Entire home
OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada
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5 bedrooms3 bathroomsSleeps 10
Popular amenities
Explore the area

Islamorada, FL
- History of Diving Museum8 min walk
- Florida Keys Brewing Co.2 min drive
- Theater of the Sea3 min drive
- Marathon, FL (MTH-Florida Keys Marathon)40 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
2 Queen Beds
Bedroom 4
1 Queen Bed
Bedroom 5
2 Single Beds
3 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Spaces
Deck or patio
Garden
About this property
OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada
82754 Overseas Highway - OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering five bedrooms and three full baths on two living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully equipped kitchen with the dining room overlooking a lush private garden. The spacious living room features a natural "keystone" wall-framed fireplace with cypress mantle, a full wet bar, and separate bath, which also opens to the pool area.
The private, downstairs south wing offers three bedrooms and one full bath with a 5th bedroom off the kitchen. The 2nd level master bedroom suite with private vanity & master bath has its own fireplace & bayside veranda.
The downstairs sliding glass doors open to the bayfront pool & elevated deck with hot tub. There are multiple decks for sunbathing and spectacular sunset-viewing. The expansive dock with its own fish cleaning table wraps around the basin for boats, water toys, and great fishing fun! The beach offers a wade-in area for snorkeling in the bay or an easy launch for kayaks.
This vacation home is secluded yet situated in a perfect location for walking to restaurants & local shops! Sorry, no pets allowed.
VACATION RENTAL LICENSE: 24-0308 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.
If booking more than a year in advance current prices may not reflect annual cost of living increase.
Many of our guests’ re-book the same property on an annual basis. No reservation is confirmed until you speak with us.
Please note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.
The private, downstairs south wing offers three bedrooms and one full bath with a 5th bedroom off the kitchen. The 2nd level master bedroom suite with private vanity & master bath has its own fireplace & bayside veranda.
The downstairs sliding glass doors open to the bayfront pool & elevated deck with hot tub. There are multiple decks for sunbathing and spectacular sunset-viewing. The expansive dock with its own fish cleaning table wraps around the basin for boats, water toys, and great fishing fun! The beach offers a wade-in area for snorkeling in the bay or an easy launch for kayaks.
This vacation home is secluded yet situated in a perfect location for walking to restaurants & local shops! Sorry, no pets allowed.
VACATION RENTAL LICENSE: 24-0308 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.
If booking more than a year in advance current prices may not reflect annual cost of living increase.
Many of our guests’ re-book the same property on an annual basis. No reservation is confirmed until you speak with us.
Please note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.
Property manager
Freewheeler Vacations
Premier Host
Languages
English
Add dates for prices
Amenities
Pool
Washer
Dryer
Outdoor space
Fireplace
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House Rules
Check in after 3:00 PM
Minimum age to rent: 23
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 not indicated whether there is a smoke detector on the property
About the area
Islamorada
Located near the beach, 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 activities can be experienced at Islamorada Brewery & Distillery and Florida Keys Brewing Co.. Take the opportunity to explore the area for water adventures such as kayaking.

Islamorada, FL
What's nearby
- Islamorada Brewery & Distillery - 6 min walk - 0.5 km
- History of Diving Museum - 8 min walk - 0.7 km
- Florida Keys Brewing Co. - 2 min drive - 2.1 km
- Theater of the Sea - 3 min drive - 3.3 km
- Bud n' Mary's Dive Center - 4 min drive - 4.7 km
Getting around
Restaurants
- Lorelei Restaurant & Cabana Bar - 14 min walk
- Islamorada Fish Company - 2 min drive
- Wahoo's Bar & Grill - 2 min drive
- Green Turtle Inn - 3 min drive
- Florida Keys Brewing Co. - 2 min drive
Frequently asked questions
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About the host
Hosted by Freewheeler Vacations

Languages:
English
Premier Host
They consistently provide great experiences for their guests
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