Vacation Rentals & House Rentals in Florida Keys

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268 house rentals

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$373

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

Match: Shared outdoor pool (unheated) Swimming pool

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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

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$300

Luxury Vacation Rental Oceanfront in Key Largo, nr, Islamorada, Florida Keys

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Great place to stay” We stayed at Sally and andrew´s place for a week. When we looked for a place to stay, we wanted a place not to far of Key West and Miami, and this place was just great! There were lots of places to eat out, things to see, and Key West and Miami was not to far away. The apartment was great, Andrew was too! Everthing regarding the stay were done in a professionel way. Both before the stay and after. The way of paying could have been easier though, but that is not a big problem We had a great time, all four of us visiting from Norway. If anyone should ask me where to stay in that erea, I have absolutely no problem telling them about Sally and andrew´s place! Ps: Make shure to have the time to eat at Mrs Mac´s Kitchen...

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$207

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

Match: Shared outdoor pool (unheated) Swimming pool

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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

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$300

Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$573

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

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$300

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$1,950

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

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$300

Home w/Gourmet Kitchen- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$638

Atlantic Paradise Found modern luxury Best pool in Key West fine finishes

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$1,374

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

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$300

One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$339

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$745

Expertly Decorated-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$578

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

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$300

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

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$300

Key West Affordable Ocean View Condo. Clean priced well on the Atlantic

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$745

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$1,374

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$1,145

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$974

“The perfect place to stay in Key West” This property is just 1 block off Duval -- but closer to the quiet, quaint side. I was so impressed with the accomodations -- fully equipped! We could have stayed there a month! The grounds are beautiful, lush, tropical and quiet. Staff was super friendly -- it is also very private with a large locking wrought iron gate keeping the units apart from the street -- we loved everything about it! We will stay here again on our next visit for sure!~

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$796

Clean & Pristine Home - Marina Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$638

Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$859

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$859

Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$859

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$764

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$912

Hidden Gem Sunset Views-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$1,368

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$1,847

Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$840

BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$134

Ocean View Monthly Rental at 1800 Atlantic- Open Nov, December & January

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$172

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$912

Boutique Resort w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$638

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 48 minutes

Match: Shared outdoor pool (unheated) Swimming pool

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Price per night from

$107

Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swimming pool

All filters match

Price per night from

$859

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rentals in Florida Keys

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