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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Bar (on property)
A modern kitchen with a coffee station, a television, and a display case with baked goods.
A white decorative sculpture in a garden area with a white fence and a building in the background.
A modern kitchen with a granite countertop, white cabinetry, and a coffee machine.
A motel with a porch, white chairs, and a signboard.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Parking available
  • Bar
The current price is $175
$155 nightly
$175 total
Total with taxes and fees
Aug 16 - Aug 17

Explore the area

View in a map
1321 Simonton Street, Key West, FL, 33040
  • Place, Duval Street
    ‪3 min walk‬
  • Place, South Beach
    ‪3 min walk‬
  • Place, Southernmost Point
    ‪5 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Room options

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down comforters, pillowtop beds, iron/ironing board

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(112 reviews)
  • 250 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, iron/ironing board

Standard Room, 2 Queen Beds

8.6 out of 10
Excellent
(84 reviews)
  • 400 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Deluxe Room

Premium bedding, down comforters, pillowtop beds, iron/ironing board

Deluxe Room

10.0 out of 10
Exceptional
(7 reviews)
  • 300 sq ft
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, iron/ironing board

Standard Room, 1 King Bed

8.4 out of 10
Very good
(124 reviews)
  • 300 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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The price is $235
Aug 17 - Aug 18
Total with taxes and fees
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About the neighborhood

Key West

With a stay at Southwinds Motel in Key West (Old Town Key West), you'll be steps from South Beach and 3 minutes by foot from Duval Street. .This hotel is 0.2 mi (0.3 km) from Southernmost Point and 0.6 mi (0.9 km) from Ernest Hemingway Home and Museum.

What's nearby

  • Duval Street - 3 min walk - 0.2 miles
  • South Beach - 3 min walk - 0.2 miles
  • Southernmost Point - 5 min walk - 0.3 miles
  • Clarence S. Higgs Memorial Beach Park - 9 min walk - 0.5 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles

Getting around

  • Key West Intl. Airport (EYW) - 8 min drive

Restaurants

  • ‪Circle K - ‬6 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬5 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬5 min walk
  • ‪Southernmost Point Bar in the USA - ‬5 min walk

About this property

Southwinds Motel

Southwinds Motel offers 58 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and hair dryers. Each accommodation is individually furnished and decorated. Pillowtop beds feature down comforters and premium bedding. Guests can make use of the in-room refrigerators and microwaves. Bathrooms include showers and complimentary toiletries.

32-inch LED televisions come with cable channels. Business-friendly amenities include phones along with free local calls (restrictions may apply). Housekeeping is provided on request.

2 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

Make yourself at home in one of the 58 individually decorated guestrooms, featuring refrigerators and microwaves. Your pillowtop bed comes with down comforters and premium bedding. 32-inch LED televisions are provided, with cable programming available. Private bathrooms with showers feature complimentary toiletries and hair dryers.
Make use of convenient amenities such as concierge services, a picnic area, and a vending machine.
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 7:00 AM to 10:00 AM.
Featured amenities include complimentary newspapers in the lobby, a 24-hour front desk, and multilingual staff. Self parking (subject to charges) is available onsite.
A complimentary continental breakfast is served each morning between 7:00 AM and 10:00 AM.
Tipsy Rooster - This bar serves light fare only. Open daily.

Property amenities

Parking and transportation

  • Self parking on site (USD 22.50 per day)

Food and drink

  • Free continental breakfast available daily 7:00 AM to 10:00 AM
  • A bar/lounge
  • Coffee and tea in common areas

Restaurants on site

  • Tipsy Rooster

Things to do

  • 2 outdoor pools

Family friendly

  • 2 outdoor pools
  • High chair
  • In-room crib
  • In-room microwave
  • In-room refrigerator
  • Laundry facilities
  • Pool gate

Conveniences

  • 24-hour front desk
  • Free newspapers in lobby
  • Laundry facilities
  • Luggage storage
  • Vending machine

Guest services

  • Concierge services
  • Housekeeping (on request)
  • Multilingual staff
  • Proposal/romance packages
  • Tour and ticket assistance

Outdoors

  • Beach loungers
  • Beach towels
  • Outdoor entertainment area
  • Outdoor furniture
  • Picnic area
  • Pool loungers
  • Pool umbrellas

Accessibility

  • No elevator

More

  • 1 floor
  • 9 buildings
  • Designated smoking areas

Room amenities

Bedroom

  • Down comforter
  • Free crib
  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Shower
  • Towels provided

Entertainment

  • 32-inch LED TV with cable channels

Food and drink

  • Cleaning supplies
  • Coffee/tea maker
  • Microwave
  • Paper towels
  • Refrigerator

More

  • Access via exterior corridors
  • Air conditioning
  • Electrical adapters
  • Free local calls
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Phone
  • Window screens

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: midnight
Late check-in subject to availability
Minimum check-in age: 18

Check-out

Check-out before 11 AM
Contactless check-out available

Special check-in instructions

Front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets not allowed

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Free cribs are available on request at the property

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Resort fee: USD 33.75 per accommodation, per night
The resort fee includes:
  • Additional inclusions
  • Beach access
  • Beach loungers
  • Beach towels
  • Concierge service
  • In-room coffee
  • Internet access
  • Laundry facilities
  • Partner property beach club access
  • Phone calls
  • Pool access

We have included all charges provided to us by the property.

Optional extras

  • Self parking fee: USD 22.50 per day

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card 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
Minimum Spring Break check-in age is 18 years old
The name on the credit card used at check-in to pay for incidentals must be the primary name on the guestroom reservation
This property accepts credit cards, debit cards, and cash
Safety features at this property include a carbon monoxide detector and a smoke detector

We should mention

This property does not have elevators
Only registered guests are allowed in the guestrooms
Alcohol is not served at this property

Property is also known as

Southwinds Motel Key West
Southwinds Motel
Southwinds Key West
Southwind Hotel Key West
Southwinds Motel Hotel
Southwinds Motel Key West
Southwinds Motel Hotel Key West

Southwinds Motel Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 745 out of 1367 reviews
Rating 8 - Good. 372 out of 1367 reviews
Rating 6 - Okay. 161 out of 1367 reviews
Rating 4 - Poor. 58 out of 1367 reviews
Rating 2 - Terrible. 31 out of 1367 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

CONNIE

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great hotel, clean and excellent location.
Stayed 2 nights in Mar 2026
Verified

8/10 Good

Steven

Liked: Cleanliness, staff & service, amenities
Great place - can walk to most activities- place a bit dated - decent breakfast- staff super friendly- would stay again.
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect location for our family vacation to Key West! Very friendly staff, clean rooms, basic continental breakfast (all pre-packaged).
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

Deborah

Liked: Cleanliness, amenities, property conditions & facilities
Great location and comfortable stay.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Elizabeth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location! Wonderful, pleasant and informative staff.
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Diana

Liked: Cleanliness, staff & service, property conditions & facilities
Super great location
Stayed 1 night in Mar 2026
Verified

8/10 Good

Catherine

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place was good and clean. The staff were nice, and very helpful. I would stay here again. Very affordable.
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Amy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location! Walking distance to Duval Street. Love that The Tipsy Rooster bar is right next door! Will definitely stay here again.
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was very clean and the staff was great. I really enjoyed the heated pool.
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Kimberly

Wonderful location, had everything we needed!
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Thomas J

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
always a great time here
Stayed 4 nights in Jan 2026
Verified

10/10 Excellent

William

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Was as depicted, clean, fun, good price,
Stayed 2 nights in Mar 2026
Verified

8/10 Good

Rick

Liked: Cleanliness, staff & service, property conditions & facilities
Room was nice staff was nice
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Jerome

Liked: Cleanliness
All good, classic MOTOR HOTEL!
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Hailey

Liked: Cleanliness, amenities, property conditions & facilities
Perfect little place, great location!
Stayed 2 nights in Dec 2025
Verified

8/10 Good

Sally

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic location and friendly staff.
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Tatiana

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice place to stay, within 30 minute walk to all fun places in old Key West. Very weak water supply during our stay.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Karen

Liked: Cleanliness, amenities, property conditions & facilities
Clean room, friendly staff
Stayed 4 nights in Jan 2026
Verified

10/10 Excellent

Roger

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean room close the bathroom and everything
Stayed 4 nights in Mar 2026
Verified

8/10 Good

Grady

The rooms were clean, the staff was polite and helpful, and the provided light breakfast options provided were good.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Leyany

Liked: Cleanliness, amenities
Very convenient location
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Keri

Liked: Cleanliness, amenities, property conditions & facilities
Very clean, friendly staff. Super cute. Would stay again.
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Mary

Liked: Cleanliness, staff & service, amenities
Always a great stay at the Sea Oats.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Amy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband and I had a great time. The staff was friendly, this is a great location for the price. The Tipsy Rooster was fantastic, the drinks and music were perfect. We will be back
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Denna

Liked: Cleanliness, property conditions & facilities
Cute comfortable rooms great staff and great location!! Will stay again
Stayed 1 night in Dec 2025