Bay Side Vacation Rentals Florida Keys

  • Nautica $20,000 / monthly

    Nautica

    $20,000 / monthly

    Mile Marker 83. Four bedroom/four bath. Sleeps 8-10. Bayfront, pool, dockage.  

    4 beds 4 baths
    4 beds 4 baths
  • Osprey Bay $5,700-$6,500 Weekly

    Osprey Bay

    $5,700-$6,500 Weekly

    Mile Marker 82.7, 5 bedrooms, 3 baths, sleeps 10-12, dockage, pool, spa, and beautiful sunsets. Located in heart of Islamorada. VR-171  

    5 beds 3 baths
    5 beds 3 baths
  • Bayview Villas $4,600 - $5,600 weekly

    Bayview Villas

    $4,600 - $5,600 weekly

    3 Bedrooms & 3.5 bathrooms Villas 7-9 $3,960 – $7,000 Weekly depending on dates   Mile Marker 81.6 — Bayside Villas   Bayview Villas are named because they are… bayside! The closest villas to the pool, water and dockage, these villas are a set of…

    3 beds 3.5 baths
    3 beds 3.5 baths
  • Key Lime Villas $3,600 - $4,200 / weekly

    Key Lime Villas

    $3,600 - $4,200 / weekly

    3 Bedrooms & 3.5 bathrooms Villas 1-3 $3,300 – $3,850 Weekly depending on dates Mile Marker 81.6 — Bayside Villas   Key Lime Villas, aptly named for the famous Key’s citrus fruit, are a set of three brand new villas located in the heart of…

    3 beds 3.5 baths
    3 beds 3.5 baths
  • Conch Villas $3,600 - $4,200 Weekly

    Conch Villas

    $3,600 - $4,200 Weekly

    3 Bedrooms & 3.5 bathrooms Villas 4-6 $3,600 – $4,200 Weekly depending on dates Mile Marker 81.6 — Bayside Villas Conch Villas, aptly named for the famous large snails that inspired the Keys to be called the ‘Conch Republic,’ are a set of three brand…

    3 beds 3.5 baths
    3 beds 3.5 baths
  • Virga Limbo $17,000 / monthly

    Virga Limbo

    $17,000 / monthly

    MM 76. Five bedrooms/four baths. Charming bay front home. Hammocks, outdoor bar, and dockage all with views of uninhabited islands that dot the Keys. Sorry, no pets.  

    5 beds 4 baths
    5 beds 4 baths
  • Sunset Dream $12,000 / monthly

    Sunset Dream

    $12,000 / monthly

    Mile Marker 83. Five bedroom/four bath. Bayfront, pool and dockage.  

    5 beds 4 baths
    5 beds 4 baths
  • Little Bay Cottage $2,500 weekly

    Little Bay Cottage

    $2,500 weekly

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

    1 bed 2 baths
    1 bed 2 baths
  • Little Bay $2,500 weekly/unit

    Little Bay

    $2,500 weekly/unit

    Mile Marker 82, duplex (up and downstairs). Each unit has 2 bedrooms, 1.5 bath, sleeps 6, basin, dockage, snorkeling. Vacation Rental License #VR-084, & 85.    

    2 beds 1.5 baths
    2 beds 1.5 baths
  • Futura Yacht Club #403 $1,400 / Week, $1,600 Holidays

    Futura Yacht Club #403

    $1,400 / Week, $1,600 Holidays

    MM 88.5. 2 bedroom, 2 baths, sleeps 4. 4th Floor. King in master w/ 2 twins in guest. Heated pool, screened Lanai, tennis courts, basketball and volleyball courts. Optional dock for boats up to 33′. Beautiful sunsets. #VR-17

    2 beds 2 baths
    2 beds 2 baths
  • Treehouse $5,000 / monthly

    Treehouse

    $5,000 / monthly

    Mile Marker 96, 1 bedroom, 1 bath, sleeps 4, dock, beach, and sunsets.  

    1 bed 1 bath
    1 bed 1 bath
  • Captains Quarters- 4 Plex $1,250 weekly - $4,750 monthly

    Captains Quarters- 4 Plex

    $1,250 weekly - $4,750 monthly

    Mile Marker 81. Two bedroom/one bath $1,450 weekly, $4,750 monthly One bedroom/one bath $1,250 weekly, $3,500 monthly Sleeps 4-6. Dockage, Wireless Internet, New A/C. #VR-127 & #VR-128  

    2 beds 1 bath
    2 beds 1 bath
  • Futura Yacht club #302 $1,400 weekly, $1,600 Holidays

    Futura Yacht club #302

    $1,400 weekly, $1,600 Holidays

    MM 88.5. 2 bedrooms, 2 baths, sleeps 4. 3rd floor. King in master W/ queen size bed in guest. Heated pool, beautiful sunsets, and lit tennis, basketball, and volleyball courts. Optional deeded dock for boats. #VR-178

    2 beds 2 baths
    2 beds 2 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.

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