10 Best Beachfront Rentals In Islamorada, Florida - Updated 2022

Stephen
Stephen 
Updated

Islamorada takes pride as the sport fishing capital of the world, thanks to its close proximity to the Atlantic Ocean. The beautiful village lies between the high-profile Miami and Key West, which means that guests who flock here throughout the year get to have an unrivaled diversity of fishing opportunities. Tourists from each corner of the world visit this village to have fun while swimming, fishing, and scuba diving in the turquoise waters. Visit Theater of the Sea and enjoy a wonderful experience admiring sea life. If you’re planning to visit the east coast for a beach retreat, then check out this list of the best beachfront rentals in Islamorada, Florida.

1. Tipsy Turtle (from USD 391)

Known as Tipsy Turtle, this cozy home has two beautifully appointed bedrooms that can sleep up to six people. Located just a stone’s throw away from the private beach, the home has four balconies, where you can enjoy a glass of wine with the ocean vista and soak in the essence of Islamorada.

When dinner beckons, you can either cook on site in the fully functional kitchen, or head to the oceanfront restaurants, which are just a five-minute walk away. It also features a plush living area with a TV, a wonderful dining room, and guests have access to the community pool with views of the Atlantic Ocean.

Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
134 reviews  Wifi Available
House 6 Guests 2 Bedrooms 3 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
we knew the beach was not ideal but didn’t realize how perfect the pool was
the pool area is great for both adults and kids
Cleanliness:
the house was very clean and the beds were comfortable
beautiful immaculately clean home in a convenient location
Host:
the owner is an excellent communicator and responded quickly to our questions
owner cared that we were happy in our stay
the owner was so helpful with supplying information about the area as well as answering our questions
owner very good with communication
our host scott was extremely accessible and anxious to help make our stay comfortable and worry-free
Location:
great location near marina and pool
scott's place located in angler's reef was the perfect location very homey for our family
great location and great home
Read more reviews

2. Sunrise Haven (from USD 500)

This elegant condo, within a resort, is an ideal space for a family or group of six people. Once you’ve explored the condo, which comes with three bedrooms, a full kitchen, a spacious living room and a great room with a HDTV, stereo system and a wet bar, turn your attention outside. All the rooms of this condo have a balcony and large windows boasting stunning views of the ocean or pool.

Guests have access to the community pool, a hot tub and a pristine beach, which are mere moments away. Stand-up paddle boards and kayaks are available for guests’ use. Several restaurants, arts district, and the marina are easily accessible from here. Feel free to come with your furry friend as the condo welcomes up to 2 dogs less than 23 kg (50 lbs).

Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
37 reviews  Wifi Available
condo 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
loved the pool (although the water temperature was way too warm) and easy access to everything
pool and hot tub were warm and beautiful
Cleanliness:
nice experience clean and all facilities worked well
the condo was clean and well equipped and pool was great for our kids
Host:
steven is an excellent communicator and an extremely kind landlord
the property manager jeff was very responsive
the owners were very responsive and a pleasure to work with
jeff the owners son was really nice and pleasant to work with
owners communicated well throughout the booking process and were even available during our stay with any help needed
Location:
a terrific location and great property
super convenient location to dining and shopping and several marinas with charters
the location is close to lots of good restaurants
this is a great place to stay
Read more reviews

3. Bay Villa 8 (from USD 772)

Few villas feel as instantly impressive as this. Upon walking through this spacious, three-bedroom villa, the first thing that hits you is its minimal aesthetics. Painted in all-white and complete with elegant furnishings, this villa can fit up to six people. Take advantage of the gourmet kitchen to prepare sumptuous meals for your family.

It has keyless entry and exit, which allows you to easily access the house. Soak in the spectacular views of the waterfront and the golden sunsets from the private balcony. The property provides amazing amenities such as a swimming pool, free Wi-Fi, and a dock. A beautiful beach is right at your doorstep.

POOL | WATERFRONT | WALK TO RESTAURANTS | GOURMET KITCHEN | Bay Villa 8
29 reviews  Wifi Available
House 6 Guests 3 Bedrooms 4 Bathrooms

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

Top guest reviews
Cleanliness:
the property was very clean
the property is beautiful and the house was impeccably clean
we loved our villa - clean simple comfortable and spacious
both the grounds and the townhome are clean and beautifully maintained
other than that the house was extremely clean and as expected thank you for making our stay memorable
Location:
close to great restaurants and grocery stores
location is walking distances shops great restaurants and marinas
great islamorada location with plenty of restaurants nearby
little basin villas in islamorada was the perfect location to explore the keys
i highly recommend the accommodations and location
Read more reviews

4. Two-bedroom home with a heated pool (from USD 363)

With a maximum occupancy of up to six guests, this home is ideal for a family getaway. The rental is situated a few steps away from a private beach, where you can go for leisure walks. Take advantage of this location to bring your kayak or boat for a wonderful adventure. Here, you will have plenty of entertainment, thanks to the three large flat-screen TVs in the house. The home has high-speed Wi-Fi, and a heated pool to relax in.

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
72 reviews  Wifi Available
House 6 Guests 2 Bedrooms 3 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
we enjoyed many sunrises at the beach and early morning swims in the heated pool
Cleanliness:
unit was clean and everything functioned well e
the community is beautifully landscaped and the home is impeccably clean and comfortable
Host:
host was easy to reach and answered any questions we had
everyone was lovely welcoming and hospitable
the owner is very nice and helpful
owner is very easy to contact and answers back quickly
owner was very quick to respond and helpful
Location:
this place is in an amazing location
loved the property access to pool and beach were very close
Read more reviews

5. Oceanfront house with a private dock (from USD 630)

This house boasts an amazing, resort-style swimming pool that offers sweeping views of the ocean. The pool area is furnished with furniture, where you can relax and dine al fresco. The compound has a private dock, where you can go fishing, and palm-shaded hammocks, where you can relax and admire the rolling ocean waves.

If you feel like going for a romantic stroll, head to the beach and dip your toes in the white sand. Take advantage of the beach bikes to explore the area.

This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2 Sleeps 6
58 reviews  Wifi Available
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 28
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the wifi was nice plus as well
-living room had ample seating for our family and stayed very cool with a/c and fans
having the chairs picnic table umbrella and even kayaks right there for our use was absolutely perfect
plenty of fans were provided to help keep those rooms cooler
the views from the immaculate clean pool was amazing
Cleanliness:
house was clean however there were a few things that needed maintenance
we had a wonderful time the house is clean and well kept
very clean and the owners are great to deal with
the property is clean and in a peaceful location
Host:
alex the owner was great
owner is super nice and responsive
lots of memories made :) owner was extremely easy going & so accommodating
alex the owner is responsive to any questions you may have and is super kind
i contacted the owner so hopefully these items will be fixed for the next guests
Location:
location was perfect for us
the property and location was inviting and relaxing
close to many great restaurants and activities
the property is conveniently located near shops restaurants grocery stores and activities like boating and watersports
house was great property and location are great for exploring the keys
Read more reviews

6. Gorgeous abode with two beaches (from USD 325)

Marvel at the red-hued sunsets while chilling on the balcony while sipping your favorite wine. Nestled in the welcoming community of Anglers Reef, this house has two nicely decorated bedrooms and three bathrooms. From here, guests can walk to the nearby local bars, restaurants, and Snake Creek Marina.

Guests will enjoy access to the two beaches — North beach which is a short stroll away, and South beach, which has a kayak for those who want to explore the waters. There’s also a resort-style pool that invites you in for a relaxing dip.

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
119 reviews  Wifi Available
House 4 Guests 2 Bedrooms 3 Bathrooms

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 complex is right on the water with a gorgeous view from the pool
beautiful residence fully stocked to make everyone comfortable & enjoy their vacation time
perfect for 2 couples traveling together as both rooms were almost the same with their own private bathrooms
the pool and beach areas and the community as a whole is beautiful quaint and pristine
Cleanliness:
house is very clean and had everything we could need
the house was as extremely clean and we felt comfortable immediately
the inside of the house was clean and fresh
very clean and well stocked condo with boat well only 100 feet away
loved everything about this home very clean well stocked and had everything we could possibly need
Host:
craig was a great owner to work with
craig was a great host to us
the owners were extremely friendly and helpful throughout our stay
owner very helpful and responsive
craig the owner was so helpful and very responsive
Location:
the location is great very close to restaurants and family activities
loved the house and location
the location was fantastic steps away from the pool and the private beach area
great location to islamorada restaurants charter boats sand bar and local stores and galleries
the location is ideal since it was quiet and not overcrowded
Read more reviews

7. Two-bedroom condo with a balcony (from USD 219)

Looking for a place that’s close to the beach where you can stay for a week? Check out this idyllic rental nestled in a lush forest, just a short walk from the beach. Its balcony offers striking views of the vast turquoise waters. While here, take advantage of the free wireless internet connectivity to update your socials and to connect with your family back home. The property has a lovely beach surrounded by lounge chairs and palm-thatched shades.

Oceanfront Condo with PANORAMIC Ocean Views, Free WIFI
118 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)
Cleanliness:
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
Host:
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
Location:
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
Read more reviews

8. Beachfront home for eight (from USD 400)

This peaceful, beachfront home offers you the opportunity to spend your evenings on the beach with your four-legged friend. It’s pet-friendly, and located right in front of a sandy beach. The house is furnished with a 60-inch smart TV in the living room and a 40-inch smart TV in each bedroom. Furthermore, you’ll get to enjoy breathtaking ocean views from every angle of the house. The house has free Wi-Fi and air conditioning as well.

Breathtaking ocean views for your Paradise vacations
55 reviews  Wifi Available
House 8 Guests 2 Bedrooms 2 Bathrooms

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

Top guest reviews
Cleanliness:
we arrived to find the home very very clean and everything as advertised
the place was very beautiful neat and clean
extremely clean property with a great upstairs porch view
this house is amazingly clean with beautiful views
Host:
the owners were very friendly and helpful
owners were completely excellent to work with
carmen and pablo are extremely helpful and make you feel right at home from the moment you arrive
the owner was a pleasure to deal with and let us check in early
we had the pleasure of meeting the owners and they were fabulous
Location:
great location with restaurants in walking distance
incredibly quiet easy to walk to restaurants
there are great restaurants and shops all within walking distance from this property
great location this house has everything you need for a relaxing vacation we would definitely come back again
we found islamorada to be a great location with restaurants and fun places to explore
Read more reviews

9. Southern Diversion (from USD 1499)

The first thing you notice when you arrive at this estate is the lush façade lined with beautiful palm trees and a well-manicured pavement leading to the house. Relax on the enclosed balcony and enjoy 180-degree views of the Atlantic Ocean.

The house is situated on a beautiful beach equipped with lounge chairs, where you can relax and watch the sun go down. Between the beach and the house, there’s a nice pool area for unwinding. The home is suitable to sleep up to 16 guests.

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
Cleanliness:
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
Host:
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
Location:
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

10. Modern home with a private beach

Surrounded by beautiful lush trees, this is a spacious apartment that comes with modern interior and chic furnishings. With two bedrooms and two bathrooms, it can comfortably accommodate a maximum of six travelers. From its balcony, you can catch spectacular sunsets and hear the sound of rolling waves crashing against the shore.

The property sits on the white sands of the beach and offers beach facilities such as chairs, beach umbrellas, and towels. For entertainment, there’s a cable TV loaded with free Netflix and premium channels.

Oceanfront, Private Beach, Charming 2 Bed 2 Bath Beach Cottage - Kayaks Included
Islamorada, FL, US
109 reviews  Wifi Available
cottage 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 28
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
the washer dryer room in the bedroom was excellent and very convenient especially the speed wash
Cleanliness:
house smelled very clean when we first walked in
house is clean and well-maintained
the house was clean and well stocked
super clean and convenient to everything
home is very clean and very well stocked with towels toiletries etc
Location:
excellent walking path across the street from house
the location of this house was amazing- private beach was a fabulous perk
luckily our friends house up the street had a pool
nice clean and well maintained beach home property location was ideal for many activities to do in the area
Read more reviews

Explore the "Village of Islands"

Islamorada is known as the sport fishing capital of the world and it’s for a good reason. It’s a destination that’s blessed with a plethora of dazzling beaches and luxury oceanfront rentals. While in this charming village, book one of the above beachfront rentals and indulge in exciting beach activities.

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

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Stephen Kinyanjui is an IT graduate who previously worked as an IT Assistant in a BPO company. He has an insatiable desire for traveling and adventure. He’s an artist who loves drawing and...Read more

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