Vacation Rentals & Apartments in Big Pine Key

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101 apartments

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated) Pets allowed

All filters match

Price per night from

$657

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Pets allowed

All filters match

Price per night from

$1,144

Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool

Marathon Shores house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated) Pets allowed

All filters match

Price per night from

$747

New Listing! Gone Coastal-Waterfront Bring Your Boat! Cabana Club Membership

Key Colony Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Shared outdoor pool (heated) Pets allowed

All filters match

Price per night from

$218

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Thirty Three by The Sea - Vacation Rental Key Colony Beach, FL

Key Colony Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$345

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

Unit 8b, small efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$207

8c, Efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$252

Reef Resort - Peaceful Getaway 204

Marathon condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$353

Reef Resort Getaway 205

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$321

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$253

Outstanding Oceanfront Condo on the Beach!!

Marathon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

Amazing Ocean View Condo on the Beach!

Marathon apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$265

2-Story condo w/ panoramic views and balconies

Marathon condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$374

Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$309

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, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$2,300

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$5,743

Bay Pointe

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$204

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$319

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$268

Casa Turquesa

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$289

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$141

Island Time (both halves of duplex)

Big Pine Key house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$236

Island Time 2 (half of duplex)

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$148

Lafitte Landing

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$144

Margarita Villa

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$189

Manatee Bay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$151

Pirate's Cove

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$118

St. Croix

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$121

Villa Cayo

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$415

Coral House

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$218

Island Chalet

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$161

Conch Out

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$194

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$208

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$184

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Shared outdoor pool (heated), Pets allowed

1 of 2 filters match

Price per night from

$385

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rentals in Big Pine Key

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