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The Speakeasy on Chicago!

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A living room with a sectional sofa, a coffee table, a Christmas tree, and a "NO HUMBUGGING" sign on the wall.
A hallway with a white door leading to a kitchen area.
A modern kitchen with stainless steel appliances, a dining area with a Christmas tree, and a living room with a fireplace.
A compact apartment with a dining area, kitchenette, living room, and a TV.
A bedroom with a large bed, a bedside table, a TV, and a wardrobe.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Pensacola, FL
  • Place, Pensacola Interstate Fairgrounds
    ‪4 min drive‬
  • Place, Marcus Pointe Golf Club
    ‪6 min drive‬
  • Place, Five Flags Speedway
    ‪7 min drive‬
  • Airport, Pensacola, FL (PNS-Pensacola Intl.)
    ‪19 min drive‬

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About the area

Pensacola

At this holiday home, you'll be 28.8 km (17.9 mi) from Pensacola Naval Air Station and 30 km (18.7 mi) from Perdido Key Beach. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .Home features 2 bathrooms, a patio and a Smart TV. In-room dining is easy with a kitchen that comes equipped with a microwave, a stovetop and a dishwasher. A hairdryer and an iron/ironing board are also available. .Attractions within a 20-minute drive of this Northwest Pensacola holiday home include Pensacola Bay Center and University of West Florida.
View more Holiday homes in PensacolaOpens in a new window

What's nearby

  • Pensacola Interstate Fairgrounds - 4 min drive - 3.2 km
  • Marcus Pointe Golf Club - 6 min drive - 3.9 km
  • Fast Eddies Fun Center - 6 min drive - 4.9 km
  • Five Flags Speedway - 7 min drive - 6.8 km
  • Osceola Municipal Golf Course - 7 min drive - 5.7 km

Getting around

  • Pensacola Station - 8 min drive
  • Pensacola, FL (PNS-Pensacola Intl.) - 12 min drive

Restaurants

  • ‪Circle K - ‬5 min drive
  • ‪Whataburger - ‬19 min walk
  • ‪Circle K - ‬5 min drive
  • ‪McDonald's - ‬16 min walk
  • ‪Church's Texas Chicken - ‬5 min drive

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 Speakeasy on Chicago!

Enjoy a quiet location that offers easy access to everything. Pack up the provided beach chairs, beach towels, and beach wagon for fun days in the sun -Perdido Key Beach and Pensacola Reach ran he reached in no timel Your family will be close to everything when you stay at this centrally-located place.

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  • Washing machine
  • Dryer
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Property amenities

Beach

  • Beach nearby
  • Beach loungers

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Dishwasher
  • Hob
  • Microwave
  • Oven

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Smart TV

Outdoor areas

  • Garden
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift (single-level property)
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

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
  • Deadbolt lock

General

  • Garden

Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 11:00 AM

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

  • No pets 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, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadbolt lock in all accommodation.

Frequently asked questions

Are there any beaches close to The Speakeasy on Chicago! ?

The closest beach to The Speakeasy on Chicago! is Pensacola Beach Beaches (15.7 km).

Does The Speakeasy on Chicago! have a pool?

No, this holiday home doesn't have a pool.

Is there a free airport shuttle available at The Speakeasy on Chicago! ?

No, The Speakeasy on Chicago! does not offer an airport shuttle service.

What time are check-in & check-out at The Speakeasy on Chicago! ?

Check-in begins at 4:00 PM. Check-out time is 11:00 AM.

Are pets allowed at The Speakeasy on Chicago! ?

No, pets are not allowed.

The Speakeasy on Chicago! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 12 out of 12 reviews
Rating 8 - Good. 0 out of 12 reviews
Rating 6 - Okay. 0 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

9.8/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Hunter K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Yes, I especially enjoyed the waffle house right down the street.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Siesta Key F.

Liked: Check-in, communication, location, listing accuracy
Great house awesome has everything you need easy booking would stay again.
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

EBKGUARDME -.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was great very clean and nice
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

kathleen R.

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

Great stay!

The home was perfect and cozy. I would rent this again. 10 stars for sure.
Stayed 2 nights in Mar 2025
Verified review

10/10 Excellent

Katie T.

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

Clean property and responsive manager!

Very nice house that was close to everything we needed, Corry Station and the beaches! Would recommend to anyone looking :)
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Julie L.

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

Very Clean

House was perfect for our quick trip to visit my son. Very convenient to stores and restaurants nearby. The house was extremely clean. Beds were comfortable. Would stay again.
Stayed 3 nights in Nov 2023
Verified review

10/10 Excellent

stacey r.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect. Communication was great. House was exactly as listed. No issues Great area
Stayed 24 nights in Oct 2025
Verified review

10/10 Excellent

Trammell R.

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

June family trip

The property was clean and well maintained. Any minor issue we had, we sent an email and there was an immediate response. We greatly appreciate the hospitality and will definitely look to utilize the services and location again.
Stayed 2 nights in Jun 2024
Verified review

10/10 Excellent

Elijah b.

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

Amazing

The property was spacious and clean! Communication with Me. Nick the house was easy and quick response! All around a great stay!
Stayed 6 nights in Jul 2024