Charleston, South Carolina

192 East Bay 300+200

5 bedrooms8 beds4 baths16 guests4.8 (63)

About the property

Located in the heart of the French Quarter and draped in history, this private, secure 3,300 sq. ft. luxury retreat comfortably sleeps 16 guests with 5 spacious bedrooms, dual master suites, ensuite bathrooms, and upgraded luxury amenities. Enjoy gourmet entertaining spaces with soaring 18’ ceilings, exposed brick, SONOS sound system, chef’s kitchen, and multiple kitchenettes. Every bedroom features flat-screen TVs with YouTube TV, premium linens, and thoughtful comforts throughout.

Discover the best of downtown Charleston from this spacious 5-bedroom, 4-bathroom retreat in the coveted French Quarter. Perfect for groups of up to 16, the home blends historic charm with modern comfort and features a gourmet kitchen, inviting gathering spaces, and an unbeatable location just a short walk from Waterfront Park, City Market, acclaimed restaurants, and Charleston's iconic landmarks.

Sleeping Arrangements:

  • Bedroom #1: King Bed with En suite
  • Bedroom #2: Queen Bed + Queen Bed with En suite
  • Bedroom #3: Queen Bed + Queen Bed with En suite
  • Bedroom #4: Queen Bed with En suite
  • Bedroom #5: King Bed
  • West Elm Pullout Sofa with Queen Air Mattress and Additional Bedding (Available upon request)

Key Amenities:

  • Free Parking on Premises
  • Self Check-in
  • Elevator
  • Comcast Business-Class Internet and WiFi HotSpots Throughout
  • Luxury Linens & Towels Provided
  • Paper Products & Bath Amenities Included

Outdoor Living:

  • Walking Distance to Fine Dining Restaurants, Charleston's City Market, Historic Landmarks, Boutiques, Tours, Parks
  • Eye-level View of the Iconic St. Philip Church

Indoor Comforts:

  • Bathtub
  • Pack ’n play/Travel crib & High chair (Available upon request)
  • Flat Screen TVs with Streaming Capabilities on all Bedrooms
  • Dedicated Workspace
  • In-unit Laundry Room with a Full-size Washer & Dryer Including Detergent
  • Full Gourmet Kitchen Furnished with Stainless Appliances
  • All 3 floors Feature Individual Kitchenettes

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

Located in the heart of the French Quarter and draped in history, this private, secure 3,300 sq. ft. luxury retreat comfortably sleeps 16 guests with 5 spacious bedrooms, dual master suites, ensuite bathrooms, and upgraded luxury amenities. Enjoy gourmet entertaining spaces with soaring 18’ ceilings, exposed brick, SONOS sound system, chef’s kitchen, and multiple kitchenettes. Every bedroom features flat-screen TVs with YouTube TV, premium linens, and thoughtful comforts throughout.

Discover the best of downtown Charleston from this spacious 5-bedroom, 4-bathroom retreat in the coveted French Quarter. Perfect for groups of up to 16, the home blends historic charm with modern comfort and features a gourmet kitchen, inviting gathering spaces, and an unbeatable location just a short walk from Waterfront Park, City Market, acclaimed restaurants, and Charleston's iconic landmarks.

Sleeping Arrangements:

  • Bedroom #1: King Bed with En suite
  • Bedroom #2: Queen Bed + Queen Bed with En suite
  • Bedroom #3: Queen Bed + Queen Bed with En suite
  • Bedroom #4: Queen Bed with En suite
  • Bedroom #5: King Bed
  • West Elm Pullout Sofa with Queen Air Mattress and Additional Bedding (Available upon request)

Key Amenities:

  • Free Parking on Premises
  • Self Check-in
  • Elevator
  • Comcast Business-Class Internet and WiFi HotSpots Throughout
  • Luxury Linens & Towels Provided
  • Paper Products & Bath Amenities Included

Outdoor Living:

  • Walking Distance to Fine Dining Restaurants, Charleston's City Market, Historic Landmarks, Boutiques, Tours, Parks
  • Eye-level View of the Iconic St. Philip Church

Indoor Comforts:

  • Bathtub
  • Pack ’n play/Travel crib & High chair (Available upon request)
  • Flat Screen TVs with Streaming Capabilities on all Bedrooms
  • Dedicated Workspace
  • In-unit Laundry Room with a Full-size Washer & Dryer Including Detergent
  • Full Gourmet Kitchen Furnished with Stainless Appliances
  • All 3 floors Feature Individual Kitchenettes

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.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 17, 2026$775Available1
Jul 18, 2026$775Not Available1
Jul 19, 2026$724Not Available2
Jul 20, 2026$699Not Available2
Jul 21, 2026$629Not Available2
Jul 22, 2026$559Not Available2
Jul 23, 2026$1,009Not Available1
Jul 24, 2026$1,109Not Available1
Jul 25, 2026$1,069Not Available1
Jul 26, 2026$594Not Available2
Jul 27, 2026$854Not Available2
Jul 28, 2026$679Not Available2
Jul 29, 2026$599Not Available2
Jul 30, 2026$994Available1
Jul 31, 2026$1,469Available2
Aug 1, 2026$1,619Not Available3
Aug 2, 2026$689Not Available2
Aug 3, 2026$574Not Available2
Aug 4, 2026$539Not Available2
Aug 5, 2026$579Not Available2
Aug 6, 2026$1,099Not Available3
Aug 7, 2026$1,664Not Available3
Aug 8, 2026$1,624Not Available3
Aug 9, 2026$589Not Available2
Aug 10, 2026$465Available2
Aug 11, 2026$465Available1
Aug 12, 2026$465Available1
Aug 13, 2026$1,119Not Available2
Aug 14, 2026$1,699Not Available2
Aug 15, 2026$1,634Not Available2
Aug 16, 2026$559Not Available1
Aug 17, 2026$465Not Available1
Aug 18, 2026$465Not Available1
Aug 19, 2026$465Not Available1
Aug 20, 2026$989Not Available2
Aug 21, 2026$1,599Available2
Aug 22, 2026$1,554Available2
Aug 23, 2026$584Available1
Aug 24, 2026$465Not Available1
Aug 25, 2026$465Not Available1
Aug 26, 2026$465Not Available1
Aug 27, 2026$1,014Not Available2
Aug 28, 2026$1,624Not Available2
Aug 29, 2026$1,589Not Available3
Aug 30, 2026$465Available1
Aug 31, 2026$465Not Available3
Sep 1, 2026$465Not Available2
Sep 2, 2026$465Not Available2
Sep 3, 2026$904Available3
Sep 4, 2026$2,214Available3
Sep 5, 2026$2,269Available3
Sep 6, 2026$1,734Available2
Sep 7, 2026$479Available2
Sep 8, 2026$465Available2
Sep 9, 2026$465Available2
Sep 10, 2026$1,619Not Available3
Sep 11, 2026$1,999Not Available3
Sep 12, 2026$1,949Not Available3
Sep 13, 2026$864Available2
Sep 14, 2026$934Available2
Sep 15, 2026$859Available2
Sep 16, 2026$914Available2
Sep 17, 2026$1,789Not Available3
Sep 18, 2026$2,144Not Available3
Sep 19, 2026$2,074Not Available3
Sep 20, 2026$830Available2
Sep 21, 2026$884Available2
Sep 22, 2026$864Available2
Sep 23, 2026$914Available2
Sep 24, 2026$1,849Not Available3
Sep 25, 2026$2,254Not Available3
Sep 26, 2026$2,174Not Available3
Sep 27, 2026$1,039Not Available2
Sep 28, 2026$534Available2
Sep 29, 2026$509Available2
Sep 30, 2026$649Available2
Oct 1, 2026$1,934Not Available3
Oct 2, 2026$2,409Not Available3
Oct 3, 2026$2,404Not Available3
Oct 4, 2026$1,064Available2
Oct 5, 2026$979Available2
Oct 6, 2026$579Available2
Oct 7, 2026$734Available2
Oct 8, 2026$2,044Not Available3
Oct 9, 2026$2,559Not Available3
Oct 10, 2026$2,474Not Available3
Oct 11, 2026$600Available3
Oct 12, 2026$654Available3
Oct 13, 2026$624Available2
Oct 14, 2026$719Available2
Oct 15, 2026$2,129Not Available3

Amenities

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

4.8 · 63 reviews

H
Happy Guest
4 days ago

Could not be a better location to stay at in Charleston!

H
Happy Guest
June 2026

Ideal location, spacious and charming interior, excellent communication. This was our second stay; we plan to return here on on next visit to Charleston.

H
Happy Guest
May 2026

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!

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.

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

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.