2 Br Private Vacation Home Vacation Rental In Islamorada, Florida

Relax, Recharge & Explore – Detached Islamorada Cottage w/ Pool, Paddleboards & Fire Pit ☀️
Welcome to your own private cottage in paradise — perfectly located in Islamorada, just a mile from the legendary Robbie’s Marina, where feeding massive tarpon, grabbing a drink at the Hungry Tarpon, or hopping on a snorkeling charter is all part of a normal day.
This detached 2-bedroom, 1-bathroom cottage is ideal for couples, friends, solo adventurers, or small families looking for a laid-back, comfortable, and affordable Keys escape. It’s part of a quiet, boutique property with just 7 cottages total, so you get the space and peace of a private place with shared perks like a stunning pool just steps away.

Two bedrooms, both with queen beds and clean, simple decor

A full kitchen stocked with essentials – fridge, oven, microwave, pots/pans, utensils, coffee maker, and more

Comfortable living area to relax after a day on the water

Fast, reliable WiFi – whether you’re working remotely or uploading your snorkeling videos

Air conditioning throughout the space

Fresh linens, bath towels, and starter toiletries provided.
🌴 Outdoor Living – Florida Keys Style
You’ll have your own:
✔️ Fire pit – light it up for s’mores, a nightcap, or just to unwind under the stars
✔️ Grill – perfect for cooking up the day’s catch or some island-style BBQ
✔️ Outdoor seating surrounded by tropical greenery
This is your spot to sip your morning coffee or enjoy a cocktail after a day of exploring.
🏊‍♂️ Resort-Style Pool (Without the Crowds)
The pool area is a gem – beautifully maintained and shared with only 6 other cottages, so it’s never crowded. Plenty of space to lounge, float, soak up the sun, or take a dip before heading out to dinner.
🛶 Free Paddleboards Included
Want to explore the crystal-clear waters the Keys are famous for? We include paddleboards FREE for guest use! You can easily launch from a nearby ramp and head out to discover mangroves, spot wildlife, or just glide across the turquoise sea. No rentals, no hassle – just grab and go.
📍 Location, Location, Location
You’re right in the heart of Islamorada, known as the Sportfishing Capital of the World, but there's so much more here than just fishing.
✔️ Robbie’s Marina – just 1 mile away! Feed the tarpon, rent a boat, book a jet ski, or shop the quirky local market
✔️ Anne’s Beach – a beautiful, family-friendly stretch of sandy coastline just a 5-minute drive
✔️ The Art District – home to local galleries, artisan shops, cafes, and laid-back island vibes
✔️ Close to amazing restaurants and tiki bars – fresh seafood, sunset views, tropical cocktails
✔️ Easy access to snorkeling, diving, kayaking, and boat tours
Whether you’re here to explore or just kick back with a drink in your hand, you’re in the perfect spot.
☀️ What Guests Love About the Cottage:
It’s private, peaceful, and relaxed

The pool is beautiful and never crowded

You can paddleboard without having to rent anything

The outdoor firepit and grill make it feel like your own little backyard in paradise

The location makes it easy to get anywhere on the island – beaches, marinas, restaurants, all nearby

🧳 Other Things to Note:
Parking is included and right outside your door

Pool towels are provided

No smoking inside the cottage

We’re happy to give local recommendations – we live here and love it!

Located by the sea, this vacation home is in Matecumbe, a neighborhood in Islamorada. Keys History & Discovery Center and History of Diving Museum are cultural highlights, and some of the area's activities can be experienced at Robbie’s of Islamorada and Bud n' Mary's Dive Center. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven.