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The Speakeasy on Chicago!

Photo gallery for The Speakeasy on Chicago!

A living room with a sofa, ottoman, and a dining area with a table and chairs.
A single-story brick house with a front porch, a small front yard, and a wooded backdrop.
A single-story house with a brick exterior, a front porch, and a driveway leading to the entrance.
Property grounds
A single-story brick house with a wooden deck and a sliding glass door leading to an outdoor patio.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Private garden
    A rare find — relax in the peaceful, private garden space.
4 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Deck or patio
  • Free Wi-Fi

Explore the area

View in a map
Pensacola, FL
  • Place, Pensacola Interstate Fairgrounds
    ‪4 min drive‬
  • Place, Marcus Pointe Golf Club
    ‪5 min drive‬
  • Place, Five Flags Speedway
    ‪8 min drive‬
  • Airport, Pensacola, FL (PNS-Pensacola Intl.)
    ‪18 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds

2 bathrooms

Bathroom 1

Soap · Towels provided · Bathtub or shower · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Bathtub · Shampoo

Spaces

Deck or patio
Kitchen
Garden

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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 3600569vb
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

About the area

Pensacola

Located near the beach, this holiday home is in Northwest Pensacola, a neighbourhood in Pensacola. The area's natural beauty can be seen at Johnson Beach and Pensacola Beach Beaches, while Saenger Theatre and National Museum of Naval Aviation are cultural highlights. Looking to enjoy an event or a game while in town? See what's going on at Pensacola Bay Center, or consider a night out at Vinyl Music Hall.
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Map
Pensacola, FL

What's nearby

  • Pensacola Interstate Fairgrounds - 4 min drive - 3.2 km
  • Marcus Pointe Golf Club - 5 min drive - 3.9 km
  • Brent Athletic Park - 8 min drive - 5.3 km
  • Five Flags Speedway - 8 min drive - 6.8 km
  • Splash City Adventures - 9 min drive - 8.5 km

Getting around

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

Restaurants

  • ‪Whataburger - ‬19 min walk
  • ‪McDonald's - ‬16 min walk
  • ‪Circle K - ‬4 min drive
  • ‪Culver's - ‬18 min walk
  • ‪Taco Bell - ‬17 min walk

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 2.5 mi (4.1 km) from Fast Eddies Fun Center and 2.9 mi (4.7 km) from Brent Athletic Park. Barnes Shopping Center and Brentwood Shopping Center are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

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

10/10 Excellent

Beth F.

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

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

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

10/10 Excellent

Alicia W.

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

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

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

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

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
Response from VrboOwner on 5 Dec 2023
Julie was the perfect guest. Thank YOU for your family’s support of your son and his military service. Please come back anytime!
Verified

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

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
Verified

10/10 Excellent

Ashley A.

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

About the host

Hosted by Nick Pacino

Host profile image
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