Holiday rentals in Historic District, St. Augustine

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

Guests agree: these stays are highly rated for location, cleanliness and more.

Superhost

Apartment in St. Augustine

5 out of 5 average rating, 3 reviews

"St Augustine Beach Retreat" Oceanfront Resort!

“St Augustine Beach Retreat” Oceanfront resort that is the ideal homebase for your St. Augustine Vacation Enjoy access to an abundance of resort amenities ~🌴 Impeccably maintained and secure resort ~ 🛜Complimentary high-speed WiFi ~ 🍔BBQ grilling and picnic area ~ 🏊Exquisite swimming pools ~ 👙Five outdoor hot tubs ~ 🎾 Four tennis courts ~ 🏓Pickleball courts ~ 🧑‍🦯Shuffleboard courts ~ 🎣Catch-and-release pond ~ 🛖Clubhouse with a spacious outdoor deck ~ 🪩Bocce ball ~ 🏖️Beautiful Beach

Guest favourite

Flat in St. Augustine

4.92 out of 5 average rating, 12 reviews

Beachside Ocean & Pool View- New Listing!

Experience the charm of our beachfront condo, where the ocean's waves greet you. Steps from the white, sandy beach, enjoy ocean views, sunrises, and sunsets from our balcony. Our two-story condo overlooks a large pool and ocean waves in a quiet, family-friendly area. Newly remodeled, king bedrm looks out to the beach, 2 full bathrms, & bright kitchen. Close to historic St. Augustine's exquisite dining, shopping, and the charm of historic streets. Perfect place to stay to visit Nights of Lights!

Guest favourite

Home in St. Augustine

4.98 out of 5 average rating, 168 reviews

Serenity Now - On The Beach

Welcome to Serenity Now! This immaculate beachfront home was completely renovated with beautiful, new furniture and comfortable beds. Sleeps 10 easily in 5 bedrooms, 2.5 baths & hot, outdoor shower. Fully equipped kitchen & BBQ for easy family meals. Enjoy covered, wrap around decks & ocean views from nearly every room! Keyless entry & self check-in. *Service/emotional support animals not allowed b/c our family is severely allergic. 5/27-8/17 weekly rentals; but inquire for shorter stay.

Guest favourite

Townhouse in St. Augustine

4.91 out of 5 average rating, 125 reviews

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

Come and escape to the Florida sun and beaches at Paradise Retreat! This completely renovated home is only a few minute's walk to the beach with access to miles of tranquil, quiet stretches of beautiful sand, abundant sea seashells and a fantastic blue ocean. It is located in a quiet residential neighborhood, perfect for bike riding and evening walks under the stars. Paradise Retreat is your peaceful getaway only minutes to everything Vilano Beach and historic Saint Augustine has to offer.

Guest favourite

Cottage in St. Augustine

4.94 out of 5 average rating, 371 reviews

Perfect location- Cottage Retreat in historic area

This charming two story gem with a wrap around front porch is perfect for your stay while visiting historic St. Augustine. Situated within walking distance of the Fountain of Youth and the Old Town Trolley Tours, you can easily explore all the city has to offer! It’s in a perfect location near the city’s downtown area featuring Castillo de San Marcos (1 mile away) and many local shops and restaurants. Check out the featured guidebook which references many nearby points of interest.

Guest favourite

Bungalow in St. Augustine

4.96 out of 5 average rating, 193 reviews

Updated Cottage in Heart of Town / Park & Walk

Located in the Historic Abbott District of St Augustine, Florida in the heart of it all. Walk to everything, you will never need your car! This 2-bedroom cottage has all the historic charm was lovingly updated with an open floor plan is beautifully decorated and tastefully furnished. Enjoy a five-minute walk through the neighborhood to famed Castillo De San Marcos (the fort) and Historic St. George Street in the ancient “Colonial Quarter”. Extremely clean, and well-maintained.

Guest favourite

Apartment in St. Augustine Beach

4.95 out of 5 average rating, 114 reviews

Newly renovated! Steps to BEACH & POOL!

Our little slice of paradise is situated in the heart of St. Augustine Beach right on A1A Beach Blvd. Our unit, recently renovated, is just steps from the beach and closest building to the pool! 2 outdoor pools (1 heated in winter), 5 hot tubs & tennis courts. Perfect location to enjoy our beautiful beaches & all that Anastasia Island has to offer! Historic St. Augustine is less than 7 miles away. Unit is equipped with everything you need for a perfect beach vacation!

Superhost

Home in St. Augustine

4.9 out of 5 average rating, 124 reviews

Vilano Vibes *Luxury*King Beds HotTub+Walk 2 Beach

NEW! Luxury BeachHouse has everything you would want for your dream vacation! Large Hot Tub, BBQ Grill+Outdoor Dining is perfect for relaxing after a day exploring! Perfectly located - Beach is one way & Intracoastal Waterway the other - both just a short stroll. Premium Mattresses w/Luxury Bedding- King Beds + BunkBeds for Kids. Dog friendly* Fully Stocked Kitchen. Oversized 2Car Garage. New Luxury BeachHouse has it all w/nothing missed * Book Today & Save$

Guest favourite

Apartment in Saint Augustine

4.99 out of 5 average rating, 73 reviews

Sand In My Shoes -1 min to Beach-Close to Downtown

Sand in my Shoes - in just seconds you will be walking on pristine sandy beach & minutes from exploring 17 Century watch towers & history, this 2 bedroom 2.5 bath townhouse condo sleeps 6 and won’t disappoint. Kitchen equipped for any occasion, amenities galore. 3 TV/DVDs. Private keyless entry. Don't miss WORLD FAMOUS "NIGHT OF LIGHT" ranked as one of the top 10 places IN THE WORLD to see Christmas lights, every November 20, 2021 through January 31, 2022.

Superhost

Apartment in St. Augustine

4.64 out of 5 average rating, 53 reviews

The Place to Bee. Make your memory with us!

The Place to be🐝 St.Augustine and this condo! Our location is perfect any time of the year. One of kind condo experience: a setting which is a short walk to the beautiful flat beaches or free parking next to the pier. All your beach needs: umbrella,towels, beach chairs...and a beach cart! As a fellow vacationer explains: it’s the 🐝hive to begin your exploration of the most ancient city in America! So many adventures if you choose to partake or not🦄

Guest favourite

Townhouse in St. Augustine

4.93 out of 5 average rating, 42 reviews

Crescent Cove at St. Augustine

Escape to this charming townhome for an unforgettable beach getaway near Crescent and St. Augustine beaches! Discover the perfect retreat with its inviting ambiance and convenient location, just a short drive away from the historic downtown. Relax in the hammock in the serene backyard, take a leisurely stroll to the beach via the walkway across A1A, or explore the nearby Fort Matanzas National Monument. Your dream vacation awaits!

Guest favourite

Villa in St. Augustine

4.98 out of 5 average rating, 253 reviews

Perfect location 2 Bedroom Private Hot Tub

Couples retreat, grill out in your own private courtyard while listening to the relaxing water fountain. “Wine” down and watch the sunset. Private brand new 4 person hot tub. Beautiful courtyard night lighting. 0.5 miles walking distance to the bridge of lions and historic downtown. Off-street parking. Food bars and fun within 300 feet location is directly off the downtown boulevard entrance. Special requests are available.