Villa in Upper Matecumbe Key, FL
8 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this villa rental
Villa by the Bay – Your Islamorada Escape for Sunsets, Fishing & Island Living
Bring your heart, your family, and your fishing gear to Villa by the Bay, a charming island retreat tucked inside the quaint gated community of Coral Cove in the heart of Islamorada. With just eight homes in the community, this peaceful getaway offers the perfect blend of privacy, comfort, and easy access to everything that makes the Florida Keys unforgettable.
Whether you're planning a world-class fishing adventure, a relaxing family getaway, or a romantic escape, Villa by the Bay is your ideal home base.
Breathtaking Bayfront Sunsets
End every day the way island life was meant to be enjoyed—watching the sun melt into the bay from the dock area. Gentle ocean breezes and vibrant sunset colors create a relaxing atmosphere you’ll look forward to every evening.
A Fisherman’s Paradise
Islamorada is known as the “Sport Fishing Capital of the World,” and Villa by the Bay puts you right where you want to be.
Direct ocean access
Private dockage available (upon request & trailer parking offsite can give recommendations )
Easy access to deep-sea fishing, backcountry fishing, and sandbars
Perfect for bringing your own boat or chartering a local guide
Spend the day chasing sailfish, mahi, snapper, or tarpon, then return home to relax by the pool and relive the day’s best catches.
Private Heated Saltwater Plunge Pool
After a day on the water or exploring the Keys, unwind in your private heated saltwater plunge pool. The soothing waterfalls and tranquil sounds create a relaxing oasis perfect for evening cocktails, family time, or a quiet morning coffee.
Community Amenities
Coral Cove is a quiet gated enclave designed for peaceful island living. Guests enjoy access to:
Community swimming pool
Community dock with water and electricity
Gated privacy
Beautiful bay views throughout the property
With only eight homes, the atmosphere remains calm, welcoming, and uncrowded.
Walk to Islamorada’s Best Restaurants & Bars
One of the best parts of staying at Villa by the Bay is the central location. Many of Islamorada’s favorite spots are within walking distance.
Enjoy fresh seafood, tropical cocktails, and live music at nearby local favorites. Whether you're craving sunset dining, casual tiki bars, or a lively night out, it’s all just steps away.
No long drives—just pure island convenience.
Relaxed Island Living
Villa by the Bay was designed for easy, comfortable stays where you can truly unwind.
Wake up to warm tropical breezes.
Spend afternoons fishing, boating, snorkeling, or paddleboarding.
Return home for a refreshing swim in the plunge pool.
Then end the day watching spectacular Florida Keys sunsets over the bay.
This is the laid-back Keys lifestyle people come back for year after year.
Thoughtful Guest Amenities
To help you settle in comfortably, we provide initial starter supplies, including:
Coffee
Paper towels
Basic toiletries for each guest
For longer stays, additional supplies can easily be purchased locally and are the responsibility of the guest.
Optional Private Dockage
Bringing your boat? Private dockage available upon request. Please inquire ahead of your stay to confirm availability and details. (Up to a 42 ft boat)
Why Guests Love This Home
✔ Private heated saltwater plunge pool with waterfalls
✔ Beautiful sunset views from the dock area
✔ Gated community with only 8 homes
✔ Walkable location to restaurants and nightlife
✔ Community pool and dock
✔ Optional private dockage for boaters
✔ Centrally located in Islamorada
✔ Perfect for fishing trips, couples, or family vacations
✔️ Decorating with fine art & noise canceling blinds and curtains for a restful night sleep Your Keys Adventure Starts Here
Whether you’re casting lines at sunrise, exploring the turquoise waters of the Keys, or enjoying sunset drinks on the balcony, Villa by the Bay delivers the authentic Islamorada experience.
Relax. Fish. Explore. Repeat.
Ready, set… book your unforgettable stay at Villa by the Bay today!
License #26-0059
Bring your heart, your family, and your fishing gear to Villa by the Bay, a charming island retreat tucked inside the quaint gated community of Coral Cove in the heart of Islamorada. With just eight homes in the community, this peaceful getaway offers the perfect blend of privacy, comfort, and easy access to everything that makes the Florida Keys unforgettable.
Whether you're planning a world-class fishing adventure, a relaxing family getaway, or a romantic escape, Villa by the Bay is your ideal home base.
Breathtaking Bayfront Sunsets
End every day the way island life was meant to be enjoyed—watching the sun melt into the bay from the dock area. Gentle ocean breezes and vibrant sunset colors create a relaxing atmosphere you’ll look forward to every evening.
A Fisherman’s Paradise
Islamorada is known as the “Sport Fishing Capital of the World,” and Villa by the Bay puts you right where you want to be.
Direct ocean access
Private dockage available (upon request & trailer parking offsite can give recommendations )
Easy access to deep-sea fishing, backcountry fishing, and sandbars
Perfect for bringing your own boat or chartering a local guide
Spend the day chasing sailfish, mahi, snapper, or tarpon, then return home to relax by the pool and relive the day’s best catches.
Private Heated Saltwater Plunge Pool
After a day on the water or exploring the Keys, unwind in your private heated saltwater plunge pool. The soothing waterfalls and tranquil sounds create a relaxing oasis perfect for evening cocktails, family time, or a quiet morning coffee.
Community Amenities
Coral Cove is a quiet gated enclave designed for peaceful island living. Guests enjoy access to:
Community swimming pool
Community dock with water and electricity
Gated privacy
Beautiful bay views throughout the property
With only eight homes, the atmosphere remains calm, welcoming, and uncrowded.
Walk to Islamorada’s Best Restaurants & Bars
One of the best parts of staying at Villa by the Bay is the central location. Many of Islamorada’s favorite spots are within walking distance.
Enjoy fresh seafood, tropical cocktails, and live music at nearby local favorites. Whether you're craving sunset dining, casual tiki bars, or a lively night out, it’s all just steps away.
No long drives—just pure island convenience.
Relaxed Island Living
Villa by the Bay was designed for easy, comfortable stays where you can truly unwind.
Wake up to warm tropical breezes.
Spend afternoons fishing, boating, snorkeling, or paddleboarding.
Return home for a refreshing swim in the plunge pool.
Then end the day watching spectacular Florida Keys sunsets over the bay.
This is the laid-back Keys lifestyle people come back for year after year.
Thoughtful Guest Amenities
To help you settle in comfortably, we provide initial starter supplies, including:
Coffee
Paper towels
Basic toiletries for each guest
For longer stays, additional supplies can easily be purchased locally and are the responsibility of the guest.
Optional Private Dockage
Bringing your boat? Private dockage available upon request. Please inquire ahead of your stay to confirm availability and details. (Up to a 42 ft boat)
Why Guests Love This Home
✔ Private heated saltwater plunge pool with waterfalls
✔ Beautiful sunset views from the dock area
✔ Gated community with only 8 homes
✔ Walkable location to restaurants and nightlife
✔ Community pool and dock
✔ Optional private dockage for boaters
✔ Centrally located in Islamorada
✔ Perfect for fishing trips, couples, or family vacations
✔️ Decorating with fine art & noise canceling blinds and curtains for a restful night sleep Your Keys Adventure Starts Here
Whether you’re casting lines at sunrise, exploring the turquoise waters of the Keys, or enjoying sunset drinks on the balcony, Villa by the Bay delivers the authentic Islamorada experience.
Relax. Fish. Explore. Repeat.
Ready, set… book your unforgettable stay at Villa by the Bay today!
License #26-0059
Amenities at Islamorada Florida Bay! Plunge Pool, Boat Dock, Sunset Views & Near fine dining
Non-smoking
Pets allowed
Family friendly
Map of Upper Matecumbe Key, FL
Ratings and reviews
10 / 10Outstanding·Jul 2026
My family and I had a wonderful week stay. The house was very clean upon arrival and was stocked with everything we would need. The location of the house was also great, central to all the restaurants and beach stores. We arrived by boat and the docking situation was easily accessible and smooth. The owners of the property quickly responded to any questions we had. Islamorada is our favorite Key and we will definitely be back!
10 / 10Outstanding·Jan 2024
The house was perfect for our family. We loved the layout and the pool in the back was perfect after a day on the water. Great location to everything in Islamorada. Hope to be back again soon.
8 / 10Excellent·May 2023
Great house, super friendly and responsive hosts. Boat dock gave great access to the bay and oceanfront was a short drive away. This unit is the first off of the highway, so it was a little noisier than preferred, but it is priced under the others in the complex. Would rent it again.
$$$$
Top rated by guests
9.4Outstanding
(4 Ratings)
"My family and I had a wonderful week stay. The house was very clean upon arrival and was stocked with everything we would need. The location of the house was also great, central to all the restaurants..."
Dana A.Don't miss out! Price and availability may change
