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Vacation Rentals & House Rentals in Islamorada

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75 house rentals

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Sea view

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Price per night from

$1,720

NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 31 minutes

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Price per night from

$206

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!

Match: Sea view

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Price per night from

$259

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. 16 minutes

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Price per night from

$667

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$422

Paradise Beach Sandy Oceanfront

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 25 minutes

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Price per night from

$1,261

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$310

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$158

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

Match: Sea view

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Price per night from

$382

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. 1 hour 25 minutes

Match: Sea view

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Price per night from

$1,261

2 Acres on the Atlantic Ocean in Islamorada, Florida

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 49 minutes

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Price per night from

$373

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. 1 hour 25 minutes

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Price per night from

$1,261

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$376

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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Price per night from

$333

Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

Islamorada villa

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$1,151

Islamorada Florida Cozy Cottage

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 4

Responds fast! avg. 2 hours 8 minutes

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Price per night from

$327

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

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$150

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$227

3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$273

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$286

Peacock Shores Oceanfront Islamorada

Islamorada townhouse

2 bedrooms / 3 bathrooms / sleeps 4

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Price per night from

$366

Great rentals within 20 miles that match your search

A Piece Of Paradise

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$75

Paridise Found

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 13

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Price per night from

$779

Paradise on the water

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 36 minutes

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Price per night from

$578

Waterfront Key Largo Bayside Cottage Paradise

Key Largo cottage

2 bedrooms / 4 bathrooms / sleeps 4

“Hidden Treasure” This cottage is one of our favorite place to stay. Clean, well equipped, private, and so relaxing. A great place to spend a relaxing vacation. We love the outdoor kitchen and sitting area.

Responds fast! avg. 1 hour 45 minutes

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Price per night from

$179

Key Largo Beautiful House

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 27 minutes

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Price per night from

$288

Your New Happy Place in Key Largo

Tavernier townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Match: Sea view

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Price per night from

$227

Match: Sea view

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Price per night from

$211

Waterfront Home w/EZ Ocean Access*Boat Slip*Roof Top Deck*Hot Tub*28 nt min

Key Largo house

3 bedrooms / 4 bathrooms / sleeps 6

“Great Key Largo Rental” We rent homes on the water in the Keys frequently. By far this is the best home we have rented. House is immaculate, fully equipped,and only a short ride to the ocean. On water gas super close. Restaurants within walking distance. Management company is awesome, very responsive and prompt.

Responds fast! avg. 55 minutes

Match: Sea view

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Price per night from

$205

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Sea view

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Price per night from

$287

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

$240

Key Largo Rental Fantastic Views

Key Largo condo

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$345

Tropical Island Getaway-Keys

Key Largo condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$277

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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Price per night from

$1,959

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

Key Largo yacht

3 bedrooms / 3 bathrooms / sleeps 6

Match: Sea view

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Price per night from

$1,614

Key Largo 2/2 Tropical Daze Oceanfront Condo

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. 1 hour 27 minutes

Match: Sea view

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Price per night from

$276

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

1 bedroom / 1 bathroom / sleeps 4

Match: Sea view

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Price per night from

$258

Comfortable Clean HouseBoat in an amazing location

Tavernier boathouse

1 bedroom / 2 bathrooms / sleeps 5

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Price per night from

$402

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rentals in Islamorada

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