22

Summerland 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

    $6,000 Per Month

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

    22777 Jolly Roger Dr, Summerland Key, FL 33042

    Property Id: 1197908Canal 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

    22777 Jolly Roger Dr, Summerland Key, FL 33042
  • /7

    $3,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    4166 Dorn Rd, Summerland Key, FL 33042

    Property Id: 2728964This Very Nice Home is available on a 28 day minimum term. 2 bedroom, 2 bath home in a quiet neighborhood with 60 Ft dock. Deep water access to gulf or Atlantic. Fully furnished. Please email, call or text questions if interested. Tours are not available.All excellent appliances, gas stove with convection/electric oven, and bait freezer downstairs.

    4166 Dorn Rd, Summerland Key, FL 33042
  • /18

    $3,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • House for Rent

    1635 Pandorea Ln, Big Pine Key, FL 33043

    Welcome to your ideal rental in Big Pine Key, Florida! This charming property offers a perfect environment for those seeking a peaceful lifestyle close to nature and conveniences.Key Property Features include a spacious living area designed for comfort, ensuring you have plenty of room to relax and entertain. Enjoy the benefit of central heating and air conditioning, complemented by

    1635 Pandorea Ln, Big Pine Key, FL 33043
  • /27

    $5,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,360 Sq Ft
    • House for Rent

    133 Indies Rd, Summerland Key, FL 33042

    Fully furnished and ready to live in, single story ocean access home in Breezeswept Beach Estates.Complete with fully remodeled kitchen, plates, utensils and appliances. Seating for 8 in a gourmet eat in kitchen. This home offers a split floorplan with complete privacy. RV parking with water, power and sewer hookups. 120' of canal frontage with concrete seawall, davits, and basin for

    Harold Viera Global Luxury Realty LLC

    133 Indies Rd, Summerland Key, FL 33042
  • /41

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 6,098 Sq Ft
    • House for Rent

    280 Airport Dr S, Summerland Key, FL 33042

    *** Private Airstrip *** Welcome to your slice of paradise in the Florida Keys! For aviation enthusiasts, the allure of this property is further enhanced by its location within a private airpark community (FD51 Summerland Key Airport). Nestled on a serene, clear wide canal with direct access to the Atlantic Ocean with no bridges, within a private airpark community, this home offers the

    Lisa Guirguis Genesis Realty Team

    280 Airport Dr S, Summerland Key, FL 33042
  • /81

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,443 Sq Ft
    • House for Rent

    441 La Fitte Rd, Summerland Key, FL 33042

    ** SHORT-TERM RENTAL ** Stunning open water house with high ceilings, open floor plan, covered screen porch, and open deck for the sun lovers! New deck with a heavy-duty boat lift in place (15,000 pounds) in one of the cleanest waters in the FL Keys! Metal roof, New A/C, Water Heater, and a Front aluminum fence with beautiful landscaping This home is located in one of the best neighborhoods in

    Carolina Gil Caralex Intl Realty Group Corp

    441 La Fitte Rd, Summerland Key, FL 33042
  • /49

    $5,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    3770 Park Ave, Big Pine Key, FL 33043

    Welcome to Caribbean Cove located in Big Pine Key. Located in the lower keys, 30 minutes from Key West. This stunning waterfront three bedroom/two bath home features an open floor plan, with a fully furnished living area and a modern kitchen. The kitchen is a culinary dream, equipped with stainless steel appliances and an oversized quartz island, surrounded by eight comfortable seats, perfect for

    Mary Jo Selden DomainRealty.com LLC

    3770 Park Ave, Big Pine Key, FL 33043
  • /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. Available starting Aug, 2027. 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
  • /19

    $4,500 Per Month

    • 2 Beds
    • 1 Bath
    • 884 Sq Ft
    • House for Rent

    27346 Martinique Ln, Summerland Key, FL 33042

    Welcome to your private slice of paradise in the Florida Keys. This fully remodeled, exquisitely furnished 2-bedroom, 1-bathroom waterfront home is a true island escape. Where turquoise waters, swaying palms, and golden sunsets become your everyday view. Enjoy direct ocean access from your private dock, no bridges to slow you down. Lounge by the heated pool, dine under the stars, and feel the

    Alicia Rufino Island Living Realty, LLC

    27346 Martinique Ln, Summerland Key, FL 33042
  • /15

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • House for Rent

    813 Hawksbill Ln, Summerland Key, FL 33042

    If you want to Rent a home with Canal View that leads to the Bay. This is your perfect home. Has a Lift and a great view from the second story Porch, Fishing is always near

    Miguel Riveron Douglas Elliman

    813 Hawksbill Ln, Summerland Key, FL 33042
  • /34

    $11,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,352 Sq Ft
    • House for Rent

    Unlisted Address

    **Exclusive Waterfront Luxury Home in Big Pine Key** (minimum 6 months, available Sept 1.)Experience the ultimate Florida Keys getaway in this newly built, four-level, all-concrete waterfront home in beautiful Big Pine Key. Designed with luxury and comfort in mind, this spacious and light-filled property features 4 bedrooms and 2.5 bathrooms, with custom, high-end finishes and top-of-the-line

    Unlisted Address
  • /13

    $6,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,418 Sq Ft
    • House for Rent

    1540 Lantana Ln, Big Pine Key, FL 33043

    Fishermans Dream House! Bring your boats to this beautiful canal front home in Big Pine Key. Secluded on a corner lot with 190 ft of seawall. Boat ramp is less than a mile away. Enjoy swimming in the pool, relaxing on the deck, cocktails at the outside bar, or meeting the adorable friendly Key Deer roaming the neighborhood .SLEEPS 8 PRICE WILL CHANGE NOV.1ST Call Andrea for bookings

    1540 Lantana Ln, Big Pine Key, FL 33043
  • /20

    $3,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • House for Rent

    3930 Gordon Rd, Big Pine Key, FL 33043

    BRAND NEW CONSTRUCTION.LONG-TERM RENTAL AVAILABLE NOW.Pets welcome!Let your clients be the first to live in this newly constructed home. This house has a large porch facing the canal, with over-dead fans to keep your family cool.This 1350 sq. ft. house is fully tiled throughout.The bedrooms and the closets are spacious, and the ceilings are 9 feet high throughout the

    Mark Peterson Mark F. Peterson Licensed Real Estate Broker

    3930 Gordon Rd, Big Pine Key, FL 33043
  • /49

    $5,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    3770 Park Ave, Big Pine Key, FL 33043

    Welcome to Caribbean Cove located in Big Pine Key. Located in the lower keys, 30 minutes from Key West. This stunning waterfront three bedroom/two bath home features an open floor plan, with a fully furnished living area and a modern kitchen. The kitchen is a culinary dream, equipped with stainless steel appliances and an oversized quartz island, surrounded by eight comfortable seats, perfect for

    Mary Jo Selden DomainRealty.com LLC

    3770 Park Ave, Big Pine Key, FL 33043
  • /13

    $6,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,418 Sq Ft
    • House for Rent

    1540 Lantana Ln, Big Pine Key, FL 33043

    Fishermans Dream House! Bring your boats to this beautiful canal front home in Big Pine Key. Secluded on a corner lot with 190 ft of seawall. Boat ramp is less than a mile away. Enjoy swimming in the pool, relaxing on the deck, cocktails at the outside bar, or meeting the adorable friendly Key Deer roaming the neighborhood .SLEEPS 8 PRICE WILL CHANGE NOV.1ST Call Andrea for bookings

    Andrea Lennon Vylla Home

    1540 Lantana Ln, Big Pine Key, FL 33043

Frequently Asked Questions

How much does it cost to rent a single-family home in Summerland Key, FL?
The median rent for a single-family home in Summerland Key, FL is $6,125 per month, though prices vary by neighborhood, size, and property type. As of July 2026, single-family homes tend to be the most affordable option.
How much do you need to make to afford rent in Summerland Key, FL?
To comfortably afford the median rent in Summerland Key, FL, a household needs to earn roughly $245,000 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 $6,125 per month in Summerland Key, FL, renters typically need to show $18,375 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 Summerland Key, FL?
In Summerland Key, FL, the price-to-rent ratio is 15.0, 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
22
Median Single Family Home Rent
$6,125
Median 3 Bedroom Single Family Home Rent
$7,500
How to Rent a Home