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Houses Islamorada

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84 houses

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 44 minutes

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$488

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 25 minutes

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$343

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

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$4,122

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

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$107

Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom / 1 bathroom / sleeps 2

“AMAZING!!!!!!!” Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips when we asked. The studio was so well stocked with all the essentials and then even the ones you forgot! It was wonderful to see a manatee swim up past the dock our first morning there. A very magical spot with generous hosts. It had everything we wanted and then some. After a week there and driving around the whole Keys it was 100% the most perfect choice for us. I miss those hammocks!

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$580

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 25 minutes

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$679

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

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$292

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. 3 hours 28 minutes

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$994

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

“Just what the family needed” The accommodations were just what we needed. Chris was a gracious host; she was available for anything we needed. The location and amenities fit our needs perfectly. We were able to swim and kayak in the channel, hang out in the tiki hut, play cards and share meals in the large kitchen. We were close enough to family members, restaurants, and attractions. The trip to Key West wasn't too bad either. Overall, a perfect rental!

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$522

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

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$580

RIOLO VILLA

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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$143

ANTIGUA PLACE

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

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$207

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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$215

Gorgeous waterfront home

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

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$464

WEST LAKE PLAZA

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

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$200

San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 41 minutes

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$1,821

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool

Islamorada house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 41 minutes

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$1,507

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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$456

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 25 minutes

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$382

Cozy Keys Cottage Islamorada FL.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 44 minutes

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$348

AZALEA WARTERFRONT

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 6

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$395

Islamorada cottage on deep water canal

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

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$290

Boater's Paradise

Lower Matecumbe Key house

4 bedrooms / 3 bathrooms / sleeps 10

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$377

Bayview house with bayviews. Pool with Spa, dock center of town great fishing !!

Islamorada house

2 bedrooms / 1 bathroom / sleeps 6

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$829

Waterfront Home, 20ft Boat Ramp

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

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$232

New Listing! Luxury Oceanfront Estate in Islamorada - Booking now for 2023

Lower Matecumbe Key house

6 bedrooms / 7 bathrooms / sleeps 14

Responds fast! avg. 2 hours 16 minutes

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$1,855

Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn

Islamorada house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 59 minutes

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$696

The PERFECT Escape with pool & jacuzzi

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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$386

Beachfront Islamorada Villa with Dockage and Bay Views

Lower Matecumbe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$332

New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 38 minutes

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$922

Majestic estate, 200' of private oceanfront beach & pool, ideal wedding venue

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$1,469

Great rentals within 20 miles that match your search

Private Beachfront -Perfect for Families and Events Historic Shadow Point Estate

Key Largo house

6 bedrooms / 5 bathrooms / sleeps 16

“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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$2,087

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.

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$140

Bayside Retreat. Pool, Boat and Beach

Key Largo house

5 bedrooms / 4 bathrooms / sleeps 10

“SPLENDID VACATION” I had the opportunity to stay here with my family in March. The house was spacious and the beach and pool were exactly what we wanted for a private family vacation. The house manager, Kevin, could not have been more accomodating in seeing that all of our vacation needs were taken care of. I could have sat on the porch and watched the sunset views forever. Watch for the manatees when you are there, they are a lifetime experience.

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$1,275

Waterfront Vacation Beach House Rental Home Bayside Steps from the Water

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 9

“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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$522

Waterfront Home In Florida Keys

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 4

“Perfect Holiday in Tavernier” We had a wonderful time at Dan and Penny's home. They were very accommodating! The home is absolutely pristine and in a nice neighborhood. There wasn't a day that we did not see manatee and tarpon in the canal in front of the house. Perfect location for restaurants, shopping and activities either by land or water. Beautiful home with everything you need for a perfect vacation in the Keys!

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$194

Beautiful Private Home with Beach Access

Key Largo house

2 bedrooms / 1 bathroom / sleeps 6

“Great place for a family” Wonderful place to stay! My family of 5 enjoyed the clean rooms and full kitchen. Easy access to private beach, restaurants, grocery store. Very safe neighborhood. The house was fully provided for our stay, Great access to John Pennycamp and the Everglades. We would definitely stay here again. Daniel A. was very easy to work with. We enjoyed coming home after a busy day of snorkeling to make supper and lounge on our own deck or wander down to the private beach to enjoy the evening. Having this home made our vacation very relaxing and enjoyable.

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$69

Clean Keys 3/3 w/Davits Clear Canal Bay Side/Views Fenced 2Level Tavernier Home

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 12

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Price per night from

$250

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