Monthly Vacation Rentals

Our monthly Key West vacation Rentals are perfect if youre looking for a home away from home during your stay here in the beautiful Keys. Choose from one bedroom cottages to our larger, more spacious four-bedroom rentals, perfect for groups or large families.

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Starting at (USD)

$350.00

A Bit of Heaven
Key West, FL
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: A Bit of Heaven (Monthly)
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Starting at (USD)

$250.00

All in South (Monthly)
Key West, FL
  • 5 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: All In South (Monthly)
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Starting at (USD)

$350.00

Almost Southernmost
Key West, FL
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Almost Southernmost (Monthly)
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Starting at (USD)

$556.00

Aloha- Monthly Rental
Key West, FL
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Aloha (Monthly)
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Starting at (USD)

$215.00

Anna Maria Haven
Key West, FL
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Anna Maria Haven (monthly)
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Starting at (USD)

$415.00

Backyard Oasis (Monthly)
Key West, FL
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Backyard Oasis (Monthly)
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Starting at (USD)

$166.00

Bahama Breeze
Key West, FL
  • 6 Guests
  • 3 Bedrooms
  • 4 Bathrooms
  • Code: Bahama Breeze (monthly)
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Starting at (USD)

$315.00

Blue Sun
Key West, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Blue Sun (Monthly)
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Starting at (USD)

$210.00

Caribbean Cottage
Key West, FL
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Caribbean Cottage (Monthly)
  • Pets Allowed
View Rental
Starting at (USD)

$345.00

Casa Blanca
Key West, FL
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Casa Blanca (Monthly)
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Starting at (USD)

$200.00

Casa Cayo Hueso
Key West, FL
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Casa Cayo Hueso (Monthly)
  • Pets Allowed
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Key West, FL
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Casa Dulce (Monthly)
  • Pets Allowed
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Starting at (USD)

$345.00

Casa Lima
Key West, FL
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Casa Lima (Monthly)
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Starting at (USD)

$85.00

Cocomo Cottage
Key West, FL
  • 2 Guests
  • 1 Bedrooms
  • 1 Bathrooms
  • Code: Cocomo Cottage (Monthly)
  • Pets Allowed
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Starting at (USD)

$145.00

Conch Cigar Home
Key West, FL
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Conch Cigar Home (monthly)
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Starting at (USD)

$245.00

Conch Easy Livin' Monthly Vacation Home
Key West, FL
  • 6 Guests
  • 2 Bedrooms
  • 3 Bathrooms
  • Code: Conch Easy Livin` (Monthly)
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Starting at (USD)

$225.00

Conchy Tonk
Key West, FL
  • 6 Guests
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Code: Conchy Tonk (Monthly)
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Starting at (USD)

$275.00

Cottage Charm- Monthly Rental
Key West, FL
  • 8 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Cottage Charm (Monthly)
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Starting at (USD)

$158.00

Esperanza Suite
Key West, FL
  • 4 Guests
  • 1 Bedrooms
  • 2 Bathrooms
  • Code: Esperanza Suite (Monthly)
  • Pets Allowed
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Starting at (USD)

$158.00

Haven House (Monthly)
Key West, FL
  • 2 Guests
  • 1 Bedrooms
  • 2 Bathrooms
  • Code: Haven House (monthly)
View Rental
Starting at (USD)

$245.00

Higgs Beach Hideaway
Key West, FL
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Higgs Beach Hideaway (Monthly)
  • Pets Allowed
View Rental
Starting at (USD)

$350.00

Key Lime Cottage (Monthly)
Key West, FL
  • 4 Guests
  • 2 Bedrooms
  • 3 Bathrooms
  • Code: Key Lime Cottage (Monthly)
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Starting at (USD)

$195.00

Key West Conch
Key West, FL
  • 6 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Key West Conch (Monthly)
  • Pets Allowed
View Rental
Starting at (USD)

$245.00

Knot A Worry  Monthly Vacation Home
Key West, FL
  • 6 Guests
  • 2 Bedrooms
  • 3 Bathrooms
  • Code: Knot A Worry (Monthly)
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Key West, FL
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Living the Dream (Monthly)
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