Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach

Choose dates to view prices

Where to?

Dates

July 2025

August 2025

2 outdoor pools, pool umbrellas, sun loungers

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

Standard Room, 1 King Bed

Very good

300 sq ft
Sleeps 3
1 King Bed

1 bedroom, premium bedding, down comforters, pillowtop beds

Deluxe Room

Exceptional

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

Standard Room, 2 Queen Beds

Excellent

400 sq ft
Sleeps 4
2 Queen Beds

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

Pool
Breakfast included
Pet friendly
Free WiFi

$138 nightly

Aug 3 - Aug 4

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 Jul 15, 2025, prices found for a 1-night stay for 2 adults at Southwinds Motel on Jul 16, 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 parking available on site 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.

Does Southwinds Motel have a hot tub?

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, you won't find 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

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

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

10/10 Excellent

Cynthia

Apr 16, 2025

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

We love this place. Will be back.

Stayed 1 night in Apr 2025

8/10 Good

james

Traveled with family

Apr 15, 2025

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

Great location Nice staff and breakfast

Stayed 5 nights in Apr 2025

10/10 Excellent

Debra

Traveled with group, Traveled with family

Apr 12, 2025

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

Great motel! Loved the location and the staff. Would stay here again.

Stayed 3 nights in Apr 2025

8/10 Good

Linda, Downers Grove

Traveled with group, Traveled with partner

Apr 12, 2025

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

The staff is excellent. Standard continental breakfast. While the property is older it was very clean and comfortable. The bathroom is a bit small. Loved the bar attached to the property with live music.

Stayed 3 nights in Apr 2025

10/10 Excellent

david

Apr 10, 2025

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

Nice area. Very convenient. Wi-Fi not reliable in room but strong signal outside. Wasn't a problem.

Stayed 1 night in Apr 2025

10/10 Excellent

Susan

Apr 9, 2025

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

Stayed 4 nights in Mar 2025

10/10 Excellent

Bruce T

Traveled with family

Apr 9, 2025

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

Great place to stay!

Very clean and very convenient to get to the beach and Duvall. Perfect location. We'll definitely stay again!

Stayed 3 nights in Apr 2025

10/10 Excellent

david

Apr 9, 2025

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

Been here before, very convenient.

Stayed 1 night in Apr 2025

6/10 Okay

sherry

Apr 4, 2025

Stayed 2 nights in Feb 2025

10/10 Excellent

Amy

Traveled with group

Apr 3, 2025

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

Our bathroom needed a little TLC….nothing major but still needs a little attention Room 36 It won’t keep us from staying again for sure!! Southwinds vibes are perfect in KW! The beds and pillows are amazing!! And ‘Z’ at the Tipsy Rooster is pretty cool and on her game!!!

Stayed 6 nights in Mar 2025

6/10 Okay

Dawn

Traveled with family

Apr 3, 2025

Liked: Staff & service

The breakfast was a treat. The pool was nice. Property is very walkable to attractions. Complimentary laundry did not work.

Stayed 1 night in Apr 2025

10/10 Excellent

Kelly

Traveled with family

Apr 1, 2025

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

Key West

Clean and wonderful location

Stayed 6 nights in Mar 2025

10/10 Excellent

stacey

Apr 1, 2025

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

Fun music next door

Stayed 1 night in Mar 2025

8/10 Good

Edwin

Mar 31, 2025

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

Stayed 4 nights in Mar 2025

10/10 Excellent

LAURYN

Traveled with family

Mar 30, 2025

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

Walk to beach and southern most point. The motel breakfast propided as perfect and plentiful. I will be going back.

Stayed 2 nights in Mar 2025

10/10 Excellent

Don

Traveled with partner

Mar 30, 2025

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

I would stay here again. The location was good - easy walking to things but also quiet. The pool was nice.

Stayed 2 nights in Mar 2025

4/10 Poor

Joy Smith

Traveled with family

Mar 30, 2025

Disliked: Cleanliness, amenities

Very basic property .smalls r very small not cleaned enough. Washrooms are tiny...no hot breakfast option. Not value for money considering it's a motel

Stayed 1 night in Mar 2025

8/10 Good

Lora

Traveled with group, Traveled with partner

Mar 28, 2025

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

Check in was easy. Staff very friendly. Bed comfortable. Only negative is the small bathroom.

Stayed 2 nights in Mar 2025

10/10 Excellent

JEFF

Traveled with group

Mar 28, 2025

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

We absolutely love this place! We had four couples with us and we all loved it. Very quaint, tropical, and convenient. A bar on one side and ice cream parlor on the other. Room was your basic motel but cute and clean. Will definitely be staying here again.

Stayed 1 night in Mar 2025

8/10 Good

Kimberly

Traveled with group, Traveled with family

Mar 25, 2025

Liked: Staff & service, amenities

Staff was great and very helpful. They will book excursions, take care of golf cart rentals and have bike rentals onsite. Roosters, the bar attached to the motel was perfect with music every night. The rooms are small, especially the bathroom but fine for a few nights. I'm not sure I could stay here long term, but again, perfect for a short stay.

Stayed 3 nights in Mar 2025

6/10 Okay

Ian

Mar 24, 2025

Liked: Cleanliness

Disliked: Property conditions & facilities

Overpriced old school motel, shabby but clean.

This would be a $150 a night place anywhere else. 3x as much in Key West. It's a typical old school motel. Showing its age a lot. It was clean and has a great location. The biggest annoyance was it has a functioning kitchen but not a single spec of any pots, silverware or anything at all. I had to forage in the breakfast room to find a few plates and plastic silverware.

Stayed 3 nights in Mar 2025

8/10 Good

Elke

Mar 23, 2025

Liked: Cleanliness, staff & service

Downtown sehr gut mit Shuttlebus erreichbar.

Stayed 1 night in Mar 2025

10/10 Excellent

Keri

Traveled with family and small children

Mar 23, 2025

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

Great location! Just a walk away from everything! Nice rooms, just a little dated. No utensils or dishes in kitchen. Otherwise great staff, very kind & helpful. Great continental breakfast. 2 pools, great for families! Free laundry on site!

Stayed 2 nights in Mar 2025