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Islamorada Rentals by Owner

(60 rentals)
Islamorada Villa
Sleeps 4, 2 bedrooms, 2 bathrooms
14 reviews

Distance to beach: 5 miles to Anne's Beach

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Welcome to The Nest Villa & Marina in the heart of beautiful IslamoradaNestled on a picturesque 1-acre lot overlooking the stunning Florida Bay in the Florida Keys, the Nest Villa offers a perfect blend of privacy and proximity. This exclusive residence is one of seven privately owned villas,...

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Featured review

"Amazing location, view, and super clean!"

My 18 yr old son and I stayed here at the end of September and it was a fantastic trip!We have been going to the keys for 14 years several times a year. This unit is the cleanest we have ever seen!...

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$325
avg per night
Islamorada Townhome
Sleeps 4, 2 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking...

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Featured review

"Great Location"

This condo was very conveniently located. We could snorkel at John Pennekamp and kayak the mangroves of Islamorado. Plenty of close good seafood restaurants in vicinity. Spend the day at Bahia Honda.

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$283
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Great house! Great location!HOUSE ON CANAL… 34 foot concrete dock with fish cleaning stand, water and electricity. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. We are also...

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Featured review

"Excellent vacation rental"

This house is beautiful. Right on a canal where we kept our boat for the week. Manatees came by to visit daily. Caught keeper mangrove snapper right there. Neighbors were amazingly friendly. Everything...

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$297
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Named one of the most romantic destinations in the world, this Magnificent brand new home in the heart of Islamorada is nestled between Cheeca Lodge Resort and Caribbean Resort offers a unique and luxurious experience for those looking for a private getaway. This 4 bedroom/4.5 bath home services from...

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Featured review

"Great House, Great location"

Had a great time! The house was amazing and well-appointed. We grilled, we cooked, amd we walked to several great dinner spots. The pool was excellent with the grandchildren. Highly recommended!

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$1,150
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you...

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Featured review

"Outstanding view and amenities. Will return soon!"

Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.

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$318
avg per night

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Islamorada Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs...

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$183
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and...

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Featured review

"Bayside Paradise Perfection"

Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt...

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$978
avg per night
Islamorada Townhome
Sleeps 6, 2 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy breathtaking sunsets on the private beach while staying in this beautifully remodeled corner unit. The unit was completely gutted in 2021 and features 2 bedrooms plus a built out loft and 3 full bathrooms.The unit has a huge master with a king bed plus a bathroom/walk-in closet and...

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Featured review

"A perfect place to relax and unwind"

Spending the month of December at this beautiful condo with my family was an unforgettable experience. The condo itself was warm, cozy, and inviting, with all the amenities we could possibly need for a...

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$175
avg per night
Islamorada Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

We are delighted to offer this 2 story, 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! There are a limited number of oceanfront townhomes available at Planation By The Sea! Enjoy the breathtaking views off of all 3 balconies catching the sunrise and sunset. The main living area and upstairs bedroom...

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Featured review

"Beautiful waterfront Condo"

We had a wonderful month in Islamorada at this outstanding waterfront condo with pool and sauna, dock etc. The views were gorgeous from the 3 decks in this corner unit. The area is exciting and near both...

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$184
avg per night
Islamorada Cottage
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove...

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$290
avg per night
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