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Vacation Rentals & House Rentals in Islamorada

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391 house rentals

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” The unit was great, the views of the sunrise were amazing. Enjoyed our stay! The owner Deanna L unit 303 .

Price per night from

$221

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$174

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,727

75731 Overseas Highway

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. Brandi at Freewheeler Realestate was wonderful. She was prompt with answers to questions, friendly and professional. The home-owner obviously wants to see to it that the people staying in their home are well taken care of. Everything was great all the way down to the fluffy beach towels. We will definitely look at staying at this home again.

Price per night from

$1,227

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

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 38 minutes

Price per night from

$167

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 23 minutes

Price per night from

$402

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

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 49 minutes

Price per night from

$204

Dream Escape in Islamorada at Anglers Reef

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 8 minutes

Price per night from

$349

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$430

Islamorada Tropical Canalfront Paradise

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 40 minutes

Price per night from

$319

THE PERFECT GETAWAY

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

“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.

Price per night from

$465

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 39 minutes

Price per night from

$1,411

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 47 minutes

Price per night from

$172

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

$263

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$86

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$113

Futura Yacht Club # 205

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$148

Summer Sea #418

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$153

107 San Remo Drive

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$344

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$262

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!

Responds fast! avg. 1 hour 41 minutes

Price per night from

$262

140 Atlantic Lane

Islamorada house

5 bedrooms / 4 bathrooms / sleeps 10

“Great vacation” We visited over Christmas.All nine of us! The main house and guest house configuration worked out great for our multi- generational group, giving the younger group the opportunity to stay up later and sleep in later. The house had everything we could have needed,including a washer/dryer which came in very handy. Big patio doors let in the ocean breezes and kept the house bright. Quiet location right on the canal and on the beach. No beach, Beautiful, multi hued, water to gaze upon, with easy access to the water for swimming etc. rented kayaks, fished right off the pier and enjoyed the resident chameleons in the mangroves out front. The management was very friendly and responsive to all our questions. Great location, offers peace and quiet yet only an hour and a half drive to Key West for a day trip. Lots of restaurants and shops nearby. A table on the balcony would be nice for outdoor eating, but not a huge problem.Overall, wonderful!

Price per night from

$492

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$349

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. 42 minutes

Price per night from

$614

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$883

Executive Bay G-5

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$115

$2500 A MONTH FOR OCTOBER AND NOVEMBER. OCEANFRONT 2 BEDROOM/2 BATH CONDO

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing view! Absolutely gorgeous!” My two teenage daughters and I stayed at this condo and it worked out perfect for us! The view is stunning, and I loved to just sit in the living room and look out at the ocean. The condo was very clean, and really nicely decorated. There were some beach chairs on the balcony that we used at the beach which was nice to have since we had flown to Florida. There were also beach towels to use. The kitchen was cute with everything you would need to cook, although we mainly just ate breakfast there. It is located away from traffic so nice and quiet. I swam in the pool once and it was warm like a bathtub. Felt good after a day at the beach. This was our first trip to the Keys, and I liked that we were centrally located. We were a couple hours from Fort Lauderdale where we flew in from, and a couple hours from Key West where we went for a day trip. We loved John Pennekamp State Park which is only about 20 minutes away, and swam with a manatee at Canon Beach. We also snorkeled with Robbie's in Islamorada which is 20 min. the other way from us. I would definitely stay there again if I return to the keys.

Responds fast! avg. 1 hour 47 minutes

Price per night from

$126

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

“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.

Responds fast! avg. 1 hour 3 minutes

Price per night from

$1,718

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$150

LITTLE BAY - Upper Duplex

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

“Classic Islamorada - Amazing Property” Little Bay was a perfect property for us! The setting is idyllic and classic keys - Huge backyard on the Bay with excellent dock area, hammocks and view of the bay. Covered porch was the full width of the house and was a great place to hang out morning and evening. The property had everything that we needed, was centrally located and have plans to visit again! Service provided by rental agency was top notch and very attentive - they showed us around, accepted packages on our behalf and were friendly and helpful throughout our entire rental experience - from planning to checkout. This is definitely on our To Re-Do List.

Price per night from

$393

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

$211

152 Valencia Drive

Islamorada house

4 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$267

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 35 minutes

Price per night from

$582

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

102 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$126

Islamorada 2-bedroom Condo

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic Views” This 6th floor unit has all you need for a relaxing vacation. Close proximity to local attractions and fantastic Seafood Restaurants. The Hospital is one mile from the condo and has an excellent rehab and emergency. The complex has a private heated poool, work out room and sauna. The grounds are cleaned every morning and the manager responds to needs promptly. We will again stay here in 2013. repeat customers. That will be our 6th year in a row at Sea Gulls.

Price per night from

$188

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

$368

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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

100' Private Beach Front Ocean Front Estate
Beach Paradise

The location was perfect and loved the privacy that this property offered us! The owner and the local property manager were very helpful and quick to respond! … see more
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
$2500 A MONTH FOR OCTOBER AND NOVEMBER. OCEANFRONT 2 BEDROOM/2 BATH CONDO
Oceanfront condo

Fantastic views and great accommodations. A great place for a base in the Keys. The complex was affected by the hurricane and is almost back to better than before. … see more
Islamorada Luxury Waterfront Condo with Boat Slip
Great Keys Condo

Owners are very responsive. Great condo with boat slip and very good location. Very well provisioned. The condo even has a freezer chest for bait and ice. … 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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