6

Cudjoe Key, FL Houses for Rent

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  • /70

    $12,500 Per Month

    • 4 Beds
    • 4 Baths
    • 2,952 Sq Ft
    • House for Rent

    21640 Overseas Hwy, Summerland Key, FL 33042

    Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    21640 Overseas Hwy, Summerland Key, FL 33042
  • /8

    $5,750 Per Month

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • House for Rent

    22777 Jolly Roger Dr, Summerland Key, FL 33042

    Property Id: 1197908 Canal front pool home with a double fenced in lot. Enough room for all your boats and toys. Large saltwater pool perfect for soaking up the sun and enjoying a peaceful afternoon. The split layout provides privacy with your own separate areas to unwind. Bring your 4 legged family members. Bonus room could be the 4th bedroom or office. Large AC storage area or workshop and

    22777 Jolly Roger Dr, Summerland Key, FL 33042
  • /16

    $4,750 Per Month

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • House for Rent

    22961 John Avery Ln, Summerland Key, FL 33042

    Florida Keys Boater's pardise now available for rent! 2 bedrooms 2 bathrooms with direct ocean access, boat slift, double jetski lifts, RV hook up, shore power, fish cleaning station. Just Bring your toys! One year lease minimun. This beautiful home is also available for sale. Call listing agent for questions.

    Rayden Vega Casa Miami Real Estate

    22961 John Avery Ln, Summerland Key, FL 33042
  • /17

    $4,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • House for Rent

    22860 Blackbeard Ln, Cudjoe Key, FL 33042

    Enjoy the Florida Keys lifestyle in this beautifully upgraded 3-bedroom, 2-bathroom canal front home, now available for long-term rental in the highly desirable community of Cudjoe Key. Situated on a quiet dead-end street, this home offers privacy and minimal traffic, making it an ideal retreat.Boaters will appreciate the 10,000-pound boat lift, commercial ice maker downstairs, and quick,

    Maria Sanchez LoKation Real Estate

    22860 Blackbeard Ln, Cudjoe Key, FL 33042
  • /12

    $3,700 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    21074 Hamilton Ave, Cudjoe Key, FL 33042

    Enjoy the Florida Keys lifestyle in this spacious 3 bedroom, 2 bath waterfront duplex located in the desirable Cudjoe Gardens community. Step outside and enjoy dock space with direct boating access, making it easy to spend your days on the water. The property is conveniently located just seconds from the local marina.Please note that this is a duplex, so there are some shared

    Halley Haack Coldwell Banker Schmitt RE Co.

    21074 Hamilton Ave, Cudjoe Key, FL 33042
  • /19

    $11,600 Per Month

    • 5 Beds
    • 3 Baths
    • 2,528 Sq Ft
    • House for Rent

    142 Sawyer Dr, Summerland Key, FL 33042

    Welcome to Paradise!Enjoy this beautiful 5-bedroom, 3-bathroom waterfront rental featuring 120 feet of private dockage--perfect for boating enthusiasts and families alike. Shore power would be an additional charge.This fully furnished home is move-in ready and offers everything you need for a comfortable and relaxing stay. Whether you're planning a vacation getaway or an extended

    Tracey Petrusha Venture Realty Group

    142 Sawyer Dr, Summerland Key, FL 33042

Frequently Asked Questions

How much does it cost to rent a single-family home in Cudjoe Key, FL?
The median rent for a single-family home in Cudjoe Key, FL is $4,895 per month, though prices vary by neighborhood, size, and property type. As of August 2026, single-family homes tend to be the most affordable option.
How much do you need to make to afford rent in Cudjoe Key, FL?
To comfortably afford the median rent in Cudjoe Key, FL, a household needs to earn roughly $195,800 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $4,895 per month in Cudjoe Key, FL, renters typically need to show $14,685 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Cudjoe Key, FL?
In Cudjoe Key, FL, the price-to-rent ratio is 17.3, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Home Trends

Number of Houses for Rent
6
Median Single Family Home Rent
$4,895
Median 3 Bedroom Single Family Home Rent
$4,895
How to Rent a Home