Vacation Rentals & House Rentals in Florida Keys

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111 house rentals

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) Swing set or jungle gym

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Price per night from

$206

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Swing set or jungle gym

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Price per night from

$286

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Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

Florida Keys Splendor at Hammer Point

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Winter Paradise!” My wife and I stayed at this great place in January 2014 and it was wonderful. It was very clean and well maintained. The canal was great to watch the fish jump and we saw Manatees almost every day. We especially liked the kayak and did a lot of site seeing from the ocean side. Migdy was great to work with and very accommodating. We would highly recommend this place to anyone.

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$157

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$264

Coastal Key Largo Townhome with Ocean Views, Pool & Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$390

Penthouse Sunsets and Tropical Breeze in Key Largo

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place for a family of 5” Loved the condo, it was family friendly and very spacious. We had a great view from our deck. The owner was very friendly and very helpful. The facility had a great tennis court and we loved the lagoon. This unit was a great value and the owner makes it affordable for the average family to be able to spend time there.

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$315

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$457

Luxury 4-Bedroom Home with Resort Privileges

Tavernier villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,663

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$402

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$213

Beautiful condo with ocean view(distant)

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$258

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$364

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$286

BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$252

“Fantasic wedding on paradise!!” We picked Shadow Point because of it's fabulous secluded view and beautiful gardens on 2.5 acres. The house and cottage held up to 16 of us and was wonderfully decorated with period antiques. Our guests loved playing at their beach and kayaking and swimming around Key LargoSound. Our wedding was perfect with the full moon rising over our reception. We danced the night away in paradise.

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$2,408

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$159

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 2 hours 56 minutes

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$327

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 59 minutes

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$544

BREATHTAKING Ocean views await at Tropical Daze

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$286

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$258

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$184

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: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

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: Swing set or jungle gym, 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: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$271

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: Swing set or jungle gym, 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: Swing set or jungle gym, 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: Swing set or jungle gym, 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: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$422

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: Swing set or jungle gym, 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: Swing set or jungle gym, 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: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

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: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

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: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 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

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$339

Luxury 3-Bedroom Home with Resort Privileges

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,548

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$859

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: Swing set or jungle gym, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$577

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