Vacation Rentals & Apartments in Big Pine Key

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142 apartments

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$263

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Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$316

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$975

Islamorada Waterfront Paradise Getaway!

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$574

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$4,015

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$915

Clean & Pristine Home - Marina Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$640

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$1,821

Home w/Gourmet Kitchen- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$640

Hidden Gem Sunset Views-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$1,349

Roof Top Water Views - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$640

Family Friendly w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$579

Terrace & Roof Top Deck-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$579

Expertly Decorated-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$579

Boutique Resort w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$640

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$640

Attn:Couples, 3 Kings - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$579

Couples Getaway, Suites-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$579

4 Bd w/Pool, Bayside - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$1,821

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$346

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$523

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$525

Florida Keys Beach Home Pool Fishing Diving

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful stay” Post hurricane and still a spectacular place to stay. Office staff was great. Free use of tennis court, rackets, and balls. Pool and jacuzzi were very excellent. TG

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$2,295

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$912

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$912

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

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Price per night from

$392

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$654

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$622

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$471

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$510

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$444

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$667

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Staffed property

1 of 2 filters match

Price per night from

$525

Bay Pointe

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Pets allowed

1 of 2 filters match

Price per night from

$204

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Pets allowed

1 of 2 filters match

Price per night from

$268

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Pets allowed

1 of 2 filters match

Price per night from

$318

Manatee Bay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Pets allowed

1 of 2 filters match

Price per night from

$151

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Staffed property, Pets allowed

1 of 2 filters match

Price per night from

$141

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rentals in Big Pine Key

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