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Entire home

The Speakeasy on Chicago!

Photo gallery for The Speakeasy on Chicago!

Living area
Exterior
Exterior
Property grounds
Terrace/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.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
4 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Patio
  • Air conditioning
  • Washer
  • Internet
  • Onsite parking available
  • Microwave

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 Twin 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.

Add dates for prices

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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 # 3600569
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 indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Pensacola

Located near the beach, this vacation home is in Northwest Pensacola, a neighborhood in Pensacola. Fort Pickens is a notable landmark, and the area's natural beauty can be seen at Johnson Beach and Pensacola Beach Beaches. 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 Seville Quarter.
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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
  • Fast Eddies Fun Center - 8 min drive - 4.9 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 Intl. Airport (PNS) - 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 does it cost to stay at The Speakeasy on Chicago! ?

As of Jun 20, 2026, prices found for a 1-night stay for 2 adults at The Speakeasy on Chicago! on Jun 30, 2026 start from $293, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite 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! ?

Check-out is at 11:00 AM.

Where is The Speakeasy on Chicago! located?

Located in Northwest Pensacola, this vacation 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 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 11 out of 11 reviews
Rating 8 - Good. 0 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 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 Dec 5, 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

About the host

Hosted by Nick Pacino

Host profile image
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