House in Upper Matecumbe Key, FL
10 guests · 5 bedrooms · 3 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
OSPREY BAY VILLA – Your private bayfront escape in the heart of Islamorada, Florida Keys!
Relax and enjoy incredible panoramic bay and sunset views from this elegant yet casual "Old Keys Charm" home, designed for the perfect family or group getaway. With a heated pool, hot tub, and deep-water dock, you’ll experience the best of island living—whether you’re soaking up the sun, exploring by boat, or strolling to local restaurants and shops.
KEY FEATURES:
*5 bedrooms, sleeps 10–12 guests
- 2 king bedrooms (including master suite)
- 1 queen bedroom
- 2 bedrooms with 2 queen beds
* 3 full bathrooms
- Master bath with separate vanity room
- Full bath with bathtub + separate shower, double sinks
- Pool-level bath with shower + direct outdoor access
* Fully equipped gourmet kitchen with open dining room and atrium garden
* Spacious living room with coral rock fireplace + wet bar
* Second-level master suite with private bayfront veranda + fireplace
* Multiple sunning decks, heated pool, and hot tub
* Deep-water dock + boat basin (perfect for boating, snorkeling, kayaking & paddleboarding)
* Lush tropical landscaping + private sandy beach area for wading
* Incredible sunset views from expansive waterfront lawn and outdoor spaces
* Secluded yet walkable to iconic Islamorada restaurants and local shops
Come, Relax & Enjoy!
Your perfect Florida Keys vacation awaits.
Relax and enjoy incredible panoramic bay and sunset views from this elegant yet casual "Old Keys Charm" home, designed for the perfect family or group getaway. With a heated pool, hot tub, and deep-water dock, you’ll experience the best of island living—whether you’re soaking up the sun, exploring by boat, or strolling to local restaurants and shops.
KEY FEATURES:
*5 bedrooms, sleeps 10–12 guests
- 2 king bedrooms (including master suite)
- 1 queen bedroom
- 2 bedrooms with 2 queen beds
* 3 full bathrooms
- Master bath with separate vanity room
- Full bath with bathtub + separate shower, double sinks
- Pool-level bath with shower + direct outdoor access
* Fully equipped gourmet kitchen with open dining room and atrium garden
* Spacious living room with coral rock fireplace + wet bar
* Second-level master suite with private bayfront veranda + fireplace
* Multiple sunning decks, heated pool, and hot tub
* Deep-water dock + boat basin (perfect for boating, snorkeling, kayaking & paddleboarding)
* Lush tropical landscaping + private sandy beach area for wading
* Incredible sunset views from expansive waterfront lawn and outdoor spaces
* Secluded yet walkable to iconic Islamorada restaurants and local shops
Come, Relax & Enjoy!
Your perfect Florida Keys vacation awaits.
Amenities at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
Non-smoking
No pets allowed
Family friendly
Map of Upper Matecumbe Key, FL
Ratings and reviews
Summary of reviewsOutstanding waterfront property with spacious accommodations, well-equipped kitchen, stunning views, and a variety of activities including swimming, boating, fishing, and snorkeling. Excellent communication with the host and a truly memorable experience for families and friends. Highly recommended!
10 / 10Outstanding·Jul 2026
Perfect for our family of 8 adults two little children. Location was great, dock with power and water for our boat was very convenient. Communication with host was excellent. Would highly recommend!
10 / 10Outstanding·Jul 2026
We had a wonderful week at Osprey Bay! Judy was a great host and had much to offer in terms of boating/restaurant recommendations. Centrally located in Islamorada, all of the restaurant favorites are 10 minutes drive. The house is located down a long driveway, offering a great deal of privacy. Inside, everything you need is available and extremely clean. We enjoyed the beautiful pool and swimming from the dock. There is a school of parrotfish that live in and around the dock, along with occasional manatee sightings. The protected basin offers easy navigation while boating with multiple access points to the Atlantic. In every direction the water is always 4-10 feet deep with lots of seagrass and top to bottom visibility. We were able to reach Alligator Reef within 30 minutes from the backyard dock. Finally, you have a world class seat for each magnificent sunset.
10 / 10Outstanding·Jun 2026
This was a treat for our entire family. The boys fished from the dock. Our two grand boys frequented the pool. The kitchen is absolutely completely equipped. A cooks dream. Wonderful is the the only appropriate description.
10 / 10Outstanding·Jun 2026
We loved the layout and location of the house! It was perfect for our family vacation of 8. There was plenty of space! The pool and dock was private and lively.
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Top rated by guests
10Outstanding
(92 Ratings)
Outstanding waterfront property with spacious accommodations, well-equipped kitchen, stunning views, and a variety of activities including swimming, boating, fishing, and snorkeling. Excellent communication with the host and a truly memorable experie...
From real guest reviews summarized by AIDon't miss out! Price and availability may change
