Lilo's In The Keys

20/10/2026

Halloween in the Keys has its own kind of magic 🎃🌴

If you’re staying at Lilo’s In The Keys during the last part of October, there are some really fun local events happening nearby — from beachside trick-or-treating and Halloween carnivals to a sunset dolphin experience, costume contests, and family activities.

We put together this late-October guide to make it easy to see what’s happening around Key Colony Beach and Marathon while you’re here.

Island days, spooky nights 🎃 and plenty of Keys fun in between. 🧡

01/10/2026

🌴October 2026 Events🌴

🌴🎃In the beautiful Florida Keys 🌴🎃

🐠🐠🐠🐠🐠🐠🐠🐠🐠🐠🐠🐠🐠🐠

01/10/2026

Just another evening in paradise at Lilo’s In The Keys 😍

30/09/2026

🌴 **FALL DIRECT BOOKING SPECIAL AT LILO’S IN THE KEYS** 🌴

We have **three 7-night stays available** this fall in beautiful Key Colony Beach:

**October 31 – November 7, 2026**

**November 7 – November 14, 2026** - ~~~~BOOKED ~~~~

**November 14 – November 21, 2026**

✨ **Save 10% when you book directly through our page!**

Come enjoy a relaxing week in the Florida Keys with:

🏊 Private heated saltwater pool - poolside lounging!
🌴 Private tiki hut with TV, refrigerator & fans - relax and enjoy the views!
🌊 Waterfront canal location - Bring your boat or rent one!
🎣 Private dock & fishing - catch dinner, watch manatee!
🛶 Kayaks included - get out on the water!
🔥 Grill & outdoor living space - cook up your fresh catch!
🌅 Beautiful canal sunsets - breathtaking views!

November is a beautiful time to enjoy the Keys before the busy winter season arrives.

📍 **Lilo’s In The Keys | Key Colony Beach, Florida**

💰 **10% DIRECT BOOKING DISCOUNT**
**7-night minimum**

Message directly through our page for pricing and booking details.

24/09/2026

🌴 Upcoming Local Events Near Lilo’s in the Keys 🌴

Kilts in the Keys
Sunday, September 27, 2026 | 5–7 p.m.

📍 Dockside at Boot Key Harbor
35 Sombrero Blvd., Marathon

Enjoy a casual waterfront evening featuring harbor views, Celtic culture, food, drinks and live music from The Skallywagz.

• Admission: No cover charge is listed; food and drinks are available for purchase.
• Reservations: None required.
• Helpful tip: Arrive early—waterfront seating may fill quickly.

🏴󠁧󠁢󠁳󠁣󠁴󠁿 🏴󠁧󠁢󠁳󠁣󠁴󠁿 🏴󠁧󠁢󠁳󠁣󠁴󠁿 🏴󠁧󠁢󠁳󠁣󠁴󠁿

Florida Keys Premier Swordfishing Experience
October 2–4, 2026

📍 Two Conchs Sportfishing
11499 Overseas Highway, Marathon

An exceptional experience for serious anglers! Spend three full days learning directly from the Two Conchs crew and swordfishing expert R.J. Boyle. Participants will learn deep-drop rigging, bait preparation, drift setup, electronics, fish care and techniques for targeting swordfish in approximately 1,300–1,800 feet of water.

• Price: Call 305-481-0495 for current pricing.
• Registration: Advance arrangements are required.
• Schedule: Exact departure times and daily details are provided by the organizer.
• Booking note: Space is limited and this experience may sell out, so interested anglers should call promptly.

🎣 🌊 🐟 🎣 🌊

Marathon Community Theatre Annual Fundraising Gala
October 9–10, 2026

📍 Marathon Community Theatre
5101 Overseas Highway, Marathon

Enjoy a special Keys-style date night featuring live entertainment by Jaimie Roberts and Michael Kramer, catered hors d’oeuvres, live and silent auctions, a ch*****ne toast and dessert. Attire is “Keys formal.”

• Doors open: 6 p.m.
• Hors d’oeuvres: 6:30 p.m.
• Show begins: 7:30 p.m.
• Tickets: $75 for assigned seating or $95 for VIP preferred seating, including one drink ticket.
• Reservations: Required online or through the box office at 305-743-0994.
• Booking note: Preferred seating and the Saturday performance may sell out, so advance reservations are recommended.

🎭 🎭 🎭 🎭 🎭

21/09/2026

26/08/2026

A huge shout-out to Lil Deb L Do It! ❤️

I want to take a moment to recognize someone who is very important to us and who plays such an important role in helping us care for Lilo’s In The Keys.

I’ve always referred to Deb as our caretaker and friend, rather than simply our house cleaner, because what she does goes far beyond cleaning. She genuinely helps us care for our home and she has also become someone I’m very grateful to call a friend.

One of the things we value most is trust. When you own a vacation rental and can’t always be there yourself, having someone you can completely rely on is priceless. Deb is incredibly trustworthy, dependable, conscientious, and someone we know we can count on.

Her attention to detail is exceptional. She notices the little things others might overlook, takes pride in making sure everything is just right, and consistently goes the extra mile without needing to be asked. She doesn’t simply come in, clean, and leave—she genuinely looks out for the home and helps make sure it is welcoming, cared for, and ready for every guest.

Having someone who cares about Lilo’s the way Deb does means more to us than I can say. That kind of care, reliability, integrity, and dedication is hard to find.

If you’re in the Key Colony Beach or Marathon area and are looking for someone you can truly trust to help care for your home, vacation rental, or property, I wholeheartedly recommend Lil Deb L Do It.

Look to Deb also ~ for any shuttle needs! She goes back-and-forth to Key West, around town, to the Miami airport …. she does it ALL and she does it with enthusiasm and she makes every ride entertaining. 🤩

Thank you, Deb, for everything you do for us and for Lilo’s and for the community. We appreciate you more than you know! ❤️🌴

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Full service Vacation Rental Property Care, Commercial Cleaning
&
Transportation & Courier Svcs

20/08/2026

I've said it before BUT I will say it again ~ Reviews are one of my favorite things! There is nothing like hearing about the Keys experiences of our treasured guests and what they liked about Lilo's! We have the absolute best guests ~ TRULY! 💛💙💛💙

This one really melted my heart:

10/10 Excellent
This place was even better than we imagined! Our family of four had the best stay. LeAnn was wonderful to communicate with and made everything so easy from start to finish. The home was spotless and thoughtfully stocked with everything we needed. The outdoor space truly felt like having our own private resort. We would absolutely stay here again and highly recommend it to anyone looking for a relaxing getaway.

Liked: cleanliness, check-in, communication, location, listing accuracy, value for money

And from another amazing guest ~ who we enjoy having visit as often as they can ~ sent amazing photos from their trip (with permission to share) so I will share a few now. Thank you, Tracey and we will look forward to having you visit again next year! ❤️

I hope everyone is having a fantastic day!!! 🦀🦞🌴🌞🌺

13/08/2026

🌴 Who says summer gets to have all the fun?

Some of our favorite months in the Florida Keys are still ahead! ☀️🌊

If you’ve been waiting for an excuse to sneak away to the Keys, the next few months bring plenty of reasons to do it — and a little more room to slow down and enjoy island life.

🍹 SEPTEMBER — Warm water, laid-back island days and that wonderful slower Keys pace after the summer rush.

🎃 OCTOBER — Things start getting a little spooky! Witches in the Hammock comes to Crane Point in Marathon on October 17, and of course October brings all kinds of Halloween fun throughout the Keys.

🌴 NOVEMBER — Sunshine, warm weather and palm trees while much of the country is pulling out winter coats. We can think of worse ways to spend November. 😉

And honestly? You don’t even need an event to have a pretty great day here.

🎣 Fish right from the dock
🛶 Grab a kayak and head out on the water
🏊‍♀️ Spend the afternoon in your own private pool
🌴 Relax under the tiki hut
🔥 Grill dinner outside
📺 Catch the game at the outdoor TV
🌅 Or do absolutely nothing at all — you’re on Keys time!

Lilo’s In The Keys is our little waterfront piece of paradise in Key Colony Beach, just minutes from Marathon and about 5 miles from beautiful Sombrero Beach.

So here’s the important question…

👇 If you were planning a fall escape to the Keys, which month would you choose — September, October or November?

Maybe it’s time to put a little island time on the calendar. 🌴☀️

08/07/2026

🌴 Lilo’s In The Keys ~ Would You Rather🌴

You can only choose ONE… 😬

🦟 Never get bitten by a mosquito or no-see-um again

OR

🎣 Catch a trophy fish every single day you’re in the Keys

No cheating… you only get one! 😂

👇 Which one would you choose & why! 👇