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Little Bay Upper - Image 1
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Islamorada, Florida

Little Bay Upper

2 bedrooms4 beds2 baths4 guests

Welcome to Little Bay!

Offering panoramic views and world famous sunsets, Little Bay is a hidden waterfront gem on the Florida Bay located at MM 82, in the heart of Islamorada. This secluded and intimate property offers three homes independent of each other on the same gated property. Situated among lush tropical landscaping on 1-acre, this slice of paradise is perfect for large families, reunions and even weddings. 

The shared common area offers complimentary boat dockage with power and fresh water, an array of lounge furniture for both shade and sun loving guests, BBQ grills, filet table, hammocks, chickee hut, and much more.

Little Bay Upstairs: 2 bedrooms & 2 baths with a large porch overlooking the beautiful Florida Bay. Full kitchen, laundry, and family room offers plenty of space! Little Bay Upstairs can accomodate up to 4 guests.

Please contact Coastal Vacation Rentals of the Florida Keys for pricing on stays less than 7 nights. 

Instant quote prices and calendar availability is subject to change without notice and is not guaranteed. Please contact Coastal Vacation Rentals of the Florida Keys to speak to one our our associates to confirm pricing and availability.

Love Little Bay but your dates are not available? There are three cottages on this property! Give us a call and we will be more than happy to assist you in your Florida Keys vacation home search.

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (excl. fees and taxes)AvailabilityMin Stay (nights)
Nov 12, 2026$429Not Available7
Nov 13, 2026$429Not Available7
Nov 14, 2026$429Available7
Nov 15, 2026$429Available7
Nov 16, 2026$429Available7
Nov 17, 2026$429Available7
Nov 18, 2026$429Available7
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Nov 23, 2026$429Not Available7
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Nov 26, 2026$429Not Available7
Nov 27, 2026$429Not Available7
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Nov 30, 2026$429Available7
Dec 1, 2026$429Available7
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Dec 22, 2026$429Not Available7
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Jan 1, 2027$429Not Available7
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Feb 1, 2027$429Not Available7
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What this home offers

BBQ Area
Air conditioning
Bathtub
Bed linens
TV

Where you’ll be

Islamorada, Florida, 33036, United States

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Check-in & check-out

Check-in after 4:00 PM.

Check-out before 10:00 AM.

Property rules

Children welcome (2–12 years).

Infants welcome (under 2).

Maximum 4 guests.

No pets allowed.

No parties or events.

Cancellation policy

Add your trip dates to get the cancellation details for this stay.