Island Management Vacation Rentals

01/05/2026

🌴 Welcome to Green Flash in beautiful Islamorada 🌴

This gated single-family home has it all—private pool, small boat dock, and space for the whole family.

✨ 4 Bedrooms | 2,500 sq. ft. | Sleeps 8
✨ Monthly only: $22,000 (28-day minimum)
✨ Pets considered 🐾

Your Keys escape starts here!

📞 305-842-1151
🌐 islandmanagementvacationrentals.com

01/04/2026

85 E Second Street – MM97, Key Largo

VACATION RENTAL‼️

Cozy island living with water access and everything you need to relax in paradise 🌴☀️
This charming 1.5-bedroom single family home sleeps up to 4 guests and includes a boat dock for your next Keys adventure 🚤

From $4,800/month | 28-day minimum
$225 Cleaning Fee + 12.5% Tax
King Bed + Double Bed | 1 Bath | 750 sq. ft. | Pets considered

01/03/2026

Islamorada Direct Bayfront

Now Available Vacation Rental
Wake up to endless bay views at this beautiful 3-bedroom waterfront retreat in Lower Matecumbe 🌊🌴
Sleeps up to 6 guests with spacious living areas upstairs and down—perfect for your extended Keys stay

Located at 76200 Overseas Highway
From $10,000/month | 28-day minimum
Two baths | Three King Beds + Bunks | Unbeatable Bayfront Location

01/02/2026

🌴 Your Islamorada getaway starts at Bay Harbor 110C 🌴

Enjoy paradise living in this spacious 2-bedroom condo with a boat slip, community pool, and spa!

✨ $2,300 weekly | $8,000 monthly
✨ Sleeps 4 | 1,500 sq. ft.
✨ King bed + 2 twins
✨ Saturday–Saturday (7-day minimum)

📍 Mile Marker 74, Islamorada
📞 305-842-1151
🌐 islandmanagementvacationrentals.com

01/01/2026

🌴 Dreaming of your next getaway? 🌊✨

Whether you’re planning a family trip, a romantic escape, or a month-long retreat, Island Management Vacation Rentals has the perfect Keys property waiting for you.

From waterfront condos with boat slips 🚤 to private homes with pools 🏊, we make your stay in Islamorada unforgettable.

📍 Located in Islamorada, FL
📞 305-842-1151
🌐 islandmanagementvacationrentals.com

12/15/2025

Open due to cancellation
10% off January and February
Weekly or monthly
Call rich 305-842-1151

3-bedroom with boat slip
For more info, photos and booking visit https://www.floridarentals.com/8959

This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamora

12/04/2025

Open January and February
Weekly or monthly
Call Rich 305-842-1151

3-bedroom with boat slip
For more info, photos and booking visit https://www.floridarentals.com/8959

This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamora

11/12/2025

We’re Hiring Agents in the Florida Keys! 🌴💼

Join our growing team and help guests discover their dream vacation rentals in the beautiful Florida Keys! We’re looking for enthusiastic and dedicated agents to provide top-notch service and make every guest’s stay unforgettable.

Ready to work in paradise? Apply now at www.islandmanagementrentals.com and start your career today!

11/11/2025

🏝️ Island Management Vacation Rentals – Your Home in Paradise 🌅

From oceanfront villas to cozy canal-side cottages, Island Management Vacation Rentals offers the best stays across the beautiful Florida Keys. Enjoy private pools, dock access, and unbeatable waterfront views — all managed with local care and island hospitality.

✨ Stay longer, relax deeper, and experience the Keys like a local.

📞 (305) 842-1151
🌐 islandmanagementrentals.com

11/10/2025

🌴 The Green Flash – Your Private Islamorada Retreat 🌅

Escape to paradise at Green Flash, a stunning 4-bedroom single-family home in the heart of Islamorada. This 2,500-square-foot oasis sleeps up to 8 guests and features a private gated pool, small boat dock, and beautiful tropical surroundings — perfect for your next extended getaway.

💰 From $22,000/month (28-day minimum)
🛏️ 4 Bedrooms | 3 Baths | Sleeps 8
🐾 Pets Considered | 🛥️ Small Boat Dock | 🏡 Private Pool

📞 Call (305) 842-1151
🌐 islandmanagementrentals.com