Flamingo Crossing

Homemade ice cream and the softest freshest giant cookie I've ever had. I thought it would be too…read morerich and sweet but it was not. Don't get me wrong, it was sweet but the flavors were well balanced. Service was phenomenal. We asked what flavor the worker thought was the best and her favorite was the toasted coconut. Immediately yes. It was perfect. Creamy but not too sweet. The toasted coconut flavor was very nice. I will be definitely be making this a must do stop on any future visits to Key West. Mattheessen's is a local ice cream and cookie bakery in Key West. They have a few locations dotted around the island. This location we went to was small with a small counter with a couple stools but that's it for seating so plan to stand inside or walk outside to eat.

AMAZINGGGGG!! Enjoyed everything we had here, but specifically went back multiple times for the…read moregigantic cookies. We tried the peanut butter, chocolate chip, and the peanut butter cookie with fudge and peanut butter on top. All three were perfection, so moist, and still fresh tasting the next day. I also loved the frozen key lime pie slice dipped in chocolate!

Key lime

Slice of Key Lime Pie

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Wicked Lick

4.0(105 reviews)

0.6 mi

Watched the ice cream guy make two flavors of ice cream using the nitrogen process in the mixers…read more It was an experience that actually persuaded me to buy ice cream tonight. Each of the people I was with had a different flavor but I chose the pistashio ice cream in a waffle cone which was excellent.

Great little ice cream spot. I got the vegan coconut agave which was delicious. Not overly sweet…read moreand very smooth. My kids enjoyed their vanilla and strawberry. Best part was the home made berry drizzle that the owner had made for it. You can tell he really puts a lot of effort into his craft. Would love to see even more vegan/ dairy free options. Definitely will be back!!

Cookie Butter Pecan

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Blueberry cobbler

Gladiators Ice Cream

4.6(115 reviews)

Refreshing on a hot June day. Delicious options to chose from. I loved the coconut and mango cream,…read morewas feeling kinda tropical. A must try.

Gladiators is a family owned ice cream shop that boasts being homemade since 1918. Their ice cream…read moreis made from scratch, all natural, no preservatives or colorants added, and no industrial mixes used. With that being said, if you want super creamy and heavy ice cream then this is not the place for you. It has a lighter, icier texture that melts faster than commercially made ice cream. I really enjoyed it and appreciated the natural quality of their product. Service was quick and friendly and the owner is proud to let you know his ice cream is homemade and natural. There are two small bistro tables in the sidewalk where you can sit and enjoy and watch the people pass by.

Gladiator's store front.

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Ice cream shop

Rainbow Cone

5.0(5 reviews)

Pros: Very convenient location, right off of Duval…read more Couldn't be any easier to get here if you're visiting Key West. Service was quick and efficient. The ice cream itself was very high quality. The flavors were well represented without tasting fake or like extract. Cons: No cons. Tips: Get the rainbow cone! It's too fun not to get it. Would love to come back.

Short, sweet, simple, to the point. That is how my visit was, and that is how my review will be…read more Right off the main street in Key West, you walk in, you wait in a very fast-moving line, you get your Tik Tok trending ice cream cone, and you race to eat it as you continue to walk down Duval. This was a happy surprise for me, because I had never heard of this thing and had no idea it was trendy with the kids. The Rainbow Cone (Our famous cone made with slices of Chocolate, Strawberry, Palmer House, Pistachio & Orange Sherbet). Very photogenic. And surprisingly, it was also delicious! Somehow, all of these flavors melded together in my mouth into one cohesive bite. I was a fan. I would definitely come back.

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Key Lime Pie Bakery

4.2(391 reviews)

There are a few spots in Key West that claim to be the original creators of the Key Lime Pie--this…read moreplace included. It's close to Mallory Square, and they even have their own space where the pies are made. I chatted briefly with the staff, and they told me that yes, this really is the place where it all started. They also mentioned that many other spots claiming to be "the original" actually get either their ingredients or their pies from here. Overall, it's a cute little spot. Besides pies, they sell cupcakes, coffee, and a variety of general goodies and touristy items. We grabbed a small, cozy two seater high table by the window and enjoyed their tart pie. And yes--be ready for that sharp tang that hits your jaw at first and then grows on you! There are benches outside too, and it felt peaceful sitting there. The pie costs $7.

It just so happens that Key lime pie happens to be my second most favorite dessert and it's hard…read morefor me to find one that I don't like. I am a stickler though on the fact that I will refuse any specimen that is green in color since it's screams inauthentic. One of my local friends even handed me a coupon for this place, so it was one of three pie concoctions that we sampled during our vacation. Lucky us! The staff here are welcoming and able to handle crowds efficiently and kindly. The store is incredibly cute and has a wide array of Key lime products as well as souvenir type inventory. Great place to perhaps do one-stop shopping if customers are pressed for time or just don't like to spend time at multiple places. The pie was delicious. Tart, sweet, fresh, cool, refreshing, and nice crust. Highly recommend!

Front of the key lime pie bakery

Exterior

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Kilwins Ice Cream - Chocolate - Fudge

4.3(130 reviews)

0.5 mi

Stopped in for an ice cream treat while on vacation and it did not disappoint. I got the chocolate…read moresalted carmel in a waffle cone and it was perfect. My Husband got some kind of mud and he really enjoyed it. No pictures bc it was just too good and was gone before I even thought to take any. There are alot of different flavors and many other desert options. The service was also great not rushed to pick a flavor at all which I appreciated.

I've visited several Kilwins locations over the years, and it's always a reliable spot for dessert…read moreafter dinner. While their chocolate confections aren't my favorite, their ice cream and fudge are excellent. We stopped in for a couple of cones, and they were delicious. The stores are well designed and festive, and the staff are consistently friendly.

Cappuccino Chocolate Chip for the Win!

Inside

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Specials

Mattheessen’s - Key West

4.4(150 reviews)

Raspberry sorbet was delicious! We came after lunch and didn't get a chance to try all of the yummy…read morelooking treats but it smelt amazing. We were in and out and the ice cream was just what we needed for a quick cool down.

Got a large cookie. It was early evening. Didn't taste like it was made same day. A little dry and…read morecrumbly. Would have taken it back, but didn't feel like walking back. My only experience, but not a good one.

Menu

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Menu

Carpe Diem

4.3(15 reviews)

Cool little spot in Mallory Square for all your sweets cravings! Ice cream, shaved ice, rolled ice…read morecream, giant chocolate chip cookies, and milkshakes... you name it! It's nice to see this cute little establishment after working so hard riding your bike around town. It is absolutely refreshing. The gentleman who works there is very friendly! Great stop before you go and see the sunset across the street!

I had heard this spot that's fairly new was a no frills ice cream spot near the end of Duval…read more And this is exactly what "Carpe Diem" is to a T. We were walking around semi-aimlessly at the north end of Duval, and had actually just done a lap around Mallory Square and the cruise ship area. We were pretty tired from all the walking. Nothing charges me up as much as a bowl of Ice cream so we popped in. Service was nice enough, straight forward. We got just what we wanted(a snickers ice cream and a peppermint) at the price we thought we would get(a touristy price). It's not right on Duval so you have to walk around to find it. And it's not well marked so even better for the line. In fact when we got there I thought there would be a large line, it was perfect ice cream weather. But since it is not obvious to find, there was no line at all. If you needing a cup or a cone at the north end of the strip, it's a good quick stop.

Shaved ice

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Chocolate covered keylime pie

Better Than Sex

4.5(1.7k reviews)

0.1 mi

I have a sweet tooth, a tremendous sweet tooth indeed, For…read moreice cream and desserts are the things that I need. I've had dessert in the desert near Area 51, And underground in Antarctica, far from the sun. I've had it in graveyards, beneath moonlight so fair, And even in a dessert restaurant, yes, I've had dessert there! At Better Than Sex, the Fever was mine, And it tasted so splendid, so luscious, divine. I tried one of their special coffees as well, And it was so delicious, I nearly swooned under its spell. But the night's grandest moment, the finest display, Was when our waiter arrived with the desserts on a tray. He looked straight in my eyes as he named each delight, With a confidence both curious and wonderfully bright. My dessert was a huge phallus, impressive and grand, With two giant balls resting beneath it in hand. It was covered in "splooge sauce," a curious sweet stream, A dessert of such drama it belonged in a dream! I truly enjoyed this place and would gladly return If I lived nearby, where the sweet candles burn. They are masters of dessert, of flavor and flair-- A deliciously mischievous treasure tucked away there.

We went to Better Than Sex after eating a full meal at Duffy's right in front, so there wasn't much…read moreroom left in us. But oh man was it amazing. An extremely unique ambience and decoration. But it's not too much or too little. The seating is comfortable and private. Our server was very nice, he checked in at all the right times and was sweet. We only ordered one dessert and it got there promptly. Everything on the menu looked excellent and delicious. We settled on the cookie nookie cake, it was super fresh with many contrasting flavors that made every bite a pleasure. Overall had an amazing time and recommend this place for anything from a late night dessert or a full dessert meal. If we're ever around again, we are definitely going back and trying a lot more than just one dessert.

Cream in my coffee

Red velvet cheesecake

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Moscato, white chocolate rimmed glass

Rooster Treats

4.2(29 reviews)

0.2 mi

This is a super cute truck in the area of the Southernmost Point that offers soft serve ice cream…read moreor mini donuts with toppings! The service was quick and there was some seating outside with some sand so even though it is a few blocks inland there was still a relaxed, beach feel to the place. I got the coconut joy mini donuts and my boyfriend got the chocolate paradise ice cream. The mini donuts did get a little soggy from the toppings so I would maybe eat a little faster than I did (though I didn't take an unreasonable amount of time) or go for the ice cream. For Key West, they seemed reasonably priced and hit the spot for something sweet. If you're already in the area and looking for something sweet, I would stop here.

We stopped in on our last night in Key West after trying several of the ice cream shops during our…read morestay. I think Rooster Treats is a fun change of pace from the more traditional storefronts lining Duval Street. Instead of a typical shop, it operates out of a permanent trailer. You order from a raised deck platform, then head down to enjoy your treat at one of the tables set up in a makeshift sandy beach area. The whole setup works surprisingly well. It gives you that relaxed, toes-in-the-sand feeling, almost like you're unwinding right by the water. It has a great vibe. We're not huge fans of soft serve, mainly because the flavors and textures can feel limited. Rooster Treats makes up for that with the generous amount of toppings you can add. I ordered the Chocolate Paradise, which came with chocolate drizzle, sprinkles, and Oreo crumbs. It was delicious, and the portion size was very good. Glad we checked it out before heading home.

Sandy "beach"

Just add your favorite toppings!

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Relax and enjoy your soft serve ice cream or freshly made mini donuts

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17 reviews that are not currently recommended

The reviews below are not factored into the business's overall star rating.

Phillip Z.

Elite 26

270

838

551

1 year ago

We had a fantastic treat at Flamingo Crossing Ice Cream in Key West! Our kids loved the wide variety of flavors -- they were so excited to be able to taste three different options before making their choice. In the end, they both stuck with classic strawberry, which made them happy. My partner also sampled three flavors and ended up trying one of the boozy options. He warned us that it was quite sweet and pretty strong, but he really enjoyed it! This spot is a well-loved local favorite, and several locals recommended we check it out -- now we see why! I especially appreciated the outdoor seating with picnic tables, perfect for relaxing and enjoying the warm Florida weather. Plus, watching the chickens roam around added a fun, authentic touch to the experience. All in all, a delightful stop with great flavors, friendly atmosphere, and a true Key West vibe. We'd definitely return next time we're in town! read more

Maddie C.

0

12

2

1 month ago

The ice cream itself is good, but unfortunately the customer service completely ruined the experience. We arrived about 30 minutes before the posted closing time, only to find the doors already closed. If your posted hours say you're open until 11PM, customers should reasonably expect to be served until then, or the hours should be updated to reflect when you actually stop serving. The staff was also very rude and dismissive. We were told the milkshake machine wasn't working, which honestly came across as an excuse to avoid making anything because they were trying to close early or just not wanting to make it. (We had gotten them earlier this day) Good ice cream isn't enough to make up for poor service and unreliable hours. If you're planning to come here, definitely arrive well before 10PM, or save yourself the frustration and go somewhere else. read more

K T.

1

281

575

9 years ago

Was a cold January evening but how to say no to ice cream with flamingos in the name. They have some unusual flavors and I wanted to try many flavors but stuck to more normal key lime and mango. The flavors were good but the bad thing is there is only one small indoor table to sit, which was taken so had to sit outside in the unusually cold temperature for key west. The service could use some improvement as the server guy appeared to be very disinterested in serving but did it anyways. Would come back to try other flavors and hopefully he will cheer up when it's not as cold. read more

Bill S.

1

69

4

15 years ago

This place is awful. AVOID, AVOID AVOID!! The ice cream is mediocre at best, Rite Aid has better ice cream than this dump. Also it is way, way overpriced almost $6 for a small one scoop, get real, and the rude little foreign man who works behind the counter is a total A-hole. I will never go back, They count on tourists so they are not concerned about repeat business or keeping their customers happy and it shows. There are plenty of better ice cream options in Key West, so do your self a favor and skip this dive. read more

Alex G.

30

7

1

8 years ago

The guy asked for my order, I asked for vanilla with Carmel, dude shook his head in disbelief and didn't say anything, after he gets done scooping my order he says "you can have x y z" no Carmel... Would've been nice to know that before you scooped it. Ice cream was good. Customer service left something to be desired. Also staff should be wearing gloves. Was a little grossed out by the dude grabbing someone's waffle cone with his bare hands. read more

Mark H.

5

46

12

9 years ago

As a few other reviews have mentioned, you may run into a crappy attitude in this place. If it is a female working, you're probably fine. The 60ish man is a prick. We walked out, don't need to spend our tourism dollars on that. read more

Stella Z.

0

5

1

6 years ago

Great spot for stopping for a refreshing ice cream if you are walking throughout Duval St heading to southernmost point area or coming back from it. They have the best Key Lime pie Ice cream. Super Creamy. read more

Ryan J.

69

11

7

1 year ago

Ever encounter someone who hates there job? Well we found one Monday afternoon 3/14! Maybe he was having a bad day? We left after the poor customer service. If you own this shop talk to your employee! read more

Will L.

0

2

0

13 years ago

What I like most about this place is they make much of their own ice cream and they have tropical fruit flavors that you can't get elsewhere on the island read more

Michael M.

0

13

0

6 years ago

Best ice cream in key west. Creamy creamy creamy. Great flavors. Nice staff. Conveniently located in the more calm side of Duval st.

Ali V.

Elite 15

16

124

4

15 years ago

Nothing special. Strawberries and cream ice cream is delicious, but other than that not too special of a place.

Melissa B.

1

28

2

14 years ago

Some of the flavors are amazing, others not so much. Wish they had cherries for the sundaes. read more

Deanna H.

74

12

5

13 years ago

What delicious ice cream. Too bad the help isn't very friendly.

Amy J.

79

21

7

13 years ago

Delicious! Try the Cuban Coffee gelato.

Otto G.

3

8

10

15 years ago

It's OK flavors were a little dull read more

Anthony P.

39

89

25

13 years ago

Love the key lime pie ice cream

J H.

110

6

0

14 years ago

Sour Sop is delicious!

Flamingo Crossing - icecream - Updated September 2026

People who viewed Flamingo Crossing also viewed

Wicked Lick

4.0

(105 reviews)

Watched the ice cream guy make two flavors of ice cream using the nitrogen process in the mixers…read more It was an experience that actually persuaded me to buy ice cream tonight. Each of the people I was with had a different flavor but I chose the pistashio ice cream in a waffle cone which was excellent.

Great little ice cream spot. I got the vegan coconut agave which was delicious. Not overly sweet…read moreand very smooth. My kids enjoyed their vanilla and strawberry. Best part was the home made berry drizzle that the owner had made for it. You can tell he really puts a lot of effort into his craft. Would love to see even more vegan/ dairy free options. Definitely will be back!!

La Michoacan Ice Cream

4.8

(24 reviews)

Amazing service, it was just one man who helped us out but everything was phenomenal. We liked all…read morethree of the items we ordered. We are from California and came to the Keys for vacation. Will be coming back the days we're here for our vacation. This business deserves more foot traffic! It was empty when we came in but about 3 other customers trickled in while we were there. If you come you should ask them about the menu. It's a Mexican shop but contains some Nicaraguan treats ;) Thank you so much sir! Hope the best for your business

Soooooo insanely delicious, the mango berry was to die for. Could not recommend this place enough,…read morehug portions as well

Gladiators Ice Cream

4.6

(115 reviews)

Refreshing on a hot June day. Delicious options to chose from. I loved the coconut and mango cream,…read morewas feeling kinda tropical. A must try.

Gladiators is a family owned ice cream shop that boasts being homemade since 1918. Their ice cream…read moreis made from scratch, all natural, no preservatives or colorants added, and no industrial mixes used. With that being said, if you want super creamy and heavy ice cream then this is not the place for you. It has a lighter, icier texture that melts faster than commercially made ice cream. I really enjoyed it and appreciated the natural quality of their product. Service was quick and friendly and the owner is proud to let you know his ice cream is homemade and natural. There are two small bistro tables in the sidewalk where you can sit and enjoy and watch the people pass by.

Mattheessen's

4.3

(42 reviews)

Holy cookie Batman! We're walking by this location on our way to another stop in the area. I happen…read moreto see an extra large chocolate chip cookie that I decided I must have. Staff was super friendly as soon as we walked in. The cookie was easily the size of four or five cookies combined but was still warm and freshly baked. It had a great flavor to it and wasn't overwhelmingly sweet and hit the right spot for a cookie lover like me. The store itself is very small, but we just took our cookie on our continuing walk towards our next destination. Given the size of the cookie it was very reasonably priced. Overall: A+ An absolute must stop for anybody with a sweet tooth. Definitely give the gigantic cookie a go. I'd recommend sharing it, but let's be real you could very much fall in love with eating it all by yourself!!

This was the best chocolate covered key lime pie I've ever had in Key West. The crust was so…read morebuttery, I'm still dreaming about it. I love that they're open late, so you can get your sweet treat sugar craving fix in even after visiting a few bars on Duval. The worker at the register was kind, and the shop was well lit, so you can look over the dessert case. I'll be back to try more!

Rooster Treats

4.2

(29 reviews)

This is a super cute truck in the area of the Southernmost Point that offers soft serve ice cream…read moreor mini donuts with toppings! The service was quick and there was some seating outside with some sand so even though it is a few blocks inland there was still a relaxed, beach feel to the place. I got the coconut joy mini donuts and my boyfriend got the chocolate paradise ice cream. The mini donuts did get a little soggy from the toppings so I would maybe eat a little faster than I did (though I didn't take an unreasonable amount of time) or go for the ice cream. For Key West, they seemed reasonably priced and hit the spot for something sweet. If you're already in the area and looking for something sweet, I would stop here.

We stopped in on our last night in Key West after trying several of the ice cream shops during our…read morestay. I think Rooster Treats is a fun change of pace from the more traditional storefronts lining Duval Street. Instead of a typical shop, it operates out of a permanent trailer. You order from a raised deck platform, then head down to enjoy your treat at one of the tables set up in a makeshift sandy beach area. The whole setup works surprisingly well. It gives you that relaxed, toes-in-the-sand feeling, almost like you're unwinding right by the water. It has a great vibe. We're not huge fans of soft serve, mainly because the flavors and textures can feel limited. Rooster Treats makes up for that with the generous amount of toppings you can add. I ordered the Chocolate Paradise, which came with chocolate drizzle, sprinkles, and Oreo crumbs. It was delicious, and the portion size was very good. Glad we checked it out before heading home.

Icestream At Morning Joint

4.5

(12 reviews)

What a cute little place for ice cream in the Keys. Variety of daily and months flavors listed…read morealong with the option for shakes, sundaes, cones and toppings. Behind the trailer they have cornhole, darts, tables and umbrellas. Even areas for dogs while you enjoys your in-house made ice cream. Right next door is a Morning Joint coffee house and a cute shop. The airstream opened at two until 930 when we were there on a Friday afternoon in late June. I tried Thai tea because they were out of snickers, a friend had a brownie sundae and another friend had sea salted munchies. Thai tea was very tasty, if sweet and friends said theirs was good but also very sweet. Saw the owner making a new batch of ice cream in house. Our server was kind enough to take out picture for us outside. Friendly service and a cool place to stop with 25 miles north of Key West

Kids loved the ice cream…read more Got the crème brûlée sundae.... Let's just say it wasn't quite what everyone said. Super Gooey top was more like snot consistency than brûlée..... took a few bites and threw it away. For single scoop once cream kids say yes.

Key Lime Pie Bakery

4.2

(391 reviews)

There are a few spots in Key West that claim to be the original creators of the Key Lime Pie--this…read moreplace included. It's close to Mallory Square, and they even have their own space where the pies are made. I chatted briefly with the staff, and they told me that yes, this really is the place where it all started. They also mentioned that many other spots claiming to be "the original" actually get either their ingredients or their pies from here. Overall, it's a cute little spot. Besides pies, they sell cupcakes, coffee, and a variety of general goodies and touristy items. We grabbed a small, cozy two seater high table by the window and enjoyed their tart pie. And yes--be ready for that sharp tang that hits your jaw at first and then grows on you! There are benches outside too, and it felt peaceful sitting there. The pie costs $7.

It just so happens that Key lime pie happens to be my second most favorite dessert and it's hard…read morefor me to find one that I don't like. I am a stickler though on the fact that I will refuse any specimen that is green in color since it's screams inauthentic. One of my local friends even handed me a coupon for this place, so it was one of three pie concoctions that we sampled during our vacation. Lucky us! The staff here are welcoming and able to handle crowds efficiently and kindly. The store is incredibly cute and has a wide array of Key lime products as well as souvenir type inventory. Great place to perhaps do one-stop shopping if customers are pressed for time or just don't like to spend time at multiple places. The pie was delicious. Tart, sweet, fresh, cool, refreshing, and nice crust. Highly recommend!

Gelateria Nuovo Fiore Key West

4.4

(18 reviews)