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Summerland Key, FL Homes for Rent

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  • /42

    $5,490 per month

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

    31547 Avenue D, Big Pine Key, FL 33043

    Come see this immaculate 2 Bedroom 2 Bath Big Pine Key Waterfront home with its Wonderful Water Views! It is available for a seasonal rental, so come on down and enjoy the Florida winter weather! It has a well equipped kitchen for your convenience and is only 5 years old. Please see the attached photos. You'll be glad you did! Only 30 miles to Key West and all of the other Points of Interest in

    Philip Vias LoKation

    31547 Avenue D, Big Pine Key, FL 33043
  • /35

    $4,800 per month

    • 3 Beds
    • 1.5 Baths
    • 1,247 Sq Ft
    • House for Rent

    29283 Coconut Palm Dr, Big Pine Key, FL 33043

    Welcome to Coconut Palm Drive--a hidden gem in one of Big Pine Key's peaceful residential neighborhoods. This 3 bedroom, 1.5 bath island home offers vaulted ceilings, crown molding, and an open-concept layout that brings in natural light and a spacious feel. The tropical backyard is fully fenced for privacy and features mature banana trees. A generous downstairs storage area offers endless

    Lisa Cattran Engel & Volkers Marathon

    29283 Coconut Palm Dr, Big Pine Key, FL 33043
  • /20

    $3,525 per month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • House for Rent

    29822 Frostproof Rd, Big Pine Key, FL 33043

    Property Id: 2218567Enjoy comfort and privacy in this elevated 2-bedroom, 2-bath home featuring an extra bedroom, open floor plan and vaulted ceilings for a bright, airy feel. The living room and master bedroom each open through French doors onto a balcony, while the bonus bedroom offers its own private sliding door access. Central A/C and heat keep the home comfortable year-round. Relax

    29822 Frostproof Rd, Big Pine Key, FL 33043
  • /10

    $4,200 per month

    • 4 Beds
    • 2 Baths
    • 1,431 Sq Ft
    • Property for Rent

    30964 Nathalie Rd, Big Pine Key, FL 33043

    Unfurnished long term rental. Nicely upgraded and available for occupancy now.

    Roberta Mira Sunshine State Realty Services

    30964 Nathalie Rd, Big Pine Key, FL 33043
  • /34

    $5,500 per month

    • 3 Beds
    • 3 Baths
    • 1,380 Sq Ft
    • Property for Rent

    59 Palm Dr, Key West, FL 33040

    Enjoy the Keys lifestyle in this stunning canal-front 3-bedroom, 3-bathroom elevated modular home, located in the desirable Bay Point neighborhood, just behind Baby's Coffee. Available for $5,900 per month, this 2015-built home offers modern amenities and a spacious layout perfect for comfortable living.The lower level features a bedroom with a full bath, 9-foot ceilings, and access to a covered

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    (645) 241-5597

    59 Palm Dr, Key West, FL 33040
  • /19

    $3,600 per month

    • 2 Beds
    • 1 Bath
    • 774 Sq Ft
    • Property for Rent

    29656 Constitution Ave, Big Pine Key, FL 33043

    Newly renovated ground level half duplex on a fantastic boating canal in Pine Channel Estates on Big Pine Key. 2 bedrooms and 1 bathroom. Large screened porch with canal views and with washer/dryer. No pets. No smoking. Tenant pays utilities. Each adult prospective tenant must fill out an application and undergo a credit and background check. F/L/S $3600. Rental is managed by owner.

    Karen Quist Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    29656 Constitution Ave, Big Pine Key, FL 33043
  • /20

    $5,300 per month

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • House for Rent

    24827 Park Dr, Summerland Key, FL 33042

    Property Id: 2171726Enjoy the best of island living in this elevated, Newer Home. 3-bedroom, 2-bath canal front home on Summerland Key. Designed for comfort and coastal style, the bright open layout features luxury vinyl plank flooring, and a chef's kitchen with quartz countertops, stainless steel appliances, and plenty of space to cook or entertain. The spacious primary suite offers

    24827 Park Dr, Summerland Key, FL 33042
  • /7

    $5,000 per month

    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft
    • House for Rent

    Unlisted Address

    3 bedroom/3 bathroom 1500 sqft canal front home. This property includes 45' of dockage in addition to a 15,000 pound boat lift. Inside you will find two en suite bedrooms & baths, and an open living and kitchen. There is also a large sized screened in covered porch overlooking the yard and canal. Pets are allowed with an additional one time pet fee of $250. Utilities paid by tenant (water and

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    Unlisted Address
  • /2

    $1,450 per month

    • Property for Rent

    29859 Overseas Hwy Unit A14, Big Pine Key, FL 33043

    🌴 Big Pine Key Lot for Rent - RV or Tiny Home Ready! 🌴Enjoy the Florida Keys lifestyle in this beautiful lot located in a desirable condominium community in Big Pine Key, just off U.S. 1 and close to everything!🏝️ Community Features:Heated pool for year-round enjoymentWasher/dryer available for tenantsSafe, friendly neighborhoodSteps from the bus stop, shops,

    Graciela Lozano KeysLifestyle Real Estate (KW)

    29859 Overseas Hwy Unit A14, Big Pine Key, FL 33043
  • /17

    $5,000 per month

    • 3 Beds
    • 2 Baths
    • 1,565 Sq Ft
    • House for Rent

    24840 Park Dr, Summerland Key, FL 33042

    { WOW } Try and find a rental in the Lower Florida Keys! Then, yet again, one with 3 bedrooms, 2 Full baths and spacious Kitchen, Livingroom, Dinning open concept layout. Welcome to living in Summerland Key Cove.Live where others vacation -- in Summerland Key Cove, just 25 miles from Key West. Whether you're a boater, pilot, fisherman, or someone who simply enjoys walking their dog by the water,

    Thomas Murphy LAER Realty

    24840 Park Dr, Summerland Key, FL 33042
  • /8

    $2,700 - $3,000 per month

    Coco Palms

    2 Beds

    21585 Overseas Hwy, Cudjoe Key, FL 33042

    Discover our newly constructed community at Coco Palms in Cudjoe Key, Florida. The leasing team will assist you in finding your new place. A selection of amenities are waiting for you: hurricane windows and doors, dishwashers, washers and dryers and convenient on-site parking options. Contact us today to see available floor plans and find your new place at Coco Palms.

    21585 Overseas Hwy, Cudjoe Key, FL 33042
  • /33

    $6,500 per month

    • 3 Beds
    • 2 Baths
    • Property for Rent

    18 W Circle Dr, Key West, FL 33040

    This beautifully remodeled 3-bedroom, 2-bath stilted home sits canal-side behind Baby's Coffee, offering open water views and great opportunity. Built in 2000, it features a durable metal roof, impact windows, and sliding glass doors for comfort and great insurance options. Launch your boat from your own private ramp or use the community ramp nearby, then relax in the sparkling pool or tinker in

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    (645) 205-0296

    18 W Circle Dr, Key West, FL 33040
  • /14

    $6,000 per month

    • 7 Beds
    • 6 Baths
    • 3,249 Sq Ft
    • House for Rent

    21660 Overseas Hwy, Summerland Key, FL 33042

    Private Oceanfront Beach House - Annual Rental Available.Your private slice of the Florida Keys, just 20 minutes from Key West. This direct oceanfront home offers sweeping Atlantic views and the ultimate coastal escape.Inside, you'll find an airy layout with plenty of natural light, stainless steel appliances, French doors, impact-rated sliders, doors, and windows, plus updated AC units for

    Kelly Gardner Bluescape Real Estate

    21660 Overseas Hwy, Summerland Key, FL 33042
  • /20

    $6,552 per month

    • 3 Beds
    • 2 Baths
    • 1,431 Sq Ft
    • Condo for Rent

    886 Loggerhead Ln Unit ID1297829P, Summerland Key, FL 33042

    Loggerhead Lagoon is a stunning, tropically themed 3-bedroom 2-bathroom home located on a large private lot that offers covered parking, a boat dock, and direct access to the Gulf of Mexico. This rare find boasts a lush outdoor area full of beautiful palms, sun loungers, and tons of Florida sunshine. Located in Sugarloaf Key, just 19 miles from Key West and the world-famous Duval Street, this

    886 Loggerhead Ln Unit ID1297829P, Summerland Key, FL 33042
  • /20

    $4,950 per month

    • 2 Beds
    • 1 Bath
    • 893 Sq Ft
    • Condo for Rent

    18954 Acosta Rd Unit ID1297838P, Summerland Key, FL 33042

    Escape to paradise at this serene 2-bedroom, 1-bath home in beautiful Sugarloaf Key. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Inside, the home sleeps up to 6 guests, featuring two bedrooms and two twin sleeper sofas in the living

    18954 Acosta Rd Unit ID1297838P, Summerland Key, FL 33042
  • /68

    $4,800 per month

    • 3 Beds
    • 1 Bath
    • 1,116 Sq Ft
    • House for Rent

    27316 Cayman Ln Unit 1,2, Summerland Key, FL 33042

    House in the Lower Keys Seasonal Rental. Available Sept 15, 2025 – Villa Marquesa, Lower Keys waterfront retreat! Spacious furnished home ideal for families, multi-gen living, or work-from-paradise. Corner lot on 2 wide canals with deep water access & 2 private docks (45’ & 15’). Upstairs: 3BR/1BA, 1,200 SQF, open kitchen, dining, living & TV rooms, water views. You can also rent downstairs unit,

    Hamlet Garcia Proxy Realty Group LLC

    27316 Cayman Ln Unit 1,2, Summerland Key, FL 33042
  • /70

    $12,500 per month

    • 4 Beds
    • 4 Baths
    • 2,952 Sq Ft
    • Property 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)

    (786) 442-3255

    21640 Overseas Hwy, Summerland Key, FL 33042
  • /13

    $5,500 per month

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

    28515 Channel View Dr, Little Torch Key, FL 33042

    Current resident moving out on 10/31/25.This is a waterfront 3 story, 2 bedroom, 2.5 bathroom unfurnished townhome for rent on a year lease. It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated

    Joseph Danieli AKT Realty LLC

    28515 Channel View Dr, Little Torch Key, FL 33042
  • /65

    $6,995 per month

    • 4 Beds
    • 3 Baths
    • 3,116 Sq Ft
    • House for Rent

    30825 Ortega Ln, Big Pine Key, FL 33043

    Welcome to your slice of paradise in Big Pine Key! This stunning property offers peace and privacy on a quiet street,just minutes from world class fishing, boating, and the natural beauty of Bahia Honda State Park. This charminghome comes fully furnished and features an open-concept layout, modern updates, and coastal finishes throughout. relax on the coveredporch, entertain on the

    Walter Vargas Cervera Real Estate Inc.

    30825 Ortega Ln, Big Pine Key, FL 33043
  • /20

    $3,900 - $5,500 per month

    Little Torch Cottages

    2 Beds

    28501 Channel View Dr, Little Torch Key, FL 33042

    In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

    28501 Channel View Dr, Little Torch Key, FL 33042
  • /20

    $8,500 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 RENTALS TOO. DISCOUNTED PRICES FOR MULTIPLE MONTH RENTALS AND OFF SEASON.

    Andrea Lennon Vylla Home

    1540 Lantana Ln, 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 in Big Pine Key! This waterfront getaway is located in the National Key Deer Refuge, just 30 minutes away from Key West. This three-bedroom/two-bath home features an open floor plan, a fully furnished living area, and a modern, fully equipped kitchen. The kitchen is a culinary dream, featuring stainless steel appliances and an oversized quartz island, surrounded by eight

    Mary Jo Selden DomainRealty.com LLC

    3770 Park Ave, 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
  • /23

    $4,900 per month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    74 Pelican Ln Unit 1, Big Pine Key, FL 33043

    Completely remodeled property, 2024 roof, new floors, termite treatment done 2025, fully furnished, with an excellent location 30 minutes from Key West, restaurants, schools, beaches, recreational centers and everything you need for a quiet and pleasant life, all nearby

    Yunior Molina My Realty Group, LLC.

    74 Pelican Ln Unit 1, Big Pine Key, FL 33043
  • /14

    $3,950 per month

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

    28511 Channel View Dr, Little Torch Key, FL 33042

    Current resident moving out on 12/31/25.This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent on a year lease.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

    Joseph Danieli AKT Realty LLC

    28511 Channel View Dr, Little Torch Key, FL 33042
  • /9

    $13,500 per month

    • 4 Beds
    • 3 Baths
    • 2,855 Sq Ft
    • House for Rent

    28502 Channel View Dr, Little Torch Key, FL 33042

    This is a 3 story furnished 4 bedroom 3 bathroom home with a water view of the gulf in the Little Torch Cottages community of townhomes. There are 2 heated and chilled community pools, a gym, a sauna, a marina with boat ramp, bbq, exterior yard games and boat slip available for an extra charge. Kayaks and paddle boards are available for community usage.

    Joseph Danieli AKT Realty LLC

    28502 Channel View Dr, Little Torch 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

Frequently Asked Questions

What are the most popular zip codes in Summerland Key, FL for renters?
The most popular zip codes in Summerland Key, FL for renters include 33042, 33043 and 33040.
How to Rent a Home