Entire home

The Pineapple Pad | EastBay Historic District Home

Photo gallery for The Pineapple Pad | EastBay Historic District Home

Interior
Interior
Fridge, microwave, oven, stovetop
Interior
5 bedrooms, desk, iron/ironing board, travel cot
Nestled in the heart of Charleston's historic French Quarter, this award-winning three-story home offers a luxurious retreat for 16 guests. With its massive gathering space, fully equipped kitchens, and TVs in every bedroom, you can unwind in style while being within walking distance to great restaurants and historical sights.

Reviews

9.6 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 16

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Air conditioning
The current price is NZ$1,959
includes taxes & fees
1 Oct - 2 Oct

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

The Pineapple Pad | EastBay Historic District Home

Summary:
Welcome to your Charleston sanctuary where historic charm meets spacious luxury. This 5-bedroom retreat offers a generous 3,000 square feet of beautifully appointed space. Ideal for families or groups who want elegant design, room to spread out, and a prime location in the French Quarter just steps from dining, culture, and waterfront views.

The Space:
Newly-renovated 5 bedroom/4 bath condo in the popular, French Quarter neighborhood. Ideal for a large group of friends or family gatherings. Steps from great restaurants & historical sights.

Please note there are 3 listing advertisements for this property, this is the 5 bedroom option (entire unit)

Bedroom #1: King Bed + En suite
Bedroom #2: Queen Bed + Queen Bed + En suite
Bedroom #3: Queen Bed + Queen Bed + En suite
Bedroom #4: Queen Bed + En suite
Bedroom #5: King Bed

Common Space: Pullout Sofa (sleeping space for 2 guests)

Only 2 blocks from City Market
20 minutes from Charleston Int'l Airport
20 minutes from local beaches

Permit Number: BL012726-10-2018

This 5 bedroom / 4 bathroom home is situated in the most desirable location in all of downtown Charleston; walking distance to fine dining restaurants, Charleston's City Market, historic landmarks, boutiques, tours, parks, and so much more. This home's unique features + ideal location are unparalleled and intended for guests who wish to travel comfortably while being fully immersed in the middle of everything Charleston.

We can comfortably accommodate 16 guests. 14 in beds + 2 additional guests on our queen-size super comfy West Elm pullout sofa. Comcast Business-Class Internet and WiFi HotSpots throughout the home ensure full connectivity for guests in every corner of this private and secured 3,300 sq ft luxury home.

All bedrooms are furnished with linens, towels, and pillows.

All bedrooms feature flat screen TVs with YOUTUBE TV

Each of the two master suites feature dual queen-size beds and full bathrooms en suite. Graber roller shades, Vornado fans and sleep machines are included for additional comfort.

A top-floor bedroom features a king-size bed and an eye-level view of the iconic St. Philip Church steeple through the bedroom window.

The fourth bedroom features a king size bed and en suite full bathroom with powder room vanity.

The fifth bedroom features a king size bed and en suite full bathroom.

The spectacular common space on the bottom floor features a full gourmet kitchen furnished with stainless appliances and all the amenities expected of a high-end luxury vacation rental. Dishes, smallwares, and cookware are top notch and plentiful; perfect for comfortably entertaining up to 14 guests.

The gracious living room features exposed interior brick, original heart pine hardwood floors and 18' ceilings. The dining area features a live-edge dining table with seating for 8 plus, a full bar with seating for 4 more and ample seating for additional guests throughout. A high-end SONOS sound system controlled by iPad and a 75" flat screen TV with premium channels lend to a common area perfect for comfortably entertaining up to 14 guests.

All 3 floors feature individual kitchenettes with brand new full-size refrigerators and ice-makers on each of the bottom two floors. The in-unit laundry room features a full-size washer and dryer including detergent.

Guest Access:
Guests will have exclusive access to this three level condo in the building. Easily accessible and well lit for your safety right next door to the famous SNOB Restaurant. You can pull your car off the street and into a parking lot with a reserved space, located right down the street, which makes parking a breeze. For additional parking there is a paid public garage right behind the building.

The Neighborhood:
The French Quarter is the oldest section of Downtown Charleston, bounded on the south by Broad Street and the north by the City Market. It is home to the Charleston Art Walk, an evening held many times a year where Charleston residents and visitors alike enjoy gallery hopping and wine tasting along its storied streets. Here you will also find theaters like the famed Dock Street, churches, inns and secret gardens waiting to be discovered. Charleston's historic French Quarter is a small neighborhood on the Southeastern corner of the peninsula, with Broad, Meeting, East Bay, and South Market streets acting as perimeters. The neighborhood is filled with historic churches and museums, theaters, art galleries and even some haunted cemeteries. The French Quarter may be the most romantic of Charleston's districts, and is perfect for leisurely walks, exploring historic sites, and immersing yourself in centuries of city history.

Getting Around:
You can walk anywhere and everywhere in Downtown Charleston, but just in case, here is a list of the top transportation services:

Uber and Lyft
Charleston Black Cab Limo Company (Can accommodate 1-200 people)

Downtown:
Charleston Pedicab
Bike Taxi
Charleston Rickshaw

Other Things to Note:
YOURPAD Charleston is full-service property management company here in Charleston, operating over 80 different properties throughout the heart of Downtown! To view all of our homes, please search YOURPAD Charleston on your preferred search engine!

Interaction with Guests:
Our team is available 24/7 by messenger, text, or call during your stay. We're happy to provide any recommendations during your vacation as we love making sure you have a wonderful time!

You'll receive all of your check-in details, lock code, emergency contacts, and a list of our favorite nearby restaurants seven days prior to your stay.

THIS PROPERTY IS LEGAL & LICENSED BY THE CITY OF CHARLESTON, Permit Number: BL012726-10-2018

Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 5 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 4 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Towels provided

Entertainment

  • Stereo
  • TV with cable/satellite channels

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Hardwood flooring in public areas
  • Lift
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

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

Rules

A $250 fine will be applied if any of the below rules are broken. • No tape, adhesives or anything that will cause damage can be used or placed on...

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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 is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
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

Property is also known as

64596a28618980003dc51e39

About the area

Located in Charleston, this holiday home is in the city centre. The area's natural beauty can be seen at Waterfront Park and Riverfront Park, while South Carolina Aquarium and Patriots Point are popular area attractions. Check out an event or a game at North Charleston Coliseum and Performing Arts Center, and consider making time for USS Yorktown, a top attraction not to be missed.
Map
Charleston, SC

What's nearby

  • Waterfront Park - 1 min walk - 0.2 km
  • Port of Charleston - 3 min walk - 0.3 km
  • Charleston City Market - 3 min walk - 0.3 km
  • College of Charleston - 10 min walk - 0.9 km
  • South Carolina Aquarium - 17 min walk - 1.4 km

Getting around

  • Charleston Station - 20 min drive
  • Charleston, SC (CHS-Charleston Intl.) - 25 min drive

Restaurants

  • ‪Carmella's - ‬1 min walk
  • ‪Charleston Crab House - ‬3 min walk
  • ‪The Vendue - ‬2 min walk
  • ‪Church and Union - ‬3 min walk
  • ‪Burwell's Stone Fire Grill - ‬3 min walk

Frequently asked questions

Is The Pineapple Pad | EastBay Historic District Home pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Pineapple Pad | EastBay Historic District Home?

As of 18 Sept 2025, prices found for a 1-night stay for 2 adults at The Pineapple Pad | EastBay Historic District Home on 1 Oct 2025 start from NZ$1,959.20, 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.

What time is check-in at The Pineapple Pad | EastBay Historic District Home?

Check-in begins at 4:00 PM.

What time is check-out at The Pineapple Pad | EastBay Historic District Home?

Checkout is at 10:00 AM.

Where is The Pineapple Pad | EastBay Historic District Home located?

Located in Charleston Historic District, this holiday home is within a 5-minute walk of Charleston City Market, Port of Charleston and Waterfront Park. College of Charleston and South Carolina Aquarium are also within 1 mile (2 km).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

The Pineapple Pad | EastBay Historic District Home Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 81 out of 93 reviews
Rating 8 - Good. 7 out of 93 reviews
Rating 6 - Okay. 4 out of 93 reviews
Rating 4 - Poor. 0 out of 93 reviews
Rating 2 - Terrible. 1 out of 93 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Kristen E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Super place

This was an amazing place to spend time with friends and explore Charleston. Just like home and so close to everything. It was just great!
Stayed 4 nights in Apr 2025

10/10 Excellent

Meagan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location is unbelievable!

Just stayed here with a group of couple friends to celebrate my sister’s birthday, and our trip was elevated by the amazing location of this property! We could walk to all of our restaurant reservations and fun bars, and had beautiful views to while
Stayed 2 nights in Feb 2025

8/10 Good

Nikole T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding Weekend

This property hosted my large wedding party for my wedding weekend! It was a little warm throughout the house and the bathrooms had poor lighting but other than that it was a great stay!
Stayed 3 nights in Apr 2025

10/10 Excellent

Paige S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

High-end and luxurious stay with amazing location

I stayed here with my friends and we all loved this place. The location was the best part for us. But it was also very clean, and felt high-end and luxurious which was amazing. The hosts were very communicative and responsive. Highly recommend to anyone looking to be right in the center of downtown historic Charleston!
Stayed 3 nights in Mar 2025

10/10 Excellent

Kathleen S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Kathy S

Great location great accommodations
Stayed 3 nights in May 2024

10/10 Excellent

Julie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Locatiin.

Place was beautiful and close to everything. We walked everywhere. Really enjoyed ourselves.
Stayed 3 nights in Nov 2024

10/10 Excellent

Christine D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Superior service

The rental itself was perfect but even more than that, the customer service and communication as well as the ability to accommodate multiple requests from us was superior. Well done!
Stayed 2 nights in Jan 2025

10/10 Excellent

Edward H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ideal location for restaurants and bars as well as city sights.

We had a great week in Charleston and made the most of the locations proximity to all of the city attractions.
Stayed 7 nights in Apr 2024

10/10 Excellent

Janet F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay in Charleston SC

Excellent location - in the heart of the historic district!! Wonderful amenities and lots of space for guests. Very comfortable! Our group of ladies had a fabulous vacation.
Stayed 3 nights in Sep 2024

10/10 Excellent

Cindy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good location

We were looking for a location close to some of our favorite restaurants and centrally located to historic area. This place is perfect for us.
Stayed 2 nights in Dec 2023

10/10 Excellent

cris s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

We loved the location and was perfect for our large group of moms and daughters
Stayed 4 nights in Mar 2024

10/10 Excellent

Kim T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay

Amazing location! Very clean
Stayed 8 nights in Feb 2023

10/10 Excellent

Rick H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic location

The place worked great as a home base for our guys weekend, being able to walk everywhere within downtown Charleston for restaurants, bars and even pickleball!
Stayed 4 nights in Oct 2023

10/10 Excellent

Spencer G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best Property EVER

This place was VERY VERY clean. Its location was the BEST!!! Everywhere we went. We were able to walk to. This area is also a very safe area and did not have to worry about anything. The host was very accommodating and very helpful with instruction on everything. The host was even helpful with providing info on nearby grocery stores. The pictures and info listing were very helpful with knowing how many people we could have. Lots of bathrooms. Hand down one of the best properties I've ever stayed in. HUGE THANKS to the host for making my stay in Charleston a great time!!!
Stayed 3 nights in Jan 2025

10/10 Excellent

Pat R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect

Beautiful home in perfect location! We enjoyed our stay very much!!
Stayed 3 nights in Nov 2019

10/10 Excellent

Keri B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location!

Beautiful place right in the heart of the Market area. Never grabbed the car. Walked all over. Loved the stay!
Stayed 2 nights in May 2024

10/10 Excellent

Bruce G., Mount gilead nc

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charleston bays st apt

Amazing location and historic apartment. Very clean and comfortable. Near great restaurants and shopping. We travel often with the same 3 couples. One of the best properties we’ve seen.
Stayed 3 nights in Jan 2020

10/10 Excellent

Sherri W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls Teip

Great location and layout was perfect for friends stay. Parking is a but challenging when loadingvand unloading your vehicle. Thermostat settings are challenging too but overallca great stay. We'd go back!
Stayed 3 nights in Nov 2023

10/10 Excellent

Lisa O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location and Luxury Details Makes This a 10!

The location of this rental made it perfect for exploring the city on foot. That alone made any additional cost we may have saved at a less ideal location. But, coming from a bed snob, the luxurious mattress and linens really put this charmer over the top! The amount of space was perfect for our group of 7 and the living room made for a perfect dance floor for our Just Dance game we brought! The overall decor and vibe of the place was so charming & added the best touches to our Bachelorette weekend! 10/10 would stay here again!”
Stayed 4 nights in Jul 2024

10/10 Excellent

Pat D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

YaYa trip

This home was beautifully decorated and very clean. The location was fabulous. There was a problem with the hot water heater making a lot of noise, Megan said they will fix it.
Stayed 4 nights in Nov 2019

8/10 Good

Kurt Z., Madera, California, USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Very nice property and perfect layout for our family, three couples and a child. We stayed during a cold snap, 19 degrees one day so the weather did not cooperate. We all enjoyed the family room/kitchen open space and can highly recommend. Walked to all of downtown, aquarium, the Battery, restaurants.
Stayed 6 nights in Dec 2022

10/10 Excellent

Jessica W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

House was wonderful!

The house is perfect for large groups. Four separate bedrooms spread across two floors with a living room on the lowest level. Could have used another hair dryer (one was broke ) and more towels (only 4 given per room) but overall it was great!
Stayed 3 nights in Mar 2022

10/10 Excellent

Katy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Annual Cousin Weekend

We made The East Bay Home our “home” for our annual cousin/aunt weekend. We all live in different areas of the country and enjoy when we can all be together. The East Bay Home was exactly as expected. Clean and comfortable on every level, room, and bathroom. The location was in the heart of Charleston. We were able to walk to absolutely everything. The host had thought of every detail to make our stay more comfortable, also responsive and helpful. We look forward to coming back!
Stayed 3 nights in Jan 2024

10/10 Excellent

Tracy A., Myrtle Beach, USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location / perfect rental

This unit has a very unique style. The multi level floor layout provided a spacious atmosphere for our family. It was very clean, beds / linens were extremely comfortable, and It was stocked with everything we needed. The host provides a variety of coffees and laundry detergent; which were very convenient. I would definitely return and recommend this to others.
Stayed 2 nights in Jul 2020

10/10 Excellent

Robin N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

GREAT LOCATION - BEAUTIFUL HOME

Home is beautiful and has a lot of character! The location was right next door to a really good restaurant (SNOB) and to a pizza restaurant that was also good! We were a group of 11 ladies and were able to walk everywhere downtown that we wanted to go from this house. Most of the bedrooms had an ensuite bathroom. It is three stories so you need to be sure that no one would have a problem with the stairs. The host could not have been anymore responsive. :) Overall, a very nice home in a great location! Highly recommend!!
Stayed 4 nights in Apr 2024