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

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A spacious living area with a wooden ceiling, a bar with stools, and a large window offering a view of palm trees and the ocean.
A kitchen with wooden beams, a bar area with stools, and a dining area with a bed and window.
A bedroom with a large bed, a TV, a fireplace, and a balcony with a view of the ocean.
A waterfront property with multiple houses, a dock, and a swimming pool.
A modern kitchen with white cabinetry, granite countertops, and a central island.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Family fun awaits
    Top-rated for families.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Islamorada Brewery & Distillery
5 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Private pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a map
Islamorada, FL
  • Place, Islamorada Brewery & Distillery
    ‪7 min walk‬
  • Place, History of Diving Museum
    ‪10 min walk‬
  • Place, beach near Islamorada
    ‪12 min walk‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪47 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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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

Property # 189714vb
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 indicated that there is a carbon monoxide detector on the property
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Islamorada

Located in Matecumbe, a neighbourhood in Islamorada, this holiday home is near a water park and on the waterfront. 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. Consider Lorelei Restaurant & Cabana Bar for a night out or MoradaWay Arts & Cultural District if you're travelling with kids. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours.
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Map
Islamorada, FL

What's nearby

  • Islamorada Brewery & Distillery - 7 min walk - 0.7 km
  • History of Diving Museum - 10 min walk - 0.9 km
  • beach near Islamorada - 12 min walk - 1.1 km
  • Keys History & Discovery Center - 14 min walk - 1.2 km
  • Lorelei Restaurant & Cabana Bar - 16 min walk - 1.4 km

Getting around

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

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬15 min walk
  • ‪Hog Heaven - ‬5 min drive
  • ‪Lazy Days Restaurant - ‬5 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪Islamorada Fish Company - ‬3 min drive

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.

How much does it cost to stay at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!?

As of 19 Aug, 2026, prices found for a 1-night stay for 2 adults at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! on 15 Oct, 2026 start from S$13,759, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

No, pets are not allowed at this property.

How much is parking at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!?

On-site parking is available at the 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

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English
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