Vacation Rentals & House Rentals in Florida Keys

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80 house rentals

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.

Match: Bicycles available Swing set or jungle gym

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Price per night from

$157

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

Match: Bicycles available Swing set or jungle gym

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Price per night from

$327

Match: Bicycles available Swing set or jungle gym

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Price per night from

$457

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available Swing set or jungle gym

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Price per night from

$286

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Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$172

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$144

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, Bicycles available

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Price per night from

$338

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$207

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$367

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, 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: Bicycles available, 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: Bicycles available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$315

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$401

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$458

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: Swing set or jungle gym, Bicycles available

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Price per night from

$352

Reef Resort Getaway 205

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$320

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$516

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$447

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$344

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$974

Oceanfront Condo w/Lake, Kayaks, Paddleboards & Bikes

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$447

The Butterfly Cottage

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$251

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$331

“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: Bicycles available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$2,405

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$158

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: Bicycles available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$544

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Bicycles available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$258

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...

1 of 2 match: Bicycles available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$206

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: Bicycles available, Swing set or jungle gym

1 of 2 filters match

Price per night from

$286

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$401

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$401

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$172

Islamorada Waterfront Paradise Getaway!

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$573

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$287

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$561

“Beautiful property” This place is way nicer then the pictures. The property itself is breathtaking and its right on the water with a beautiful deck. I love that we had access to kayaks whenever we wanted. No one else but our party was there. The house seemed pretty clean but I wish it had a quick sweep again before we got there. The barstools had lots of dead flies. Which is weird because we didn’t have any flies around even while cooking outside. I loved that we could fish right off the deck. Just wished there was a pipe outside to wash up before going in. It’s definitely heaven, I woke up at 6 one day and enjoyed the sunrise n watching Dolfins and manitees. I would definitely stay here again.

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$315

Key Largo Rental Fantastic Views

Key Largo condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$401

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Bicycles available

1 of 2 filters match

Price per night from

$487

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