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Vacation Rentals & House Rentals in Islamorada

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308 house rentals

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

Oceanfrontparadise: 209

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$285

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

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 24 minutes

Price per night from

$200

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,700

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 55 minutes

Price per night from

$202

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

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$430

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

Bay and Beach Beauty

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 56 minutes

Price per night from

$397

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$248

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$340

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$113

Oceanfront Oasis - Pinch me am I dreaming!!!

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 53 minutes

Price per night from

$6,158

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$86

82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$982

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

$429

Futura Yacht Club # 205

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$161

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!

Price per night from

$259

Executive Bay G-5

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$115

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

Price per night from

$667

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$262

107 San Remo Drive

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$393

Bayside Condo, marina, pool and beach

Islamorada condo

3 bedrooms / 2 bathrooms / sleeps 6

“The Best Keys Location” My family stayed at this lovely Futura Yacht Club Condo for three weeks this July. We have stayed at many other units in this complex over the years but this unit was one of the nicest we have seen. The unit has been remodeled and it has everything you would need for a great Keys vacation. Futura Yacht club has a big heated pool, tennis courts and if you are a boater a great marina with its own boat ramp which made it easy for us to enjoy our boat and jet ski's. It is a gated complex with security, centrally located to all the activities & restaurants in the area. We found the owner most helpful, accommodating and easy to deal with. We are looking forward to our next stay!!

Price per night from

$154

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

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

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

Bay Harbour C-312

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$328

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$168

LITTLE BAY - Cottage

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$429

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$117

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

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$423

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$352

102 Columbus Drive

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$126

141 Ocean Lane

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$210

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

“Just what the family needed” The accommodations were just what we needed. Chris was a gracious host; she was available for anything we needed. The location and amenities fit our needs perfectly. We were able to swim and kayak in the channel, hang out in the tiki hut, play cards and share meals in the large kitchen. We were close enough to family members, restaurants, and attractions. The trip to Key West wasn't too bad either. Overall, a perfect rental!

Price per night from

$585

Paradise Beach Sandy Oceanfront

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 25 minutes

Price per night from

$1,360

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$306

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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

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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