5

Cudjoe Key, FL Homes for Rent

Section Image
  • /8

    $5,500 Per Month

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

    22777 Jolly Roger Dr, Summerland Key, FL 33042

    Property Id: 1197908 Long term 12 month lease plus renewable. 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

    22777 Jolly Roger Dr, Summerland Key, FL 33042
  • /14

    $3,693 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,080 Sq Ft
    • Townhouse for Rent

    28508 Channel View Dr, Little Torch Key, FL 33042

    This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent.It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, stackable washer and dryer, hurricane windows and doors, two balconies, 2 heated and chilled community pools, gym, sauna, marina with boat ramp, outdoor games, bbq, kayaks and paddle

    Joseph Danieli AKT Realty LLC

    28508 Channel View Dr, Little Torch Key, FL 33042
  • /12

    $3,300 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    21076 Hamilton Ave, Summerland 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 water views. The property is conveniently located just seconds from the local marina. Please note that this is a duplex, so there are some shared outdoor/common areas while still offering your own private living space. Property Features: 3

    Halley Haack Coldwell Banker Schmitt RE Co.

    21076 Hamilton Ave, Summerland Key, FL 33042
  • /12

    $3,600 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 LoKation Real Estate

    142 Sawyer Dr, Summerland Key, FL 33042

Why Live in Cudjoe Key

Cudjoe Key, FL, is a small community known for its waterfront properties and unique attractions. The island, which began as a U.S. Air Force base in the late 1950s, features a mix of single-family homes and resort rentals, with much of the land remaining undeveloped. The National Key Deer Refuge, a 9,000-acre preserve, protects the endangered Key deer on the island. A notable feature is the aerostat site at the northern tip, where a large white blimp, nicknamed “Fat Albert,” hovers. Residential areas like Cutthroat Harbor Estates and Cudjoe Gardens offer stilt homes and canal-front properties, with prices ranging from $600,000 to over $3 million. The island lacks traditional parks, but residents enjoy water activities such as deep-sea diving, boating, and fishing. Bahia Honda State Park, located 15 miles away, provides additional outdoor recreation with its beach, hiking trails, and snorkeling sites. Dining options include Broil, a gourmet steakhouse, and The Bent Prop, known for its happy hour specials. For groceries, Murray’s Market is 2 miles away on Summerland Key, and a Winn-Dixie is 9 miles away on Big Pine Key. Students attend highly rated schools like Key West High School and Big Pine Academy. The Overseas Highway connects Cudjoe Key to Key West, 20 miles south, and Marathon, 30 miles north. Residents face high home and flood insurance premiums due to the island's susceptibility to hurricanes.

Frequently Asked Questions

How much does it cost to rent a home in Cudjoe Key, FL?
The median rent for a home in Cudjoe Key, FL is $4,550 per month, though prices vary by neighborhood, size, and property type. As of September 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 $182,000 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 $4,550 per month in Cudjoe Key, FL, renters typically need to show $13,650 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 19.8, 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.
What neighborhoods in Cudjoe Key, FL are best for renting a home?
The best neighborhood for renting in Cudjoe Key, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include New Town, Mid Town and Old Town, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
5
Median Rent
$4,550
Median Single Family Home Rent
$4,895
How to Rent a Home