Island Management Vacation Rentals

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Islamorada, FL
Island Management Vacation Rentals

Full Service Real Estate & Vacation Rental services.

09/02/2025

Rent Your Piece of Paradise in the Florida Keys! 🏝️🌞

Escape to the Florida Keys with a beautiful vacation rental that suits your style—whether it’s a beachfront bungalow or a luxurious villa, we have the perfect home for your tropical getaway. 🌊🌴

Book your dream vacation today at www.islandmanagementrentals.com and start your adventure in paradise!

08/28/2025

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

08/27/2025

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

08/26/2025

🌴 Escape to Islamorada 🏝️✨ Stay in one of our vacation homes or condos and experience the best of the Florida Keys! Feed the tarpon at Robbie’s 🐟, relax at the iconic Islamorada Sandbar 🌊, and explore the historic Alligator Lighthouse 🛟—all just minutes from your rental. Your perfect island getaway starts here! 🪸☀️

islandmanagementrentals.com
305-842-1151

08/22/2025

🌴 Bay Harbour 307B | MM 74.5 | Lower Matecumbe Key, Islamorada

Experience the Florida Keys lifestyle in this beautiful 2-bedroom condo, perfect for up to 4 guests. Nestled in Lower Matecumbe Key, this waterfront escape offers comfort, relaxation, and stunning island views.

✨ Rates:
• From $2,400 weekly 🏝️
• $8,000 Monthly 🌊
• Saturday to Saturday 📆 7-day minimum

💲 Additional Fees:
• $100 Condo Fee 🏡
• $275 Cleaning Fee 🧹
• 12.5% Tax 💰

🌊 Make Bay Harbour 307B your next island retreat!

🌅 🐬
🚤 🌴
🌊 🏡
🍹 🌞

08/21/2025

🌴 Greenflash | Lower Matecumbe Key, Islamorada

Indulge in luxury at Greenflash, a stunning 4-bedroom single-family home perfect for up to 8 guests. Located in Lower Matecumbe Key, Islamorada, this spacious home offers the ultimate Florida Keys experience with premium amenities and breathtaking views.

✨ Rates:
• From $25,000 Monthly 🏝️ (28-day minimum)
• $325 Cleaning Fee 🧹
• 12.5% Tax 💰

🏡 Live the dream at Greenflash—your perfect island retreat!

🌅 🚤
🏡 🌴
🌊 🏝️
🍹 🌟

08/20/2025

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

08/19/2025

Buy your next home with us, or find the perfect escape with Island Management Vacation Rentals 🏝 Whether you’re searching for your dream Keys property or a short-term getaway, we’ll make island living a reality.

📞 (305) 842-1151
💻 islandmanagementrentals.com

08/18/2025

🏡 Greenflash | Lower Matecumbe Key, Islamorada

4-Bedroom Single-Family Home | Sleeps 8
💰 Monthly Only from $25,000 (28-Day Minimum Stay)

Indulge in luxury living with this stunning 4-bedroom single-family home on Lower Matecumbe Key. With ample space for up to 8 guests, this spacious home offers the ultimate Keys experience, perfect for an unforgettable getaway.

🔹 Fees:
✔️ $325 Cleaning Fee
✔️ 12.5% Tax

📲 Contact us today or visit realtyonegroupengagethekeys.com to book your stay!

08/17/2025

🏡 Bay Harbour 307B | MM 74.5, Lower Matecumbe Key, Islamorada

2-Bedroom Condo | Sleeps 4
💰 From $2,400 Weekly | $8,000 Monthly
📅 Saturday to Saturday | 7-Day Minimum Stay

Relax in style at Bay Harbour 307B, a beautiful 2-bedroom condo with breathtaking waterfront views and resort-style amenities. Enjoy the best of Islamorada’s island lifestyle in this exclusive community.

🔹 Fees:
✔️ $100 Condo Fee
✔️ $275 Cleaning Fee
✔️ 12.5% Tax

📲 Contact us today or visit realtyonegroupengagethekeys.com to book your stay!

Address

81579 Old Highway
Islamorada, FL
33036

Website

http://www.islandmanagementrentals.com/

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