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Vacation Rentals & House Rentals in Islamorada

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74 house rentals

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 8 minutes

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Price per night from

$401

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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$344

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / sleeps 5

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$168

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 3 minutes

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$574

Fabulous 6bedroom /4bathroom Waterfront Pool Home in Islamorada - 3/2 Each Level

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 33 minutes

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$382

Paradise at Islamorada

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

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$161

Recently Remodeled Beautiful Pool Home with Private Dock with Beach Access

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

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$421

Beautiful Pool Home with Private Dock with Beach Access

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

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$403

Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Islamorada townhouse

2 bedrooms / 3 bathrooms / sleeps 6

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$333

Mile Marker 87 - Mina Bay - Oceanfront "Million Dollar View"

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

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$150

Islamorada Florida Cozy Cottage

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 2 hours 8 minutes

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$327

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

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$227

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 6

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$286

Great rentals within 20 miles that match your search

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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$78

Spectacular open Bay views in beautifully remodeled home 2/2 or 4/3 you choose

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

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$624

Island Conch Cottage

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$146

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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$174

Beautiful Private Home with Beach Access.

Key Largo house

2 bedrooms / 1 bathroom / sleeps 6

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$58

Key Largo Beautiful House

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 27 minutes

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$288

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$211

Private Beachfront Paradise

Matecumbe Key house

4 bedrooms / 3 bathrooms / sleeps 8

“Nicest rental property we have ever stayed in!!” Beautiful home on spotless white beach! Property has been updated with upscale furnishings throughout. Granite, leather furniture, redone bathrooms. Well stocked for all your vacation needs -- towels, beach chairs, beach toys, kitchen full of everything you need, 2 grills. Outside patio was amazing for our meals, sunrises and after dinner activities. The backyard was the beach filled with palm trees for natural shade. Hammock and volleyball court, beautiful pool with waterfall, tables and chairs everywhere for meals or for just relaxing. We traveled as two families and there was more than enough room for all of us. We felt right at home right away. Highly recommend this paradise!

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$824

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.

Responds fast! avg. 3 hours 37 minutes

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$132

Luxury Bayside Resort Home

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 11

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Price per night from

$306

Del Valle Houseboat Getaway

Key Largo boathouse

1 bedroom / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$239

Private Key Largo Bayside Canalfront home

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 30 minutes

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$167

Sailing Catamaran in the Florida Keys, Sailing, diving, adventure experience.

Key Largo yacht

3 bedrooms / 3 bathrooms / sleeps 6

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$1,612

Penthouse Paradise | Developer Unit w/ Every ★ Upgrade Possible!!

Layton apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 7 minutes

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$1,437

Cypress House 3bed/2bath with 40ft of dockage

Matecumbe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 28 minutes

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$443

A Coastal Getaway the most beautiful modern house in Key Largo!!!

Sunset Point house

6 bedrooms / 5 bathrooms / sleeps 18

Responds fast! avg. 28 minutes

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$621

Blue Water Escape 2 bed 2 bath includes Kayak and paddleboard, Sunsets are Free

Tavernier house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 28 minutes

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$221

A Pirates Great Escape ~ 3bed/2baths Ocean View Slip ~LKKB

Layton condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 28 minutes

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$336

LICENSED MANAGER - MODERN 2/2 SUITE - AREA'S MOST LUXURIOUS OCEANFRONT RESORT!

Key Largo villa

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful condo in a great location” The Mariners Club has great potential. Jose made our stay as comfortable as possible with some great entertainment recommendations! Unfortunately not all the amenities listed were functional due to hurricane damage but we still had a great time. I would definitely come back to this location, but not until it was fixed up.

Responds fast! avg. 2 hours 37 minutes

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Price per night from

$247

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

1 bedroom / 1 bathroom / sleeps 4

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$258

Comfortable Clean HouseBoat in an amazing location

Tavernier boathouse

1 bedroom / 2 bathrooms / sleeps 5

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$401

OCEAN VIEW 1BR APARTMENT! PRIVATE BEACH, TENNIS, POOL, PARKING, HOT TUB!

Tavernier apartment

1 bedroom / 1 bathroom / sleeps 4

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$160

FLORIDA KEYS GETAWAY! COMFY OCEAN VIEW 1BR! PRIVATE BEACH, MARINA, POOL, BBQ

Tavernier apartment

1 bedroom / 1 bathroom / sleeps 4

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$160

BEACH VACAY STARTS HERE! OCEAN VIEW, 1BR APT! PRIVATE BEACH, TENNIS, POOL

Tavernier apartment

1 bedroom / 1 bathroom / sleeps 4

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$160

PRIVATE BEACH OPEN!! Comfy Ocean View 2BR/2BA with Balcony, Pool, Tennis!

Tavernier apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$171

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