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Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!

Photo gallery for Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!

Pool
Outdoor dining
Living area
Room
Terrace/patio

Reviews

10 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 10488.2 sq m

Popular amenities

  • Parking available
  • Dryer
  • Air conditioning
  • Washer

Explore the area

View map
Islamorada, FL
  • Islamorada Brewery & Distillery
    ‪6 min walk‬
  • Florida Keys Brewing Co.
    ‪2 min drive‬
  • Theater of the Sea
    ‪4 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.

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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
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
No Jet Skis, Wave Runners, or Ultra Light Gliders are Allowed. No RV's and/or Motor Homes are Allowed.
Property must be booked Saturday to Saturday for a minimum of 7 nights, otherwise we cannot accept the booking.

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.
Map
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

  • Marathon, FL (MTH-Florida Keys Marathon) - 40 min drive

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

Does Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!?

Check-in begins at 4:00 PM.

What time is check-out at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!?

Checkout is at 10:00 AM.

Where is Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! located?

This family-friendly Islamorada holiday home is located on the waterfront, within a 10-minute walk of History of Diving Museum and Islamorada Brewery & Distillery. Keys History & Discovery Center and Matecumbe United Methodist Church are also within 1 mile (2 km).

About the host

Hosted by Judy Moeller

Host profile image

Why they chose this property

What makes this property unique

Languages:

English