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Vacation Rentals & House Rentals in Islamorada

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295 house rentals

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

Islamorada house

4 bedrooms / 2 bathrooms / sleeps 14

Price per night from

$401

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. 1 hour 51 minutes

Price per night from

$573

Keys Kottage

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$269

Discover the Charm of Island Living

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 10 minutes

Price per night from

$229

Beacon Reef 404

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$164

76004 Overseas Highway

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

“Wonderful accommodations” Aside from being rainy for the majority of our stay, the accommodations were amazing. We will certainly be going back to this house. This house sleeps 8-10 adults comfortably. Freewheeler Realty was a pleasure to do business with and was the only company that was responsive to my inquiries. The house has an amazing view, full laundry, kitchen upstairs and downstairs. My favorite part were the stairs that go directly into crystal clear water to snorkel!

Price per night from

$328

BEACON REEF 306

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$123

ANTIGUA PLACE

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$207

Windy Cove #1

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$328

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$287

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$100

102 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$126

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$982

Conch & Lobster Homes

Islamorada house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$916

Windley Key, FL Keys

Islamorada caravan/mobile home

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$115

LITTLE BAY - Lower Duplex

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful House in the heart of Islamorada” My kids and I stayed on the property and rented the lower duplex. We had an amazing time and the dock for our boat was perfect. The kids and I went paddleboarding right off the back of our house and the dog also loved the large yard. The kids could snorkel right out back and it was located right next to everything. We never used our car to get around since we had the boat right in our back yard. We will most certainly be back.

Price per night from

$429

PALMS 301

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$93

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$148

BEACON REEF 501

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$133

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$133

PALMS 314

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Wow, what a beautiful view” This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the daytime the view would take your breath. However, at night the lights from the parking lot would shine into our bedroom. Alas, with the flip of a switch an outside shutter would roll down and the room was completely dark. Talk about sleeping well! As for the complex, everyone was very friendly and we made some very good friends. The pool was heated and the hot tub was always warm and enjoyable. We have already made plans to go back next year. If you have the chance to rent a unit there, GO, you will not be sorry.

Price per night from

$80

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$123

LITTLE BAY - Cottage

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$429

Gorgeous waterfront home

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$458

Waterfront Home With Ramp

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

Bay Harbour C-312

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$328

137 LeSerra Lane

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

“The best house we have rented in the keys!” This is the best house we have ever rented in the keys! The furnishings are modern, up-to-date and comfortable, the layout is perfect, the house is well-equipped and well-maintained, and the view is fabulous! Water on all sides, either the canal, ocean or bay, so no matter what room you are in you have a fantastic view! The location at MM 76.4 Is very convenient to everything in Islamorada including some great restaurants, and if you have a boat, you are only one house in from the ocean. I would definitely rent this house again!

Price per night from

$393

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$107

PALMS 417

Islamorada apartment

1 bedroom / 2 bathrooms / sleeps 2

“Paradise on the ocean” We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay side with amazing sunsets. People in surrounding condos were very friendly; and one condo owner gave us some lovely smoked fish. Some road noise but we soon got used to it as the condo and location soon out weighted any small negative of the road noise. Holiday Keys Rentals agency went out of their way to assist us. And would definately rent one of their properties again; esp Palm 417.

Price per night from

$70

132 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

“Fantastic getaway” This is a great vacation rental property for a couple or small groups of 4 or less people. First of all, you can't beat the panoramic view of the water and what's more, the water is just 10 ft away. The front yard is one of the best if not the best with a lot of gardening and the antiques placed in the garden easily beats the boring gnomes. The interior of the house has a very wood cabin like feel to it and if you're looking for modern furniture, you'll be disappointed but if you're into a quaint little cottage like atmosphere, this will not disappoint. The 2 bedrooms are well kept and there are tons of pictures on the wall from the owners' travels all over the world and they're very interesting. There is no flat screen TV but the old color TV is more than sufficient - it has cable with most big channels you'll need (no premium ones except maybe Encore). They also have a ton of Dvds and Music CDs for your entertainment if you ever get bored of the views from the wrap around deck :-) The sunrises from this deck are awesome if you can wake up early - no sunsets cuz that's on the other side but you can always walk/drive over to the Overseas highway within minutes to catch the sunsets from there. The other amenities worth mentioning are the inground hot tub/spa they have which was awesome - you can view the ocean from the spa. If that wasn't close enough a view, you can pick up the huge Kayak they have and walk right into the water and row away. If there was any drawback, it was these bugs called no-see-ums that come out in full force in the evenings and if you aren't taking necessary protection, they will wreak havoc on your skins, but the owners/realtors can't do much about this. Just get some Off spray or something and you'll be fine. Overall this was a memorable trip for us and we hope it will be for you too. Thanks!

Price per night from

$328

Futura Townhome #731

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$252

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$117

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

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$153

RIOLO VILLA

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$143

Executive Bay G-5

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$115

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$292

107 San Remo Drive

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$410

BROCK HAUS ON THE GULF

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Absolutely Beautiful and convenient for boaters!” Our family stayed here for a week in late March. We had plenty of room and everything we needed was available. This is a gorgeous condo overlooking the Florida Bay. You get to see an awesome sunset every day. We also brought our boat and the dock is literally right across the condo and ocean access is not too far away by water. Manatees visited the dock about every day, you can see picture below. We looked at other condo options and by far this was the best that suited our needs. The service provided was excellent. They were a phone call away if we needed anything. We will definitely be staying here again. Thank you so much!

Price per night from

$228

Viewing 38 of 295
rentals in Islamorada

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About Islamorada

Islamadora, or "Village of Islands", refers to the collection of islands in the Florida Keys including the Keys of Tea Table, Upper and Lower Matecumbe, Plantation, and Windley. Every destination in Islamadora offers access to the very best of this island paradise. The beautiful beaches, emerald golf courses, luxurious spas, and charming local museums in Islamadora make this the perfect place for a family vacation. Islamadora also offers easy access to Everglades National Park, an ecological destination that draws visitors from all over the world to see its dazzling biodiversity and elusive marine life. Come to Islamadora to play, explore, learn about the culture and history of the Florida Keys or simply relax. After the sun goes down, experience the world-class seafood restaurants and laid back vibe of Islamadora's night life.

Here are a few additional suggestions as you plan your trip:

  • Visit the Theater of the Sea: This place is a nature center, aquarium, and theater all rolled into one. Come here to learn about the marine ecosystems of the Florida Keys and interact with dolphins and sea lions.
  • Explore the wharf: Go fishing, rent a boat, or feed the gigantic tarpon at Robbie's marina. There are also sport fishing marinas in Islamadora where you can schedule charter trips and pursue large game like swordfish.
  • Visit the History of Diving Museum: The interactive displays and extraordinary collection of artifacts at the diving museum provide a great way to learn about maritime history and culture.
  • Take an eco-tour: Explore the Everglades National Park by boat, one of the best ways to see marine plants and animals in their natural habitats.
  • Play on the beach: Annie's Beach offers a clean stretch of beautiful white sand and blue ocean waves, perfect for a relaxing day with children. Go swimming, surfing, parasailing, rent a boat, or just sunbathe with a good book.
  • Visit the Windley Key Fossil Reef Geological State Park: This park is known for its hiking trails but more so for its incredible fossilized coral reefs.

Finding a place to stay will be easy in Islamadora, even if you arrive during the height of the summer. Find a quaint cottage for a romantic getaway, a summer home big enough for your whole family, or a luxury beach villa for you and some friends. No matter what you plan to do while you're here, you'll be able to find the perfect vacation rental to meet your needs.

Top Destination reviews

SANCTUARY IN PARADISE
A truly perfect setting

This is a spectacular area to scuba dive, snorkel, catch lobster, fish, jet ski, boat or just hang out at the beach. The kitchen in the upstairs is equipped to feed whatever you catch to a crowd and was great to work from. We had 10 people ages 2-90 in the three units and it was so nice to be able to stay together on one property.see more
The PERFECT Escape with pool & jacuzzi
Great keys get-a-way! Pool and canal front make it awesome

This home is in the great area of Venetian shores, huge dock on canal with direct ocean access. The pool makes this the perfect keys vacation home. … see more
THE PERFECT GETAWAY
The owner was understanding and worked with us

I was scheduled to rent from Dec 29th to Jan 4th and expected 7 friends to join me. For multiple personal reasons four of the seven had to back out and it is not the place you want to be without the full group. I was very concerned and as soon as I knew there would only be three of us I contacted the owner and explained what had happened and asked if I could reschedule. He immediately responded that he would be willing to reschedule. Not only have I told my guests, but several friends who frequently rent in the Hilton Head/ Daufuskie area how accommodating this owner has been. We are looking forward to our visit there.see more
Oceanfront Oasis - Pinch me am I dreaming!!!
Relax in Luxury

Great Location. Lots of nearby restaurants. Owners were extremely helpful in recommending attractions. A stunningly beautiful home with plenty of room for my large family to spread out. Pool was great. Swimming in warm shallow waters off of our own private beach was perfect for the kids. Pictures don't do it justice. Plenty of amenities - snorkeling gear, paddle boards, kayaks, pool toys, karaoke machine, portable waterproof sound system, etc. I have been to Florida many times always renting houses. This was by far the best.see more
Newly refinished condo open water views very nice
Paradise

Staying at this Condo on the 5th floor was awesome. From the 5th floor you have an incredible view that seems to be difficult to find in the keys. This gated community is quiet and laid back. If you want a quiet, easy vacation this is definitely a place to consider. I’ll be going back. … see more
Islamorada cottage on deep water canal
Comfortable, peaceful home in the Keys

We found the place very comfortable and peaceful. Spent a lot of time sitting under the nice canopy right on the canal, and did a little fishing there also. Had our morning coffee and ate our meals on the screened porch whenever weather permitted. It is an older home but very well maintained and updated. Nice décor with a lot of personal touches . Caretakers and owners quick to respond the few times we had questions. We really enjoyed using the kayaks . Saw manatees, porpoise, lots of colorful and interesting fish. Close to grocery store, so many great places to eat , but everything needed in the kitchen for those like us that also like to cook. Since the rental is in Islamorada we only needed to present our rental agreement to have free entry to the wonderful Founder's Park just over a mile away. Already booked for next year.see more

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