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US FL Monroe County Islamorada Vacation Rentals

2 Br Private Vacation Home Vacation Rental In Islamorada, Florida

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Experience the beauty of Islamorada in this 2BR upper-level with stunning water views.

Type Private vacation home
Bedrooms 2
Bathrooms 2
House Rules
  • Pets allowed: dogs less than 20 lbs per pet (limit one pet total)
  • Adults only
  • Smoking is not permitted
  • No events allowed
Max Occupancy 4
Host Language English
Property Id 4555932

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Little Bay Upper Level - 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. The Upper Duplex is a 1,500 sq ft unit with two bedrooms, two full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the Bay. Master bedroom: king and twin murphy bed. Guest bedroom: two twins. Living room: sofa sleeper

This unit comes equipped with central a/c and ceiling fans. The Upper Duplex shares with the other two units so there are loads of outdoor furniture and BBQ, 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! The Upper Duplex can be rented individually or in combination with the entire Little Bay Compound.

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.

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.

VR-24-0334 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.
Matecumbe, a neighborhood in Islamorada, is home to this vacation home. Hurricane Monument and Indian Key Historic State Park are local landmarks, 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.
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    Policy

    Pet policy

    • 1 total (up to 20 lbs per pet)
    • Pets allowed
    • Service animals are welcome, and are exempt from fees
    • Welcoming dogs only

    Check out time

    • 10:00 AM

    Check in policy

    • Check-in time starts at 3:00 pm
    • Minimum check-in age: 22

    Payment policy

    • Localcurrency: USD

    Check out policy

    • Check-out before 10:00 am

    Check in start time

    • 3:00 PM

    Check in instructions

    • Information provided by the property may be translated using automated translation tools
    • You will receive an email from the host with check-in and check-out instructions

    Special instructions

    • 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
    • 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
    • Onsite parties or group events are strictly prohibited
    • Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
    • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
    • This property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

    Children and extra bed policy

      • This property does not allow children.
    Amenities

    Popular amenities

    • Ac
    • Balcony
    • Barbecue
    • Dryer
    • Extra bed
    • Free parking
    • Internet
    • Kitchen
    • Laundry
    • Microwave
    • No smoking
    • Tv
    • Washer

    Property amenities

    • Pets:
      • 1 total (up to 20 lbs per pet)
      • Pet friendly
      • Welcoming dogs only
    • Dining:
      • Dining table
    • Safety:
      • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
      • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
    • Bedroom:
      • 2 bedrooms
      • Sofa bed
    • General:
      • Property does not allow children
    • Kitchen:
      • Coffee/tea maker
      • Cookware/dishes/utensils
      • Dishwasher
      • Microwave
      • Oven
      • Refrigerator
      • Stovetop
      • Toaster
    • Laundry:
      • Laundry facilities
      • Washing machine and dryer
    • Parking:
      • Onsite parking
    • Internet:
      • Free WiFi
    • Outdoors:
      • Balcony
      • Barbecue grill
      • Outdoor furniture
    • Bathrooms:
      • 2 bathrooms
      • Hair dryer
      • Shower
    • Langs Spoken:
      • English
    • Entertainment:
      • Smart TV
    • Climate Control:
      • Air conditioning
    • Suitability/accessibility:
      • Smoke-free property
 

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Updated on Jul 20, 2026

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