Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach

Choose dates to view prices

Where to?

Dates

August 2025

September 2025

Relax on the covered patio with Adirondack chairs amidst a beautifully maintained garden.

Enjoy cooking in this well-equipped kitchen with a coffee machine and TV.

Relax by the pool surrounded by lush vegetation and comfortable lounge chairs.

Stroll up the paved driveway to the front door of this two-story house, surrounded by lush vegetation and a covered porch area.

Stunning sculpture and gazebo in a serene outdoor setting, surrounded by lush greenery and tranquil atmosphere.

Overview
Rooms
Location
Policies

Excellent

Popular amenities

24/7 front desk
Bar
Laundry
Air conditioning

Explore the area

1321 Simonton Street, Key West, FL, 33040

Duval Street
‪3 min walk‬
South Beach
‪3 min walk‬
Southernmost Point
‪5 min walk‬
Key West, FL (EYW-Key West Intl.)
‪7 min drive‬

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Room options

Relax in this inviting room with a large bed, flat-screen TV, and a comfortable chair by the window.

Standard Room, 1 King Bed

Very good

300 sq ft
Sleeps 3
1 King Bed

Relax in a cozy retreat with a neatly made bed, framed artwork, and a convenient coffee station.

Deluxe Room

Exceptional

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

Two single beds with white bedding and red throw blankets, a desk with a microwave, and a television.

Standard Room, 2 Queen Beds

Excellent

400 sq ft
Sleeps 4
2 Queen Beds

Relax in a spacious room with a large bed, wardrobe, and convenient microwave.

Standard Room, 1 Queen Bed

Very good

250 sq ft
Sleeps 3
1 Queen Bed

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
Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
Mallory Square - 4 min drive - 1.3 miles

Getting around

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

Restaurants

‪El Siboney Restaurant - ‬8 min walk
‪Southernmost Beach Café - ‬3 min walk
‪Southernmost Point Bar In the USA - ‬5 min walk
‪Rum Bar at the Speakeasy Inn - ‬5 min walk
‪Banana Cafe - ‬4 min walk

About this property

Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach

Guests of Southwinds Motel enjoy access to 2 outdoor pools, coffee in a common area, and free newspapers. You'll find limited parking. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage. Additional amenities include laundry facilities, a vending machine, and a picnic area.

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.

Languages

English, Russian, Spanish

Similar properties

Relax on the covered porch with comfortable wicker chairs and lush greenery.

Pool
Breakfast included
Pet friendly
Free WiFi

$151 nightly

Aug 10 - Aug 11

Total includes taxes and fees

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
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

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

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

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

This property doesn't allow pets

Children and extra beds

Children 13 years old and younger stay free when using existing bedding
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 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

These are all of the 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

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 limited parking.

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 Aug 4, 2025, prices found for a 1-night stay for 2 adults at Southwinds Motel on Aug 11, 2025 start from $125.13, 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, there is accessible parking available.

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.

Is Southwinds Motel a good place to stay for couples?

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.

Does Southwinds Motel have connecting rooms?

No, this hotel doesn't feature connecting guestrooms.

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

8.8

Excellent

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

8.2/10

Eco-friendliness

4/10 Poor

Keith

Traveled with family

Aug 4, 2025

Disliked: Property conditions & facilities

We were asked when checking in if we used Orbitz, I said yes and she changed my room number. Room assignment was not what was shown on the website or in the photos.

Stayed 5 nights in Jul 2025

6/10 Okay

Deborah

Traveled with partner

Aug 1, 2025

Liked: Cleanliness

The staff was fine, not particularly friendly. Parking was not good. The second pool was out of order, so the one pool was crowded.

Stayed 1 night in Jul 2025

8/10 Good

Maximo

Traveled with family

Jun 17, 2025

Liked: Cleanliness, property conditions & facilities

Great location close to everything around old town key west

Stayed 4 nights in Jun 2025

8/10 Good

Russell

Traveled with partner

May 6, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Great location. Friendly staff and loved having the Tipsy Rooster there. Enjoyed the music very much.

Stayed 5 nights in Apr 2025

10/10 Excellent

MICHAEL

May 4, 2025

Liked: Cleanliness, staff & service, property conditions & facilities

Stayed 3 nights in May 2025

10/10 Excellent

Sara Irma

Traveled with partner

May 4, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

From the moment we checked in, meeting the front desk staff, they were friendly, gave us information to make our stay comfortable and worry free. Our room was towards the back, quiet, clean and parking right in front. We loved that parking is free. Another plus, besides a big coffee pot in the room, in the morning, grab and go continental breakfast in the lobby was very nice and convenient. Definitely would stay here again and I would recommend to other travelers.

Stayed 2 nights in Apr 2025

10/10 Excellent

Justin

May 2, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Place was awesome.

Stayed 1 night in Apr 2025

10/10 Excellent

Marilyn

Apr 30, 2025

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

Good except the bathroom light was a little bright

Stayed 2 nights in Apr 2025

10/10 Excellent

Sarah

Apr 30, 2025

Liked: Cleanliness

Stayed 3 nights in Apr 2025

10/10 Excellent

Peter

Traveled with partner

Apr 27, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

A hop and a skip to the Tipsy Rooster

Stayed 2 nights in Apr 2025

10/10 Excellent

laura

Apr 27, 2025

Liked: Cleanliness, staff & service, property conditions & facilities

Stayed 2 nights in Apr 2025

8/10 Good

Pamela

Traveled with family

Apr 27, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

I liked the "old Florida" feel of Southwinds. The staff was friendly and helpful. I loved having the option of the pools or the beach (with beach chairs and towels). It was a great location-close to cafes, the Tipsy Rooster (with daily live music) and the free Duval Loop Bus stop. While the bed was very comfortable, the other furniture in the room (dresser, table, chairs) was dated. Would definitely come back!

Stayed 6 nights in Apr 2025

10/10 Excellent

Barbara

Traveled with partner

Apr 26, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

It was close to everything and quiet, nice outdoor seating areas, parked our car in a safe area and walked everywhere in town

Stayed 2 nights in Apr 2025

6/10 Okay

Rognvald

Traveled with family

Apr 25, 2025

Liked: Cleanliness, property conditions & facilities

Disliked: Staff & service

Perfect location. Good value & clean. Most staff very good, but Karen on the Front Desk was rude & unprofessional when I was trying to address the return of my security deposit.

Stayed 2 nights in Feb 2025

8/10 Good

Tarabeth

Traveled with partner

Apr 24, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

The room was a bit small, but it suited our needs for the long weekend trip to Key West.

Stayed 3 nights in Apr 2025

10/10 Excellent

Annmarie

Traveled with group, Traveled with family

Apr 20, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Such nice staff! Great area! Everything you need is a short walk away. Includes access to a beach with chairs and towels too!

Stayed 1 night in Apr 2025

10/10 Excellent

Annmarie

Traveled with group, Traveled with family

Apr 20, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

The staff was incredibly kind and helpful! Especially with my handicap mother. Shout out to Nico and Quiana! They were wonderful! This was the least expensive motel I could find for our large group and I was nervous about the quality. While some of the rooms are very small, ours was large and comfortable. I had no reason to worry! They have 2 nice pools, clean rooms and coffee ready in the morning. It's a very walkable area. They also have parking for cars or golf carts. Close to so many things! I was very happy with everything!

Stayed 4 nights in Apr 2025

10/10 Excellent

Mary

Apr 19, 2025

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

Stayed 2 nights in Apr 2025

4/10 Poor

Brian

Traveled with family

Apr 19, 2025

Disliked: Cleanliness, amenities, property conditions & facilities

At the driveway, the trees/shrubs knocked off our sideview mirror. That will be $1,700 repair cost on top of the cost of motel - damage caused by this property. Of course the next day, the bushes/tree had been cut down !! No offer by property to help our repair costs !

Stayed 3 nights in Apr 2025

4/10 Poor

Sean

Apr 18, 2025

Disliked: Staff & service, amenities, property conditions & facilities

Small, dirty little place. But, the kicker is that they use real keys that aren’t stamped with room number all that well. This was a problem because the guy at front desk gave us 2 keys to our “room” but one was the wrong room. After it wouldn’t open the one that was actually our room, we went to what the key said (thinking the front desk guy messed up) and yup, key worked…..let my wife open up a room with another couple having sex. The guy at the front desk just said “oh sorry” and gave us a better key. So no, we didn’t feel safe in these rooms as who knows who may just walk in.

Stayed 1 night in Apr 2025

10/10 Excellent

Cynthia

Apr 17, 2025

Liked: Cleanliness, staff & service, property conditions & facilities

Excellent.

8/10 Good

Julie

Traveled with group, Traveled with partner

Apr 16, 2025

Liked: Cleanliness, staff & service, property conditions & facilities

If you don't expect too much, you won't be too let down. It's an older property, my room was very small but it had a coffee maker, mini fridge, free parking, free breakfast. The area around it is great. Personally I would try to find a higher star hotel to stay at next time, but if none were available, I'd stay here again in a pinch.

Stayed 2 nights in Apr 2025