Vacation Rentals & House Rentals in Islamorada

/ Home
/ Vacation Rentals
/ United States
/ Florida
/ Florida Keys
/ Islamorada
Book with confidence.

Updating...

age 0-16
54 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

54 house rentals

Why am I receiving these results?

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Garden

All filters match

Price per night from

$201

Bay and Beach Beauty

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 10 minutes

Match: Garden

All filters match

Price per night from

$532

Islamorada Waterfront Paradise Getaway!

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

Match: Garden

All filters match

Price per night from

$573

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$573

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$802

Gorgeous waterfront home

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$458

Match: Garden

All filters match

Price per night from

$2,127

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

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$1,145

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$457

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

Islamorada villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$1,145

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

Match: Garden

All filters match

Price per night from

$408

AZALEA WARTERFRONT

Islamorada house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$390

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$287

Keys Kottage

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$315

Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$602

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$184

Match: Garden

All filters match

Price per night from

$206

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Garden

All filters match

Price per night from

$659

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$377

Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Garden

All filters match

Price per night from

$602

New Listing! Charming Angler's Reef Home with Pool, Dockage

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$457

Match: Garden

All filters match

Price per night from

$602

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

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$784

Islamorada Townhome w/Beach View, Pool, Marina,Tennis! Perfect Family Getaway!!

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$203

Perfect Family Getaway! Waterfront Vacation Home in Islamorada, Florida Keys!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$659

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$773

BAYSIDE Villa

Islamorada villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Garden

All filters match

Price per night from

$315

Majestic estate, 200' of private oceanfront beach & pool, 3,600sqft tiki

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$1,472

Great rentals within 20 miles that match your search

Match: Garden

All filters match

Price per night from

$149

Modern house in the heart of Key Largo

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$343

Paradise in Key largo

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$286

Sunrise Waterfront Home

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$487

Waterfront Key Largo Bayside Cottage Paradise

Key Largo cottage

  • 1 bedroom
  • 2 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. 56 minutes

Match: Garden

All filters match

Price per night from

$252

Cozy Couple Getaway! or Great Family Home

Key Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

All filters match

Price per night from

$144

Unique Houseboat on Dry Lot

Key Largo houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Quaint and unique rental” The houseboat was everything I expected and needed it to be. It slept our family of four comfortably - which was all we really needed. The weather was good so really the only thing we did at the houseboat was shower and sleep. We did also do a few loads of wash - having a full size washer and dryer was convenient. I bet if we spent more time there, we would have used the back yard, it is really neat and welcoming. Maggie was a gracious hostess and everything was exactly where and how she described it. All in all a great value.

Match: Garden

All filters match

Price per night from

$98

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.

Match: Garden

All filters match

Price per night from

$172

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.

Match: Garden

All filters match

Price per night from

$86

Match: Garden

All filters match

Price per night from

$247

Viewing 38 of 54
rentals in Islamorada

×

Also consider