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The May House - Heated Pool - Historic Downtown

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Fridge, microwave, oven, stovetop - The May House - Heated Pool - Historic Downtown (St. Augustine)
Pool - The May House - Heated Pool - Historic Downtown (St. Augustine)
3 bedrooms, iron/ironing board, free WiFi, bed sheets - The May House - Heated Pool - Historic Downtown (St. Augustine)
TV - The May House - Heated Pool - Historic Downtown (St. Augustine)
Property grounds - The May House - Heated Pool - Historic Downtown (St. Augustine)
Close to Castillo de San Marcos National Monument, The May House - Heated Pool - Historic Downtown provides amenities such as laundry facilities. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms1400 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Add dates for prices

About this property

The May House - Heated Pool - Historic Downtown

  • Modern Comfort Meets Old Florida Charm at the Historic Cottage on May Street

    Tucked behind a private gate and surrounded by lush landscaping, this beautifully renovated historic cottage offers the perfect blend of modern design and vintage Florida charm. Whether you're relaxing by the heated pool or practicing your putt on the private mini putting green, every corner of this home is designed for comfort and fun.

    Step inside and discover a thoughtfully updated interior featuring a stylish modern kitchen with a pass-through window that opens onto a spacious deck. The built-in outdoor bar makes it easy to enjoy sunset cocktails or a casual evening grilling with friends and family.

    Just minutes from both historic downtown St. Augustine and the shores of Vilano Beach, this home is ideally located in a quiet neighborhood that offers a peaceful retreat from the hustle and bustle. Walk to iconic local attractions like the Fountain of Youth and The Old Jail, or take a scenic stroll through uptown St. Augustine toward the historic district. Along the way, stop at CookieBird Ice Cream Bar or grab a frozen margarita at Boat Drinks—local favorites just around the corner.

    Highlights include:

    Private pool (heating available for an additional charge)

    Mini putting green

    Outdoor deck with built-in bar

    Modern kitchen with Nespresso pods

    Fireplace for cozy nights

    Outdoor grill and water filtration system

    Self check-in for added convenience

    Family- and pet-friendly accommodations

    Whether you're planning a romantic getaway, a family vacation, or a relaxing retreat with friends, 9 May Street offers the charm, comfort, and location to make your St. Augustine stay unforgettable.

Property amenities

Pool/Spa

  • Pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • TV

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • Up to 23 kg per pet

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift (single-level property)
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Safety features

  • No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Unit size: 1,400 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age - 18

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you to complete the following before checking out:

Load and start the dishwasher

Gather used towels

Remove personal items, remove leftover food and drinks and take out the rubbish

Turn off the lights and lock the doors

Failure to complete these may result in a negative review from the host.

Pets

Pets are allowed

Service animals are welcome, and are exempt from fees

Welcoming dogs only

1 total (up to 23 kg per pet)

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

Uptown, a neighbourhood in St. Augustine, is home to this holiday home. Castillo de San Marcos National Monument is a notable landmark, and the area's natural beauty can be seen at Vilano Beach and Anastasia State Park. World Golf Village and St. Augustine Pirate and Treasure Museum are also worth visiting. Visit our St. Augustine travel guide
View more Holiday homes in St. Augustine
Map
St. Augustine, FL

What's nearby

  • Ponce de Leon's Fountain of Youth Archaeological Park
    Ponce de Leon's Fountain of Youth Archaeological Park
    5 min walk - 0.3 miles
  • Ripley's Believe It Or Not
    Ripley's Believe It Or Not
    17 min walk - 0.9 miles
  • St. George Street
    St. George Street
    19 min walk - 1.0 mile
  • St Augustine, Florida, USA Downtown Skyline Aerial
    Flagler College
    3 min drive - 1.3 miles
  • Castillo de San Marcos National Monument
    Castillo de San Marcos National Monument
    5 min drive - 1.9 miles

Getting around

  • St. Augustine, FL (UST-Northeast Florida Regional)
    11 min drive

Restaurants

  • McDonald's
    13 min walk
  • Bronx House Pizza
    14 min walk
  • Ann O'Malleys
    20 min walk
  • Village Inn
    18 min walk
  • Castillo Craft Bar + Kitchen
    17 min walk

Frequently asked questions

Does The May House - Heated Pool - Historic Downtown have a pool?

Yes, this property has a pool.

Is The May House - Heated Pool - Historic Downtown pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much is parking at The May House - Heated Pool - Historic Downtown?

On-site parking is available at the property.

What time is check-in at The May House - Heated Pool - Historic Downtown?

Check-in begins at 4:00 PM.

What time is check-out at The May House - Heated Pool - Historic Downtown?

Checkout is at 11:00 AM.

Where is The May House - Heated Pool - Historic Downtown located?

Located in Uptown, this holiday home is within 1 mile (2 km) of Davenport Park, St. George Street and Castillo de San Marcos National Monument. Old Jail Museum and Florida Heritage Museum are just steps away.

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The May House - Heated Pool - Historic Downtown Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

10

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

Christina W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property is beautiful and was perfect for our St. Augustine getaway! Modernly designed with still an old Florida feel. Accommodation’s on point. I would recommend staying here when visiting the St. Augustine area!
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Tom and Sandy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a wonderful experience. Damon was a fabulous host. Beautiful home with superb amenities.This was a 50 year college reunion with girlfriends. The five days together did not disappoint. We all LOVED The May House. Thank you Damon! Sandra
Stayed 5 nights in Feb 2026
Verified

10/10 Excellent

Allie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay and overall a very positive experience at this property. The owner’s communication was fantastic before, during, and after our trip—responsive, helpful, and easy to work with.The beds and linens were very comfortable, and we appreciated how well-stocked the home was with essentials like toilet paper, paper towels, and trash bags. Those little details make a big difference when traveling.The pool was absolutely amazing and truly the highlight of our trip—we spent so much time enjoying it!A couple helpful notes for future guests: the king bed is not in the primary bedroom with the attached bathroom (I overlooked that in the listing), so just be aware of the layout when booking. Also, there were quite a few mosquitoes outside during our stay, so bringing bug spray is definitely recommended. It may be worth considering mosquito treatment for the property.Overall, we had a great stay and would absolutely recommend this home to others!
Stayed 5 nights in Apr 2026
Verified

10/10 Excellent

Dan J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property outside is a Oasis and is wonderful. It was too cool for us to utilize it much, but I can't say enough how nice it was! Very nice grill that we used one night for some Steaks.Host was very responsive to questions that we had. Property is like the pictures that are on VRBO, as advertised.Location is good, which is walkable down to St George, but we decided to drive and park to save time since it was very cool at night.Overall, this is a really nice property and we plan to use again in the future.
Stayed 4 nights in Dec 2025