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
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·May 2026
Wonderful property!!!
10 / 10Outstanding·Mar 2026
Everything was wonderful! Our family really enjoyed our stay. The house is very well equipped with everything you need. The beds are comfortable, the pool is huge, the waterfront view is amazing and the dock on the water was really nice.
10 / 10Outstanding·Feb 2026
We had a wonderful stay at Osprey Bay Villa in Islamorada from February 4th–11th. The villa was clean, comfortable, and in a perfect location for enjoying the Keys.We especially loved the pool and hot tub — both were spotless and so relaxing. The sunsets were absolutely beautiful and made each evening feel special. The property had everything we needed and felt like a true home away from home....but with better weather and views!!!!Host Judy was wonderful and very responsive.We would definitely stay here again and highly recommend it for a relaxing Islamorada getaway.
10 / 10Outstanding·Feb 2026
We had a wonderful stay. All is as described. Host is responsive and quick with communication. Will stay again
$$$$
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
