A rare find — relax in the peaceful, private garden space.
Discover nearby landmarks
Close to Islamorada Brewery & Distillery
5 bedrooms3 bathroomsSleeps 10
Popular amenities
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue
Explore the area
Islamorada, FL
Islamorada Brewery & Distillery
Place, Islamorada Brewery & Distillery
6 min walk
History of Diving Museum
Place, History of Diving Museum
9 min walk
Keys History & Discovery Center
Place, Keys History & Discovery Center
12 min walk
Marathon, FL (MTH-Florida Keys Marathon)
Airport, Marathon, FL (MTH-Florida Keys Marathon)
46 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
Toilet · Shower only
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Balcony
Separate dining area
Garden
Dining area
About this property
Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests.
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.
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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 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
Matecumbe, a neighbourhood in Islamorada, is home to this holiday home. 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.. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven. With snorkelling, fishing and swimming nearby, you'll find plenty of adventures in the water.
Islamorada Brewery & Distillery - 6 min walk - 0.6 km
History of Diving Museum - 9 min walk - 0.8 km
beach near Islamorada - 11 min walk - 0.9 km
Keys History & Discovery Center - 12 min walk - 1.1 km
Florida Keys Brewing Co. - 2 min drive - 2.4 km
Getting around
Marathon, FL (MTH-Florida Keys Marathon) - 40 min drive
Restaurants
Wahoo's Bar & Grill - 2 min drive
Lorelei Restaurant & Cabana Bar - 14 min walk
Wendy's - 10 min walk
Islamorada Fish Company - 2 min drive
Bayside Gourmet of Islamorada - 1 min walk
Frequently asked questions
Does Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests. have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests.?
As of 16 June 2026, prices found for a 1-night stay for 2 adults at Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests. on 3 October 2026 start from NZ$2,598, 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 Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests. pet-friendly?
No, pets are not allowed at this property.
How much is parking at Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests.?
On-site parking is available at the property.
What time is check-in at Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests.?
Check-in begins at 3:00 PM.
What time is check-out at Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests.?
Checkout is at 10:00 AM.
Where is Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests. located?
Located in Matecumbe, this holiday home is within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum. Lorelei Restaurant & Cabana Bar and Keys History & Discovery Center are also within 15 minutes.
About the host
Hosted by Freewheeler Vacations
Languages:
English
Premier Host
They consistently provide great experiences for their guests