Vacation Rentals & House Rentals in Key West

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61 house rentals

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Shared outdoor pool (unheated) Private outdoor pool (unheated)

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Price per night from

$2,191

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

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Shared outdoor pool (unheated) Private outdoor pool (unheated)

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Price per night from

$1,852

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Sunsets and Sand

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$149

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$774

1 of 2 match: Shared outdoor pool (unheated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$912

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$213

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$286

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$364

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$184

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$271

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$422

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$2,212

Lobster Lagoon

Stock Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Shared outdoor pool (unheated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$975

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$860

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

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: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$589

Waterfront Luxury Villa (62) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$577

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Shared outdoor pool (unheated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$500

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$258

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$700

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$516

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$602

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