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Southwinds Motel

2.0 star property

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Exterior
Deluxe Room | Living area | 32-inch LED TV with cable channels, TV
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated
2 outdoor pools, pool umbrellas, sun loungers
Deluxe Room | Terrace/patio

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Breakfast included
  • Bar
  • 24/7 front desk
  • Laundry
  • Pool
  • Air conditioning

Explore the area

Map
1321 Simonton Street, Key West, FL, 33040
  • Duval Street
    ‪3 min walk‬
  • Simonton Beach
    ‪3 min walk‬
  • South Beach
    ‪3 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Room options

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 King Bed

  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Deluxe Room

Premium bedding, down comforters, pillowtop beds, individually decorated

Deluxe Room

  • 300 sq ft
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 2 Queen Beds

  • 400 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 Queen Bed

  • 250 sq ft
  • Sleeps 3
  • 1 Queen Bed

Similar properties

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Authors of Key West Guest House

  • Pool
  • Breakfast included
  • Free WiFi
  • Air conditioning
4.5 out of 5, Wonderful, (1007)
The price is $419
per night
$494 total
includes taxes & fees
Feb 21 - Feb 22
Authors of Key West Guest House

About this property

Southwinds Motel

Hotel in Key West Historic District
2 outdoor pools, a bar/lounge, and coffee/tea in a common area are available at this hotel. Continental breakfast is free. Additionally, concierge services, laundry facilities, and a 24-hour front desk are onsite. Housekeeping is available on request.
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.

Southwinds Motel features 2 outdoor swimming pools. A bar/lounge is on site where guests can unwind with a drink. Guests can enjoy a complimentary breakfast each morning.

This Key West hotel also offers a vending machine, multilingual staff, and tour/ticket assistance.

Southwinds Motel has designated areas for smoking.

A complimentary continental breakfast is served each morning between 7:00 AM and 10:00 AM.
Tipsy Rooster - This bar serves light fare only.

Languages

English, Russian, Spanish

Property amenities

Parking and transportation

  • Limited onsite parking
  • Wheelchair-accessible parking available

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
  • Bicycle rentals

Family friendly

  • 2 outdoor pools
  • Free crib
  • Highchair
  • 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

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No elevator
  • Wheelchair-accessible parking

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

Access methods

Staffed front desk

Pets

Pets not allowed

Children and extra beds

Children are welcome
Children up to the age of 13 years can stay for free if using existing beds when occupying the parent or guardian's room
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 28.13 per accommodation, per night
The resort fee includes:
  • Beach access
  • Beach loungers
  • Beach towels
  • Concierge service
  • In-room coffee
  • Internet access
  • Laundry facilities
  • Partner property beach club access
  • Phone calls
  • Pool access
  • Self parking

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

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

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

8.8

Excellent

Rating 10 - Excellent. 607 out of 1067 reviews
Rating 8 - Good. 278 out of 1067 reviews
Rating 6 - Okay. 117 out of 1067 reviews
Rating 4 - Poor. 43 out of 1067 reviews
Rating 2 - Terrible. 22 out of 1067 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

8/10 Good

DPL

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place is not new. Staff is helpful and they have an outdoor bar with live music every nite. And food is available in the area and all over town. And lots of bars. Walk to Southernmost marker and Hemingway House. Near south end of Duval St. Long walk to seaport. Desk told us about public transport, great!! And they can book some activities if available. JET SKI around Key West!!!! Watch the weather. Lots of waves during Rapheal! We had a good 4 days.
Stayed 3 nights in Nov 2024

10/10 Excellent

Sally

Liked: Cleanliness, staff & service, property conditions & facilities
Nice location
Stayed 3 nights in Nov 2024

10/10 Excellent

LISA MARIE, Greensboro

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay
Stayed 4 nights in Oct 2024

8/10 Good

Stacy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great rate for Key West. Bar on property. We actually had the room attached to the bar. We sleep with a sound machine & didn't hear a thing. Pool had lots of leaves in the filter. Room was basic, but you don't need much more in Key West. Bed very comfortable.
Stayed 1 night in Oct 2024

6/10 Okay

Sherree, Lady lake

Traveled with group, Traveled with partner
Disliked: Amenities, property conditions & facilities
Was a confusing checkin. Only did room service every 3 days but that was not explained so used and hung towels, went and grabbed pool towels to use. Carried out own garbage to the dumpster and had a one use shampoo bottle to use for the two of use for 3 days.When you pay almost $300 a night and resort fee .... You do not even get room cleaned or towels. C'mon be better than this! We loved Key West and Carlos (employee) was amazing!!! Also gave me some shampoo/clean towels on day 4...
Stayed 3 nights in Nov 2024

10/10 Excellent

denise

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Easy to walk around and two pools were great!
Stayed 4 nights in Oct 2024

10/10 Excellent

Denise

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone and everything was fabulous.
Stayed 3 nights in Oct 2024

10/10 Excellent

Darren

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 5 nights in Oct 2024

2/10 Terrible

John

Traveled with partner
Disliked: Amenities, property conditions & facilities
My plans had changed and one month before the 10/24 reservation, I submitted a request for a cancellation with full refund to Expedia. You rejected the request. I emailed the manager Umberto, explaining that you could easily resell the room since it was a month before and this was Fantasy Fest. He refused. So if a I cancelled with no returned you could resell the room and get paid for it twice. This is just wrong. He still refused. The room did not look anything like the room in the ad. The tiles in the bathroom were moving and about to fall through. The pressure in the shower was very low.
Stayed 3 nights in Oct 2024

10/10 Excellent

Kerry

Liked: Cleanliness, staff & service, property conditions & facilities
Will definitely be back - a small jem right by Duval St and the Southernmost Point!!
Stayed 3 nights in Oct 2024

2/10 Terrible

Simon

Disliked: Cleanliness, staff & service, property conditions & facilities
NOTHING!! I WILL NOT STAY THERE AGAIN, DO NOT RECOMMEND IT FOR ANYONE ELSE!!
Stayed 2 nights in Oct 2024

10/10 Excellent

Rebecca Ruth

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything you could ask for right in one place. Motel amenities are superb. The staff are unbelievably friendly and kind. There is a liquor store and bar on site as well as a yummy donut shop. A market and small restaurant across the street make for extra convenience. Location is close to must see attractions.
Stayed 4 nights in Oct 2024

8/10 Good

Loretta

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice affordable Key West getaway.
A nice place to stay with a nice outdoor bar and ice cream and snack bar. The room was comfortable for two people however the bathroom is very small.
Stayed 11 nights in Oct 2024

10/10 Excellent

Jayne

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 3 nights in Oct 2024

8/10 Good

Jacqueline, Rockland

Traveled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
Berg loud bar on property. Unfortunately my room was right near the band and they played until 1:30 AM. My only complaint, but a deal breaker for me for future stay.
Stayed 3 nights in Oct 2024

8/10 Good

Victoria

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The location is good- near the southernmost point, walkable access to the main area on Duvall. The rooms are spacious and clean, property has 3 pools and parking. There’s a resort fee but you have that wherever you stay in key west! They also have complimentary breakfast items in the lobby. Would stay here again.
Stayed 3 nights in Oct 2024

6/10 Okay

Evert Randall

Stayed 3 nights in Oct 2024

10/10 Excellent

Cynthia

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Aug 2024

10/10 Excellent

Aimee

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Oct 2024

10/10 Excellent

dawn zargarling

Traveled with family
Liked: Cleanliness, amenities
Very small. Clean , friendly and close to everything.
Stayed 7 nights in Oct 2024

8/10 Good

Maureen

Traveled with group, Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place was exactly what we were looking for when it came to location and price. It is an older hotel and the furnishings show it but, it was the most comfortable bed I have ever had at a hotel.
Stayed 4 nights in Sep 2024

6/10 Okay

Iva

Traveled with partner
Liked: Cleanliness, staff & service
Friendly staff, great location. Rooms are a bit tired and dated but clean. Bed is comfortable. Washroom is very small so if you are a larger person it maybe too tight. It worked ok for us.
Stayed 2 nights in Oct 2024

10/10 Excellent

Kevin

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
A gem in the Keys!
The moment I stepped into the Southwinds Motel, it felt like it was going to be a great place to be in Key West. I was greeted by a nice gentleman called Carlos, he was so helpful and gave me some great tips! The room was not on the big side, but was clean & all we needed. On site free laundry, ice cream van & so close to all the places we wanted to see. To top things off the evening's we had at the Tipsey roster were relaxed with great music & a great choice served by the delightful Alice. Highly recommend & will be back ourselves in the near future 😎
Stayed 3 nights in Oct 2024

10/10 Excellent

Theodore

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Room was right next to the bar, the pool was clean and we were close to everything within scooter distance. Staff was very nice and friendly. Had a blast for the wife’s birthday, definitely worth the money and plan on coming back soon!
Stayed 3 nights in Oct 2024

8/10 Good

tammy

Traveled with partner
Liked: Cleanliness, staff & service
Stayed 1 night in Oct 2024