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Summerland Key, FL Homes for Rent

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  • /34

    $6,000 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) 205-0832

    59 Palm Dr, Key West, FL 33040
  • /20

    $3,950 - $4,200 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
  • /14

    $4,200 per month

    • 3 Beds
    • 2 Baths
    • 1,048 Sq Ft
    • Property for Rent

    29267 Cypress Dr, Big Pine Key, FL 33043

    Located in the Eden Pines community, this unfurnished single-family home offers 2 bedrooms plus a bonus room previously used as a third bedroom. Enjoy canal-front living with a boat lift and plenty of storage, including an enclosed downstairs area and separate shed. Washer and dryer included. Pet-friendly with deposit. 6-8 month lease preferred. Utilities not included. Background and credit check

    Melissa Gibbins Expert Realty LLC (HQ)

    29267 Cypress Dr, Big Pine Key, FL 33043
  • /9

    $2,400 per month

    • 1 Bed
    • 1 Bath
    • 528 Sq Ft
    • House for Rent

    31020 Avenue B, Big Pine Key, FL 33043

    Property Id: 2043481Cozy 1 Bedroom, 1 Bath Mobile Home This well-maintained mobile home features laminate flooring, a screened-in back porch, and a small fenced side and backyard. It includes washer/dryer hookups and an on-demand water heater. The home is unfurnished, and utilities are not included. Lease Terms: Maximum 2 people $2,400.00/ per month 12-month lease First month, last month,

    31020 Avenue B, Big Pine Key, FL 33043
  • /25

    $3,650 per month

    • 3 Beds
    • 2 Baths
    • 1,285 Sq Ft
    • House for Rent

    3717 Palmetto St, Big Pine Key, FL 33043

    Nice remote 3/2 in the heart of big pine key with a canal in the back where you would be able to dock your boat; beautiful location, a relaxing getaway, close to the open water, less than an hour away from Key West, minutes away from shopping, schools, and park. Call Now. Background and Credit Report (we will provide you with a link, and your customer will pay for the fee), Proof of employment,

    George Assal ASLO Real Estate

    3717 Palmetto St, Big Pine Key, FL 33043
  • /12

    $3,100 per month

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • House for Rent

    31167 Ave G, Big Pine Key, FL 33043

    Property Id: 2043505If your between homes, or construction, or here for a shorter period, here is a fully furnished home. Available now, 6mos + few days rental. Nice spacious, furnished home on a double lot, with fenced back yard. Utilities not included. Above ground pool. Close to local amenities. 3bd/2bth 1528 sq. ft. home with laundry room. Central AC & Heat. Monthly yard care

    31167 Ave G, Big Pine Key, FL 33043
  • /12

    $3,950 per month

    • 2 Beds
    • 3 Baths
    • 1,100 Sq Ft
    • Property for Rent

    31111 Hibiscus Dr Unit lot 31, Big Pine Key, FL 33043

    Come live the island life in this immaculately kept 2 bedroom 3 full bath with additional room on ground floor.If you love nature Big Pine is for you. Close enough to enjoy both Marathon and Key West for the nights where you want to see the local action but far enough away for peace and tranquility. Home sits on a spacious 60 ft of canal front lot with quick access to Gulf or Atlantic from Bogie

    Kimberley Frazier Keller Williams Key West Compass Realty

    31111 Hibiscus Dr Unit lot 31, Big Pine Key, FL 33043
  • /11

    $5,000 per month

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    467 W Shore Dr, Summerland Key, FL 33042

    Property Id: 1850307Welcome to your dream home in the heart of Summerland Key! Located at MM25 in the coveted Summerland Key Cove neighborhood conveniently located near restaurants, shopping, and boat ramps. This spacious property features modern amenities such as a stainless steel appliances, central AC, and in ground swimming pool. Extra large driveway with plenty of off street parking

    467 W Shore Dr, Summerland Key, FL 33042
  • /32

    $6,000 per month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    1655 Sunrise Dr, Big Pine Key, FL 33043

    Your clients will love having their morning coffee in the family room and watching the Sun rise over No Name Key.This back yard pool is completely private and perfect for family and guests. Sit in the Tiki Bar, sip a Margarita and enjoy the ocean and pool views. The tropical trees and setting will make you feel like you are living at a Caribbean Resort. Dock you boat at the cut-in boat slip, and

    Mark Peterson

    1655 Sunrise Dr, Big Pine Key, FL 33043
  • /14

    $2,700 per month

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

    29720 Journeys End Rd, Big Pine Key, FL 33043

    Property Id: 2012413Unfurnished, Spacious stilt home featuring 2 bedrooms and 2 full bathrooms. Enjoy outdoor living on the screened porch—perfect for relaxing or entertaining. Home includes skylights for natural lighting and a storage area beneath the house for added convenience.$8,100 to move in (First, Last and Security) $2700 X 3Monthly Lawn maintenance is

    29720 Journeys End Rd, Big Pine Key, FL 33043
  • /36

    $5,000 per month

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

    27316 Cayman Ln Unit 1, Summerland Key, FL 33042

    Presenting Villa Marquesa — the perfect opportunity to lease a charming private villa in the heart of Ramrod Key, located in the picturesque Lower Keys. This fully furnished 3-bedroom, 1-bath tropical retreat offers stylish South Florida beach decor, a fully equipped kitchen, and two spacious living areas for ultimate comfort. Ideal for tenants seeking privacy, relaxation, and a resort-style

    Gilbert Garcia Proxy Realty Group LLC

    27316 Cayman Ln Unit 1, Summerland Key, FL 33042
  • /22

    $3,900 per month

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • House for Rent

    29172 Rose Dr, Big Pine Key, FL 33043

    Freshly remodeled waterfront home! Located in a lovely neighborhood with a boat ramp right around the corner! Exterior of property has open parking as well as covered parking for multiple vehicles. Below home is surrounded by lattice to give additional shade and privacy. So much potential downstairs for outdoor entertainment.The main living area has gone through a full renovation. Kitchen boast

    29172 Rose Dr, Big Pine Key, FL 33043
  • /40

    $5,000 per month

    • 3 Beds
    • 2 Baths
    • House for Rent

    3635 Tradewinds St, Big Pine Key, FL 33043

    Beautiful Waterfront Home for Rent in the Florida Keys - Boater's Paradise!Ready to move in! This stunning 3-bedroom, 2-bathroom home is perfect for boat lovers and anyone seeking the ultimate Keys lifestyle. Located on a peaceful canal with direct access to open water, this home offers the ideal setting for fishing, boating, and relaxing walks.Property Features:3 spacious bedrooms, 2 full

    Michel Luna Lifestyle International Realty

    3635 Tradewinds St, Big Pine Key, FL 33043
  • /24

    $4,000 per month

    • 2 Beds
    • 2 Baths
    • 1,258 Sq Ft
    • Property for Rent

    29487 Ranger Ave, Big Pine Key, FL 33043

    Unfurnished canal-front 2 bed, 2 bath home in a quiet neighborhood, just minutes from shopping, restaurants, marina, bait shop, and local parks. Enjoy fantastic boating with easy access to both the ocean and backcountry--bring your boat!Home features an open layout, primary bedroom with ensuite bath, laundry closet, and a covered screened porch. The fully fenced yard offers plenty of space for

    Melissa Gibbins Expert Realty LLC (HQ)

    29487 Ranger Ave, Big Pine Key, FL 33043
  • /65

    $10,995 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 spacious deck,

    Walter Vargas Cervera Real Estate Inc.

    30825 Ortega Ln, Big Pine Key, FL 33043
  • /10

    $4,000 per month

    • 2 Beds
    • 2 Baths
    • 1,464 Sq Ft
    • Property for Rent

    61 W Cahill Ct, Big Pine Key, FL 33043

    Long-term canalfront rental on Big Pine Key. Great location for boaters! Primary bedroom with en-suite bathroom on 2nd floor. Add a bed to the office downstairs to create a 2nd bedroom. Furnishings negotiable - home is currently mostly furnished. Screened porch overlooks the 75 ft wide canal with 60 ft of seawall. Fenced yard. Unobstructed sunset views over the wetlands across the street. Plenty

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

    61 W Cahill Ct, Big Pine Key, FL 33043
  • /8

    $4,500 per month

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

    24317 Caribbean Dr W, Summerland Key, FL 33042

    Welcome to Casa Caribe, a long-term rental, comfortable 2 bed, 2 bath vacation home on Summerland Key. Located on one of the best canals on the island, and conveniently across the canal from the Summerland Marina, this home provides quick boating to the blue water as well as the prime diving areas of the Gulf and Looe Key National Marine Sanctuary out front. Large boats will tie up easily at

    Mary Conklin Action Keys Realty of the Lower FL Keys LLC

    24317 Caribbean Dr W, Summerland Key, FL 33042
  • /18

    $3,600 per month

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

    Unlisted Address

    Wonderful renovated waterfront 1/2 Duplex for rent! This one is the left side of duplex and has spacious 2 bedrooms and 1 full bath with open floor plan for living. Completely renovated and gorgeous inside! Beautiful Quartz countertops and stainless appliances in kitchen, all new fixtures and flooring thru-out. Stylish barn doors in both bedrooms with ample closet space. Screened in back porch

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    Unlisted Address
  • /16

    $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 HOUSEBRING YOUR BOATS TO THIS AMAZING 3/2 HOUSE SECLUDED ON A CORNER LOT WITH 190FT. SEAWALL .BOAT RAMP BLOCKS AWAY.ENJOY THE POOL, COCKTAILS AT THE OUTSIDE BAR AND THE ADORABLE KEY DEER ROAMING THE NEIGHBORHOOD.ICE MAKER AT BAR. SLEEPS 8.MULTIPLE MONTHS AND OFF SEASON MONTHS OFFERED AT DISCOUNT RATES.$7500/mo for April-June

    Andrea Lennon Palm Paradise Realty Group

    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 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
  • /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
  • /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

    $4,600 per month

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

    28543 Channel View Dr, Little Torch Key, FL 33042

    Current resident moving out on 9/30/25.Water view from balcony.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

    Joseph Danieli AKT Realty LLC

    28543 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
  • /2

    $4,000 per month

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

    29050 Rose Dr, Big Pine Key, FL 33043

    This spectacular FL Keys home is available for rent with direct access to a canal that goes to the ocean.

    Evelyn Brito Lifestyle International Realty

    29050 Rose Dr, Big Pine Key, FL 33043

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