Name: Winslow's Bungalows - Key West Historic Inns
Address: 725 Truman Avenue, Old Town Key West, Key West, Florida, United States of America, Key West, Monroe County, US
Price range: $158–$694 per night
Rating: 8.8

What guests think

At Winslow's Bungalows - Key West Historic Inns, travelers praise the lush, resort‑like grounds, multiple small pools with a bar, and a walkable, quiet‑yet‑central location, while service is frequently described as warm, responsive, and accommodating.

Guests highlight the generous continental breakfast with fresh items like juices and wellness shots, plus occasional live music. Room experiences vary: some are spacious and charming, while others feel small or dark, with noisy or uneven AC, musty odors, thin walls, or soft flooring. Pool seating and towels can run short, and street‑facing rooms may hear traffic; a few reviews note housekeeping inconsistencies and surprise parking fees. Expect a tropical, boutique stay with character and some quirks.

Facilities

Cleanliness

Rooms

Service

Location

Dining

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AI-generated summary based on recent guest reviews

Facilities

Lush grounds with several small pools, a pool bar, shaded seating and occasional live music create a relaxed vibe; water refill stations and bike delivery assistance are noted. Downsides include limited loungers or towels and paid or limited on-site parking.

Related guest reviews

8

Leslie

Apr 29, 2024

·

Stayed 5 nights

Nice quiet property, enjoyed our stay. Was able to walk to Duval Street and all the shops there. Only complaint was that seating and lounging options around the pools were limited. Most were snatched up early and saved all day. Would have been nice to have a closet and more space in the bathroom.

10

Kristina

Mar 17, 2025

·

Stayed 3 nights

The property was clean with many amenities. The pools were great with plenty of chaise lounges. We were sorry there wasn’t a hot tub.

10

juliette C

Mar 8, 2025

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Stayed 5 nights

Nice to have your own little bungalow and outside seating area with privacy. The bar and two pools wee also very nice and convenient as well as the ability to rent bikes there as well. Great breakfasts! And bar !

10

Mary

Apr 10, 2025

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Stayed 4 nights

The hotel was very nice except it needed more lounge chairs poolside.

10

Ruta K

Jan 3, 2025

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Stayed 4 nights

Property was fantastic-bungalos amazing for privacy and space. 3 piols, bar, morning breakfast! Staff super helpful from management, front desk, housekeeping and bar. So close to shops.

10

Renee

Aug 22, 2025

·

Stayed 3 nights

Beautiful property with several private pools. The front desk was very helpful in helping us get bikes delivered. They were always helping people and answering questions.The breakfast is perfect to get your day started. We will definitely return.

10

Bradley

May 28, 2025

·

Stayed 4 nights

Wow! This was a great place to stay in Key West. The grounds are gorgeous, and the rooms are quaint. It’s the perfect key west experience- the pools are also a nice touch- they aren’t huge, but there are 3!

10

Rebecca

Jul 28, 2025

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Stayed 2 nights

Lovely property!! Only Complaint is there are rarely available towels for the pool. They can’t seem to keep up. Other than that, we love this property!

10

Adam

Jun 19, 2025

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Stayed 4 nights

Our stay here was magical! We arrived around midnight due to flight issues and were met by a friendly Manager to check us in. The grounds are gorgeous and there's little areas all over the property to tuck yourself away and read a book or enjoy a drink. We stayed in the Annex across the street. It was so cute and we had our own little pool all to ourselves the entire time. It's a very quick walk to the "main" pool by the bar and restaurant. The complimentary buffet for breakfast was wonderful and the drinks at the bar were delicious! I really appreciated the purified water stations for refilling our bottles. The location of the Winslow is hard to beat. Your right smack dab in the middle and can be anywhere on the island in 5 minutes to 15 minutes via bike. Definitely rent a bike, it's so much fun to cruise around!

8

Thomas C.

Mar 15, 2025

·

Stayed 3 nights

Historical buildings but well maintained. Small swimming pools for lounging and cooling off. A/C in our bungalow had a loud motor.

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Cleanliness

Most guests find rooms and grounds very clean, but several report musty or mildew odors, occasional mold, humidity issues, or missed housekeeping.

Related guest reviews

10

patrick

Oct 3, 2025

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Stayed 5 nights

Comfortable bed, very clean room and service. Breakfast was excellent

6

Troy Alan

Feb 2, 2025

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Stayed 8 nights

Poor room cleanliness

10

Lynn

Jul 15, 2024

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Stayed 3 nights

Loved every minute here! Beautiful property, exceptionally clean and staff was wonderful. The breakfast is a lovely way to start the day. This was a great place to stay in a great location. Can’t wait to return!

6

phyllis

Oct 3, 2024

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Stayed 4 nights

The property location is great for walking to many restaurants and attractions. Building is beautiful but has some repairs needed. Room was ok but didn’t cooldown for comfortable sleeping at night. I was put in a room upstairs far away from the bar, ice, and breakfast. Room maid service had to be requested and then was not done well. Floors were filthy. The daily resort amenities fee of $35?! For what? Relaxing at the pool when the staff started power washing! Not worth the extra costs! There are many other choices close by. Very disappointed

8

Linda

Mar 13, 2025

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Stayed 5 nights

The gardens and pools were beautiful and well maintained. The property was very walkable to Duval St. The room itself had very little storage for our belongings and had a very strong mildew smell. I would suggest the property owners install dehumidifiers or whatever needs to be done to eliminate the mildew smell, as it really detracted from the experience, especially at the price point.

10

Rachel

Nov 25, 2025

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Stayed 3 nights

Room was extremely clean and spacious

4

Flavia

Jul 21, 2025

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Stayed 1 night

The room was humid and smelled bad. They had the AC going on plus a fan and an extra AC when we checked in. The loud floor AC blew air directly onto the bed, and the wall thermostat didn't work. The bed linens felt wet. This was not a four-star room.

4

dominick

Apr 19, 2025

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Stayed 6 nights

The housekeeping was terrible, our room was only cleaned once during our stay. We had to call for towels every day because the room wasn’t cleaned! Three pools are advertised but they are tiny, and one of them is across the street! The air conditioner sounded like a freight train! I would not recommend staying there!

8

Francia

Aug 30, 2024

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Stayed 2 nights

Beautiful property and great customer service. The breakfast was good. Unfortunately there was a sewage smell at my bungalow coming from the bathroom and mold in the shower. I only stayed there 2 nights.

10

Freddy

Jul 30, 2025

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Stayed 4 nights

This is one of the nicest hotels I have stayed in for a very long time. It was very clean, and the staff was very friendly. They loved my dog. I will definitely be staying here again in September. and considering that it has a lot of trees, there is not one mosquito on the property.

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Rooms

Rooms range from spacious, quiet bungalows to very small or dark units with limited storage; decor is charming but variable in these historic buildings. Recurring comments cite loud or ineffective AC, thin walls, musty air, and occasional soft flooring.

Related guest reviews

8

Brenda Jeanne

Jun 9, 2025

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Stayed 1 night

Property was in good location. Beautiful grounds. Good breakfast. Room was very small. No closet.

4

David

Feb 4, 2025

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Stayed 4 nights

It's a historic hotel so I expected the smaller rooms. But what I didn't expect was the secondary lock on the room door not to work. I didnt expect to have to jiggle the door in order for it to close properly. I didnt expect to see drops of white pain on the floor or the smokey/musty smell. It is clear the hotel has not undergone a hotel renovation in years. I can see why Kimpton left. There is much better value to be had at hotels closer to Duval.

8

Vimal

Feb 22, 2025

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Stayed 2 nights

Property was charming and lush, location was very walkable to local attractions, breakfast buffet was varied and beds were comfy. Our room was just big enough for the four of us to move around, though we had no window, sink was so tiny with no counter that we kept splashing water on the floor, and we had a tough time figuring out how to work the AC because it was mounted too high on the wall to read the settings. Pools were charming but hard to get chairs given how small the pool areas were.

6

Lenore

Apr 10, 2025

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Stayed 4 nights

The property was cute, grounds were very nice, it was clean and a nice breakfast. However the rooms were relatively small and it was a bit further from areas we frequented than ideal. Additionally, we had to switch rooms at 4am due to faulty smoke alarm battery that was an issue during the day before and not properly fixed. Our room also had hot water for only 3 minute showers and the AC sounded like a jet engine. We complained about these things (along with mold on shower tiles). None of those items were fixed. The second room we were transferred to was lovely, so maybe we were unlucky with room 22. They did apologize and remove our resort fees for our stay.

10

Dorit

Jun 3, 2025

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Stayed 1 night

AC was too loud

4

Margaret

Jan 1, 2025

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Stayed 5 nights

The room that we were given (Room 61) was extremely tiny, and had no natural light (no windows). It also did not have anywhere at all to hang clothes, no closet, or even hooks other than one in the bathroom that had two robes on it. The room air conditioner was set on high when we arrived which I soon realized was to hide the overall musty smell. As our 5 day vacation went on, it became more uncomfortable, as it is increasing hard to come back after a long day out to a dark, musty and tiny room. Definitely not the experience we thought we would have at Winslow's Bungalows. It looked so nice in the ads and the landscaping was very nice. But is it even legal to rent a room without windows? I think they should at least have it posted it in the ad for these rooms that they are tiny and windowless. Then people know what they are getting. We came home with our luggage filled with musty clothes, including the winter coats we wore from home, as well as the inside of our luggage. I would not recommend staying here unless you are assured that you will not be assigned this room or any other like this as there may be more than one! We loved Key West though and can't wait to return, but will stay elsewhere for sure. I am very disappointed and feel deceived by Winslow's Bungalows.

8

Kevin

Jun 24, 2025

·

Stayed 4 nights

Property is turn of the century Florida, which we loved. Flooring had some weak spots in the bedroom. The room was updated. Loved the sitting areas outside the rooms and variety of swimming pool options on site.

8

Garrett

Aug 8, 2025

·

Stayed 4 nights

My wife and I stayed here for a getaway together and absolutely loved it. The staff were very friendly and welcoming. The property was absolutely beautiful, quiet, relaxing. We loved the vibes and atmosphere. The included breakfast was above average. Gut health shots, chia pudding, boiled and deviled eggs to start off your day with good protein and nutrition. It was conveniently located to walk to all of the downtown restaurants and sites. The one thing that was subpar was the room itself. These buildings are from the 1800’s so it’s understandable that not everything is going to be perfect but the floor was mushy in a few spots and caving in like the subfloor was rotten. The air conditioning was not very cold despite us cranking it all the way down. These things could have been just our room/bungalow so it’s not necessarily a thumbs down because everything else was wonderful. Honestly if we vacation in Key West again we will most likely stay at Winslow’s again!

10

Chris

Sep 6, 2025

·

Stayed 6 nights

Great room, spacious and private

10

Beverly

Aug 7, 2025

·

Stayed 3 nights

We especially liked the delicious breakfast. The beds were clean and comfortable. The room could use better lighting, an iron and a microwave.

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Service

Service is widely praised as friendly, attentive, and accommodating, with staff proactively assisting with requests and room moves. A few guests mention slow or uneven housekeeping and rare front-desk issues.

Related guest reviews

10

Jennifer Todd

Aug 18, 2025

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Stayed 3 nights

The staff is amazing! They always go above and beyond getting fast results if you need an item, need a recommendation, etc. Keep coming back year and year!

10

Nicole

Aug 7, 2025

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Stayed 3 nights

Beautiful property, great location and the staff were all incredibly nice and genuinely wanted to ensure that you had a fantastic stay.

2

Jennifer

Sep 1, 2025

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Stayed 3 nights

This was the worst lobby experience and treatment. I had planned to stay again next year same weekend and reserve 3 rooms for 4 nights. We will not stay here again. The front desk lobby was and their “visitor” was close to be reporting to police as her behavior was atrocious. I am so disappointment and we were very much looking forward to another stay.

10

Maureen

Jun 27, 2024

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Stayed 4 nights

We thoroughly enjoyed our recent stay. The room was clean and quaint, the property was very pretty and well-kept, the free breakfast was awesome. They arranged for bikes to be delivered to the property which we used for transportation the whole stay. The pools were great. And the location was perfect. It wasn’t in the middle of the party but close enough to get there. Staff were kind and accommodating.

10

Chesla Ann

Aug 3, 2025

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Stayed 4 nights

Amazing in every way!!!!

2

Kyle

May 18, 2025

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Stayed 4 nights

Got downgraded even though I paid for a higher end room. The next day they said they were going to “upgrade me” to a room with a balcony at no additional charge. That’s the room I paid for, it wasn’t an “upgrade” it was simply the room that I paid for. They acted like they did a favor and that annoyed me. She told me I didn’t book a room with a balcony, I showed her the reservation and she said “well that must be an issue with hotels.com, because thats not what was booked. Okay, well that’s between the property and hotels.com, not me then. Extremely unprofessional. I am a Marriott business traveler with over 800 nights in hotels and I never complain. But let me tell you this was honestly the worst stay in my lifetime of traveling. House keeping came in and made the bed. Didn’t bother to remove the trash. The walls were super thin so I could hear my neighbors yelling behind me at 2am. I thought it would be a cute place, I was very wrong. Just stay somewhere else.

10

William Kraus Joseph

Oct 27, 2024

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Stayed 3 nights

The front desk was amazing! Sonya really made the trip stress free

10

Alexa

Nov 1, 2024

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Stayed 5 nights

Property was well maintained. Our first night the people above us were really loud so we talked to the front desk and they asked if we’d like to be moved. They moved us the next day and made sure they checked on us throughout the stay. I would definitely give them a 10/10 and would stay again.

8

Scott A

Jun 10, 2024

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Stayed 6 nights

The bungalows and property are amazing and have very beautifully landscaped gardens. Great private bungalows nestled into a scenic tropical paradise. We also used the swimming pool every midday after touring numerous beaches, historic sites, and restaurants. It's perfectly located in the middle of Old Town where all the fun starts. You can Uber anywhere for around 10 dollars and they are only minutes away when requested. The only negative is the cleaning service was hit or miss, so request maid service every day. The staff is very helpful and quick to rectify any needs or issues.

10

Anne B

Nov 12, 2024

·

Stayed 3 nights

Teqila and Ursula at the front desk were AMAZING! They insured that our Key West experience exceeded all our expectations. The property is wonderful from the comfy bedding to the delicious breakfast! Highly recommend!!

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Location

Walkable Old Town setting near Duval Street, attractions and dining, with many noting a quiet feel despite the central spot. Some mention street-facing noise and that upper-floor rooms require stairs with no elevator.

Related guest reviews

10

barton

May 25, 2025

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Stayed 3 nights

Great property, very good location, walkable to Duvall St.

10

Christianne

Nov 27, 2025

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Stayed 4 nights

I loved this hotel. It’s about a 8 to 10 minute walk to Duval Street in a great location. The staff are so nice and helpful and the pools, bar and breakfast are all terrific features.

10

Erin

Jan 29, 2025

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Stayed 2 nights

Very nice property. It is a long walk from Duvall street but do-able.

10

Gwen C.

May 12, 2025

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Stayed 7 nights

This is our 5th time to Key West and the Winslow Bungalow's were wonderful. The location is close to Duval Street but just enough off the side street so it's quiet. There was some traffic noise on Truman, but nothing to complain about. The layout was super cute with all the bungalows, paths, sitting areas, pools, etc. The breakfast was fine to us as we are not big eaters, but if you are looking for a big breakfast, then you may want something else. Our room was #11. It was clean, just the right size, had a cute outside patio in the back, which we loved. The only thing I would change is request a single bungalow or a 2nd floor room as our neighbors above us had very heavy feat at 3 am and were loud. But this happens and not a game changer. Overall, it was great and would definitely love to stay again at this property. Thanks for a wonderful week! :)

10

Theodore

Sep 14, 2024

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Stayed 4 nights

We stayed in a free standing bungalow. We loved the peace and privacy of it. The property is great, with little pathways and lots of tropical landscaping, two pools and an outside bar. It's also a couple blocks from the main drag on Duval St. Great spot.

10

rebecca

Nov 2, 2024

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Stayed 6 nights

Loved the location…quiet but soooo close to everything!

10

Alice

Apr 27, 2025

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Stayed 4 nights

Walking distance only 2 blocks to Duval St for shopping and restaurants.

8

Jessica

Oct 28, 2024

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Stayed 3 nights

Loved the property but if you can’t do stairs you need to tell them. We were on the third floor, which worked for us but definitely wouldn’t have for everyone in our party. Luckily they got rooms on the first floor. No elevators.

8

Carole

May 17, 2025

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Stayed 2 nights

A lovely oasis to relax in away from the busy town, but close enough to walk everywhere.

10

Maria

Apr 9, 2024

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Stayed 3 nights

Not one but two swimming pools. Very clean, quiet, and everyone was very friendly. Duval St. and all the action within a short walk distance. Fantastic experience!

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Dining

Breakfast is a highlight with fresh, varied options such as juices, wellness shots, fruit and waffles, and the pool bar is popular, sometimes with live music. Some find breakfast seating limited or the spread carb-heavy, and note extra charges for omelets.

Related guest reviews

10

Camille

Aug 13, 2025

·

Stayed 1 night

We loved our stay! The grounds are well kept and very tropical. We only had one day to stay, Winslow made it feel like a true vacation. Don’t miss the continental breakfast! Really nice choices and beautiful live music Sunday morning. You also get a complimentary drink from the bar upon arrival. Overall, I would definitely stay here again.

10

paul

Nov 8, 2024

·

Stayed 7 nights

The breakfast is awesome different everyday. Wellness shots and fresh juices. Staff is amazing very friendly and always accommodating. I’ve been coming to key west quite a bit lately and this stay was the best. Hope to return asap. Property is really cool too

10

Shannon

Jul 22, 2025

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Stayed 2 nights

Absolutely amazing resort . Breakfast was included in the rate and it was perfect . Definitely will be coming back !

6

Navit

Aug 1, 2024

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Stayed 4 nights

Bungalows were kinda small but nice. The continental breakfast wasn’t great and there’s a $15 up charge for an omelet?! The worst part was the loud banging at all times of the day but even more at night. Apparently there are avocado trees and they fall and land on the roof and it makes a VERY loud noise. Also being called to the room for no reason at 6am was not cool. We barely slept thanks to the loud noises.

10

Andrew

Jul 28, 2024

·

Stayed 4 nights

This place is so amazing and completely exceeded my expectations! The staff were so friendly and very accommodating, the whole place is super cute and quaint, was not super busy or overwhelming, so tranquil. The included breakfast was so good and the options had slight alterations everyday so it never got boring! They also offered delicious fresh fruit and smoothies every morning including a wellness shot which was so awesome. The location is so perfect and is right next to Duval street. We rented bikes and got everywhere in 10 min or less including beaches, but we also walked all of Duval street and it wasn’t bad! The three pools were super nice, there’s tons of places on the property to sit and read and many areas are shaded. The bar was also great and the food we ordered was awesome! It was the best experience I have ever had at a hotel and I have been to big fancy resorts. If you are considering a larger resort or hotel in the Keys I seriously would recommend looking into this place for the location, caring staff and the incredible charm. We will be back and I recommend this place to everyone I talk to!

10

Mark

May 26, 2025

·

Stayed 2 nights

Charming. Great atmosphere and solid breakfast

10

Frances

May 1, 2025

·

Stayed 3 nights

We would definitely recommend this hotel. It was cozy and the grounds were beautiful. The bartender was fabulous and we could have had a drink ever night at the bar it was a nice place to relax and meet fellow travelers.

10

Janet

Mar 21, 2024

·

Stayed 3 nights

Upon arrival there had been a misunderstanding on size of room, but they accommodated us and were very nice and attentive to the situation. The grounds are lovely. Nice staff, bar area and food court. The pools were clean and well supplied with towels. The breakfast selection was well equipped and had nice options. There was also small selection of lunch foods offered at the bar, prices were very affordable and food was fresh. I would definitely visit again.

10

Joseph Dominic

Apr 25, 2025

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Stayed 4 nights

The property was beautiful and relaxing. The two pools were nice and clean. The breakfast was great.

6

Melinda

Feb 26, 2025

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Stayed 4 nights

Rooms were extremely small with almost no storage. Very disappointing, especially as we like to unpack when on vacation. Outside of the rooms was nice, and the staff at breakfast were very friendly. Note that the breakfast is extremely carb heavy, including pre-sweetening the yogurt, overnight oats and hot oats. Grateful for the hard-boiled eggs and ham, but would have preferred to exchange a couple of the extensive carb options for more protein (e.g. plain yogurt)

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AI-generated summary based on recent guest reviews

Month	Average price
January	$453
February	$544
March	$524
April	$423
May	$343
June	$249
July	$253
August	$235
September	$204
October	$293
November	$310
December	$363

Su	Mo	Tu	We	Th	Fr	Sa
		1	2	3	4	5
6	7	8	9	10	11	12
13	14	15 $268	16 $158	17 $158	18 $189	19 $187
20 $159	21 $158	22 $159	23 $159	24 $163	25 $191	26 $193
27 $158	28 $161	29 $161	30 $163

Su	Mo	Tu	We	Th	Fr	Sa
				1 $161	2 $251	3 $250
4 $186	5 $186	6 $186	7 $186	8 $256	9	10
11 $198	12 $199	13 $198	14 $207	15 $251	16	17
18 $317	19 $318	20 $384	21 $450	22	23	24 $694
25 $198	26 $202	27 $198	28 $222	29 $218	30 $344	31 $305

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Monthly average prices

About this property

Location

Room options

King Suite with Sofa Bed

Annex King Mobility

Single Queen

Classic King

Premier King with Patio Or Balcony

Bungalow King

Treehouse King Suite

King Mobility

King Suite with Soaking Tub

Annex King

Two Queens

Guest reviews

Fabulous

Who stays here?

What guests think

Property Policies

Check-in instructions

Security deposit

Good to know

Optional extras

FAQs about Winslow's Bungalows - Key West Historic Inns

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