Relax in a Cozy Retreat 3 Minutes from St. Augustine Beach

Enjoy a Private Backyard, Fire Pit, and 450 sq. ft Game Room

Historic Coastal Retreat 3 minutes to Sand

Welcome to The Stay on May your inviting historic single-level home. This thoughtfully designed 100 year old retreat offers a private fenced backyard, fire pit, and 450 sq ft. game room with curated local art inspired by St. Augustine ensuring a comfortable and memorable stay for families, couples, or friends.

St. Augustine, FL, United States
8 guests
3 bedrooms
2 bathrooms

What this place offers

Common

  • Air conditioning
  • Cleaning products
  • Cooking basics Pots and pans, oil, salt and pepper
  • Dishes and silverware
  • Dryer In the building, free or for a fee
  • Essentials Towels, bed sheets, soap, toilet paper, and pillows
  • Hair dryer
  • Heating Central heating or a heater in the listing
  • Kitchen Space where guests can cook their own meals
  • Dedicated workspace
  • TV
  • Washing Machine In the building, free or for a fee
  • Wifi

Entertainment

  • Arcade machine
  • Sound system
  • Theme room

Kitchen and dining

  • Baking sheet
  • Blender
  • Coffee
  • Coffee maker
  • Dining table
  • Freezer
  • Microwave
  • Mini Fridge
  • Oven
  • Refrigerator
  • Stove
  • Toaster

What this place offers

Common

  • Air conditioning
  • Cleaning products
  • Cooking basics Pots and pans, oil, salt and pepper
  • Dishes and silverware
  • Dryer In the building, free or for a fee
  • Essentials Towels, bed sheets, soap, toilet paper, and pillows
  • Hair dryer
  • Heating Central heating or a heater in the listing
  • Kitchen Space where guests can cook their own meals
  • Dedicated workspace
  • TV
  • Washing Machine In the building, free or for a fee
  • Wifi

Entertainment

  • Arcade machine
  • Sound system
  • Theme room

Kitchen and dining

  • Baking sheet
  • Blender
  • Coffee
  • Coffee maker
  • Dining table
  • Freezer
  • Microwave
  • Mini Fridge
  • Oven
  • Refrigerator
  • Stove
  • Toaster

Bathroom

  • Bathtub
  • Body soap
  • Conditioner
  • Hot Water
  • Shampoo
  • Shower gel

Bedroom and laundry

  • Bed linens
  • Drying rack for clothing
  • Extra pillows and blankets
  • Hangers
  • Iron
  • Room-darkening shades
  • Clothing storage

Family

  • Board games
  • Fireplace guards

Home safety

  • Carbon monoxide detector
  • Fire extinguisher
  • First aid kit
  • Smoke detector

Heating and cooling

  • Ceiling fan
  • Portable fans

Outdoors

  • Fire pit
  • Garden or backyard
  • Hammock
  • Outdoor seating
  • Patio

Parking and facilities

  • Free parking on premises
  • Private living room
  • Single level home No stairs in home

Location features

  • Private entrance Separate street or building entrance

Accessibility

Neighborhood

Located in a safe, charming, and walkable neighborhood, this home offers the perfect balance of comfort and convenience. Enjoy a peaceful, well-kept setting just minutes from St. Augustine’s historic downtown, beaches, local shops, restaurants, and top attractions—making it easy to explore and unwind.

Guest Access

The entire home is yours to enjoy during your stay — from the bedrooms and sunroom to the backyard fire pit and classic front porch. Included is a detached climate controlled building with 450 sq. ft. game room and family hang out!

Good to know

⭑Master Bedroom:⭑ ✔ Queen bed with premium bedding, extra pillows & blankets ✔ Full closet, dresser, and decorative curtains ✔ SmartTV for personalized entertainment ⭑Second Bedroom:⭑ ✔ Queen bed with premium bedding, extra pillows & blankets ✔ Full closet, dresser, and decorative curtains ✔ SmartTV for personalized entertainment ⭑Third Bedroom:⭑ ✔ Queen bed with premium bedding, extra pillows & blankets ✔ Full closet, dresser, and decorative curtains ✔ SmartTV for personalized entertainment ⭑The Sunroom:⭑ ✔ Queen bed with premium bedding, extra pillows & blankets ✔ A quiet, peaceful space with soft natural light ✔ Board games and activities available for fun, downtime, or rainy days ⭑Living Room:⭑ ✔ Bright, open-concept space with cozy seating ✔ Smart TV with top streaming apps to connect and decorative curtains ✔ Stylish décor with a convenient charging station ⭑Kitchen and Dining Area:⭑ ✔ Fully equipped kitchen with refrigerator, freezer, electric stove, single oven, microwave ✔ Coffee maker (drip & Keurig), toaster, blender ✔ Cooking basics: pots, pans, baking sheet, oil, salt & pepper ✔ Dishes, silverware, bowls, plates, cups ✔ Dining table with seating for 6 ⭑Bathrooms:⭑ ✔ Two full bathrooms with fresh towels and complimentary toiletries ✔ Hair dryer and starter bath kit provided ⭑Outdoor Space:⭑ ✔ Fully fenced backyard with open grassy area ✔ Fire pit, outdoor furniture, and hammocks ✔ Private porch for morning coffee or a night cap ⭑Additional Amenities:⭑ ✔ High-speed Wi-Fi ✔ Dedicated workspace for remote work ✔ In-unit washer & dryer, iron, and ironing board ⭑Safety and Security:⭑ ✔ Smoke detector, carbon monoxide alarm, fire extinguisher, and first aid kit ✔ Private entrance and keypad self check-in ⭑Entertainment and Connectivity:⭑ ✔ Smart TVs in every room to connect streaming services ✔ High-speed internet for streaming and work ⭑Heating and Cooling:⭑ ✔ Central air conditioning and heating for year-round comfort ⭑Parking and Facilities:⭑ ✔ Free parking on premises ✔ Single-level home with no stairs ⭑Services:⭑ ✔ Self check-in with keypad and door code ✔ Essentials kit: towels, linens, soap, toilet paper Your stay at The Stay on May promises relaxing comfort, unbeatable convenience, and a true taste of St. Augustine charm. Book now and start your historic adventure in style! ⭑Conclusion⭑ Experience the best of St. Augustine with a stay at The Stay on May. Reserve your dates today and enjoy comfort, privacy, and easy access to the city’s top attractions! About the Area Located in the heart of St. Augustine, just steps from historic sites, vibrant dining, and local shops. Nearby Attractions • Castillo de San Marcos (Fort) – 3 minutes • St. George Street – 5 minutes • Lightner Museum – 6 minutes • Flagler College – 6 minutes • Fountain of Youth – 2 minutes • Vilano Beach – 6 minutes • Anastasia State Park – 9 minutes • St. Augustine Beach – 12 minutes • St. Augustine Lighthouse – 8 minutes • Ripley’s Believe It or Not! – 4 minutes • Old Town Trolley Stop #1 – 3 minutes • Pirate & Treasure Museum – 4 minutes

Check availability

Reviews

Madison
April 2026
The Stay on May is the BEST Airbnb ever. Jeremy and Cindy were phenomenal hosts, and so quick to respond every time. The whole trip, from check in to check out they were so kind to us and easy to communicate with. They gave us recommendations, answered all of our questions quickly, and helped us with everything we needed. I booked this house for my birthday weekend with friends I hadn't seen in a long time, and the porch and game room were perfect for hanging out, laughing, and catching up. We spent hours just drinking coffee and sitting outside, it was so relaxing and perfect. The house was so clean and we were even provided with a snack basket when we checked in. The location was phenomenal, with the beach and downtown just a few minutes away. We made lifelong memories in this house, and if I ever find myself staying in St Augustine again I will be booking the Stay on May. It was truly the best weekend ever and I would recommend this place to anyone!
Chris
April 2026
We absolutely loved the place! It was clean, comfortable and added a lot of fun to our wet and chilly spring break. The game room was fantastic for our 14 year old to stay active and fun when we were stuck inside. All the seating was great for each of us to find our favorite little spot. The kitchen was easy to cook in. Just a wonderful place for our trip away. Added bonus was being able to hear the peacocks nearby!
Alisen
April 2026
We had a delightful time at Jeremy and Cindy’s place. It’s very conveniently located (quick to downtown and the beach) and had everything we needed for our stay. Our kids loved roasting marshmallows in the fire pit out back, hanging out on the front porch, and walking around the neighborhood. We would definitely stay here again!
Lauren
March 2026
Perfect location. We walked to restaurants and bars, 5 minute drive to the beach. Loads to do at the home itself, from the games room to the outdoor seating area we were very happy. Truly a wonderful stay!
Sean
February 2026
We had a wonderful stay at Jeremy and Cindy’s place. Our trip was so memorable and the location of the home was absolutely perfect! We walked to just about everything. Our kids absolutely loved the added game room too. We definitely plan to be back!
Dillon
December 2025
We had a fantastic stay at this Airbnb! The home was beautiful and in a great location. We were able to walk into town every night with ease. The hosts were extremely kind and responsive. They also provided great recommendations. The home itself was clean, decorated well, and fit all of our needs. They included games and we enjoyed a fire one night in the backyard. We will definitely be looking to stay here again when we return to St. Augustine.
Courtney
December 2025
They were amazing hosts. Super attentive, friendly and accommodating. Any time we had questions or messaged them, they were there to help. Would highly recommend staying and would come back!

Find us

Getting around is easy and convenient. You can walk to the nearby trolley stop and ride into historic downtown, or take a short walk or quick drive to the beach. Bikes and golf carts are also a great way to explore, with plenty of space to park them safely at the home.

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Approximate location. Full address will be provided on booking.