Islamorada Beachfront Rentals

(31 rentals)

6 BR | 5 BA | Sleeps 14 | Quick View

$1500

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool

About this property

Welcome to Caribee Beach House!This estate is the perfect mix of old school Islamorada combined with present-day, stylish luxuries. This hidden gem is a special slice of heaven, nestled in downtown Islamorada, boasting with 200 feet of exclusive water frontage, 100’ dock, and fabulous views ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner

About this property

The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...

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Property Type

Islamorada Apartment

"Perfect stay"

This was our second stay at Jerry’s apartment. We already want to go back. The privacy and beauty of the place can not be overstated. Highly recommended!

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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 50 yards to Private sunning beaches at Anglers

$433

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Vacation Rental License 097. Welcome to Anglers Reef, a very special community of vacation homes with UNOBSTRUCTED OCEAN VIEWS FROM EVERY ROOM!We are new to this site so no reviews yet, BUT MANY AT OUR DIRECT SITE (SEE "LINKS" TAB ON THE LEFT) AND 12 YEARS of top reviews ON VRBO PROPERTY ...

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Property Type

Islamorada Villa

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$930

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Welcome to The Snook House at Tarpon Point!This impressive home is tastefully decorated and features an open floor plan, soaring ceilings, an unimpeded, nearly 180 degrees of breathtaking ocean vistas and four oversized bedrooms, each with their own bathroom.On the main level, you will find the ...

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Property Type

Islamorada House

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5 BR | 5 BA | Sleeps 14 | Quick View

$748

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

One of the only white sandy beaches in the Fl Keys and 1 mile whole of it!Newly built,state of the art,beautifully done 5 bedroom home, 4 master suites w/ king beds and facing open water! Magnificent indoors and out! Each bathroom is exquisite,very large stone,glass and hand picked tiles. The ...

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Property Type

Islamorada House

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4 BR | 4.5 BA | Sleeps 8 | Quick View

2
LAST MINUTE DEAL 6/11 - 6/18: REDUCED 6/11-6/18 for $5900/wk

$753

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

‘The Beach House’ at Tarpon Point in Islamorada‘The Beach House’ is a luxurious oceanfront home in a private gated enclave of only 12 houses. This end home offers privacy and beautiful ocean views including of Indian Key Historic State Park. Enjoy morning coffee and a phenomenal ...

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Property Type

Islamorada House

"Highly Recommended"

This home is stunning from top to bottom and all around. Our family, ranging from 18-75 years of age, found this home to be spacious, comfortable, and well equipped for cooking, relaxing, and having fun ...

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DEAL

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This is our NEWEST rental, so no reviews on VRBO yet, check Google for others.This majestic property is over 2.75 acres of landscaped beauty. There is more white sand on this private lot than any in all of the keys! There are over 100 palm trees with about 60 of them lit up at night, some of the ...

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Property Type

Islamorada House

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3 BR | 2 BA | Sleeps 6 | Quick View

9
Owner special: Last minute cancellation , Saturday July 16th to Saturday July 23rd , available now.

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6 Pure High End Luxury with all the Bells and Whistles Boat Friendly Vacation Rental with DockVilla Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. ...

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Property Type

Islamorada House

"Perfect, quiet, and secluded"

This was a spectacular vacation! The house was clean and comfortable, and the location was quiet and the setting perfect. I could write a novel about the host and the house, but in a few words the host ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool

About this property

Tropicaly furnished ALL ROOMS Tiled floors, 2 bedrooms carpeted All appliances, cookware included Linen all included Under cover parking Pool, beach, workout room, tiki hut Near Publix, CVS, Sopping 50 ft from Ocean with 300 ft dock

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Enjoy these spacious, 2 & 3 bedroom townhomes at EXECUTIVE BAY in the heart of ISLAMORADA. Each unit features large living areas, gourmet kitchens, comfortable bedding, outdoor patios perfect for BBQing, secured private parking and many extras!This amazing WATERFRONT TOWNHOME COMMUNITY has ...

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Property Type

Islamorada Townhome

"Amazing !"

We recently stayed at Beacon reef in January of 2022 .What a wonderful time we had! The condo was excellent, modern ,clean , just beautiful ! The grounds, immaculate .The exercize room was top notch.It ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located ...

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Property Type

Islamorada Townhome

"Winter getaway"

Had a wonderful 3 weeks in Islamorada. The unit was perfect location to restaurants, activities etc. we will be returning in 2023

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3 BR | 3 BA | Sleeps 6 | Quick View

$879

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

About this property

MM 81.5.  BRAND NEW construction located in the Heart of Islamorada!  Coral Cove is a gated, secluded and intimate community of 8 homes on the Florida Bay.   Featuring both a private pool in the back, and a community pool on the bay, Coral Cove also features 3.5 bedrooms, 3.5 baths, bay ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Minimum Rental: 28 Days"Beacon Reef 222" is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. ...

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Property Type

Islamorada Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

1

$500

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

About this property

Mile Marker 75 – Bayside4 bedroom 3 bathPalm Cottage South, is a charming, modern home directly on the canal with a heated, private pool, dockage, and access to the Port Antigua community sandy beach. Dockage for 24′ boat max on the lift pictured.Elevated for great breezes and ...

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Property Type

Islamorada Villa

"House was great with all the amenities!"

Great house, pool, and area. Lots of attractions and wonderful restaurants. Also, great people to work with.

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7 BR | 4 BA | Sleeps 14 | Quick View

$733

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

About this property

Mile Marker 77 – Oceanfront – Lower Matecumbe Key. Seven bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on the private beach, ...

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Property Type

Islamorada Estate

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4 BR | 4 BA | Sleeps 8 | Quick View

$2143

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Pool

About this property

$15,000 Weekly, Call for holiday rates***Note: Brand new furnishings are due early this winter. In the photos, you will see the furniture style sheets to depict what will be in the final home presentation.***Introducing Maison Residences Unit 202, Oceanfront & Poolside… A world-class ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Beachfront

About this property

Minimum Rental: 1 Month Everything in this unit is lovely - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool

About this property

This charming, island style beach house on Lower Matecumbe Key is the perfect spot for your next Florida Keys vacation. This home can sleep up to 9 guests, with 4 bedrooms and 2 1/2 baths. The main living space features a fully equipped kitchen and an open floor plan with vaulted ceilings, tons of natural ...

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Property Type

Islamorada House

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4 BR | 2.5 BA | Sleeps 8 | Quick View

$800

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

About this property

Mile Marker 75 – BaysideLarge, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal.The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut, grill and outdoor seating ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 28 Days "My Paradise" is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The ...

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Property Type

Islamorada House

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4 BR | 3 BA | Sleeps 8 | Quick View

1

$1286

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Private pool

About this property

Mile Marker 83 – OceanfrontTwo adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and skiff dock. Relax at the beach or cool down in the beachside pool.The front home ...

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Property Type

Islamorada Cottage

"Osprey Bay January"

Just finished a week at Osprey Bay nice house a little too much up and down with all the steps but spacious Need a larger trash can in the kitchen put it next to the wall near toaster Also new pillows ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Wake up to the sun rising over the ocean and relax by the pool, in the spa or on the sandy beach in a safe gated community. This nicely appointed 2 bed (one king, two twins, also has sofa bed), 2 bath condo is fully furnished with everything you need to enjoy your stay in the Keys. Amenities include a ...

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Property Type

Islamorada Condo

"Blown away by the condo"

I would recommend this condo to everyone Very spacious, clean stocked etc. View is stunning. Grounds are immaculate. Tanya was very accessible thru my entire stay. I would come back in a heart beat ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

About this property

Sunrise is a spectacular unit within the Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach.Dockage can be obtainable through Islamorada ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Introducing Maison Residences Unit 403, Oceanfront & Poolside. A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living ...

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Property Type

Islamorada Condo

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4 BR | 4 BA | Sleeps 8 | Quick View

$2143

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

About this property

$15,000-$17,500 WeeklyA world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just a short 90-minute ...

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Property Type

Islamorada House

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2 BR | 2 BA | Sleeps 4 | Quick View

$167

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...

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Property Type

Islamorada Apartment

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Oceanfront Estate on 3.5 PRIVATE Acres in the Heart Of Islamorada. Features include: Private Boat Basin with 100 of feet of dockage for any size boat, private boat ramp and fishing pier. HUGE salt pool and hot tub, 3rd floor private master suite w/ office, master bathroom and private balcony. This huge ...

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Property Type

Islamorada House

"WOW is all we can say!!! Amazing rental."

We have been renting in the Keys for 22 years, this one topped them all. The grounds are SO secluded and private, makes you feel like your staying in the Jungle. Peacocks, exotic birds, and cool lizards ...

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2 BR | 2.5 BA | Sleeps 6 | Quick View

2

$400

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

2 Bed & 2.5 Bath Villa in Anglers Reef with Boat slip.Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious ...

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Property Type

Islamorada Villa

"Great accomodations"

Beautifully decorated house in the Keys. Very spacious and comfortable. Kitchen was fully stocked. Plenty of linens and extra towels. The community dock has kayaks we used. There are lobsters under ...

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5 BR | 3.5 BA | Sleeps 17 | Quick View

1

$2544

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Private pool

About this property

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat ...

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Property Type

Islamorada Estate

"Great stay"

Perfect location in town with plenty of private space to enjoy the pool, beach, dock, etc. Would definitely stay here again.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Anglers Reef Villa Resort 2 Bedroom and 2.5 Bath Villa, in Anglers Reef with Boat Slip. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch ...

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Property Type

Islamorada House

"Perfect Family Vacation Spot!"

We absolutely loved this charming community! It was the perfect place for our family to unwind after the unusual spring and summer! We rented a boat slip and it was an easy - peezy trip to the the sandbars ...

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Islamorada Vacation Rentals