10 Best Vrbo Vacation Rentals In Islamorada, Florida - Updated 2022

vrbo islamorada

Islamorada is an incorporated village situated in Monroe, Florida. The name is of Spanish origin and it literally means “Island Home.” Although there are times that it is also called “Purple Isle.” It boasts of having beautiful and awe-inspiring coral reefs that will surely leave any visitor’s mouth agape. Having numerous islands composing the whole village, it does not lack any food that comes from the seas. Visitors may partake in fishing activities as well as indulge in the delectable and sumptuous feasts that the sea offers. Here are some properties where you may stay and enjoy everything Islamorada can offer. Keep reading to learn about the best Vrbo accommodations in Islamorada, Florida.

1. Condominium unit with ocean views (from USD 279)

This unit is located at the best location of Islamorada’s Oceanfront Condominium. It has a bright and breezy atmosphere and it also has panoramic views of the ocean. It is only minutes away from multiple places; Old Tavernier Restaurant, the PADI certified Florida Keys Dive Center, Theater of the Sea, the quaint Wild Bird Center and a lot more. For those who do not enjoy traveling around, they may indulge in the comforts of the unit with a high-speed WiFi router, high definition television, Bluetooth speakers, and the condominium’s very own swimming pool.

Oceanfront Condo with PANORAMIC Ocean Views, Pool, FREE WIFI
112 reviews  Wifi Available
condo 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Bed was very comfortable plenty of towels in bathroom pool at condo is
The beds provided excellent sleep and sweet dreams
The pool is immaculate and the charcoal grills on the beach were great
Everything was pretty much as advertised
but both have features (en suite bathroom in one; big sliding door to balcony in the other)
It was very clean and bright
Very nicely furnished and very clean
The owners also had plenty of informational notebooks and pamphlets to assist with "Things-to-Do" and/or
The unit is very clean and well appointed and Donna is a pleasure to work with
The condo itself is extremely clean very comfortable and boy
She returned all emails and text messages very quickly and answered all questions
We had great communication with the owner
that make them balance out
Hopefully she will have us back in the future
We met several really nice people at the pool
Perfect location for a quiet getaway Off the main highway just enough
The location was just perfect also
Many restaurants and shops Overall wonderful
It's a great location
/walk along long white sugary sandy beaches
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2. Tropical property near the ocean (from USD 249)

Situated near the ocean, this tropical bungalow gives off the feeling and atmosphere of being disconnected from the toxicity of life. Despite that, it is near luxurious restaurants, pubs, marinas, and shopping centers. It is only two blocks away from the ocean where guests may enjoy fishing, boating, kayaking, and other water activities.

Islamorada Escape – Bungalow #4 – Cozy, clean, tropical oasis!
61 reviews  Wifi Available
House 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
It was very nicely equipped with a functional kitchen and modern bathroom with shower
It was wonderful and had everything we needed included
The unit itself was also smaller than we were expecting
you wont be sorry
updated and pool was nice Home can be a little noisey at night because of the highway
well decorated and up to date) and perfectly appointed; towels linens
Our bungalow was we clean and had everything we needed
It was very clean and comfortable
I loved the simplistic beachy feel of the cottage and found the place to be clean and well equipped
We like having personal recommendations to guide us while on vacation
" The owner Caitlin was very attentive to any questions we had with speedy responses
great clean new fun great pool
so we checked out many of the places suggested in the welcome packet
All info regarding the home was honest and accurate Couldn't ask for better weather which always helps a review
Outdoor activities and restaurants are close by
and we enjoyed it several times
The bottle of Prosecco was a nice surprise
My family enjoyed the activities snorkeling parasailing
The location is very close to all restaurants food stores and fun places to visit Recommend you visit Founders Park
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3. Child-friendly property in front of the ocean (from USD 150)

This two-bedroom property can hold up to four individuals. It is close enough to the ocean that guests may enjoy various water sports and satisfy their inner surf dudes. Workout maniacs would love the place as it has a state-of-the-art workout gym. In addition, it has a sauna that can help relieve the muscles after a long and strenuous workout. Guests are also free to bring their boat or even rent one as the place has a free dockage for such.

Oceanfront Islamorada Condo with T-Dock FREE boat dockage
7 reviews  Wifi Available
condo 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 28
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Although the unit is not the best location in terms of the water it is fine
Great condo Close to pool ocean and boat slip
all Pat as well as her family were very quick to help with anything that came up or answer any questions that we had
We took so many excursions even a garden tour and still have lots left for next year
Pat left us was invaluable
We rented our condo for February to avoid winter We wanted to be on the ocean with swimming pool and hot tub with beautiful gounds and a gate for safety
Five star condo property in Islamorada
it stays cool Unit itself is like a well loved family cottage that has everything needed
As it does not get afternoon sun
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4. Newly renovated villa by the bay (from USD 325)

This newly renovated villa has two bedrooms which can accommodate up to six individuals. It has a fully equipped kitchen, a full-size washing machine and dryer, a cable television, and a dining room. What’s better is that it is only 30 feet (9 m) away from the water. That means that the guests may enjoy the cool sea breeze while contemplating about life. In the evening, guests will be greeted with the mesmerizing view of the Everglades and the golden crown of the sunset. At night, they may enjoy cooking and feasting on grilled delicacies as the property has an enclosed patio with an outdoor grill and dining.

See Special Fall Rates
22 reviews  Wifi Available
House 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
The boat basin is perfect
Sunset Happy Hour is a never miss for me
The other renters were fun to be with
The Bayview Villa is everything you will need in the Keys
Not only are the accommodations outstanding
The views are amazing and the villa is updated and clean
Mr Mitchell was a great host
Marina super convenient for those with boats
We met some fantastic people and of course the fishing was awesome and let me not forget to mention the fresh key limes for my pies Looking forward to the same time next year
We can't wait for next year
and it's also well prepared for those who like to fish or have a boat
Tackle is also within walking distance
Thank you Bob and Pyllis for another great time
You are secluded from the busy world and it is the perfect place to de-stress
We had a manatee swim up to the dock for a drink of fresh water--a great surprise
But why would anyone want to leave this adorable house and patio????
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5. Private villa facing the Everglades (from USD 275)

This two-bedroom villa can house up to four people. Located in the lush tropical hammock in a quiet residential area, visitors are sure to have a peaceful, quiet, and relaxing vacation. Only approximately 50 feet (15 m) away from the water, watching the waves crash onto each other can be a good way to pass time. It also has its own wading beach and marina, complete with night lights, power, and water. Entertainment includes cable television, a VCR, and a fully equipped kitchen.

Mitchell's Keys Villa - Private, Secluded House on the Bay
52 reviews  Wifi Available
House 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
The villa is very comfortable and had all the amenities of home
but it was very comfortable
The landscaping was immaculate and the other visitors on the property were all so nice
That was a game changer for us to be able to turn the key and go
You can fish off the pier
It is kept very clean and
The villa was very clean and updated
The house was "cozy" for a family of 4 full grown people
The 1 bedroom villa was clean and spacious and very comfortable
hammer head sharks sea horses
Mr Mitchell was a wonderful host
The hosts were very gracious and always available for any questions Thanks for a nice stay
The property well taken care of
The marina was nice calm easy
There are so many restaurants and stores within walking distance or more less than a 5 minute drive away
This home is in a great location and just steps from the water
In 35 minutes we were at K-Mart in Key Largo and 15-20 minutes to Win-Dixie in Tavenier (which I found to be cheaper than Publix and maybe better stocked )
The location of the villa in Islamorada is amazing you can walk to numerous shops bars and restaurants We loved being able to moor our boat in the marina and enjoyed many peaceful afternoons rela...
This vacation was by far the best
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6. High-end condominium with oceanfront views

This two-bedroom condominium unit can accommodate up to six individuals. It boasts of having a high-end interior design and appliances. It has a kitchen, fully equipped with high-end appliances and cookware. Furniture is also, of course, upscale; it has a pottery-barn sofa and Prana mattress among others. The location is just a walking distance away from luxurious restaurants, thrilling water activities, as well as, the shopping district. To top it all off, it has a swimming pool that is heated up during the winter season.

Luxury Ocean Front Condo in Islamorada
4 reviews
condo 6 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
Other tenants / owners are awesome
The view out the front of her condo is mesmerizing Also to watch the sunrise in the early morning is just spectacular
The owner Sandy was very helpful to us with anything we needed
Owner Sandy is awesome Condo is awesome
Beautiful condo and the owner is so easy to work with Definitely will stay again
Most are done in fairly cheap beachy
Although there is still quite of bit of damage to the keys from the previous hurricane we did not have a problem finding plenty of places to go out to eat and there was plenty of staff around to he...
which is only a half mile away there are numerous things over there to take advantage of such as 1 Heated olympic swimming pool 2 tennis courts 3
a sandy beach on the bay
It is so nice that many days you can be content just to sit around the condo The condo has a very nice albeit small pool Because of the small size it is generally very warm which is really nice ...
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7. Tropical bungalow with a whole list of activities

This two-bedroom tropical bungalow can house up to four individuals. It is situated in the perfect location to experience everything Islamorada has to offer. The owners are even kind enough to patch up a whole list of activities, restaurants, and places to go to. It is also freshly renovated after typhoon Irma struck. It is, however, important to take note that pets are not allowed in the property.

Bungalow Blue ~ Tropical Keys Home w Pool, WiFi, Bikes & Grill.
116 reviews
House 2 Guests 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
The living room was comfortable
visiting bahia honda state park
It had everything we needed to make our vacation comfortable cozy and easy
The home is immaculate and has everything you could possibly need Very tastefully decorated with comfortable beds and nice linens
We loved the kitchen & grill for cooking
The bungalow was neat and clean and the owners were a joy to work with
which I think we occupied each evening
The neighborhood was nice and clean
The community is very clean and quiet Will definitely be back for another visit
Personally we went kayaking and parasailing--both which were amazing
They also have an excellent binder with great reviews of things all around the Keys for you to enjoy Very very thoughtful and responsive owners
That heated pool is the best
We met some of the residents and they were very nice and had good advice for local restaurants Would definitely recommend this cottage
We absolutely adored the swimming pool
The owners Bill and Maggie were very responsive to all of our questions we had along the way
We felt very safe at this location and were within 30-45 minutes of many things to do and within probably 60-90 minutes of Key West depending on traffic
It really was a home from home which was in a quiet area and local to shops and great restaurants
The house was just want we were looking for
Having a washer and dryer was a huge bonus and allows you to pack a little less than you normally would We took advantage of the bikes that Bill and Maggie provided taking daily bike rides to diff...
We rented two additional bikes and rode to Robbie's a number of times for
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8. Tiny paradise complete with pool

This listing is located beneath the owner’s apartment. Despite its location, the guests have total autonomy on the property and complete privacy as the owners prefer not to meddle with the guests’ activities. The house itself has a mini kitchenette and refrigerator. What’s best, however, is the pool, spa, barbecue grill, and Tiki hut that is available for the guests to use.

185 Plantation Dr
11 reviews
studio 4 Guests 0 Bedrooms 1 Bathroom

9. Penthouse overlooking the serene blue waters

This property is a penthouse with two bedrooms and it can sleep up to four persons. That being said, its high location gives the best sightseeing view of the blue and fresh waters of Islamorada. It is perfect for boaters as the listing also features deep water dockage and an on-site boat ramp. Also, storage for the boat trailers is provided with no extra expense. In addition to that, the owner is kind enough to offer to hook up the guests with charter boats and the best of the best boat captains.

Futura Yacht Club- Penthouse Views- Prices slashed for Dec and Jan due to cancel
36 reviews
condo 5 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The kitchen was amazing with real china
Condo was comfortable with a beautiful view
Everything was spotless and the beds and the furniture were all comfy
Everything that you need was in the unit
The unit has all of the updated amenities to enjoy comfort and relaxation
The premises were well kept with good facilities and lovely sea views
Love the pool marina and gardens of the property
It is huge and also nice and warm
The Yacht club property was great with pool and marina
we rented a boat and dock in marina and had a great time again
The owner is very nice and very easy to work with Very close to everything Will definitely be back
bars and shops to choose from in area
Really liked the security of a gated community
We especially loved the picnic and BBQ area
Location was easy for walking to restaurants or driving in either direction
The pool is a short walk from the building which is good for Senior citizens
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10. Private and gated townhouse

This townhouse listing is located in the Florida Keys. It is part of the Exclusive Bay Club that provides daily free access to amazing amenities and facilities. Guests may access and use two tennis courts, a swimming pool, a clubhouse, a private beach area and a fishing dock. In addition to that, all of these are within the gated vicinity of the neighborhood. The townhouse itself has a fully equipped kitchen, a flat screen television in every room, and a barbecue grill and picnic tables.

Family Friendly Executive Bay Townhome, Heated Pool, Dock Beach, Tennis, Near Attractions & More!
18 reviews
townhome 6 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The down stairs bathroom with a small shower was adequate
There is only one pot in the kitchen
It was also nice that there were some chairs and an umbrella for the beach
The back padio was a plus and a wonderful spot to set outside and enjoy the suroundings however follage that surounds the padio is in need to trimming and cleaning up Spiral stairs to the second ...
We have twin 7 yr olds and a 8 month old
but we didn't use Tennis rackets and balls
place was clean and very efficient
It was clean and nice
and we were very comfortable there
The tennis court is right beside the unit
We contacted the manager and hopefully they will be available for the next guest
We felt very welcome by everyone in the complex
coffee machines are all in good order More small appliances in stock
nice and warm Garbage is picked up promptly People are very friendly
Kitchen - more than enough dishes and utensils and of good quality Fridge stove
The location was perfect for attractions
The best beaches were close
plus there is plenty of activities and shopping within 15 minutes either direction
A dock and beach are a 2 minute walk from your front door
We spent the month of March 2019 in this townhouse at the Executive Bay Club
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The village of islands

Islamorada is quite famous as the sport-fishing capital of the world. Unsurprisingly, it is the place to be for people who love the ocean or enjoy playing around in the water. Consisting of various islands and bays, this is just perfect for all kinds of tourists- both casual goers and hardcore ocean lovers. Whichever you are, Islamorada has something in store for you.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Christian is a young and free willed adventurer and writer. He mostly enjoys feeling the salty and cool sea breeze kissing his tanned skin, while lying down on a white-sand shore. Writing humorous...Read more

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