Vacation Rentals & House Rentals in Islamorada

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31 house rentals

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!

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Price per night from

$575

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$518

Experience the Florida Keys like never before!!!

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$246

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$460

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$287

Great rentals within 20 miles that match your search

Motel Room #1, Private Entrance, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$213

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$81

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$144

Unique Houseboat on Dry Lot

Key Largo houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Quaint and unique rental” The houseboat was everything I expected and needed it to be. It slept our family of four comfortably - which was all we really needed. The weather was good so really the only thing we did at the houseboat was shower and sleep. We did also do a few loads of wash - having a full size washer and dryer was convenient. I bet if we spent more time there, we would have used the back yard, it is really neat and welcoming. Maggie was a gracious hostess and everything was exactly where and how she described it. All in all a great value.

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Price per night from

$98

Spacious 1 Bedroom Duplex, Full Kitchen, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$282

1 Bedroom, Full Kitchen, Mini Split Air, Beach and Marina Apt #1

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$282

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 20 minutes

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Price per night from

$403

Tropical Island Getaway-Keys

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$335

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.

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Price per night from

$173

“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.

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Price per night from

$2,415

Waterfront Vacation Beach House Rental Home Bayside Sunset Cove Access

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Abbsolutly Fantastic !!” This is our second year staying a week. Can not say enough about how much we love this house. It's not often you ca stay somewhere for this amount of time and feel like you are are coming home when you arrive for vacation. The house has all the amenities you will need to include fishing rods and 1 and 2 person Kayaks. toys for the kids etc. The location is also great near restaurants, marinas etc. The only complaint once you stay here you are hooked ! We were already ready to book for next year immediately after this vacation. If you want a stress free place for a vacation this is it.

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$575

“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.

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Price per night from

$317

Key Largo Rental Fantastic Views

Key Largo condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 20 minutes

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Price per night from

$403

Private Key Largo Bayside Canalfront home

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$202

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$282

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Price per night from

$374

Sleeping Room, Private Entrance and use of RV Park Bathrooms, Beach and Marina

Key Largo private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$144

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$282

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$317

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

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Price per night from

$287

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...

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Price per night from

$207

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Price per night from

$367

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.

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Price per night from

$317

Motel Room #2, Private Entrance, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$212

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$367

Spacious 1 Bedroom, Full Kitchen, Central Air, Beach, Marina and Docks

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Tranquil and friendly” This was a place we found after months of searching and having another owner cancel out on us. We came in with a pre judgement of the place and BOY were we wrong. Everyone is super nice, everyone there(employees and guests) are very caring and friendly. The apartment was very comfy and well equipped, although anextra blanky or throw would have been nice to have for the sofa lounging. We are only 4 days into it but all is great!

Responds fast! avg. 1 hour 37 minutes

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Price per night from

$281

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