Key West, FL Homes for Rent

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  $5,200 Per Month

  • 4 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • NEW PRICE!! Move in Ready Single Family Home - 4 bedroom - 1.5 Bathroom on Stock Island

  H16 Miriam St, Key West, FL 33040

  Great Family Home Located on Stock Island with water view. This unfurnished single-family 4 bed / 2 - half baths plus adjoining tub/shower stilt home offers central AC, washer/dryer, ample off street parking and fully fenced yard. All pets welcome! $5,200.00/mo plus utilities. Available mid-June for a 12 month rental. First/Last/Security. At Historic Key West Annual Rentals, we strive to

  H16 Miriam St, Key West, FL 33040
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  $3,100 Per Month

  • 1 Bed
  • 1 Bath
  • 718 Sq Ft
  • Oceanfront Condo!

  2601 S Roosevelt Blvd, Key West, FL 33040

  Attractive one bedroom, one bath oceanfront unit featuring breaktaking views of Smather's Beach and the turquoise water that surrounds Key West. Located at Key West By The Sea with gated access, one parking spot, 2 pools, and 2 tennis courts. Interior features include: Kitchen with dishwasher, ice maker, full bath with shower, 2 ductless AC units, hurricane windows, balcony facing the ocean, and

  2601 S Roosevelt Blvd, Key West, FL 33040
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  $3,100 Per Month

  • 2 Beds
  • 2 Baths
  • Fully Furnished 2BR/2BA at Las Salinas with Pool, Gym & Parking for Two

  3930 S Roosevelt Blvd, Key West, FL 33040

  Step into effortless island living with this beautifully appointed 2-bedroom, 2-bathroom residence at Las Salinas. Fully furnished and thoughtfully designed, this home offers the perfect blend of comfort and style, ideal for those looking to move right in without the hassle.Enjoy a bright, open living space, a well-equipped kitchen, and spacious bedrooms that provide a relaxing retreat at

  3930 S Roosevelt Blvd, Key West, FL 33040
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  $14,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Condo for Rent

  918 Southard St Unit 205, Unit 205, Key West, FL 33040

  Art-Filled 1,700SF 3BR/2BA Old Town Key West Home with 2 Decks, Pool, ParkingLarge art-filled, two story Key West condo boasts 2 large inviting bedrooms, including a king bed, queen bed, and large office or third bedroom for extra flexibility. Guests enjoy living and dining rooms, 2 full bathrooms, one with a large shower and one with bathtub, high ceilings throughout, wrap around porch in lush

  918 Southard St Unit 205, Unit 205, Key West, FL 33040
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  /19

  $3,400 Per Month

  • 2 Beds
  • 1.5 Baths
  • 836 Sq Ft
  • Fully Furnished 2 Bed 1.5 bath Home in the Key West Golf Club Community

  67 Spoonbill Way, Key West, FL 33040

  It doesn't get better than this! This stylishly decorated, fully furnished 2 bedroom 1.5 bath townhome is located in the Key West Golf Community and features Central AC, a flat screen TV, and a full size washer & dryer. This home boasts upper and lower, front and back porches. Enjoy the lush view of the beautiful golf course from both your large master bedroom and living room porches. This

  67 Spoonbill Way, Key West, FL 33040
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  $2,700 Per Month

  • 2 Beds
  • 2 Baths
  • 696 Sq Ft
  • 2 Bedroom 2 Bathroom in Santa Clara Condo

  3312 Northside Dr, Key West, FL 33040

  2 bedroom 2 bathroom unfurnished unit at Santa Clara Condominium has a 3rd floor Enjoy stunning sunsets off the living area balcony. This home has Luxury Vinyl Plank Flooring throughout with the spacious bedrooms This unit has central air conditioningThis modern 2-bedroom condo includes private gated parking, guest parking, heated swimming pool, tennis courts, grill area for

  3312 Northside Dr, Key West, FL 33040
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  $3,950 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,060 Sq Ft
  • $3950 - Furnished partial year rental Private Pool! 2 Bedroom / 2.5 Bathroom

  58 Golf Club Dr, Key West, FL 33040

  Tropical Townhome with Private Pool in Key West Golf Club – Furnished 6+ Month RentalPets Considered!Escape to your own island retreat in the gated Key West Golf Club community. Available Today - flexible dates, but rental should be 6 months plus 1 day or longer to avoid 12.5% tax. The lease must end around January. furnished lease, this beautifully updated 2-bedroom, 2.5-bath

  58 Golf Club Dr, Key West, FL 33040
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  $3,450 Per Month

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft
  • Condo for Rent

  3655 Seaside Dr Unit 423, Key West, FL 33040

  Available for annual lease starting August 1st, 2026, this 2 bedroom, 2 bathroom fourth-floor condo is located in the desirable SaltPonds community in Key West. The condo offers a comfortable split floor plan, with each bedroom featuring its own ensuite bathroom, making it ideal for privacy and convenience. The primary bedroom also includes a walk-in closet.Enjoy a peaceful view from the private

  3655 Seaside Dr Unit 423, Key West, FL 33040
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  /10

  $3,300 Per Month

  • 2 Beds
  • 2 Baths
  • 805 Sq Ft
  • Ocean View 2 bedroom 2 bathroom Las Salinas Condo

  3930 S Roosevelt Blvd, Key West, FL 33040

  Wake up to stunning ocean views every day in this spacious 2-bedroom, 2-bathroom unfurnished condo at Las Salinas. Designed for both style and convenience, the home features sleek, easy-to-clean tile flooring throughout. A brand-new stackable washer and dryer add modern efficiency to your daily routine.This coastal retreat offers a 1-year lease with the option to renew, making it perfect

  3930 S Roosevelt Blvd, Key West, FL 33040
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  /19

  $3,450 Per Month

  • 2 Beds
  • 1.5 Baths
  • 6+ MONTH RENTAL-Temporarily discounted to $3000 for this season!

  121 Golf Club Dr, Key West, FL 33040

  Available May to November - Decorated with island charm, this 2-bedroom 1.5 bath home is located in the Key West Golf Community and is offered fully furnished. The home features Central AC, a full size washer & dryer, and a flat screen TV. The screened deck off the living room and the master bedroom balcony both offer beautiful views of the golf course.The Key West Golf Club HOA is a gated

  121 Golf Club Dr, Key West, FL 33040
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  $3,250 Per Month

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft
  • Waterfront Island Living at Staples Duplex

  2627 Staples Ave Unit A, Key West, FL 33040

  Experience the relaxed side of Key West living from this canal-front duplex with access to both the Gulf and Atlantic. Enjoy off-street parking, nearby bike paths, easy access to beaches, waterfront restaurants, grocery stores, and all the everyday conveniences that make island life easy.Perfectly positioned in a quiet neighborhood close enough to enjoy Old Town and Duval Street, while

  2627 Staples Ave Unit A, Key West, FL 33040
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  /19

  $3,000 Per Month

  • 2 Beds
  • 2 Baths
  • 803 Sq Ft
  • Las Salinas 2 Bedroom 2 Bathroom

  3930 S Roosevelt Blvd, Key West, FL 33040

  This 2 bedroom 2 bathroom condo is located in Las Salinas. This unit has a central ac unit and stackable washer/dryer unit appliances including a fridge, oven and dishwasher. There is a shared pool at this complex. There is one assigned parking space.

  3930 S Roosevelt Blvd, Key West, FL 33040
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  $4,900 Per Month

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • AVAILABLE NOW!! Furnished 2 bed/2 bath Home with Pool and on Canal

  3017 Airport Blvd, Key West, FL 33040

  Furnished 2 bed/2 bath private home. This charming residence offers a private pool, perfect for enjoying the warm Florida weather. With two off-street parking spaces. The central AC ensures a comfortable living environment year-round. Situated on a canal, this home provides a tranquil atmosphere and stunning water views. The kitchen is equipped with a stove, refrigerator, microwave, and

  3017 Airport Blvd, Key West, FL 33040
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  $3,250 Per Month

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft
  • Waterfront Island Living at Staples Duplex

  2627 Staples Ave Unit B, Key West, FL 33040

  Experience the relaxed side of Key West living from this canal-front duplex with access to both the Gulf and Atlantic. Enjoy off-street parking, nearby bike paths, easy access to beaches, waterfront restaurants, grocery stores, and all the everyday conveniences that make island life easy.Perfectly positioned in a quiet neighborhood close enough to enjoy Old Town and Duval Street, while

  2627 Staples Ave Unit B, Key West, FL 33040

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