Bay Side Vacation Rentals Florida Keys

Happy Ours $30,000 / monthly

Happy Ours

$30,000 / monthly

Mile Marker 74.5 – Open Bayfront Six Bedroom/ Six Bath Ultra-Luxurious, Open water front estate with more than 5,000 square feet under air and 4,500 of covered terraces and deck.  Walk out the back door to the world famous Port Antigua gated community beach!  The…

6 beds 6 baths

Contact for more details, Located at mile market 81 and convenient to all properties!  305-664-3333   $900 a week for boats up to 27 feet. $1,400 a week  for boats up to 40 feet. Must arrange ahead of arrival and fill out paperwork.

Coral Cove, Islamorada, Florida Keys $6,000 weekly Call for Holiday Rates

Coral Cove, Islamorada, Florida Keys

$6,000 weekly Call for Holiday Rates

MM 81.5.  BRAND NEW construction located in the Heart of Islamorada!  Coral Cove is a gated, secluded and intimate community of 8 homes on the Florida Bay.   Featuring both a private pool in the back, and a community pool on the bay, Coral Cove…

3 beds 3.5 baths

Fantasy Point Villa $25,000 / monthly

Fantasy Point Villa

$25,000 / monthly

Mile Marker 73 – Bayfront observation pier / Boat basin dockage   Four bedroom/ four bath home located on a bay front parcel with fantastic protected boat basin dockage.  Best of both worlds!  Dock multiple boats in your protected boat basin steps from the villa,…

4 beds 4 baths

Osprey Bay $7,700-$8,700 Weekly

Osprey Bay

$7,700-$8,700 Weekly

Mile Marker 82.7 – Bayfront A quaint 5 bedroom home bay-front with some of the best sunsets in the Florida Keys!  Fully equipped home with heated pool, dockage, and large spacious living quarters.  Located in heart of Islamorada. 5 bedrooms, 3 baths, sleeps 10-12, dockage,…

5 beds 3 baths

Gulfview $13,000-$15,000 Monthly Call for holiday rates


$13,000-$15,000 Monthly Call for holiday rates

The private home features 3 modern bedrooms and 2 updated baths and sleeps 6 adults.  The master bedroom features a king size bed and stunning bay and sunset views.  Two guest bedrooms, one with a king bed and one with a queen bed makes this house ideal for friends or family.  An additional bunk room with a bunk and day bed provides plenty of room for accompanying children.  

3 beds 2 baths

Conch Villa @ Little Basin Villa $4,360 - $5,100 Weekly, Call for holidays

Conch Villa @ Little Basin Villa

$4,360 - $5,100 Weekly, Call for holidays

3 Bedrooms & 3.5 bathrooms Villa 6 $3,600 – $4,200 Weekly depending on dates Mile Marker 81.6 — Conch Villa Conch Villa, aptly named for the famous large snails that inspired the Keys to be called the ‘Conch Republic,’ is located in the heart of…

3 beds 3.5 baths

Little Bay $3,000 weekly/unit

Little Bay

$3,000 weekly/unit

Mile Marker 82 – Bayfront Multiple units available, including the Duplex (up and downstairs).  Located bayside, Little Bay has some of the best sunsets in Islamorada.   Great dockage, wildlife, and snorkeling makes this property even more beautiful. Each unit has 2 bedrooms, 1.5 bath, sleeps…

2 beds 2 baths

Little Bay Cottage $3,000 weekly

Little Bay Cottage

$3,000 weekly

Mile Marker 82 – Bayside One bedroom/two bath with Florida room. Newly remodeled. Vacation Rental License #VR-086.  

1 bed 2 baths

Nautica $20,000 / monthly


$20,000 / monthly

Mile Marker 83 – Bayfront Welcome to your dream waterfront rental home in Islamorada, located in the heart of the Florida Keys. This stunning 4 bedroom, 4 bathroom home sits on the bay and offers breathtaking views of the water and world class sunsets.  …

4 beds 4 baths

Reservation Procedure

A 30% security deposit is required along with the rental agreement and application within 24 hours to insure your booking.  The security deposit is payable by credit card.  A $75.00 reservation fee, cleaning fee and 12.5% sales and county tax are additional to the rental amount.  The balance due is payable by check or wire transfer within 90 days prior to check in  Cancellations will be refunded in full 90 days prior to check in.  The 30% security deposit will be refunded within 30 days after your departure if the property is found in satisfactory condition.  


Please be advised that during the event of a hurricane, your deposit is fully refundable without penalty. You may also use your deposit toward a future rental at a different date.


Status of properties and prices are subject to change. If owner changes status of property, a substitution will be made or refund given. Check-in is 4 PM. Check-out is 10 AM.

Contact Us


    Amenities Desired / Comments


    Subscribe to our newsletter

    Stay up to date