29

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

    $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
  • /18

    $3,250 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
  • /14

    $3,500 Per Month

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

    3693 Landers St, Big Pine Key, FL 33043

    Property Id: 2514237 Annual Canal-Front Rental on Big Pine Key! Utilities not included. This charming 2-bedroom, 2-bath home sits on a desirable corner lot with water access, offering a relaxed island lifestyle. Enjoy peaceful views. House is on a corner cana. Nice screened-in back porch with sliding doors to living and dining areas.—perfect for morning coffee or evening unwinding. Open

    3693 Landers St, Big Pine Key, FL 33043
  • /41

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,068 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 your vacation rental! 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

    Lisa Guirguis Genesis Realty Team

    280 Airport Dr S, Summerland Key, FL 33042
  • /20

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    1540 Lantana Ln, Big Pine Key, FL 33043

    FISHERMANS DREAM HOUSE! BRING YOUR BOATS TO THIS AMAZING 3/2 HOUSE SECLUDED ON A CORNER LOT WITH 190FT OF SEAWALL. BOAT RAMP MINUTES AWAY. ICE MAKER AT THE OUTSIDE BAR.ENJOY THE POOL, OPEN DECKS, COCKTAILS AT THE OUTSIDE BAR, AND THE ADORABLE KEY DEER ROAMING THE NEIGHBORHOOD. SLEEPS 8. AVAILABLE FOR MONTHLY AND ANNUAL RENTALS.

    Andrea Lennon Vylla Home

    1540 Lantana Ln, Big Pine Key, FL 33043
  • /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
  • /14

    $6,500 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    31226 Hollerich Dr Unit 1, Big Pine Key, FL 33043

    Exceptional waterfront rental opportunity available yearly or seasonally (minimum 28-day rental). This beautifully maintained 3-bedroom, 2-bath villa is located in the heart of Big Pine Key and offers direct water access with a private dock, making it ideal for boating, fishing, kayaking, and enjoying the Florida Keys lifestyle.Relax on the waterfront and take in the spectacular sunset views

    Annie Mora Tellado The Opulence Group Brokerage

    31226 Hollerich Dr Unit 1, 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
  • /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

    $7,500 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 just a few blocks 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 .Available for annual and monthly rentals.

    1540 Lantana Ln, Big Pine Key, FL 33043
  • /47

    $11,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • House for Rent

    28577 Peg Leg Rd, Summerland Key, FL 33042

    Make the most of winter in the Florida Keys from this fully furnished waterfront retreat on Little Torch Key. Whether you're planning a seasonal stay, considering a move to the Keys, or looking for a comfortable home base while searching for a property of your own, this 3-bedroom, 2-bath home offers an easy way to settle in and experience island living.Located on the Atlantic side in

    Micaela Eleicegui Ocean Sotheby's International Realty

    28577 Peg Leg Rd, Summerland Key, FL 33042
  • /37

    $5,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,654 Sq Ft
    • House for Rent

    31490 Avenue F, Big Pine Key, FL 33043

    Brand-New Waterfront Home in the Florida KeysDiscover the ultimate Florida Keys lifestyle in this stunning brand-new construction, perfectly designed for those who love boating, waterfront living, and the beauty of the Gulf. This exceptional property features 3 spacious bedrooms, 2.5 bathrooms, and a private boat dock, providing direct access to the Gulf for unforgettable days on the water.The

    31490 Avenue F, Big Pine Key, FL 33043
  • /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
  • /16

    $4,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,079 Sq Ft
    • House for Rent

    53 Barry Ave, Summerland Key, FL 33042

    This is a 2 story furnished or unfurnished single family house with a private pool, fenced in yard, screened patio, 2 bedrooms, 2 bathrooms with showers, stainless steel appliances, hurricane windows, washer and dryer, tile and wood floors. You are also able to use the amenities at our property next door such as 24 hour community gym and sauna. marina with boat ramp, outdoor games, bbq, kayaks

    Joseph Danieli AKT Realty LLC

    53 Barry Ave, Summerland Key, FL 33042
  • /30

    $4,400 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
  • /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
  • /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 Summerland Key, FL?
The median rent for a single-family home in Summerland Key, FL is $9,500 per month, though prices vary by neighborhood, size, and property type. As of August 2026, townhouses tend to be the most affordable option while single-family homes are currently more expensive.
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 $380,000 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 $9,500 per month in Summerland Key, FL, renters typically need to show $28,500 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 9.6, 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
29
Median Single Family Home Rent
$9,500
Median 3 Bedroom Single Family Home Rent
$9,500
Median 5 Bedroom Single Family Home Rent
$11,600
How to Rent a Home