House in Upper Matecumbe Key, FL
10 guests · 5 bedrooms · 6 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
Little Bay Compound - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people.
The Upper & Lower Duplex are each 1,500 sq ft units, each with two bedrooms, two full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the bay. Each unit accommodates 6 people (upper master bedroom: king and twin murphy, Guest bedroom: two twins, sofa sleeper) (lower master bedroom: queen and twin murphy, guest bedroom: two twins, sofa sleeper)
The Cottage is a bright and airy 1,250 sq ft unit with a huge master bedroom (king & sofa bed), 2nd sunroom with sofa bed and twin murphy bed, two full baths, laundry room, and combined family room, kitchen, & great room. The Cottage accommodates 6 people.
All units come equipped with central a/c and ceiling fans, loads of outdoor furniture and BBQs for each unit, large private boat basin with 12' X 25' Chickee hut and 12' X 25' Pergola, bait prep station, freshwater shower and power on the dock. The spacious front yard is enhanced by Tropical Landscaping and offers a large circular driveway with plenty of parking for cars and trailers. Located in the heart of Islamorada within walking distance to water & land activities, restaurants, shops, and more!
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.
VR#- 24-0336, 24-0334, 24-0335 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.
The Upper & Lower Duplex are each 1,500 sq ft units, each with two bedrooms, two full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the bay. Each unit accommodates 6 people (upper master bedroom: king and twin murphy, Guest bedroom: two twins, sofa sleeper) (lower master bedroom: queen and twin murphy, guest bedroom: two twins, sofa sleeper)
The Cottage is a bright and airy 1,250 sq ft unit with a huge master bedroom (king & sofa bed), 2nd sunroom with sofa bed and twin murphy bed, two full baths, laundry room, and combined family room, kitchen, & great room. The Cottage accommodates 6 people.
All units come equipped with central a/c and ceiling fans, loads of outdoor furniture and BBQs for each unit, large private boat basin with 12' X 25' Chickee hut and 12' X 25' Pergola, bait prep station, freshwater shower and power on the dock. The spacious front yard is enhanced by Tropical Landscaping and offers a large circular driveway with plenty of parking for cars and trailers. Located in the heart of Islamorada within walking distance to water & land activities, restaurants, shops, and more!
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.
VR#- 24-0336, 24-0334, 24-0335 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.
Amenities
Non-smoking
Pets allowed
Map of Upper Matecumbe Key, FL
Ratings and reviews
Summary of reviewsBeautifully situated property with stunning bay views, ideal for groups. Convenient location near restaurants and grocery store. Perfect backyard for swimming and water activities. Guests excited to return!
10 / 10Outstanding·Jul 2025
We had 5 families of friends and all our kids stay here for a week and it was fantastic. We brought 3 boats which we were able to keep on property. The fishing was great and the sunsets were absolutely amazing. During the stay there were some issues with the AC and a tree fell in the driveway. But the management company has maintenance staff on site within a ln hour and everything was fixed quickly. 10 out of 10 would book this again.
10 / 10Outstanding·Dec 2020
We were a group of 9 adults who rented the entire compound for Christmas week. The property is stunning! It is beautifully situated with bay views and was ideal for our group,. We ate at several of the neighborhood restaurants and thoroughly enjoyed our meals. The property is situated close to Publix for groceries and is within walking distance of several restaurants. The only suggestion I have is to replace some of the bed linens and pillows which are showing signs of wear and tear. All of our guests had a bed to sleep in, but we did have an overnight guest who required use of a pull out couch and the mattress was very thin. All said, we would definitely return to this property in the future!
10 / 10Outstanding·Dec 2020
This place was amazing and we will be back for sure!
10 / 10Outstanding·Aug 2020
Location was perfect, boats fit perfectly, backyard was PERFECT. We had everything we needed and more, we able to swim, snorkel, paddle board right off the dock. I already booked for next year!
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Top rated by guests
10Outstanding
(5 Ratings)
Beautifully situated property with stunning bay views, ideal for groups. Convenient location near restaurants and grocery store. Perfect backyard for swimming and water activities. Guests excited to return!
From real guest reviews summarized by AIDon't miss out! Price and availability may change
