Top 10 Vacation Rentals In Islamorada, Florida - Updated 2023


Florida is a world-renowned tourist destination, but have you ever heard of Islamorada? This little hamlet is hidden away in the Florida Keys, a location that allows it access to the attractive coral reefs in the area. Being a small village, Islamorada is a wonderful getaway destination for those seeking a serene vacation, devoid of the general rush of the city. It’s characterized by lush tropical forests that surround the stunning holiday homes. Attractions in this area include the Lignumvitae Key Botanical State Park and the Windley Key Fossil Reef Geological State Park. Escape the crowded cities of Florida and settle down in Islamorada. Here are our suggestions for vacation rentals in this destination. Check them out below.

1. Private oceanfront house (from USD 599)

Eight guests can stay in this house, one that’s suited for a group of friends on a vacation or even a family visiting Islamorada. If you stay here, you’ll be in a serene, tropical setting in the heart of La Jolla Resort. At your disposal will be two acres (0.8 hectares) of lush lawns and exquisite tropical trees. The house itself has three bedrooms, with a total of four beds set to offer comfort to all guests staying here. The deck area outside is aptly placed to offer a breathtaking view of the ocean, visible just beyond the trees. And, of course, you get all the homely facilities from a spacious living area to a well-equipped kitchen.

3 Bedroom Private Oceanfront House - Sol
29 reviews  Wifi Available
Entire home 4 Beds 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
great location and roomy accommodations for our group
wonderful location beautiful scenery and great service
Read more reviews

2. Three-bedroom oceanfront house (from USD 699)

This is another house that’s nestled in La Jolla Resort, offering all the benefits similar to the house above. These include proximity to the stunning beach, an unfettered view of the ocean, a serene tropical garden in the compound and a luxurious home for you and your friends. This house can host eight guests. But unlike the house in the listing above, this one has a covered deck, shading you from the sun but still offering an excellent view of the ocean. Inside there’s a luxurious living room, a spacious dining area and a fully equipped kitchen, a major selling point for those intending to prepare their own meals.

4 Bedroom Private Oceanfront House - Bahia
33 reviews  Wifi Available
Entire home 5 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
clean and stylish interior
house was clean comfortable and had everything we needed
staff were very nice and were helpful
great location close to everything
Read more reviews

3. A private oceanfront cottage (from USD 225)

Stay in this private cottage that places you right at the beach. With the ocean outside your front door, you have all the reasons to spend all your time on the fine golden sands of the beach. This cottage has just one bedroom, but it still can host up to four guests. The interior is just like any other home, with a cozy living room and a spacious kitchen/ dining area. And, yes, you can prepare meals if you choose to, in this fully equipped kitchen. The bedroom has a queen bed and a large-screen television is mounted on the wall adjacent to it so you’ll be able to fall asleep while watching your favorite show.

RELAX in your PRIVATE Oceanfront Cottage!
Islamorada, Florida, United States
75 reviews Premier Host  Wifi Available
cottage 4 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
Downstairs is one bedroom upstairs
pretty much anything you need
Having a large truck also made it difficult to back boat to slip due to one palm tree which is in line with boat slip
There is a full size kitchen and a washer/dryer
but is was our own private paradise
Everything was clean and well maintained
The property was very clean spacious and provided everything we needed for our relaxing vacation
Loved our stay so clean and well kept
Was newly renovated clean and smelled amazing
The view and location was awesome and secure The property provide a large boat dock and slip which we were excited about
Carmen was awesome to work with Always very quick to respond to any questions
They answered all our questions very quick
They are the absolute best genuine people we have met :)
We spoke with Carmen and the neighbors both very nice and welcoming
's since she also has a boat ramp
it has everything you need and in a great location
Islamorada is a beautiful area with delicious restaurants and lots of shops
The owners Carmen and Pablo are very nice people
We're in the keys 3 to 4 times a year and this place has become our first pick
The location is perfect Easy access to the marinas for fishing charters and other attractions Carmen and Pablo
Read more reviews

4. Five-bedroom house (from USD 1499)

If listing four above still isn’t large enough for your party, then consider this five-bedroom house. This one can host a whopping 16 guests, meaning no one will be left behind. Have fun exploring Islamorada which is a short walk from the house. You also get a private beach area that stretches for 60 meters (200 feet). Other than the house, which is quite well decked out, you also get access to a heated pool and WiFi connectivity. This beautiful wood-clad mansion is such a welcoming rental, offering delightful views of the ocean at all times of day.

Southern Diversion Estate Islamorada
52 reviews  Wifi Available
House 16 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 16
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
towels - everything you will need for outside
Our family came here to celebrate our parents 40th wedding anniversary and it was amazing
The house had plenty of room for all our extended family including a bunch of young kiddos
The bunk room was perfect for all the cousins to sleep in
The property was just beautiful - from the tree lined drive up to the front of the home to the postcard-like views of the ocean out back
The house was exactly as described
The pool was lovely as were the views from this spacious property
The four bathrooms were great
the house is very well appointed clean large and roomy
We were able to accommodate approximately fifty guests caterers a band
The caretaker John was very helpful
They could use some more pool towels Owner not the easiest to work with
the groundskeeper was super-helpful and available whenever we needed him
well-kept responsive owner to questions and requests and a great concierge
I P experience and was very helpful in explaining the dock lift channel to bring our boat in
Conveniently located to good restaurants
The house is in the perfect location being close to restaurants and activities
The dock was a perfect This area of the island has plenty of restaurants activities bars and shopping
This property is directly across the street from an amazing spa
Very close to great dining and convenient to shopping and the tackle shop We will definitely return for another stay but longer
Read more reviews

5. Beautiful Islamorada home (from USD 895)

With a look that blends in well with the tropical landscape and a magnificent view of the ocean right from the house’s balcony, this vacation rental argues a good case as a prime home for those visiting Islamorada. It has four bedrooms and three bathrooms and can comfortably accommodate eight guests. The kitchen is meant for culinary aficionados. Spacious and well-equipped, there is nothing you can’t cook here. Of course, there’s also a large living space that’s adorned with chic furniture, a perfect place to relax after a long day. You also get a swimming pool so you have all the reason to spend time in the water.

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
Islamorada, Florida, United States
80 reviews  Wifi Available
Private vacation home 8 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
we love this community because of the view pool & the relaxing atmosphere
lovely property nice views of ocean and pool
our kids enjoyed the pool and the 'old school' video game table on the main level
the pool was well maintained and our family enjoyed the time together
the pool was warm & wonderful too
you have a beautiful and very clean home
the house was very comfortable and clean
i’m not on vacation to clean a house in better condition than when i arrived
home had everything we needed clean and well stocked
the owner was wonderful and very helpful
owner and property manage were extremely helpful and quick to respond
very enjoyable location and the accommodations were perfect
the location right at the pool and marina front made it even better
the location of anglers reef gave us great access to the ocean and bay
Read more reviews

6. Mitchell’s bay-view villa (from USD 325)

Surrounding this house are breathtaking views. On one side is the Florida Bay and the other the stunning Everglades. In the evenings, this picturesque view is colored by a stunning sunset hue. This is a representation of what paradise is, and it’s all at your disposal when you stay in this two-bedroom villa. Another reason you should book this house is that it’s just 9 meters (30 feet) from the soothing ocean waters. If you’re not yet convinced, then you’ll be glad to know that there’s a marina on the property as well as a wading beach. The house can sleep six with two bathrooms.

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????
Read more reviews

7. Rental with a private oceanfront

Elegance and sophistication, that’s the aura exuded by this four-bedroom home. Sitting in the Islamorada’s Millionaire’s Row, this accommodation will make you feel like one of the rich and famous. The beach is right outside the house and you need not worry about bumping into other beach goers as it’s exclusive to this house. Settle in and take advantage of the swimming pool which is set amidst lush tropical trees. You also get a well-fitted kitchen that boasts elegant, silver appliances. The living room is spacious, cozy and a perfect place to relax at the end of the day. You can hang out here and watch the television or sit outside on the deck and be awed by the spectacular view.

Private 150 Ft Oceanfront 2 Acre Millionaire Row Estate Saltwater Pool Spa Dock
52 reviews  Wifi Available
House 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
The house was just like the pictures and very comfortable for all seven of us
The downstairs suite was so private and the upstairs three bedrooms were laid out to perfection
The kitchen was well stocked and all appliances worked great as did the air conditioner
The driveway to the house sets the stage and the expansive yard to the ocean
The kids loved fishing off the dock while we lounged in the spa
The house was incredibly clean and well stocked with plenty of towels and beach towels as well
The house had everything we needed and the property is truly private
The ocean views and sunrises were outstanding
The pool was a huge hit with our kids and us
the owner was helpful answering any and
dock for fishing or keeping a boat clean almost new pool and spa laundry
All questions and concerns were quickly responded to and taken care of
We caught many mangrove snappers from the great dock and made yummy fish tacos two different nights
It's near to many great restaurants
Just a great vacation and the perfect location to good restaurants and charter boats
The boys took the paddle boards out on a very calm sea
we felt secluded yet close to everything
We all enjoyed the salt water swimming pool
Read more reviews

8. Executive Bay townhome

Islamorada’s heavenly beaches are a major reason you should visit and this townhome offers a quick and easy access to one such beach. Found in Executive Bay Club, the vacation rental is only a stone’s throw from the ocean. In fact, you need only stroll a few minutes to be on the fine golden sands. If you hardly ever get enough of the water, you can spend time in the pool on the property. And when you need to get your blood flowing, try a game of tennis in one of the two tennis courts available. This townhome boasts two bedrooms, each one elegantly furnished, offering a comfortable sleep for up to six guests. All the creature comforts of a modern home are available here, from a flat-screen TV in each of the bedrooms and the living room to laundry facilities.

Newly renovated Executive Bay townhome with pool, beach, next to Founders Park
Islamorada, Florida, United States
Entire townhouse 3 Beds 2 Bedrooms 2 Bathrooms

9. Luxury oceanfront condo

You obviously visit Islamorada for its proximity to the ocean and this vacation rental is one among many that allow you to be close to it. Other than the beach, you’ll also be within a walking distance of restaurants where you can indulge in the local cuisines. However, you can opt to prepare your own meals and eat in since this house is endowed with a well-equipped gourmet kitchen. If you choose to remain indoors, you can relax in the living room and watch the television or hang out on the balcony and marvel at the picturesque ocean view. There are two bedrooms here, each one furnished with a queen bed, able to sleep a total of six guests.

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 ...
Read more reviews

10. Oceanfront house at the pier

Can’t get enough of the ocean? Then check out this four-bedroom house that is the perfect place for a large group of travelers. If you’re planning a getaway with your extended family or your colleagues, then go ahead and book this lovely home. From inside the house, you’ll be constantly marveled by the view of the ocean, a view that only gets better from the deck outside. Being a modern home, you won’t lack in amenities like a beautifully furnished living area, a spacious kitchen and even WiFi. On top of these, you’ll also have access to a swimming pool on the property as well as a tennis court.

Islamorada Oceanfront Gem at The Pier
Islamorada, Florida, United States
Entire house 4 Beds 4 Bedrooms 3 Bathrooms

A dream vacation

Enjoy a dream vacation in Islamorada by booking yourself one of the vacation rentals above. You’ll be within easy reach of the beach and with plenty of amenities to ensure you live in comfort. Explore Islamorada and gather an unforgettable experience.

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

Get Trip101 in your inbox

Unsubscribe in one click. See our privacy policy for more information on how we use your data

 Want to contribute as a Local Expert?
Explore Islamorada
Good things are meant to be shared!