Entire home·Private host

The Speakeasy on Chicago!

Photo gallery for The Speakeasy on Chicago!

A living room with a sectional sofa, a coffee table, a Christmas tree, and a "NO HUMBUGGING" sign on the wall. - The Speakeasy on Chicago! (Pensacola)
A compact apartment with a dining area, kitchenette, living room, and a TV. - The Speakeasy on Chicago! (Pensacola)
A bedroom with a large bed, a bedside table, a TV, and a wardrobe. - The Speakeasy on Chicago! (Pensacola)
A hallway with a white door leading to a kitchen area. - The Speakeasy on Chicago! (Pensacola)
A modern kitchen with stainless steel appliances, a dining area with a Christmas tree, and a living room with a fireplace. - The Speakeasy on Chicago! (Pensacola)
The Speakeasy on Chicago! provides amenities, such as a garden and laundry facilities. Stay connected with free in-room WiFi.

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

Add dates for prices

About this property

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.

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

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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

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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

About the area

Located near the beach, this holiday home is in Northwest Pensacola, a neighbourhood in Pensacola. Fast Eddies Fun Center and Osceola Municipal Golf Course are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Pensacola Interstate Fairgrounds and Pensacola Children's Museum. Looking to enjoy an event or a game while in town? See what's happening at Pensacola Bay Center or Five Flags Speedway. Visit our Pensacola travel guide
View more Holiday homes in Pensacola
Map
Pensacola, FL

What's nearby

  • A large, empty stadium with tiered seating and a curved track.
    Five Flags Speedway
    7 min drive - 6.8 km
  • 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
  • Brent Athletic Park
    7 min drive - 5.3 km

Getting around

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

Restaurants

  • Chick-fil-A
    5 min drive
  • Whataburger
    19 min walk
  • McDonald's
    16 min walk
  • Circle K
    4 min drive
  • D&R Lounge
    4 min drive

Frequently asked questions

Is The Speakeasy on Chicago! pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Speakeasy on Chicago! ?

On-site parking is available at the property.

What time is check-in at The Speakeasy on Chicago! ?

Check-in begins at 4:00 PM.

What time is check-out at The Speakeasy on Chicago! ?

Checkout is at 11:00 AM.

Where is The Speakeasy on Chicago! located?

Located in Northwest Pensacola, this holiday home is within 3 miles (5 km) of Pensacola Interstate Fairgrounds, Fast Eddies Fun Center and Brent Athletic Park. Marcus Pointe Baptist Church and Osceola Municipal Golf Course are also within 6 miles (10 km).

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The Speakeasy on Chicago! Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 13 out of 13 reviews
Rating 8 - Good. 0 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

9.8

Cleanliness

10

Location

Reviews

Verified review

10/10 Excellent

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

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

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

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

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was exactly what my family needed. The house is very nice and has a large backyard. It is in a great location and close to many popular places to eat. We would love to stay here again!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

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

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

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

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved our stay at The Speakeasy on Chicago! The home was extremely clean and exactly as listed. Nick & Angela were incredible hosts!! They communicated with us before the trip with helpful recommendations and answers to questions about the area, and they continued to check in after we arrived to make sure everything was perfect.The home was ideal for our family of 5 during our 5-night stay. It had everything we needed and truly felt like a home away from home. We couldn’t have asked for a better experience and will definitely be back in the future!
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect for our family vacation! The location was perfect, everywhere we wanted to go was not far at all! The house was clean and the host was easy to get ahold of if we had any issues. If we ever find our way back to Pensacola we will definitely book again!
Stayed 5 nights in Jun 2026