Westwing

10/10

Exceptional

28 Apr 2026

Victoria

Beautiful property. Loved looking at all the different plants. Close to a bus line that runs through key west for easy access to all areas of the island, even other areas of the lower keys. We ended up getting there later than the office was open (closes at 7), but I called ahead of time and they had no problem making arrangements for an after-hours check-in.

Partner

10/10

Exceptional

22 Apr 2026

Tracy

Loved everything about this place!! Very convenient to Duvall St. Free breakfast was served daily. The staff were so friendly and helpful. The bed was comfortable. The grounds were beautiful!

Partner

10/10

Exceptional

21 Apr 2026

Jeremiah

My family and I only stayed for one night but the experience was incredible. The. Check-in process was easy and staff let us keep our luggage at the property before our room was ready. Our room was clean and spacious. The property is well maintained and offerers two pools, a water filling station, and continental breakfast. Even though the resort is in the middle of the busy downtown area, it felt like you were on your own island when sitting by the pool. I highly recommend Westwinds and I look forward to our next stay.

Family_with_children

8/10

Excellent

19 Apr 2026

Peter

Quant little bungalow in great location - heated pool and outside breakfast were very welcoming.

Partner

8/10

Excellent

19 Apr 2026

Mark

Nice place to stay, with a great location. It's clean and simple. The breakfast isn't much to speak of and the pools are ok (although one is heated, which was nice for an early morning swim).

Friends

10/10

Exceptional

18 Apr 2026

Paul

Great place to stay! Walking distance to Duval Street. Bike rental one block away. Great fish cafe one block away. Rent a golf cart! You don't need a car. Very good continental breakfast here. Staff is very friendly and accommodating. Five Stars!

Partner

10/10

Exceptional

15 Apr 2026

Cynthia

great place so cute and cozy very clean great staff thank you

10/10

Exceptional

15 Apr 2026

michael

Great place

10/10

Exceptional

14 Apr 2026

Peter

Beautiful Property !

Partner

10/10

Exceptional

13 Apr 2026

Charles

Fantastic location! Loved that they have a heated pool. Would stay there again.

Friends

10/10

Exceptional

12 Apr 2026

John

Everything was perfect! We will be back.

10/10

Exceptional

10 Apr 2026

Teresa

Breakfast was great! Pool conditions could have been better.

Friends_and_family Family

10/10

Exceptional

05 Apr 2026

Maria Rowena

Truly relaxing place to stay. We enjoyed the heated pool.

Partner

4/10

Poor

02 Apr 2026

David

For a hotel that costs $450 a night the bed sucks. Very soft like a hammock. Parking is awful. Took an hour to find a place to park on the street. Our rental car had bumper damage. The pool was dirty with leaves. Not enjoyable place to stay.

Partner

8/10

Excellent

01 Apr 2026

Louisa B.

The Breakfast menu was very dissapointing. Not much to offer and all processed food.

the Pool area was nice

Partner

10/10

Exceptional

31 Mar 2026

Katt

We arrived late so we didn’t interact with the staff , but the are room was lit up so we could find it .the room was very clean would stay again and recommend

10/10

Exceptional

30 Mar 2026

April

Everything was great, the shower floor I RM 103 seemed broken

Partner

4/10

Poor

28 Mar 2026

Michael

Said the front desk was open till 7. Arrived and 20 till and no one was there. Put my key in the late arrival box and the key didn’t work. Couldn’t go to the front desk because they were gone already. Had to call the emergency number to get someone to get a correct key. Had to wait 35 minutes for the key man to arrive. Was late for a reception because of this. When I explained what happened to the front desk the next morning the response from the gentleman at the front desk was “ it happens”. Great customer service. Besides that everything was fine

Family

10/10

Exceptional

28 Mar 2026

Jason

Wonderful Westwinds… rooms are kept spotlessly clean, outdoor space is well looked after and staff are great.

Partner

10/10

Exceptional

26 Mar 2026

Bryan

Room was clean and the staff was very friendly. Garden area and pool were peaceful. Would definitely stay here again.

Family_with_children

10/10

Exceptional

25 Mar 2026

Donna

Not applicable

Partner

10/10

Exceptional

25 Mar 2026

Nicholas

This property is beautiful and well maintained. Our room was very clean and with the exception of not having a dresser or any storage for our clothes (we were forced to live out of our suitcases for the week) the room was perfect for our stay. There is a small closet with a couple hangers. The staff was extremely friendly and helpful. We did not use the laundry facilities but the room looked clean. There is an ice machine and filtered water dispenser in the pool area. The daily breakfast offered was a nice touch and the coffee that was served was 10/10. We would definitely return.

Partner

10/10

Exceptional

25 Mar 2026

Ernest

Perfect location!

Partner

10/10

Exceptional

24 Mar 2026

Bill

Great stay, we will be back!

Partner

6/10

Pleasant

24 Mar 2026

Robert

Tiny room. Bifold door on bathroom never shut completely. Room entry door knob was almost impossible to turn.

Friends_and_family Friends

10/10

Exceptional

23 Mar 2026

Ginger

Great place to stay. Good breakfast and comfortable beds. The main pool area is beautifully landscaped and a lovely place to relax. The only issue we had was it was pretty chilly a couple of nights and they don’t have heat. The blankets are very thin and more like sheets. We had a cold night bundled up in everything warm we packed. We did get extra blankets the next night but make sure you plan ahead if it looks like it will be cold.

Partner

8/10

Excellent

23 Mar 2026

Daniel

Great location. Very clean. Interesting lay out. 2 pools.

Friends_and_family Friends

10/10

Exceptional

20 Mar 2026

Tracy

Such a lovely site. Beautiful pool area and the perfect location for exploring Key West. Very short walk to great restaurants on the water.

Partner

8/10

Excellent

20 Mar 2026

Genevieve

Great location, beautiful gardens and pool. To consider for improvement: Laundry room was not working (dryer OOS) and there was no laundry soap available, our room was in the front of the building and there was a bright light shining in our window even with the shutters closed making it difficult to sleep, there was an air conditioner in the window didn't have central air.

Partner

10/10

Exceptional

19 Mar 2026

james

Pool areas were nice.....breakfast bar was perfect

Partner

8/10

Excellent

18 Mar 2026

Brian

Great spot to explore from. Walking distance to all the local favorites. Bike rental next door. Nice space to spread out in too.

Partner

8/10

Excellent

17 Mar 2026

Timothy

Nice place, good location. Everything was walkable. But far enough away from Duval to Venice and quiet at night.

Friends_and_family Family

10/10

Exceptional

15 Mar 2026

Krista

Great stay! Our third time here!

Partner

10/10

Exceptional

13 Mar 2026

Michelle

What a wonderful place. We stayed with a group of friends and really enjoyed this property a lot. Great location central to everything. The room and property were very clean, the bed was comfortable, pool was relaxing and the atmosphere was just enjoyable overall.Typical continental breakfast by the pool (included) but there is a really good coffee shop in walking distance if you want more. Ice machine and water filling station by the pool in an added bonus.

Friendly staff are willing to accommodate you in any way they can, whether you need extra towels, another blanket or need to store your bags while you wait for your room to be ready if your flight gets in early before check-in time. Just ask!

Only complaints are that the water pressure is not ideal in the shower and the internet is subpar but I think that is typical for the area.

We will definitely be staying here again.

Friends

8/10

Excellent

11 Mar 2026

Denisse

Lovely garden location walking distance to all sites. Two lovely pools and a nice complimentary light breakfast overlooking one of them. Good coffee! Our room 503 was tiny but fine for an overnight stay. Good shower. Staff was courteous. Appreciate that they don’t charge a resort fee, and that they have a drink vending machine near the pool for water. We paid $12 to park nearby. There is a bike shop on the corner but we didn’t use it.

Friends

10/10

Exceptional

11 Mar 2026

Dyane

Great area, within walking distance to everything we wanted to do. Very comfortable room but shower was old and door didn’t close properly but that is my only complaint. Would definitely stay there again.

Family

8/10

Excellent

09 Mar 2026

Elena

Great location. Walking distance to almost everything; did not need a car. Room was clean. Pool was a special treat.

Partner

10/10

Exceptional

07 Mar 2026

Vickie

Westwinds exceded my expectations. They were a more affordable choice for my trip so I had my expectations set low. One heated pool, one unheated, continental breakfast, great bed, everything outside tucked away amidst beautiful landscaping (blooming ordchids growing on the trees). The back area was totally private from the adjoining properties. Perfectly location, close enough to walk to shopping and dining but ifar enough away that the area is very quiet (Duval St doesn't shut down til 4 am). I will stay at Westwinds again.

Partner

10/10

Exceptional

05 Mar 2026

Carmen

Beautiful property and friendly staff. Was very peaceful.

Partner

2/10

Poor

05 Mar 2026

Tyler

Front office staff was atrocious! Called several times to confirm stay with no answer. Upon arriving to the hotel staff was no where to be found for 45+ minutes at peak check in time— came back with Wendy’s. Was not helpful or informative. At check out he was on the phone watching videos, hard to get his attention. Breakfast staff was friendly and helpful. Beautiful place with proper receptionist.

10/10

Exceptional

04 Mar 2026

Amy

We loved our stay at Westwinds. It was very close to the restaurants and shopping. The pools and outside areas were beautiful. We will be coming back.

Partner

10/10

Exceptional

03 Mar 2026

Stephen

The site is compact but still provides 2 pools and quality accomodation. The rooms were clean, spacious, well maintained and bright. Continental breakfast was included with the usual cereals, pastries, toast, etc. The hotel is very central to the attractions and amenities. Offsite parking just 5 minute walk and reasonably priced. The staff were very helpful and available. We would definitely return here if we had the opportunity.

Partner

10/10

Exceptional

25 Feb 2026

sarah

Very clean and staff was friendly! Will definitely stay here again!

Partner

10/10

Exceptional

24 Feb 2026

Christian

. Breakfast was a welcome addition beside the tropical pool. Housekeeping was quick. Water pressure was spotty. Good location.

Partner

8/10

Excellent

21 Feb 2026

Larry

Room was a little cramped. No chair.
Check-in was poor. Person at desk could not even tell me that there was a parking garage one block away.
Breakfast great
Pools were nice but obviously too cool to swim in
Location was great

Family

10/10

Exceptional

21 Feb 2026

Kimberly

Everything was great.Staff very friendly. Nice breakfast by the pool.

8/10

Excellent

15 Feb 2026

Steve

yes

10/10

Exceptional

14 Feb 2026

Ben

Perfectly located within walking distance from the Key West Express port and it looks like it was totally renovated by an HGTV expert within the last year or two.

Leisure Family

10/10

Exceptional

13 Feb 2026

Richard

Great location, the two pools and outdoor area really good.
Room was very comfortable and clean.
Great value (for the area)

10/10

Exceptional

12 Feb 2026

Charlotte

Great Location - juan was wonderful - property was so nice - continental breakfast was good.

Leisure Friends

10/10

Exceptional

12 Feb 2026

Cynthia

We were there 8 days and stayed in a suite. Included a refrigerator and microwave. The additional room/porch was amazing. All windows with a couch, chair, tv, coffe machine and dinnerware. Worked great for us. The cleaning and breakfast staff were wonderful. Enjoyed everything about the place.

Leisure Partner

8/10

Excellent

04 Feb 2026

Kristen

Outdoor and pool area were magnificent!

Partner

8/10

Excellent

03 Feb 2026

Brad

The staff was great and the hotel is in a great location. Breakfast is an added bonus.

Partner

8/10

Excellent

02 Feb 2026

David R

Hotel staff was great. The location was good for walking to nearby things to do. Breakfast area needs to be better equipped for rainy days. Overall, I was happy and stay again.

Leisure Friends

8/10

Excellent

31 Jan 2026

Troy

Great staff, with a quiet quaint vibe. I’d recommend staying here.

Partner

10/10

Exceptional

28 Jan 2026

Anthony

As always, everything was great.

Leisure Partner

10/10

Exceptional

27 Jan 2026

francis

From the moment we arrived, twe were impressed by the staff, settings and accommodations. Allowed early check in and permitted us to leave our luggage after checking out while we continued to enjoy Key West. Will definitely return!

Partner

10/10

Exceptional

26 Jan 2026

Jeanette

The staff were beyond kind, the rooms were cleaned so well and the grounds were beautiful! Easy check in and check out! Would absolutely stay here again!

Partner

8/10

Excellent

25 Jan 2026

Kim

Clean room but musty smelling. Was a bit cold and tried to use the heat but didn’t work. Employees were very friendly and helpful.

Leisure Family

8/10

Excellent

24 Jan 2026

Charles M Brainerd

Beautiful property, very well kept, great location, quiet area, three blocks to Duval St and two blocks to Harbor Walk.

Leisure Friends

10/10

Exceptional

23 Jan 2026

Compton

Great place to stay. Walking distance to Duval St.

Leisure Partner

10/10

Exceptional

22 Jan 2026

Rosalie

Cleanliness, staff, great breakfast in a beautiful setting. Parking actually worked out! We loved the Bakery so much for lunch. Thanks

6/10

Pleasant

21 Jan 2026

Deborah

Breakfast should be earlier than 8am. Perfect location. Walkable. Enjoy the heated pool in January. Room 702 very small. Fridge and microwave are a plus. Need new shower head. Had to ask for extra blanket. Beds comfortable.

Friends_and_family Friends

8/10

Excellent

20 Jan 2026

Hope

Our original room was smaller than we thought it would be and we developed an issue with the shower. But, we told the front desk and they were able to upgrade us to a very nice suite. We will stay again. We just have one suggestion. Put area runners in the sides of the bed so you can make sure your feet are wiped off before climbing into bed.

Leisure Partner

10/10

Exceptional

19 Jan 2026

Lisa

Everyone and everything was excellent!

Leisure Friends

10/10

Exceptional

18 Jan 2026

Frances

This was a great location, staff is very friendly and helpful. Rooms are nice and pools areas are lovely.

Leisure Partner

8/10

Excellent

12 Jan 2026

Jean

Location

Leisure Partner

10/10

Exceptional

12 Jan 2026

Tim

It was great and great location! We will be back!

Partner

2/10

Poor

10 Jan 2026

heqing

The milk provided at breakfast was clearly spoiled — it tasted sour.

We reported this issue to the breakfast staff. At first, she appeared indifferent. We explained that the milk had gone bad and even asked her to taste it herself. We poured her a cup, but she only glanced at it and told us that it was “regular.”

To the best of my knowledge, sour milk indicates that it has spoiled. This was disappointing, especially given basic food safety expectations.

6/10

Pleasant

09 Jan 2026

Lucia

The breakfast is quite lacking, all dishes and cutlery are cardboard or compostable. Upon arrival you have to sign the acceptance of paying for loosing keys, for damaging property, etc. i mean, it is not an economical hotel. This is not at all welcoming.
Bikes were offered for the guests to use, we stayed 3 nights and never saw them, the receptionist said he could not help with that.
I have to say we were kindly allowed to check out an hour later. But it was another receptionist, who was more accomodating.

Leisure Partner

8/10

Excellent

07 Jan 2026

Eileen

Overall great, clean & close to everything, i walked everywhere! Breakfast was served promptly . Turndown service was everyday .

Front desk could be a little bit more personable. Impatient tone . Just handed me a paper map and didn’t even bother to walk me out to show the way . He just sat and kept shaking his head or shrugging his shoulders. I was the only customer checking in.

One of the pools had some mildew , no one was swimming in it !

Could offer more variety at breakfast , it was mainly processed food . Coffee can be improved.

I stayed a week and only given 1 set of toiletries , wish they replenished as they did with towels .

For the location, i would recommend it .
For what i paid i think it’s peak season rate , it is way more than what i would usually pay for a room with no beach access or view .

Self

10/10

Exceptional

02 Jan 2026

Brian

Great location, friendly staff, & a heated pool!

Friends_and_family Friends

4/10

Poor

02 Jan 2026

Cathy

No hot water

Leisure

8/10

Excellent

29 Dec 2025

Tomasz

Excellent staff

Leisure Family

8/10

Excellent

29 Dec 2025

James

The grounds were beautiful. Room was clean and looked renovated. Coffee maker and big fridge was an unexpected addition. Filtered water machine available which was great. Recommend this place!

Partner

8/10

Excellent

29 Dec 2025

Varsha

Good boitique hotel

Leisure Family

10/10

Exceptional

29 Dec 2025

Monica

Very nice room! Juan was super helpful at reception. A great experience overall. I recommend it

10/10

Exceptional

27 Dec 2025

Nadia

The pictures don’t do this property justice, beautiful grounds and it actually bigger it looks. Would definitely stay here again.

Family

10/10

Exceptional

26 Dec 2025

Scott

Beautiful and quiet amenities right in the heart of the Duval Street experience. The facility is in traditional Key West, with very tastefully, updated rooms that can’t be beat. There are also two swimming pools nestled in amongst the rooms and cobblestone pathways with lush vegetation and palm trees everywhere. The staff is top shelf. A definite must stay & experience.

Leisure Partner

10/10

Exceptional

22 Dec 2025

Cindy

Enjoyed our stay.

Leisure Partner

10/10

Exceptional

19 Dec 2025

Joe

We always feel welcomed to a cool retreat after walking. We love the peaceful backyard areas, and the warm hospitality shown by the staff.

Leisure Partner

10/10

Exceptional

14 Dec 2025

Allyson

We enjoyed our stay from check in to check out. The two gentlemen on site were welcoming and enjoyable to work with. The rooms were clean with sufficient amenities and room from the minimal amount of time spend inside. The weather was perfect. I was surprised, I did not hear any noise from surrounding guest cottages or traffic. Very quiet and peaceful. We will stay again in the future.

Leisure Partner

10/10

Exceptional

14 Dec 2025

Thomas

no ocean view

2/10

Poor

13 Dec 2025

Dianna

They weren’t still open at 7 and merely emailed me (though someone from there had called earlier yesterday) to tell me how to check in after hours - though I wasn’t there after hours, and then lied about still being open at 7, despite me calling from outside the locked and dark office before 7. I’m very disappointed in the customer service here.

10/10

Exceptional

09 Dec 2025

Tammy

Great location and loved the heated pool!

Leisure Partner

10/10

Exceptional

05 Dec 2025

jeanne

Room was clean and comfortable, great location, breakfast was perfect, heated pools nice on the cool windy day we had.

10/10

Exceptional

04 Dec 2025

jason

Great pool area. Great quick continental breakfast. Easy after hours check in. Reasonable price. Will return for sure.

Leisure Family

8/10

Excellent

28 Nov 2025

Richard

very convienent to the harbor/port where the ferry comes in. beautiful setting, very private, very clean. breakfast is cold, and minimal. staff very helpful. we had a small room (403), with a very nice bathroom and shower. however, there was no chair, no suitcase stand, no desk/counter space at all.

Partner

8/10

Excellent

28 Nov 2025

miseok

I like cleanness. But, very noise heard from upstairs.

Leisure Family

10/10

Exceptional

28 Nov 2025

Allison

We loved Westwind Inn! We have been to Key West several times, but this was our first time staying at Westwind. I loved the feel of the small cottages. The grounds were immaculate and the pools were lagoon style with all of the beautiful and rich greenery. The office staff was extremely kind and helpful. The only negative would be no on site parking. However, they did accommodate our golf cart rental parking on site. I would definitely recommend Westwind for lodging if you are staying in Key West! It’s cleanliness, uniqueness, and location are all exceptional!

Business

10/10

Exceptional

25 Nov 2025

Jeff

Great location and relaxing atmosphere

Leisure Partner

10/10

Exceptional

25 Nov 2025

Jeff

The room, the staff was excellent