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The May House - Heated Pool - Historic Downtown

Photo gallery for The May House - Heated Pool - Historic Downtown

Pool
Pool
Property grounds
Interior
Private kitchen

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Swimming pool
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Rooms & beds

3 bedrooms (sleeps 8)

Double Queen

2 Queen Beds

King Bedroom

1 King Bed

Queen Bedroom

1 Queen Bed

2 bathrooms

Bathroom 1

Soap · Towels provided · Bathtub · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo

Spaces

Deck or patio
Kitchen
Dining area

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.

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The circa 1875 Cottage overlooks the private heated pool.
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  • Kitchen
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10.0 out of 10, Exceptional, (133 reviews)
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House Rules

Check in after 4:00 PM

Minimum age to rent: 18

Check out before 11:00 AM

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Children

Children allowed: ages 0–17

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Events

No events allowed

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Pets

Pets allowed: dogs less than 23 kg per pet (limit one pet total)

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Smoking

Smoking is not permitted

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.

Important information

You need to know

Property # 4529577vb
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

About the area

St. Augustine

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 St. Augustine Beach. World Golf Village and St. Augustine Pirate and Treasure Museum are also worth visiting.
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Map
St. Augustine, FL

What's nearby

  • Ponce de Leon's Fountain of Youth Archaeological Park - 5 min walk - 0.4 km
  • Ripley's Believe It Or Not - 17 min walk - 1.5 km
  • St. George Street - 19 min walk - 1.6 km
  • Flagler College - 3 min drive - 2.1 km
  • Castillo de San Marcos National Monument - 5 min drive - 3.1 km

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.

How much does it cost to stay at The May House - Heated Pool - Historic Downtown?

As of 13 May, 2026, prices found for a 1-night stay for 2 adults at The May House - Heated Pool - Historic Downtown on 8 Nov, 2026 start from S$735, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

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
Response from VrboOwner on 20 Dec, 2025
Christina and her guests kept the place in impeccable shape. We are thankful to have guests like these that truly care about the home and left it in the shape they found it!
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

About the host

Hosted by Damon Lee

Host profile image

Languages:

English

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