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Monday 9am - 6pm Tuesday 9am - 6pm Wednesday 9am - 6pm Thursday 9am - 6pm Friday 9am - 6pm Saturday 9am - 3pm

KEYS HOLIDAY RENTALS

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Islamorada, FL
KEYS HOLIDAY RENTALS

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Welcome to Keys Holiday Rentals! Let us help you with your Keys vacation or with managing your home! We manage privately owned single family homes and condos.

Established in 2007 we have grown due to our reputation for guest satisfaction and enjoy repeat business. The properties we represent are clean and offer a variety of amenities in a variety of price ranges.

10/28/2026

A little more time in the Keys sounds pretty good right about now. 🌴☀️

Welcome to Casa Azalea, a waterfront retreat in Tavernier made for settling in and enjoying island life at your own pace.

With a comfortable single-level layout, water access and room for four, this monthly rental is a lovely home base for your next Florida Keys stay.

🏡 2 bedrooms | 2 bathrooms | Sleeps 4
📍 Tavernier, Florida Keys
📅 Monthly rental

Ready to make yourself at home in the Keys? Visit the link in our bio to explore Casa Azalea and check availability.

10/27/2026

Your morning coffee just found a better view.

Meet Beacon Reef 521, a monthly rental in Islamorada where ocean views welcome you from the balcony and poolside afternoons come with a little extra sunshine.

With two bedrooms, two bathrooms and room for four, it’s a beautiful place to settle in and enjoy more time in the Florida Keys.

Ocean views
2 bedrooms | 2 bathrooms | Sleeps 4
📅 Monthly rental https://www.keysholidayrentals.com/vacation-rentals/rental/beacon-reef-521/?utm_source=Instagram&utm_medium=Post&utm_campaign=Beacon%2520Reef%2520512&utm_term=%2523keysholidayrentals

Explore Beacon Reef 521 and check availability through the link in our bio.

10/24/2026

07/04/2026

Happy Independence Day from all of us at Keys Holiday Rentals! ⁠
⁠
Wishing you a beautiful Fourth of July filled with sunshine, salty air, and moments that remind you just how sweet life by the sea can be. Wherever you’re celebrating today, we hope it’s filled with peace, joy, and a touch of coastal magic.⁠
⁠

05/19/2026

It’s almost time for Lobster Mini-Season in the Florida Keys!🦞

Sport Season is July 30 & 31 — and if you’re planning to dive in, make sure you do it safely and legally. No snorkeling or diving within 300 feet of any improved residential or commercial shoreline, man-made/private canal, or public/private marina.

This applies July 27–August 5 — three days before Sport Season, during it, and the first five days of Regular Season.

Here are the rules:
✅ Use your dive flag
✅ Measure properly
✅ Never harvest egg-bearing lobsters

Need a place to stay? We’ve got great rentals close to the action.

📲 Check availability today: https://www.keysholidayrentals.com/

05/11/2026

Meet the real locals.

Life in the Keys means sharing your mornings with pelicans, soaking up sunsets on the dock, and living life at the speed of island time.

If this is your vibe, let’s make it happen. Our vacation homes put you right in the heart of the Keys lifestyle — steps from the water, surrounded by wildlife, and minutes from the best dining, fishing, and snorkeling.

📲 Your next getaway starts here.
https://www.keysholidayrentals.com/

05/08/2026

Quiet canals, sunny skies, and mornings spent on the water…Why the Off-Season is the Best Time to Visit the Keys!

Check Availability today!

05/06/2026

Rock Harbor Club P-8
Key Largo

Open water views, two screened balconies, and sunsets that become part of your daily routine.

A bayfront townhouse with updated interiors, open living, and space to settle in — with access to a private beach, heated pool, tennis courts, and everything that makes Rock Harbor Club feel like its own little world.

Evenings end the same way here… outside, watching the light fade over the water.

28-night stays.

https://www.keysholidayrentals.com/vacation-rentals/rental/rock-harbor-club-p8/

05/04/2026

Fisherman's Gem. Work-from-home… but make it waterfront. After work you can explore Long Key. Snorkel. Fish. Paddle. Repeat.

Then come home to your own private dock.

Fisherman’s Gem
MM74 | Islamorada
28-night minimum

https://www.keysholidayrentals.com/vacation-rentals/rental/fishermans-gem/

Address

81888 Overseas Highway Ste 5
Islamorada, FL
33036

Opening Hours

Monday	9am - 6pm
Tuesday	9am - 6pm
Wednesday	9am - 6pm
Thursday	9am - 6pm
Friday	9am - 6pm
Saturday	9am - 3pm

Website

http://www.keysholidayrentals.com/

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