KEYS HOLIDAY RENTALS

KEYS HOLIDAY RENTALS 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.

It’s almost time for Lobster Mini-Season in the Florida Keys!🦞Sport Season is July 30 & 31 — and if you’re planning to d...
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/

Meet the real locals.Life in the Keys means sharing your mornings with pelicans, soaking up sunsets on the dock, and liv...
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/

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

Rock Harbor Club P-8Key LargoOpen water views, two screened balconies, and sunsets that become part of your daily routin...
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/

Just out here cruising through the keys in our vacation best 💁‍♀️🌴This is how every week should start—barefoot, sun-kiss...
05/01/2026

Just out here cruising through the keys in our vacation best 💁‍♀️🌴

This is how every week should start—barefoot, sun-kissed, and on island time.

If you're thinking about a getaway, Keys Holiday Rentals has some seriously cute spots waiting for you. https://www.keysholidayrentals.com/

Sandglass #4 — A One-of-a-Kind Bayside EscapeThis magnificent two-story townhouse in Islamorada delivers 180-degree wat...
04/29/2026

Sandglass #4 — A One-of-a-Kind Bayside Escape

This magnificent two-story townhouse in Islamorada delivers 180-degree water views, direct lagoon access, and space for the whole crew. Located on Lower Matecumbe, Sandglass #4 is perfectly positioned for boating, paddleboarding, kayaking, and sunset watching — all right from the property.

Inside, enjoy expansive living spaces, an oversized kitchen with a large center island, and disappearing glass doors that open to an enormous screened balcony overlooking the cove. With 5 bedrooms and 3 baths, sleeping up to 12 guests, this home was designed for gathering, relaxing, and making unforgettable Keys memories.

📍 Islamorada | Mile Marker 74.9
🛏 5 bedrooms | 🛁 3 baths | Sleeps 12
🛥 Boat slip + private ramp | 7-night minimum
👉 Book your Keys getaway with Keys Holiday Rentals

https://www.keysholidayrentals.com/vacation-rentals/rental/sandglass-4/

Villa RioloIslamoradaA private, gated canal-front home designed for easy days on the water and quiet evenings back at yo...
04/27/2026

Villa Riolo
Islamorada

A private, gated canal-front home designed for easy days on the water and quiet evenings back at your own place.

Open living, two ensuite bedrooms, and direct balcony access that brings the outside in.

Out back, dockage for your boat with quick access to the ocean. Under the tiki, a place to slow down.

28-night stays.

https://www.keysholidayrentals.com/vacation-rentals/rental/villa-riolo/

We got the bungalow in July.What started as a one-month stay turned into 4th of july on the water, followed by mini lobs...
04/24/2026

We got the bungalow in July.

What started as a one-month stay turned into 4th of july on the water, followed by mini lobster season… and a stretch of days we didn’t plan, but wouldn’t trade.

The Bungalow in Islamorada — private, quiet, and right where you want to be when everything’s happening.

28-night stays only. Book now!

https://www.keysholidayrentals.com/vacation-rentals/rental/the-bungalow/

This, and chasing the perfect wave. 🌊🏄‍♂️From sunrise swells to warm turquoise waters, Islamorada is more than a destina...
04/22/2026

This, and chasing the perfect wave. 🌊🏄‍♂️

From sunrise swells to warm turquoise waters, Islamorada is more than a destination — it’s a state of mind. Whether you’re here for the thrill of the ride or the calm after, every day feels like the best day on the water.

📅 Plan your Florida Keys escape with Keys Holiday Rentals.

https://www.keysholidayrentals.com/

Address

83247 Old Highway
Islamorada, FL
33036

Opening Hours

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

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