Charleston, South Carolina

192 East Bay 300+200

5 bedrooms 8 beds 4 baths 16 guests 4.8 (61)

About the property

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. 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 Queen Air Mattress + Additional Bedding (Available upon request) 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. Managed with care by YOURPAD Vacation Rentals. We manage a large portfolio of properties across the Lowcountry. Once you experience our hospitality, we’d love to welcome you back again in the future. SOCIAL MEDIA: If you plan on sharing your experience on social media, please tag us! @yourpadstays 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. 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 Luggage storage offered Monday- Friday at our main office from 8:30am-5pm. On weekends we recommend utilizing Bounce Luggage storage. Please inquire once booking is complete for the address! 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! PROPERTY NAME: PINEAPPLE PLACE

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. 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 Queen Air Mattress + Additional Bedding (Available upon request) 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. Managed with care by YOURPAD Vacation Rentals. We manage a large portfolio of properties across the Lowcountry. Once you experience our hospitality, we’d love to welcome you back again in the future. SOCIAL MEDIA: If you plan on sharing your experience on social media, please tag us! @yourpadstays 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. 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 Luggage storage offered Monday- Friday at our main office from 8:30am-5pm. On weekends we recommend utilizing Bounce Luggage storage. Please inquire once booking is complete for the address! 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! PROPERTY NAME: PINEAPPLE PLACE

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
May 18, 2026$684Not Available2
May 19, 2026$589Not Available2
May 20, 2026$684Not Available2
May 21, 2026$1,729Not Available1
May 22, 2026$2,299Not Available1
May 23, 2026$2,299Not Available1
May 24, 2026$2,299Not Available2
May 25, 2026$549Available1
May 26, 2026$549Not Available2
May 27, 2026$549Not Available2
May 28, 2026$549Not Available1
May 29, 2026$2,299Not Available1
May 30, 2026$2,299Not Available1
May 31, 2026$1,234Not Available2
Jun 1, 2026$769Available1
Jun 2, 2026$994Not Available2
Jun 3, 2026$994Not Available2
Jun 4, 2026$2,074Available3
Jun 5, 2026$2,199Available3
Jun 6, 2026$2,199Not Available3
Jun 7, 2026$1,264Available2
Jun 8, 2026$634Available2
Jun 9, 2026$634Available2
Jun 10, 2026$634Not Available2
Jun 11, 2026$634Not Available3
Jun 12, 2026$2,264Not Available3
Jun 13, 2026$2,209Not Available3
Jun 14, 2026$1,039Not Available2
Jun 15, 2026$664Available2
Jun 16, 2026$639Available2
Jun 17, 2026$774Available2
Jun 18, 2026$2,369Available3
Jun 19, 2026$2,609Available3
Jun 20, 2026$2,534Not Available3
Jun 21, 2026$1,704Available2
Jun 22, 2026$1,454Available2
Jun 23, 2026$1,369Available2
Jun 24, 2026$1,459Available2
Jun 25, 2026$1,764Available3
Jun 26, 2026$2,584Not Available3
Jun 27, 2026$2,469Not Available3
Jun 28, 2026$1,714Not Available2
Jun 29, 2026$649Available2
Jun 30, 2026$584Available2
Jul 1, 2026$769Available2
Jul 2, 2026$1,999Available3
Jul 3, 2026$1,999Available3
Jul 4, 2026$1,999Available3
Jul 5, 2026$944Available2
Jul 6, 2026$1,479Available2
Jul 7, 2026$1,199Available2
Jul 8, 2026$804Available2
Jul 9, 2026$1,684Not Available3
Jul 10, 2026$1,864Not Available3
Jul 11, 2026$1,749Not Available3
Jul 12, 2026$1,014Available2
Jul 13, 2026$664Available2
Jul 14, 2026$934Available2
Jul 15, 2026$969Available2
Jul 16, 2026$2,569Available3
Jul 17, 2026$2,654Available3
Jul 18, 2026$2,599Available3
Jul 19, 2026$1,169Available2
Jul 20, 2026$664Available2
Jul 21, 2026$584Available2
Jul 22, 2026$709Available2
Jul 23, 2026$1,709Available3
Jul 24, 2026$1,749Available3
Jul 25, 2026$1,669Available3
Jul 26, 2026$1,134Available2
Jul 27, 2026$639Not Available2
Jul 28, 2026$534Not Available2
Jul 29, 2026$664Available2
Jul 30, 2026$1,924Available3
Jul 31, 2026$1,999Available3
Aug 1, 2026$1,999Available3
Aug 2, 2026$909Available2
Aug 3, 2026$579Available2
Aug 4, 2026$714Available2
Aug 5, 2026$629Available2
Aug 6, 2026$1,764Available3
Aug 7, 2026$1,999Available3
Aug 8, 2026$1,999Available3
Aug 9, 2026$854Available2
Aug 10, 2026$524Available2
Aug 11, 2026$489Available1
Aug 12, 2026$614Available1
Aug 13, 2026$1,744Available2
Aug 14, 2026$2,044Available2
Aug 15, 2026$1,974Available2
Aug 16, 2026$829Available1

Amenities

Elevator
Conditioner
Luggage drop off allowed
Dedicated workspace
Bath linens
Bed linens
First aid kit
Air conditioning

4.8 · 61 reviews

A
Anonymous
1 week ago

We absolutely loved our stay at The Pineapple Pad! In addition to being an incredibly cool and beautifully designed space, the location was perfect — we could easily walk to the Battery, Rainbow Row, Waterfront Park, and were surrounded by amazing restaurants, coffee shops, and boutiques. It truly felt like the ideal Charleston home base. The house itself was exceptionally well appointed. From the welcoming coffee setup to the great sound system, quality stemware, and even a blender for smoothies, everything felt thoughtful and easy. Our group of five had everything we could hope for and felt very comfortable throughout our stay. On top of all that, the property management team was fantastic. They helped us with everything from luggage storage to local recommendations, and they were consistently responsive, professional, and genuinely friendly. We would absolutely stay here again and highly recommend it to anyone visiting Charleston!

A
Anonymous
March 2026

Perfect! Location couldn’t have been better! Everything was clean and we enjoyed staying there

A
Anonymous
February 2026

The kitchen and living room areas were perfect for gathering with friends. The location was perfect! It was close to everything.

Where you'll be

Charleston, South Carolina, 29401, US

Discover Charleston’s captivating blend of historic grandeur and vibrant culture. Iconic landmarks are steps away, inviting you to explore the bustling Charleston City Market, stroll through Waterfront Park to the charming Pineapple Fountain, or savor fine dining at Magnolias. A short walk brings you to the vibrant hues of Rainbow Row and the fascinating marine life at the South Carolina Aquarium, completing your immersive Lowcountry experience.

Things to know

Cancellation policy

Contact us for cancellation policy details prior to booking.

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 16 guests.