Vacation Rentals & House Rentals in Islamorada

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49 house rentals

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$574

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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.

1 of 2 match: Jacuzzi or hot tub, Cot available

1 of 2 filters match

Price per night from

$574

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: Jacuzzi or hot tub, Cot available

1 of 2 filters match

Price per night from

$207

Islamorada Waterfront Paradise | 5br | Dock | Pool

Tavernier house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 58 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$345

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$401

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$859

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,088

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$573

Paradise on the water

Key Largo house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$574

Beautifully Designed Oceanfront Condo

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$465

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$81

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$287

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$390

2 BEDROOM 2 1/2 BATH VILLA WITH PRIVATE PATIO AND PLUNGE POOL

Duck Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 13 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$339

SANCTUARY IN PARADISE

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.

Responds fast! avg. 2 hours 52 minutes

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$984

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,492

Key Largo Beautiful House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Jacuzzi or hot tub

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: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$390

“Wonderful family vacation!” We had a wonderful time in Key Largo staying in this beautiful townhouse. The house was very clean and looked exactly like it was advertised. We have two children ages 16 and 12, and it was very enjoyable with each of them being able to have their own bedroom and bathroom. The pools and hot tubs at this resort are absolutely beautiful. Also, there is a restaurant right next to the resort that has wonderful food and music. We would definitely stay here again and highly recommend it to others.

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$373

OCEAN VIEWS ALL ROOMS ! TOP FLOOR LARGEST CONDO

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$373

“The most relax g vacation..Awesome” We stayed at Mariners Run Key Largo.the place was beautiful,clean, state of the art appliances.there was nothing Fernanado didn't think us. my entire family raved about the rental.the pool was beautiful .we had two adjoining townhouses so it work put perfect ,more than enough room.

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$402

LICENSED MGR. - LUXURIOUS OCEANFRONT CONDO! - W/STUNNING OCEAN/ISLAND VIEWS!

Key Largo hotel apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$402

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$458

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$516

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$366

Best Kept Secret,Port Largo Villas In Key Largo,FL

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$224

Key Largo Mariners Club Paradise: Largest Unit, Abundant Amenities!

Key Largo townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$689

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$574

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rentals in Islamorada

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