Entire condo
**SOUTHARD PEARL @ OLD TOWN** Condo & Community Pool + LAST KEY SERVICES…
Condo near Duval Street in Key West
Choose dates to view prices
Photo gallery for **SOUTHARD PEARL @ OLD TOWN** Condo & Community Pool + LAST KEY SERVICES…





Entire condo
Popular amenities
- Pool
- Kitchen
- Washer
- Dryer
- Pet friendly
- Free WiFi
Explore the area

Key West, FL
- Key West CemeteryPlace, Key West Cemetery2 min walk
- Duval StreetPlace, Duval Street8 min walk
- Ernest Hemingway Home and MuseumPlace, Ernest Hemingway Home and Museum11 min walk
- Key West, FL (EYW-Key West Intl.)Airport, Key West, FL (EYW-Key West Intl.)8 min drive
Room options
You may also like
Ad

Hyatt Vacation Club at Beach House, Key West
Key West
- Pool
- Hot tub
- Parking included
- Free WiFi
4.7 out of 5, Exceptional, 1,000 reviews
4.7
Exceptional
1,000 reviews
The price is CA $557
CA $557
CA $688 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Ad

Blue Flamingo Resort Key West
New Town
- Pool
- Hot tub
- Pet friendly
- Free WiFi
4.0 out of 5, Very good, 1,803 reviews
4.0
Very good
1,803 reviews
The price is CA $319
CA $319
CA $436 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Ad

Hyatt Vacation Club at Windward Pointe, Key West
Key West
- Pool
- Hot tub
- Parking included
- Free WiFi
4.8 out of 5, Exceptional, 1,001 reviews
4.8
Exceptional
1,001 reviews
The price is CA $568
CA $568
CA $701 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Ad

Oceans Edge Key West Resort, Hotel & Marina
Stock Island
- Pool
- Pet friendly
- Free WiFi
- Restaurant
4.4 out of 5, Excellent, 1,761 reviews
4.4
Excellent
1,761 reviews
The price is CA $324
CA $324
CA $449 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Ad

The Key West Hotel
Key West Historic District
- Pool
- Pet friendly
- Free WiFi
- Air conditioning
4.6 out of 5, Wonderful, 514 reviews
4.6
Wonderful
514 reviews
The price is CA $533
CA $533
CA $675 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ad

Parrot Key Hotel & Villas
Northside Resort
- Pool
- Pet friendly
- Free WiFi
- Restaurant
4.5 out of 5, Wonderful, 1,217 reviews
4.5
Wonderful
1,217 reviews
The price is CA $278
CA $278
CA $391 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Ad

La Concha Key West, Autograph Collection
Key West Historic District
- Pool
- Pet friendly
- Free WiFi
- Restaurant
4.5 out of 5, Wonderful, 297 reviews
4.5
Wonderful
297 reviews
The price is CA $546
CA $546
CA $660 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Ad

Fairfield Inn and Suites by Marriott Key West
New Town
- Pool
- Breakfast included
- Pet friendly
- Free WiFi
3.9 out of 5, Good, 1,179 reviews
3.9
Good
1,179 reviews
The price is CA $301
CA $301
CA $377 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Ad

Pier House Resort & Spa
Key West Historic District
- On private beach
- Pool
- Hot tub
- Spa
4.5 out of 5, Wonderful, 1,009 reviews
4.5
Wonderful
1,009 reviews
Ad

Ridley House - Key West Historic Inns
Key West Historic District
- Pool
- Breakfast included
- Pet friendly
- Free WiFi
4.6 out of 5, Wonderful, 860 reviews
4.6
Wonderful
860 reviews
The price is CA $490
CA $490
CA $621 total
includes taxes & fees
Jan 7 - Jan 8, 2026
About the area
Key West
Seaside stay .Within a 15-minute walk of this Old Town Key West condo, you'll find Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and Mallory Square are also within 2 miles (3 km).
What's nearby
- Key West Cemetery - 2 min walk - 0.2 km
- Duval Street - 8 min walk - 0.7 km
- Ernest Hemingway Home and Museum - 11 min walk - 1.0 km
- South Beach - 16 min walk - 1.3 km
- Southernmost Point - 17 min walk - 1.5 km
Getting around
- Key West Intl. Airport (EYW) - 15 min drive
Restaurants
- Cuban Coffee Queen Waterfront - 8 min walk
- Square Grouper Key West - 8 min walk
- Pepe's Cafe - 8 min walk
- Harpoon Harry's Restaurant and Bar - 7 min walk
- The Dive Bar Shirt Club - Grub House - 5 min walk
About this property
Entire place
You'll have the entire condo to yourself and will only share it with other guests in your party.
**SOUTHARD PEARL @ OLD TOWN** Condo & Community Pool + LAST KEY SERVICES…
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!
Among the many hidden treasures of Old Town Key West, lives a charming loft-style condo that will melt your heart from the moment you enter. SOUTHARD PEARL is a 2 bedroom second floor condo located in Southard Square, an intimate community located in the heart of the island - a few blocks from Mallory Square, Duval Street and all the attractions Key West has to offer. Best of all, your rental includes Last Key Realty’s unrivaled Five-Star Guest Services, known for providing the most treasured Key West vacations.
THE LOCATION...
Southard Square is an intimate community in the heart of residential Old Town, just a few blocks from Duval Street. Imagine being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the Historic Seaport. Take a short stroll or ride bicycles down to the best of Key West, to hit local favorites like Mangia Mangia, The Café, Willie T’s and Bob’s on Margaret. Head down Margaret Street and you’ll be at BO’s Fish Wagon or Schooner Wharf.
THE COMMUNITY POOL...
The community pool is located in the center of the complex, with some chaise loungers for the sun seekers in your group. With Southard Square being such an intimate community, there’s always room. And parents, you have an eagle-eye view of the pool from the master bedroom’s private balcony! Although you won't need a vehicle to get around from this prime location, a dedicated parking space is included with your rental.
THE LIVING AREA...
The living room of SOUTHARD PEARL features a large flat screen TV and comfortable seating, including a plush sofa and two chairs. The sliding doors open to a private balcony so you can enjoy those refreshing island breezes. Lounge on the private balcony in the Adirondack chair or at the bistro set. The kitchen is fully equipped and provides every appliance and tool you’ll need to prepare meals at home. There is dining for four setup at the kitchen bar.
THE ACCOMMODATIONS...
** Loft Style Master Suite: King bed, flat screen TV, and an en-suite bathroom with a walk-in shower. Plus a single twin bed suitable for young children.
** Guest Bedroom: King bed, flat screen TV, and access to the hallway bath with a walk-in shower.
ALL LAST KEY VACATION HOMES INCLUDE:
** Washer & Dryer
** Central Heat and A/C
** Ceiling Fans
** Flat Screen TVs in Living Room & All Bedrooms
** Fully-Equipped Kitchen
** Basic stock of spices
** Starter supply of paper products
** Starter set of cleaning products
** Linens and Towels provided
** Wireless high-speed Internet access and YouTube TV is included
** Full Time Concierge Service
In addition, this fully stocked unit also includes, but is not limited to the amenities on this list:
** Community Pool
** Electric BBQ Grill
** Off-street Dedicated Parking
Other notes:
** In person welcome
** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.
** Additional interim cleanings available
** This property will accommodate up to 9 adults
** Small Dogs Allowed - Max of 2 dogs and an additional fee of $200 per pet will apply
** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
Among the many hidden treasures of Old Town Key West, lives a charming loft-style condo that will melt your heart from the moment you enter. SOUTHARD PEARL is a 2 bedroom second floor condo located in Southard Square, an intimate community located in the heart of the island - a few blocks from Mallory Square, Duval Street and all the attractions Key West has to offer. Best of all, your rental includes Last Key Realty’s unrivaled Five-Star Guest Services, known for providing the most treasured Key West vacations.
THE LOCATION...
Southard Square is an intimate community in the heart of residential Old Town, just a few blocks from Duval Street. Imagine being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the Historic Seaport. Take a short stroll or ride bicycles down to the best of Key West, to hit local favorites like Mangia Mangia, The Café, Willie T’s and Bob’s on Margaret. Head down Margaret Street and you’ll be at BO’s Fish Wagon or Schooner Wharf.
THE COMMUNITY POOL...
The community pool is located in the center of the complex, with some chaise loungers for the sun seekers in your group. With Southard Square being such an intimate community, there’s always room. And parents, you have an eagle-eye view of the pool from the master bedroom’s private balcony! Although you won't need a vehicle to get around from this prime location, a dedicated parking space is included with your rental.
THE LIVING AREA...
The living room of SOUTHARD PEARL features a large flat screen TV and comfortable seating, including a plush sofa and two chairs. The sliding doors open to a private balcony so you can enjoy those refreshing island breezes. Lounge on the private balcony in the Adirondack chair or at the bistro set. The kitchen is fully equipped and provides every appliance and tool you’ll need to prepare meals at home. There is dining for four setup at the kitchen bar.
THE ACCOMMODATIONS...
** Loft Style Master Suite: King bed, flat screen TV, and an en-suite bathroom with a walk-in shower. Plus a single twin bed suitable for young children.
** Guest Bedroom: King bed, flat screen TV, and access to the hallway bath with a walk-in shower.
ALL LAST KEY VACATION HOMES INCLUDE:
** Washer & Dryer
** Central Heat and A/C
** Ceiling Fans
** Flat Screen TVs in Living Room & All Bedrooms
** Fully-Equipped Kitchen
** Basic stock of spices
** Starter supply of paper products
** Starter set of cleaning products
** Linens and Towels provided
** Wireless high-speed Internet access and YouTube TV is included
** Full Time Concierge Service
In addition, this fully stocked unit also includes, but is not limited to the amenities on this list:
** Community Pool
** Electric BBQ Grill
** Off-street Dedicated Parking
Other notes:
** In person welcome
** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.
** Additional interim cleanings available
** This property will accommodate up to 9 adults
** Small Dogs Allowed - Max of 2 dogs and an additional fee of $200 per pet will apply
** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
Property amenities
Pool/Spa
- Communal pool
Internet
- Available in the condo: Free WiFi
Parking and transportation
- Car not required
- Parking on site
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Ice maker
- Microwave
- Oven
- Refrigerator
- Spices
- Stovetop
- Toaster
Dining
- Dining table
Bedrooms
- 2 bedrooms
- Bedsheets provided
Bathroom
- 2 bathrooms
- Hair dryer
- Towels provided
Living spaces
- Dining table
- Living room
Entertainment
- Smart TV with cable/satellite channels
Outdoor areas
- Balcony
- Barbecue grill
Laundry
- Laundry facilities
- Washing machine
Work spaces
- Desk
- Desk chair
Comfort
- Air conditioning
- Heating
Pets
- Pet friendly
Suitability/Accessibility
- Smoking not allowed
Services and conveniences
- Iron/ironing board
Location highlights
- In a village
- In the city center
- Near a health/beauty spa
- Near a hospital
- Near the marina
- Near the sea
Things to do
- Tennis
- Basketball nearby
- Cycling nearby
- Ecotours nearby
- Fishing nearby
- Golfing nearby
- Jet skiing nearby
- Motor boating nearby
- Parasailing nearby
- Sailing nearby
- Scuba diving nearby
- Snorkeling nearby
- Swimming nearby
- Water tubing nearby
- Windsurfing nearby
Safety features
- Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
- Smoke detector (host has indicated there is a smoke detector on the property)
- First aid kit
- Fire extinguisher
General
- Unit size: 1,200 square feet
Policies
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
- Pets are welcome
- Service animals are exempt from fees
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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Property is also known as
252