Islamorada Vacation Rentals

(90 rentals)
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The Oasis

3 BR | 2.5 BA | Sleeps 8 | Quick View

$1286

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Full kitchen
  • Oceanfront
  • Pets allowed
  • Private pool
  • Rentals by owner

About this property

This majestic property is over 2.75 acres of landscaped beauty. There is more white sand on this lot than any in all of the keys! The palm trees are some of the tallest as well and their graceful presence puts you in the Jimmy Buffett mode as the cooling Atlantic Ocean winds blow your hair and alleviate ...

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Property Type

Islamorada Estate

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Palm Cottage South

3 BR | 2 BA | Sleeps 6 | Quick View

$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

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PALMS #313 Spectacular 2 Bedroom Condo with Breathtaking Oceanfront Views

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$139

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pool
  • Private pool

About this property

MINIMUM STAY: 1 Month Spectacular oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Alligator Reef Lighthouse is easily visible from your master suite or the balcony and you'll be able to watch cruise ships as they pass by the reef and ...

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Property Type

Islamorada Condo

"Stunning"
Reviewed December 12, 2020

My stay at the Palms has been one of my best vacations. The views, the fishing, the pool and great people. The condo was simply gorgeous , fully stocked and the people were oh so nice. I cant wait to ...

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...

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Property Type

Islamorada Condo

"Wonderful location and hosts."
Reviewed January 10, 2019

This home was perfect for our family of five. Spacious bedrooms, living area and bathrooms. We also had use of the storage unit for our fishing gear and coolers. The pier is breathtaking. Our thoughtful ...

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Beacon Reef #522 - Oceanfront 5th floor (top floor) condo at Beacon Reef.

$177

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Full kitchen
  • Kid friendly
  • 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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BEACON REEF 501 - Updated Condo in Oceanfront Complex in Islamorada

$145

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pool

About this property

MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You’ll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 – granite counters, stainless steel appliances, and ...

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Property Type

Islamorada Condo

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Sea Ranch

4 BR | 3 BA | Sleeps 8 | Quick View

1

$1286

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pets allowed
  • 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"
Reviewed January 30, 2021

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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Antigua Place - Charming vacation home located in Port Antigua.

$207

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pets allowed

About this property

MINIMUM RENTAL 1 MONTH: Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal. You’ll ...

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Property Type

Islamorada House

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The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip

$655

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Private pool
  • Rentals by owner

About this property

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs ...

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Property Type

Islamorada House

"Great place!"
Reviewed April 22, 2019

Arlene was wonderful to work with. The home more than accommodated our mix of four couples. Thanks.

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BOAT, POOL & BEACH HOUSE-Unity & Autonomy BOTH sides of upstairs Duplex/70' DOCK

$257

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Private pool
  • Rentals by owner

About this property

ALERT: BRAND NEW POOL JUST COMPLETED AND INSTALLED....DOWNSTAIRS IS AVAILABLE TO RENT BUT IS NOT INCLUDED IN THE PRICE feel free to ask about downstairs pricing and availability. Downstairs is an additional 3br and 2ba so the upstairs and downstairs would be a total of 7br & 4ba....THIS LISTING ...

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Property Type

Islamorada House

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Palms #309 - Exceptional condo with panoramic views of the Atlantic Ocean.

$130

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen ...

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Property Type

Islamorada Condo

"Great place to relax"
Reviewed August 3, 2019

Condo is in great location and in nice condition Everything was as was promised Loved the pool and walking in the ocean Great dining just walking distance Only thing I would ask is better kitchen ...

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Latitudes of Islamorada

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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Palms #407 - Beautiful condo with panoramic views of the Atlantic Ocean.

$129

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront

About this property

Minimum Rental: 28 Days"The Palms #407" is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. ...

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Property Type

Islamorada Condo

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Beacon Reef 406 is a Charming 2 Bedroom Condo with Views of the ocean & Complex

$143

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. "Beacon Reef 406" is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient to ...

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Property Type

Islamorada Condo

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PALMS #404 - 2 Bedroom Condo with Ocean, Pool, and Tropical Views

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Founders

$131

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pool
  • Private pool

About this property

NEW LISTING Minimum Rental 1 month. This is an exceptional 2 bedroom and 2 bath condo located in one of the most popular Islamorada condo complexes - The Palms of Islamorada. The balcony is large enough to dine or recline and offers fabulous open water views. While sipping coffee in the morning ...

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Property Type

Islamorada Condo

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Luxury Oceanfront Home, Views, Pool, Sandy Beach

$735

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Full kitchen
  • Kid friendly
  • 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"
Reviewed August 19, 2021

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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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$200

avg/night

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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

"Couldn't have been better"
Reviewed September 20, 2021

Everything was as described. Private beach was beautiful. You can snorkel right off the beach. Studio apartment was extra clean and the host was always available to answer any questions we had.

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Maison 101 - Beachfront

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

$12,500-$15,000 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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'A little Piece of Paradise" Islamorada, On the water! 3/2, 90 Ft of dock, Pool

$333

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Private pool
  • Rentals by owner

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house has been remodeled, fully furnished, with a ...

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Property Type

Islamorada House

"Amazing time In Islamorada !"
Reviewed September 1, 2021

My family and I can not say enough great things about this property / property owners Tiffany & Bill ! My husband and I always book a home in the keys for the month of august for lobster seasons ! This ...

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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks Kayaks

3 BR | 2 BA | Sleeps 6 | Quick View

9

Distance to beach: 0.5 miles to White Marlin Beach

$582

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Full kitchen
  • Kid friendly
  • 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"
Reviewed April 6, 2021

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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My Paradise - Oceanfront beach house with protected dockage.

$303

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pets allowed

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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Gorgeous waterfront home

3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Rentals by owner

About this property

Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada ...

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Property Type

Islamorada House

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Anglers

2 BR | 2 BA | Sleeps 4 | Quick View

$343

avg/night

View Details

Key Amenities

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

About this property

MM 85. 2 Bedroom & 2.5 Bath. Two spacious bedrooms and two and a half bath, sleeps six. Enjoy the Beautiful garden views and ocean breezes from these island-style villas or relax poolside. Nestled amidst quaint streets and walking paths, their design takes inspiration from Native Conch and Key West ...

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Property Type

Islamorada House

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Beacon Reef #307 - Newly Renovated Condo in Islamorada with Ocean Views

$179

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pool

About this property

Minimum Rental: 1 Month This 2 bedroom/2 bath condo with fabulous ocean views has been totally remodeled and updated. You'll love the sparkling new kitchen with stainless steel appliances and induction cook top. Store your beverages in the wine cooler. The interior is bright, spacious and clean. The ...

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Property Type

Islamorada Condo

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Maison 202 - Oceanfront

4 BR | 4 BA | Sleeps 8 | Quick View

$2143

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pets allowed
  • 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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Bay Therapy - 3 Bedroom Waterfront Home with Hot Tub and Boat Dock

$313

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly

About this property

Minimum Rental: 28 DaysHappy vacationing starts here! The owners call their special getaway “Bay Therapy” for many reasons. It is located in a great neighborhood in Key Largo. It is convenient to the mainland and is the gateway to the Keys. Since purchasing this home the owners have ...

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Property Type

Islamorada House

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Oceanviews

2 BR | 1 BA | Sleeps 4 | Quick View

1

$149

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Rentals by owner

About this property

Mai Paradise Beautiful and breathtaking ocean views in Lower Matecumbe Key in Islamorada. Private Beach AccessNOTE:CAN BE RENTED AS A 2/1 or 3/2 (contact owner for info) Master Bedroom with King size bed Second bedroom with full size bed (As a3/2 3rd bedroom is a large suite with king bed ...

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Property Type

Islamorada Apartment

"Wow! What a fantastic place."
Reviewed January 13, 2021

Well we definitely will return. Completely MORE than we expected. Very nice and the perfect amount of room for a small family or couples. Great hosts and very responsive. We could not have been any luckier.

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Hidden jewel 2/2 villa, stunning waterfront views, boat ramp & free dockage!

2 BR | 2 BA | Sleeps 4 | Quick View

10

Distance to beach: 5 miles to Anne's Beach

$279

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pets allowed
  • Rentals by owner

About this property

Two Queen Beds, sleeps 4 + (1 Bedroom / 1 Murphy Bed)/ 2 Bathrooms, Full LaundryDock your boat up to 26 ft. Free boat trailer parking!The "Nest" is located on beautiful Florida Bay (at Mile Marker 82.3) in Islamorada on upper Matecumbe Key . The Villa is a privately owned condo residence ...

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Property Type

Islamorada Condo

"More than a gem"
Reviewed January 2, 2020

The home was exactly as described but better. Every detail was attended to including instructions on how to use everything right down to the remote controls. Exceptional use of space with comfortable ...

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Beacon Reef #222 - Gorgeous condo with panoramic views of the Atlantic Ocean.

$162

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Full kitchen
  • Kid friendly
  • 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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West Plaza del Lago - Gorgeous Waterfront Home with Boat Lift and Beach Access!

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$193

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly

About this property

Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...

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Property Type

Islamorada House

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BEACON REEF #503 - Stunning Newly Renovated Condo in Oceanfront Complex

$171

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pool
  • Private pool

About this property

MINIMUM STAY: 28 DAYS This exquisite condo has been TOTALLY remodeled and updated from top to bottom. This is a 5th floor unit with ocean views from the balcony and master bedroom suite. The furnishings are all brand new. There are three TV's - one to suit everyone's preference. Dine in the ...

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Property Type

Islamorada Condo

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LITTLE BAY - Lower Duplex - Ground Level Unit on Gated Bayfront Shared Property

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Founders

$429

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pets allowed

About this property

Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up ...

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Property Type

Islamorada Apartment

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Ishmaels

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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LITTLE BAY - Upper Duplex -A 2nd Floor Duplex on Gated Bayfront Shared Property

$429

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pets allowed

About this property

Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps ...

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Property Type

Islamorada House

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Nautilus Getaway

3 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to White Marlin Beach

$250

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Private pool
  • Rentals by owner

About this property

*******Check us out on VRBO No. 2003434******** Please go to ....**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will ...

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Property Type

Islamorada House

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sea oats beach

5 BR | 5 BA | Sleeps 14 | Quick View

$600

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Full 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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Little Bay Cottage- Gated Bayfront Property Shared with 2 Other Rental Units

$429

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen

About this property

Minimum Rental: 7 Days"Little Bay's Cottage" is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area ...

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Property Type

Islamorada Cottage

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PALMS 301 - 2 Bedroom Condo with Lovely Ocean Views from Balcony

$121

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #301" is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure ...

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Property Type

Islamorada Condo

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Coral Cove 2

3 BR | 3 BA | Sleeps 6 | Quick View

$723

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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Villa Riolo - Updated home and perfect for your next holiday in Islamorada

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to Anne's Beach

$164

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly

About this property

Minimum Rental: 28 Days"Villa Riolo" is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity ...

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Property Type

Islamorada House

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Directly OceanFRONT, Panoramic Oceanviews, Wraparound Decks, Optional Boat slip

3 BR | 2.5 BA | Sleeps 8 | Quick View

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

$525

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Full kitchen
  • Kid friendly
  • 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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Sunrise Town, Maison Matecumbe, Islamorada, FL 33036

$167

avg/night

View Details

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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Waterfront Paradise on Canal W/New Pool

$395

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Rentals by owner

About this property

Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy!The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, ...

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Property Type

Islamorada House

"Waterfront Paradise"
Reviewed July 26, 2020

This was a terrific location and home. The house and amenities were excellent. The backyard was the standout for our group with the pool, dock and Tiki area....this felt like a true resort get away. The ...

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Beacon Reef #310 - Beautiful condo with lovely views of the ocean.

$154

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days"Beacon Reef 310" is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your ...

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Property Type

Islamorada Condo

"Great stay."
Reviewed January 4, 2021

Clean, well equipped, phenomenal views, and friendly residents. Realty staff was very helpful and responsive to any issues that came up. Great spot for kids as well, and very close to many top restaurants.

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Lyons Landing - Large Spacious 4/3 Home on Wide Canal with Pool, Dock & Boatlift

$315

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pets allowed
  • Private pool

About this property

MINIMUM STAY: 28 NIGHTS Lyons Landing is an exceptional single family home with pool, dock, boat lift and outdoor living area located in the prestigious neighborhood of Venetian Shores in Islamorada. Everything you need for a spectacular vacation awaits you in this extraordinary home. 3 bedrooms ...

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Property Type

Islamorada House

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Pelican Landing - Waterfront Home With Dock and Access to Community Beach

$263

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pets allowed

About this property

Minimum Rental: 3 MonthsPelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. The main floor offers 3 bedrooms and an open concept with ample seating for the entire family. The large balcony overlooks a canal where pelicans are usually seen diving into ...

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Property Type

Islamorada House

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Waterfront Elegance: Dock/Heated Pool/Spa - Ultimate Vacation Rental

4 BR | 4 BA | Sleeps 8 | Quick View

2

Distance to beach: 2 miles to Founders Park

$649

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Pets allowed
  • Pool
  • Private pool
  • Rentals by owner

About this property

This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios ...

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Property Type

Islamorada House

"Islamorada Paradise"
Reviewed March 6, 2019

My wife and I have stayed at Irish Ayes the month of February the last three years. We love it there. This three story home has it all, pool, spa, boat dock even an elevator. The third floor master suite ...

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Island Conch Cottage

2 BR | 1.5 BA | Sleeps 4 | Quick View

6

Distance to beach: 0.5 miles to Anne Beach

$133

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pets allowed
  • Rentals by owner

About this property

Island Conch Cottage A quaint ground level conch style cottage located at the end of a private street in a very quiet setting. Cottage and grounds have privacy fence and gate. The grounds are displayed as a sand beach setting. This property has 60’ of canal frontage located on an extra wide canal ...

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Property Type

Islamorada House

"ANOTHER GREAT EXPERIENCE !!!"
Reviewed September 21, 2020

This is my fourth year visiting Islamorada. Something that I look forward to each year. And every year I book this Cottage , I won't stay anywhere else!! It's always clean. If there is anything you need ...

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Lazy Daze Beach House on the Beach! 2 BR/2 1/2 BA, Sleeps 5 (Maximum 4 Adults)

$359

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Full kitchen
  • Kid friendly
  • 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

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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

$312

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo ...

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Property Type

Islamorada Condo

"Gorgeous place"
Reviewed November 22, 2020

Thank you so much for letting us stay at your condo! It is absolutely gorgeous and you have everything there we needed and more. The location was perfect and our children enjoyed the tennis courts, pool, ...

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Islamorada Vacation Rentals


Islamorada Weather

 | 

7524°  6217°
JANUARY
Ocean 7423°
7624°  6217°
FEBRUARY
Ocean 7423°
7826°  6518°
MARCH
Ocean 7624°
8228°  7021°
APRIL
Ocean 7926°
8529°  7423°
MAY
Ocean 8127°
8731°  7725°
JUNE
Ocean 8329°
8932°  7926°
JULY
Ocean 8530°
8932°  7826°
AUGUST
Ocean 8730°
8731°  7725°
SEPTEMBER
Ocean 8530°
8429°  7423°
OCTOBER
Ocean 8328°
8027°  7021°
NOVEMBER
Ocean 7926°
7624°  6518°
DECEMBER
Ocean 7625°

The “Village of Islands” awaits you: Islamorada vacation rentals by owner


Sunny, friendly Islamorada is a smart choice for those who want a quiet escape away from the hustle and bustle of the major Florida hot spots. Located between Mile Marker 91 and Mile Marker 74, Islamorada is situated halfway between Miami and Key West along Florida’s scenic Route 1. Islamorada itself is spread out over six islands, each surrounded by tranquil ocean and soft sands.

Next time you’re looking for fun & sun, skip the traditional beachside hotel and opt for a vacation rental in Islamorada instead from FloridaRentals.com. When staying in a beach condo instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our rentals even come with special amenities like a backyard pool, washer/dryer units, and bicycles. Whether you’re looking for a super-sized modern villa with an indoor pool, or a cozy beachfront bungalow, you can find it on our site.

Islamorada, Florida travel advice


This destination is a tropical paradise for those looking to get away from it all. In fact, celebrities have made the secluded Islamorada a second home for decades, including the island’s most famed resident, baseball player Ted Williams. Be careful, or you might just fall in love with the area, too.

With a tropical climate and daytime temperatures that rarely dip below the 70s (F), Islamorada is a fantastic vacation spot any time of the year. During the summer, temperatures typically hover in the upper 80s. The ocean breeze cools temps down in the afternoon, and the conditions are just perfect for fishing (more on this below).

Getting here from Miami International Airport or Key West Airport is easy with a rental car, and the views on Route 1 and connecting bridges are incredible. Worth the drive! Once you’ve arrived, island hopping via boat is a fun way to see the entire area.

Named by early Spanish explorers, Islamorada literally translates to “purple isles” – a nod to the colors one might see during one of the legendary sunsets.

Top activities and attractions


The sport fishing capital of the world, this city offers activities for anglers of all ages and skill levels. The surrounding ocean and shallow bays teem with a variety of fish, including sailfish, bonefish, swordfish, marlin and tarpon. Hop aboard a deep sea fishing charter to try your hand at grabbing one of these fish and cooking your own catch for dinner. If you’d rather stay on land, explore try fly fishing in the backcountry.

Fishing not your thing? That’s fine, there’s plenty of other activities in the area. Grab a towel and head to Anne’s Beach for a full day of sand castles and snorkeling. It’s also private and quiet, so you will feel a long way away from the crowds on South Beach. If you’re feeling adventurous, try your hand at kite surfing since the shallow waters here provide an ideal environment.

Bring your family to the Theater of the Sea and take a live snorkeling tour or swim with dolphins. If you prefer nature surroundings, Windley Key Fossil Reef Geological State Park has nature trails for hiking. Don’t miss the underwater shipwreck site at San Pedro Preserve where scuba divers love the scenery and adventure.

Music lovers enjoy warm, tropical evenings and daylong music festivals on the lawn of the outdoor, waterfront ICE Amphitheater located inside Islamorada Founders Park, a 40-acre expanse that features an Olympic-sized pool, shallow water beach, water sports rentals, ball fields, fishing jetty, exercise opportunities, skatepark and a dog park.

Dining


Known for delicious seafood, Islamorada’s restaurants serve up the day’s freshest catch. Starting at breakfast, stop in to the Midway Cafe & Coffee Bar where guests can start their day off with an omelette or pancakes. For lunch, grab a wrap at Chef Michael’s where they feature daily seafood dishes that “wow” eaters. Want to eat with a view? Grab an outside table at Morada Bay and watch the palm trees sway as you grub. Lastly, the Green Turtle Inn has more seafood dishes and soups that come with rave reviews.

Islamorada homes for rent on FloridaRentals.com


Islamorada condo rentals on FloridaRentals.com can save you up to 15% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!


FAQ

How many vacation rentals are there in/around Islamorada?

There are 90 Islamorada vacation rentals available on FloridaRentals.com. From house rentals to cottage rentals to beach condos and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Islamorada?

There are vacation rentals available in Islamorada for as low as $70 per night with an average price per night of $256.

Can I rent a house in Islamorada?

Yes, you can find house rentals in Islamorada close to Theater of the Sea, Florida Keys Brewing Company, and History of Diving Musem. Don't forget to stop in to Founder's Park or Alligator Reef.

Do any vacation rentals in Islamorada have a pool?

Yes there are 35 vacation rentals with a pool in Islamorada on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Islamorada vacation rentals on the ocean?

There are 42 oceanfront rentals in Islamorada available on FloridaRentals.com. Use our filters to search and book yours today!

What are the best vacation rentals in Islamorada?

Visitors give great reviews to these top-rated Islamorada vacation rentals available on FloridaRentals.com:
Jetson's House: 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!
Venetian Shores: The deep-water dockage is ideal for the avid boater or fishing enthusiast. Bring your boat and experience world class boating, diving, and fishing.
The Nest: The Villa is a privately owned condo residence (one of only 7 units) which is wonderfully maintained and a true hidden gem. It is a perfect place for your next Keys fishing or diving adventure or an ideal place to just kick back, relax and unwind while enjoying stunning water views.


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