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
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.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jul 17, 2026 | $775 | Available | 1 |
| Jul 18, 2026 | $775 | Not Available | 1 |
| Jul 19, 2026 | $724 | Not Available | 2 |
| Jul 20, 2026 | $699 | Not Available | 2 |
| Jul 21, 2026 | $629 | Not Available | 2 |
| Jul 22, 2026 | $559 | Not Available | 2 |
| Jul 23, 2026 | $1,009 | Not Available | 1 |
| Jul 24, 2026 | $1,109 | Not Available | 1 |
| Jul 25, 2026 | $1,069 | Not Available | 1 |
| Jul 26, 2026 | $594 | Not Available | 2 |
| Jul 27, 2026 | $854 | Not Available | 2 |
| Jul 28, 2026 | $679 | Not Available | 2 |
| Jul 29, 2026 | $599 | Not Available | 2 |
| Jul 30, 2026 | $994 | Available | 1 |
| Jul 31, 2026 | $1,469 | Available | 2 |
| Aug 1, 2026 | $1,619 | Not Available | 3 |
| Aug 2, 2026 | $689 | Not Available | 2 |
| Aug 3, 2026 | $574 | Not Available | 2 |
| Aug 4, 2026 | $539 | Not Available | 2 |
| Aug 5, 2026 | $579 | Not Available | 2 |
| Aug 6, 2026 | $1,099 | Not Available | 3 |
| Aug 7, 2026 | $1,664 | Not Available | 3 |
| Aug 8, 2026 | $1,624 | Not Available | 3 |
| Aug 9, 2026 | $589 | Not Available | 2 |
| Aug 10, 2026 | $465 | Available | 2 |
| Aug 11, 2026 | $465 | Available | 1 |
| Aug 12, 2026 | $465 | Available | 1 |
| Aug 13, 2026 | $1,119 | Not Available | 2 |
| Aug 14, 2026 | $1,699 | Not Available | 2 |
| Aug 15, 2026 | $1,634 | Not Available | 2 |
| Aug 16, 2026 | $559 | Not Available | 1 |
| Aug 17, 2026 | $465 | Not Available | 1 |
| Aug 18, 2026 | $465 | Not Available | 1 |
| Aug 19, 2026 | $465 | Not Available | 1 |
| Aug 20, 2026 | $989 | Not Available | 2 |
| Aug 21, 2026 | $1,599 | Available | 2 |
| Aug 22, 2026 | $1,554 | Available | 2 |
| Aug 23, 2026 | $584 | Available | 1 |
| Aug 24, 2026 | $465 | Not Available | 1 |
| Aug 25, 2026 | $465 | Not Available | 1 |
| Aug 26, 2026 | $465 | Not Available | 1 |
| Aug 27, 2026 | $1,014 | Not Available | 2 |
| Aug 28, 2026 | $1,624 | Not Available | 2 |
| Aug 29, 2026 | $1,589 | Not Available | 3 |
| Aug 30, 2026 | $465 | Available | 1 |
| Aug 31, 2026 | $465 | Not Available | 3 |
| Sep 1, 2026 | $465 | Not Available | 2 |
| Sep 2, 2026 | $465 | Not Available | 2 |
| Sep 3, 2026 | $904 | Available | 3 |
| Sep 4, 2026 | $2,214 | Available | 3 |
| Sep 5, 2026 | $2,269 | Available | 3 |
| Sep 6, 2026 | $1,734 | Available | 2 |
| Sep 7, 2026 | $479 | Available | 2 |
| Sep 8, 2026 | $465 | Available | 2 |
| Sep 9, 2026 | $465 | Available | 2 |
| Sep 10, 2026 | $1,619 | Not Available | 3 |
| Sep 11, 2026 | $1,999 | Not Available | 3 |
| Sep 12, 2026 | $1,949 | Not Available | 3 |
| Sep 13, 2026 | $864 | Available | 2 |
| Sep 14, 2026 | $934 | Available | 2 |
| Sep 15, 2026 | $859 | Available | 2 |
| Sep 16, 2026 | $914 | Available | 2 |
| Sep 17, 2026 | $1,789 | Not Available | 3 |
| Sep 18, 2026 | $2,144 | Not Available | 3 |
| Sep 19, 2026 | $2,074 | Not Available | 3 |
| Sep 20, 2026 | $830 | Available | 2 |
| Sep 21, 2026 | $884 | Available | 2 |
| Sep 22, 2026 | $864 | Available | 2 |
| Sep 23, 2026 | $914 | Available | 2 |
| Sep 24, 2026 | $1,849 | Not Available | 3 |
| Sep 25, 2026 | $2,254 | Not Available | 3 |
| Sep 26, 2026 | $2,174 | Not Available | 3 |
| Sep 27, 2026 | $1,039 | Not Available | 2 |
| Sep 28, 2026 | $534 | Available | 2 |
| Sep 29, 2026 | $509 | Available | 2 |
| Sep 30, 2026 | $649 | Available | 2 |
| Oct 1, 2026 | $1,934 | Not Available | 3 |
| Oct 2, 2026 | $2,409 | Not Available | 3 |
| Oct 3, 2026 | $2,404 | Not Available | 3 |
| Oct 4, 2026 | $1,064 | Available | 2 |
| Oct 5, 2026 | $979 | Available | 2 |
| Oct 6, 2026 | $579 | Available | 2 |
| Oct 7, 2026 | $734 | Available | 2 |
| Oct 8, 2026 | $2,044 | Not Available | 3 |
| Oct 9, 2026 | $2,559 | Not Available | 3 |
| Oct 10, 2026 | $2,474 | Not Available | 3 |
| Oct 11, 2026 | $600 | Available | 3 |
| Oct 12, 2026 | $654 | Available | 3 |
| Oct 13, 2026 | $624 | Available | 2 |
| Oct 14, 2026 | $719 | Available | 2 |
| Oct 15, 2026 | $2,129 | Not Available | 3 |
Amenities
4.8 · 63 reviews
Could not be a better location to stay at in Charleston!
Ideal location, spacious and charming interior, excellent communication. This was our second stay; we plan to return here on on next visit to Charleston.
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.
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
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.