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Southwinds Motel

2.0 star property
Hotel with 2 outdoor pools, steps from South Beach

Choose dates to view prices

Photo gallery for Southwinds Motel

Bar (on property)
Front of property
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated
Property grounds
Reception

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Bar

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.)
    ‪7 min drive‬

Room options

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(100 reviews)
  • 250 sq ft
  • Sleeps 3
  • 1 Queen 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

8.8 out of 10
Excellent
(73 reviews)
  • 400 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Deluxe Room

Premium bedding, down comforters, pillowtop beds, individually decorated

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, individually decorated

Standard Room, 1 King Bed

8.4 out of 10
Very good
(107 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

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About the neighborhood

Key West

Located in Old Town Key West, Southwinds Motel is adjacent to South Beach and within a 5-minute walk of other popular sights like Duval Street. This 58-room hotel welcomes guests with 2 outdoor pools, free breakfast, and a bar/lounge.

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

  • ‪Seaside Cafe at the Mansion - ‬3 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Circle K - ‬6 min walk
  • ‪Southernmost Point Bar in the USA - ‬5 min walk
  • ‪Banana Cafe - ‬4 min walk

About this property

Southwinds Motel

Hotel with 2 outdoor pools, steps from South Beach
Guests of Southwinds Motel enjoy access to 2 outdoor pools, coffee in a common area, and free newspapers. Self parking is offered for USD 22.50 per day. The 24-hour front desk has multilingual staff ready to assist with concierge services and luggage storage. Additional amenities include laundry facilities, a picnic area, and a vending machine.
Guests can expect to find 32-inch LED TVs with cable channels. Bathrooms offer hair dryers and free toiletries, and pillowtop beds with premium bedding and down comforters ensure a restful night. Other standard amenities include refrigerators, microwaves, and coffee makers. Housekeeping is available on request.
2 outdoor swimming pools are on site.

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

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Property grounds
The Palms Hotel
  • Pool
  • Breakfast included
  • Pet friendly
  • Free WiFi
8.8 out of 10, Excellent, 1,019 reviews
$404 nightly
The price is $454
Feb 4 - Feb 5
Total with taxes and fees
The Palms Hotel

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
  • Bicycle rentals

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

  • This property doesn't allow pets

Children and extra beds

  • Free cribs/infant beds are available

Property payment types

Important information

Fees

You'll be asked to pay these charges at the property:

  • 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

These are all of the charges provided to us by the property.

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

  • Self parking fee: USD 22.50 per day

This list may not be comprehensive. Fees and deposits might 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
  • Check-in: 4:00 PM—-midnight
  • Check-out: 11 AM
  • Minimum check-in age: 18
The front desk is open 24 hours a day. Driving? This property offers parking (fees apply).

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A credit card for incidental charges and 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.
  • The minimum check-in age for Spring Break is 18 years old.
  • This property accepts credit cards, debit cards, and cash.
  • The credit card used at check-in for incidentals must be in the name of the primary guest who made the reservation.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Additional information about polices, regulations, and more:

  • Registered guests are the only ones allowed in guestrooms.
  • No alcohol is served at Southwinds Motel.
  • There are no elevators.
  • No rollaway or extra beds are available.

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

Frequently asked questions

Is a free cancellation option available at Southwinds Motel?

Southwinds Motel offers free cancellation on some room rates. For specific requirements, look at the cancellation policy on Orbitz.

How much does it cost to stay at Southwinds Motel?

As of Jan 28, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Feb 2, 2026 start from $344.49, excluding 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.

What's there to do around Southwinds Motel?

This hotel is situated in Old Town Key West, just steps from Duval Street and Florida Keys Beaches, and within a short walk of South Beach. You'll also find Southernmost Point and Ernest Hemingway Home and Museum less than a mile away.

Is there parking available at Southwinds Motel?

Yes, parking is offered for USD 22.50 per day.

Does Southwinds Motel have a casino at the property?

No, Southwinds Motel doesn't have a casino.

Will I find an indoor pool at Southwinds Motel?

No, this hotel doesn't have an indoor pool; however, there are 2 outdoor pools.

What amenities will couples enjoy at Southwinds Motel?

There are plenty of amenities for couples at this hotel, including 2 outdoor pools, a bar, and proposal/romance packages.

Are there hot tubs at Southwinds Motel?

No, this hotel doesn't have a spa tub.

Does Southwinds Motel feature a restaurant that includes a breakfast menu?

Yes, Southwinds Motel serves free continental breakfast at Tipsy Rooster each morning.

Will Southwinds Motel allow pets to stay free of charge?

No, pets aren't allowed at Southwinds Motel.

Are there connecting rooms at Southwinds Motel?

No, there aren't connecting guestrooms at this hotel.

How close is the airport from Southwinds Motel?

The closest major airport to Southwinds Motel is Key West Intl. Airport (EYW), which is 3.2 mi away (8 minutes by car).

Are there rooms with balconies that I can book at Southwinds Motel?

No, there aren't any guestrooms with balconies at Southwinds Motel.

Southwinds Motel Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 736 out of 1279 reviews
Rating 8 - Good. 334 out of 1279 reviews
Rating 6 - Okay. 136 out of 1279 reviews
Rating 4 - Poor. 52 out of 1279 reviews
Rating 2 - Terrible. 21 out of 1279 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

Reviews

10/10 Excellent

Gaston

Liked: Cleanliness, amenities, property conditions & facilities
Great location and well maintained. Breakfast does the job.
Stayed 1 night in Dec 2025

10/10 Excellent

Lisa

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Our stay at Southwinds hotel was wonderful. The staff always treats as courtesy since we booked through orbits we were allowed to pick our room once we arrive there great place to stay great pick up and go breakfast in the morning and close to several fun activities.
Stayed 7 nights in Dec 2025

10/10 Excellent

Michael

Liked: Cleanliness, amenities, property conditions & facilities
grerat room at a great price
Stayed 1 night in Oct 2025

10/10 Excellent

Cristy

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A true hidden gem in Old Town - very clean, comfortable rooms, staff was wonderful!
Stayed 5 nights in Oct 2025

8/10 Good

Crystal

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
We loved our stay here. The room was clean, the staff very friendly and helpful. We loved the bar out front and the live music. And the close proximity to the beach. The pool was nice. Great location to everything we walked alot and also took an uber. Would have liked another luggage stand or somewhere for our clothes but, we knew coming that the room didn't come with dressers or a closet. We will definitely come stay here again.
Stayed 6 nights in Oct 2025

10/10 Excellent

Raquel

Traveled with partner
Liked: Staff & service, amenities, property conditions & facilities
I loved that you could get a daily pass to the beach for towels and chairs, they had laundry(free of charge) onsite that included the soap.
Stayed 6 nights in Oct 2025

10/10 Excellent

Liena

Liked: Cleanliness, staff & service, property conditions & facilities
It was a good stance, we reserved 3 rooms and were clean (as clean as possible)and the staff hepful. We recomend this motel if you plan a gateway based in to know the town since is not the updated place, however it was a nice sorprais, we would stay there again if come back to key kest.!!
Stayed 1 night in Oct 2025

10/10 Excellent

Catherine

Traveled with family
Liked: Cleanliness, staff & service, amenities
Location, location, location! The place looked questionable from the outside, but the service was great and the room was great!
Stayed 2 nights in May 2025

6/10 Okay

Barry

Liked: Cleanliness
Disliked: Staff & service
Tiny rooms. Tiny TV. The bathroom is so small you can’t even close the door while sitting on the toilet. The breakfast was just a counter with some packaged muffins, yogurt packs, packaged eggs.
Stayed 3 nights in Oct 2025

8/10 Good

Bonnie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
There was an issue with the location and facilities of the room but they were resolved with no extra effort
Stayed 4 nights in Oct 2025

8/10 Good

Nancy, Winfield

Traveled with partner
Good location and comfortable enough for the price. We did not realize there is a $25 daily resort fee so be aware. Not sure what for as bike rentals are extra. Guess maybe just for use of the pools?
Stayed 6 nights in Oct 2025

10/10 Excellent

David

Traveled with partner
We loved the island vibe of this older establishment. Everyone on the staff was pleasant, helpful, and great! On the Duval bus loop, but the entire area is an easy walk away. We had the pool to ourselves over half the time. Thank you!
Stayed 6 nights in Oct 2025

10/10 Excellent

Susan

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband and I stayed 2 nights on the property. Room was large and clean. The bathroom was small but clean. Pool was great after walking around all day. Parking was a little tight but we were so close to Duval St., we never used our car while on the island. We did rent scooters for the day which I would highly recommend to explore more of the island. Hotel does rent bikes and scooters as well.
Stayed 2 nights in Oct 2025

8/10 Good

Joanna

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 4 nights in Oct 2025

10/10 Excellent

Renee

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was great! Friendly, helpful and doing what they could to make our stay even better.
Stayed 4 nights in Oct 2025

8/10 Good

ROBIN

Liked: Cleanliness, staff & service, property conditions & facilities
Property was safe no issues. Room was clean and comfortable.
Stayed 3 nights in Oct 2025

8/10 Good

Don

Stayed 7 nights in Oct 2025

10/10 Excellent

Perry

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Location. Location. Location!

Perfect location for everything in Key West.
Stayed 2 nights in Oct 2025

10/10 Excellent

Kathy

Traveled with partner
Liked: Amenities
Very safe
Stayed 3 nights in Oct 2025

8/10 Good

Marlene

Liked: Cleanliness, staff & service, room comfort
Pool area was ok, nothing special
Stayed 4 nights in Oct 2025

10/10 Excellent

Nicole

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great place!! Centrally located to be able to walk all over and check out the Duval Street area. Suited our needs perfectly.
Stayed 3 nights in Oct 2025

8/10 Good

Eileen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Bathroom was extremely small, a little outdated. But was clean and quiet! Staff was friendly!
Stayed 2 nights in Oct 2025

10/10 Excellent

Jennie

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great little motel, staff is great & clean rooms. The bar next door is so convenient
Stayed 6 nights in Oct 2025

8/10 Good

SUSAN, Pella

Traveled with family
Disliked: Property conditions & facilities
Pool area was very small and dated.
Stayed 1 night in Oct 2025

10/10 Excellent

Terry

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
We had an amazing 5 night stay. Tipsy Rooster bar is awesome as well.
Stayed 5 nights in Oct 2025

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