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The Speakeasy on Chicago!

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A living room with a sofa, ottoman, and a dining area with a table and chairs.
A single-story house with a brick exterior, a front porch, and a driveway leading to the entrance.
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.
A modern kitchen with white cabinets, stainless steel appliances, a clock, and a coffee machine.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

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

Room options

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About the neighborhood

Pensacola

Located in Northwest Pensacola, this vacation home is within a few miles (5 km) of sights such as Pensacola Interstate Fairgrounds and Fast Eddies Fun Center. The vacation home includes a kitchen, a patio, and a microwave.
View more Vacation Homes in PensacolaOpens in a new window

What's nearby

  • Pensacola Interstate Fairgrounds - 4 min drive - 2.0 miles
  • Marcus Pointe Golf Club - 5 min drive - 2.4 miles
  • Brent Athletic Park - 8 min drive - 3.3 miles
  • Five Flags Speedway - 8 min drive - 4.2 miles
  • Splash City Adventures - 9 min drive - 5.3 miles

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
  • ‪D&R Lounge - ‬4 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.
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a patio, and there's space to spread out with 4 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine and an ironing board.

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Property amenities

Beach

  • Beach nearby
  • Beach loungers

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Dishwasher
  • Microwave
  • Oven
  • Stovetop

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 elevator (single-level property)
  • Smoking not allowed

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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 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
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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM

We should mention

Details about charges, deposits, or other important information:

  • 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, 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Frequently asked questions

What can I see within easy reach of this vacation home?

This vacation home is situated in Northwest Pensacola, close to Cordova Mall, Saenger Theatre, and Pensacola Bay Center. You'll also find Five Flags Speedway and Splash City Adventures within a short drive.

Is parking available on site at The Speakeasy on Chicago! ?

No, this vacation home doesn't offer parking.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What amenities will couples enjoy at The Speakeasy on Chicago! ?

Couples staying at this vacation home will appreciate amenities like a smart TV and a kitchen as well as a garden.

Does The Speakeasy on Chicago! have a hot tub?

No, this vacation home doesn't have a spa tub.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

No, pets aren't allowed at this vacation home.

Does The Speakeasy on Chicago! have connecting rooms available?

No, this vacation home doesn't feature connecting guestrooms.

How far is the airport from this vacation home?

The closest major airport to this vacation home is Pensacola Intl. Airport (PNS), which is 6.6 mi away (12 minutes by car). Another top airport is Gulf Shores, AL (GUF-Jack Edwards), which is around 26.1 mi away.

Are there rooms with balconies that I can book at The Speakeasy on Chicago! ?

Yes, every house at The Speakeasy on Chicago! comes with a patio.

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

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

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

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

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

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