House in Upper Matecumbe Key, FL
8 guests · 4 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Remarkable home nestled in the heart of Islamorada where you will find large outdoor spaces with outdoor dining and private lounge areas with private salt water pool and outdoor kitchen. Spacious interior with large open kitchen including convection oven, wine fridge and large island with seating area, living room with comfortable large sofa, smart TV and separate dining. Occupies 8. One Spacious bedroom with on suite and large shower downstairs and three upstairs. Master Bedroom upstairs boasts a large master bath spectacularly designed with large wet bath featuring a shower and floating bathtub for soaking in a spa like setting. Sleep in luxury with comfy linens and blackout curtains in all bedrooms all with smart TV’s, king size beds on 3 of them and 1 with 2 full size beds. Extensive upstairs terrace with access from the master bedroom and guest bedroom includes a sitting area to take in the wonderful night breezes and extraordinary sunset views. Quiet street and private beach next to the luxurious Cheeca Lodge. Walk to many restaurants and shops, close to water activities, marinas, Founders park, and wonderful cafes and shops. Supermarket nearby, golf cart rentals, bike rentals and kayaks. Show your reservation for free entry to Founders Park offering pickle ball, beach, kids playground and lots more.
OCEANSIDE IS A NEW DEVELOPED COMMUNITY AND THERE IS SOME TEMPORARY CONSTRUCTION ONGOING ON THE LAST TWO HOMES CLOSEST TO BEACH CONFINED TO SPECIFIC AREAS BUT THERE IS NO ACCESS TO BEACH/PIER CURRENTLY. DURING THIS TIME WE ARE OFFERING GUESTS PASSES TO THE ISLANDER RESORT STEPS FROM OUR PROPERTY. PLEASE INQUIRE WITH HOST. APOLOGIZE FOR THIS TEMPORARY INCONVENIENCE AND REST ASSURED IT WILL NOT AFFECT YOUR VACATION EXPERIENCE.
Visit Islamorada Chamber of Commerce website for calendar and list of local events.
https://islamoradachamber.com/
Notable residents of Islamorada:
Include Miguel Cabrera, Gene Hackman, Jimmy Johnson, and Ted Williams. If you think the area looks familiar, you may recognize it from the Netflix TV Series BLOODLINE which was filmed in Islamorada.
Islamorada is known as the Sport-Fishing Capital of the World. And recently the island was named one of the 17 most romantic destinations in the U.S.
If you are interested in golf carts this is their site islamoradaluxurycarts.com 305-394-5350 for rentals, let them know we sent you. There is also a Freebee transportation .You can download it in the App Store to get you around for free.
There are also bike and kayak rentals nearby as well as fishing charters, boat tours, tiki tours, water sports, etc. All info is in the welcome binder in the house.
OCEANSIDE IS A NEW DEVELOPED COMMUNITY AND THERE IS SOME TEMPORARY CONSTRUCTION ONGOING ON THE LAST TWO HOMES CLOSEST TO BEACH CONFINED TO SPECIFIC AREAS BUT THERE IS NO ACCESS TO BEACH/PIER CURRENTLY. DURING THIS TIME WE ARE OFFERING GUESTS PASSES TO THE ISLANDER RESORT STEPS FROM OUR PROPERTY. PLEASE INQUIRE WITH HOST. APOLOGIZE FOR THIS TEMPORARY INCONVENIENCE AND REST ASSURED IT WILL NOT AFFECT YOUR VACATION EXPERIENCE.
Visit Islamorada Chamber of Commerce website for calendar and list of local events.
https://islamoradachamber.com/
Notable residents of Islamorada:
Include Miguel Cabrera, Gene Hackman, Jimmy Johnson, and Ted Williams. If you think the area looks familiar, you may recognize it from the Netflix TV Series BLOODLINE which was filmed in Islamorada.
Islamorada is known as the Sport-Fishing Capital of the World. And recently the island was named one of the 17 most romantic destinations in the U.S.
If you are interested in golf carts this is their site islamoradaluxurycarts.com 305-394-5350 for rentals, let them know we sent you. There is also a Freebee transportation .You can download it in the App Store to get you around for free.
There are also bike and kayak rentals nearby as well as fishing charters, boat tours, tiki tours, water sports, etc. All info is in the welcome binder in the house.
Amenities
Non-smoking
No pets allowed
Family friendly
Map of Upper Matecumbe Key, FL
Ratings and reviews
10 / 10Outstanding·Apr 2026
We had the absolute best stay. Gorgeous home, and Ana was so awesome to work with. We cannot wait to go back.
10 / 10Outstanding·Jan 2026
This home is beautiful and impeccable with all the necessary amenities. Each bedroom has its own bathroom, and two of the bedrooms have access to a lovely balcony. Ani was very accommodating.
10 / 10Outstanding·Aug 2025
Great location! Very close to Robbie's and Lorelei's marinas where we booked our fishing charters, an eco tour, glass-bottom boat tour and a sunset cruise. Lots of restaurants and a Publix for groceries within a 5-10 minute drive. The house has a very spacious area for gathering inside. The kitchen layout is great. Using the induction cooktop was a bit of a learning curve, but we cooked at least one meal a day there and enjoyed having the gas grill outside. The bedrooms and bathrooms were top-notch, and everything was very clean. We spent several afternoons relaxing in the pool. Ana was an attentive host and even offered to assist in booking fishing or a golf cart rental if we needed it. She also checked in the night before our departure to see if we would like a late check-out time.
10 / 10Outstanding·Apr 2025
Loved this property. Excellent location in a wonderful town close to fishing, great food and an arts festival The property was as described and fully stocked with everything you could think of Our little ones loved pool onsite too We will be back!!
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Top rated by guests
10Outstanding
(6 Ratings)
"We had the absolute best stay. Gorgeous home, and Ana was so awesome to work with. We cannot wait to go back. "
Colleen S.Don't miss out! Price and availability may change
