Vacation Rentals & House Rentals in Key West

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Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Children's pool Fridge

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Price per night from

$343

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Fridge

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Price per night from

$158

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Waterfront luxury Villa (29) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“WONDERFUL!!!!!!!” Everything at this unit was excellent! Clean upscale unit! We are going to rent next year and planning it already. Peaceful, beautiful & clean! We couldn't have asked for anything better! Unfortunately we had to depart 2 days early due to business emergency but we will be back next year!!

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$300

Waterfront luxury Villa (19) with sunset views and boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$300

Waterfront luxury Villa (34) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$300

Waterfront luxury Villa (42) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$300

Waterfront Luxury Villa (13) with sunset views and boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$300

NEW LISTING! Waterfront Villa (35) w/ boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$300

Waterfront luxury Villa (14) with sunset views and boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$300

Waterfront luxury Villa (54) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Beautiful condo in a beautiful setting” Sitting on the front porch watching the sunset was one of the highlights of the trip. And the pool was the best we've ever swam in.

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$300

Waterfront luxury Villa (30) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$300

Waterfront luxury Villa (21) with sunset views and boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$300

Waterfront Luxury Home with Pool and Boat Dock

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$422

Waterfront luxury Villa (43) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Key West get away to Marathon” My now husband, two daughters, and myself decided to take a week during Spring Break to get out of Key West. We actually went to Marathon that week to get married! I search and searched for place. Mr. Zito was very quick to respond, very helpful, and pleasant. He even allowed us to take a drive up one day to see the villas. His wide was nice enough to show us around. When we stayed there is was very clean and in perfect condition for our arrival. I big thank you to the housekeepers! The full kitchen and grills outside allowed us to be able to grocery shop and not have to eat out every meal. A benefit when you have children! The location was very kid friendly. The sunsets were amazing! Everything was honestly perfect! We would take a monthly trip if we were able to!

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$300

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$179

Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water V

Sugarloaf Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$165

Windley Key, FL Keys

Islamorada caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Fridge

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Price per night from

$114

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$671

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Fridge

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Price per night from

$140

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$207

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$177

Grouper Therapy

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$213

Latitude Adjustment

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Fridge

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Price per night from

$173

Water's Edge

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$170

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$183

Sun Kissed

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$157

BAYSIDE Villa

Islamorada villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$314

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$205

1 of 2 match: Children's pool, Fridge

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Price per night from

$859

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$573

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$630

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$630

Waterfront luxury Villa (51) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Relaxation” My finance and I stayed at the amazing Indigo Reef, unit 51. We choose Indigo Reef, primarily for the location. We love Marathon and desired to be close to all the fantastic restaurants and the lovely Sombrero Beach. We snorkeled for the day at the Sombrero Beach lighthouse (incredible - highly recommended)! Indigo Reef was lovely, quiet, family friendly, clean, and comfortable. The pool was a nice treat, after a long day in the sun. Unit 51 treated us very well. My fiance and I enjoyed the beautiful and very clean unit. The linens were clean and beds were very comfortable. We loved the outside balcony's and back patio view of the bay!! Our favorite space in the house was the outside patio; relaxing and watching the sun set. We captured beautiful photo's of orange/pink tints to the sky. Gorgeous! The unit was spacious enough to accommodate our friends traveling from Pgh, to spend a few nights, enjoying the keys with us! We visited Key West for the day (an hour drive). My communication with John Zito, prior to our stay, was simply fantastic. Thank you for allowing us to share this lovely place with our friends. Angela and Alex

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$300

Luxury beachfront home with pool in Islamorada

Layton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

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Price per night from

$589

Waterfront luxury Villa (59) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Awesome” Our stay at Indigo Reef was excellent. The unit is everything we hoped it would be. We would definitely return.

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$300

Waterfront luxury Villa (60) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Fridge

1 of 2 filters match

Price per night from

$300

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