptor C. Adrian Pillars. Featuring multiple master suites, a baby grand piano, and even a throne for fun photo ops, this luxury home is perfect for family celebrations. Enjoy elegant interiors, a garden courtyard, and a short walk to Magnolia Avenue, Fountain of Youth, and St. George Street.
A laid-back island escape close to it all.
Located just a mile from downtown and minutes from the beach, Florida Breeze offers the best of both worlds. Surrounded by local restaurants, bars, and attractions like the Alligator Farm and Lighthouse, it’s the perfect base for exploring. After a day under the twinkling lights, come home to your cozy bungalow and unwind on the porch with a tropical drink.
Historic charm steps from the waterfront.
Built in 1905, this lovingly restored home offers comfort, style, and a fascinating backstory. With river views, kayaks for guest use, and screened porches for evening wine, it’s an ideal stay for families or groups. The fort, Visitor’s Center, and St. George Street are all within an easy walk — meaning you’ll never miss a moment of the Nights of Lights glow.
Bright, cheerful, and steps from the Matanzas River.
This charming Water Street cottage combines history and comfort just a few blocks from downtown’s light displays. Enjoy morning coffee in the private courtyard, evening strolls along the waterfront, and all the cozy touches of home. It’s a perfect retreat for couples or small families who love to be near the action but want a quiet place to recharge.
Modern luxury meets historic flair.
Brand new and beautifully furnished, this apartment offers a spa-like bathroom, river views, and a private balcony where you can soak in the city’s glow. You’ll be surrounded by live music, restaurants, and St. Augustine’s most iconic landmarks — all just steps from your door.
A brand-new home with modern comfort and a touch of history.
Located in the charming Lincolnville neighborhood, this newly built property features multiple porches, a fenced backyard, and a game room. Guests love being within walking distance of the Distillery, Winery, and Lightner Museum — and just a short stroll from the best viewing spots downtown.
Historic beauty one block from it all.
This renovated 1920 Colonial Revival cottage is right near the Visitor Center and Ripley’s Museum, making it ideal for walking everywhere. It also comes with a FREE FUN package that includes complimentary entries to top local attractions — perfect for adding extra sparkle to your Nights of Lights getaway.
Classic comfort just steps from St. George Street.
Stay in a beautifully restored vintage home just off Cordova Street. With crisp linens, modern conveniences, and a lovely back porch for evening cookouts, this property is all about comfort and location. Park once and explore the entire city on foot — it doesn’t get more convenient than this.
Southern charm with a Cajun twist.
This cozy 1930s bungalow is located in a trendy neighborhood near West King Street, close to coffee shops and restaurants locals love. Relax in the hot tub, stargaze around the fire pit, or hop on bikes to explore downtown. It’s the perfect hideaway for a cozy holiday stay.
Whether you’re looking for a luxurious historic home, a romantic riverside cottage, or a modern downtown apartment, iTrip St. Augustine has the perfect place for your Nights of Lights getaway. Book early — these popular stays go fast during the holiday season!
Check out our other blog post for tips on parking, shuttles, and things to do! Click here