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Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
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Reviews
10 out of 10
Exceptional
5 bedrooms 3 bathrooms Sleeps 10 488.2 sq m
Popular amenities
Explore the area

Islamorada, FL
- Islamorada Brewery & Distillery6 min walk
- Florida Keys Brewing Co.2 min drive
- Theater of the Sea4 min drive
- Marathon, FL (MTH-Florida Keys Marathon)52 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Double Beds
Bedroom 4
1 Queen Bed
Bedroom 5
2 Double Beds
3 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area
About this property
Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
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.
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
We should mention
A car is required for transport to and from this property
About the area
Islamorada
Located on the waterfront, this holiday home is in Matecumbe, a neighbourhood in Islamorada. History of Diving Museum and Keys History & Discovery Center are cultural highlights, and some of the area's landmarks include Hurricane Monument and Indian Key Historic State Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Islamorada, FL
What's nearby
- Islamorada Brewery & Distillery - 6 min walk - 0.6 km
- Florida Keys Brewing Co. - 2 min drive - 2.3 km
- Windley Key Fossil Reef Geological State Park - 4 min drive - 4.0 km
- Theater of the Sea - 4 min drive - 4.3 km
- Bud n' Mary's Dive Center - 6 min drive - 5.7 km
Getting around
Restaurants
- Lorelei Restaurant & Cabana Bar - 15 min walk
- Florida Keys Brewing Co. - 2 min drive
- Wendy's - 11 min walk
- Whale Harbor Restaurant Marina - 2 min drive
- The Trading Post - 18 min walk
Frequently asked questions
About the host
Hosted by Judy Moeller

Why they chose this property
What makes this property unique
Languages:
English
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