Islamorada Vacation Rentals

(89 rentals)
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

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

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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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

1 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Founders Park

$214

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air ...

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Property Type

Islamorada Condo

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Ocean Harbour Condo with breath taking views!

$208

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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

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

$125

avg/night

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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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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks Kayaks

3 BR | 2 BA | Sleeps 6 | Quick View

7

Distance to beach: 0.5 miles to White Marlin Beach

$523

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Rentals by Owner

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6Villa 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. It has three bedrooms, two bath, private home totally renovated and remodeled, new furniture ...

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Property Type

Islamorada House

"Just what we were looking for"
Reviewed December 18, 2020

EXTREMELY COMFORTABLE, CLEAN, CHEERFUL AND LOVELY HOME. Beautiful layout with lots of windows allowing natural lighting in. Loved the furniture layout with plenty of seating. Beds very comfortable ...

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

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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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$181

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

"Wonderful Winter Mini Vacation"
Reviewed January 1, 2021

The location was absolutely beautiful. Quiet and safe. The owner, Jerry, was very friendly and helpful with many restaurant recommendations. The small apartment was spotless, and amenities adequate for ...

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Gorgeous waterfront home

3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

avg/night

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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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'A little Piece of Paradise" Islamorada, Fl. On the water! 3/2, 90 Ft of dock

$211

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!'' 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 seperate and private access with full kitchen and bath. Entire house has been remodeled, fully furnished, with a 90 ft Dock. Bring ...

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Property Type

Islamorada House

"This is an exceptional property"
Reviewed January 5, 2021

We rented this newly renovated waterfront home on Lower Matecumbe Key (Islamorada) with extended family for the holidays. It's the most amazing house and location, very comfortable with lots of space and ...

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PALMS 405 - Gorgeous Remodeled 2 Bedroom Condo with Ocean Views

$146

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #405" is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living ...

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Property Type

Islamorada Condo

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PALMS 417 - 1 Bedroom Condo with Tropical and Florida Bay Views

$97

avg/night

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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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Waterfront Paradise on Canal W/New Pool

$355

avg/night

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

2 BR | 2 BA | Sleeps 4 | Quick View

10
Owner special: Just had a last minute cancelation for January 4,2021 arrival departing on January 9,2021.

Distance to beach: 5 miles to Anne's Beach

$214

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Rentals by Owner

About this property

2 Queen Beds, sleeps 4 + (1 Bedroom / 1 Murphy Bed)/ 2 BathroomsDock your boat up to 26 ft.The "Nest" is located bay-side at Mile Marker 82.3 in beautiful Islamorada. The Villa is a privately owned condo residence (one of only 7 units) which is wonderfully maintained and a true hidden ...

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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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LOCATED ON BEAUTIFUL SUNSET BEACH WITH BEAUTIFUL SUNRISE AND SUNSETS

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

I BEDROOM APARTMENT RECENTLY REMODELED CAN ACCOMODATE 4 ON SLEEPER BED NEW KITCHEN AND BATH. ADJACENT BOAT LOT ON A CANAL WITH ACCCESS TO THE OCEEAN AND BAY ONLY A FEW MINUTES AWAY. VERY QUIET NEIGHBORHOOD. CLOSE TO MANY FINE RESTAURANTS. WE DO HAVE TWO VERY FRIENDLY DOGS WE KEEP UNDER CONTROL.

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Property Type

Islamorada Apartment

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Bayside - Peaceful Home - New Dock

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Please email or call if you have questions regarding flexible dates.---MONTHLY RENTAL--- Canal front - 2,600 s.f. gated home that offers 2 levels of living space with canal views and a private third-floor rooftop sundeck offering panoramic water views located in Lower Matecumbe Key, at MM 74. Easy ...

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Property Type

Islamorada House

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Greenflash

4 BR | 4 BA | Sleeps 8 | Quick View

$600

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Facing due west this property takes full advantage of the spectacular sunset view over the bay. GreenFlash has a bayside infinity pool and dockage to help you take full advantage of the myriad of water activities available in Islamorada, the 'Sport Fishing Capital of the World.' The two story house has ...

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Property Type

Islamorada House

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EXECUTIVE BAY ISLAMORADA - 2 & 3 BDR WATERFRONT TOWNHOMES-FREE DOCKAGE!!

$179

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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 it ...

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Property Type

Islamorada Townhome

"Outstanding Place!!"
Reviewed October 31, 2020

This keys location at 87200 overseas highway is an amazing location to stay at! I highly recommend it! All types of activies to do around the area and inside the location!Theres a huge pool, actually ...

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Ocean Harbor M31

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Founder's Park

$283

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This Condo is located on Plantation Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Ocean Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a fourth floor end unit location make it easy to access your stunning ...

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Property Type

Islamorada Condo

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Lazy Daze Beach House on the Beach! 2 BR/2 1/2 BA, Sleeps 4-6 (Maximum 4 Adults)

$359

avg/night

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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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Blue Heaven Coastal Cottage

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach

$223

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

House, 3 Bedrooms, 2 Baths, (Sleeps 4-6)Spacious ground level home that will be easy on your legs--NO stairs to climb! The home is fully equipped with linens for the queen, queen, and 2 double beds. The master bedroom has its own bath. A separate media room with a flat screen TV as well as a large ...

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Property Type

Islamorada House

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Apartment with beach access.

1 BR | 1 BA | Sleeps 2 | Quick View

$143

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

The apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape. ...

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Property Type

Islamorada Apartment

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

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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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

$404

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

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

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

$302

avg/night

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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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Bay Harbor 110C​

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 1 miles to Anne's Beach State Park

$286

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

This Condo sleeps 4 and comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key, Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks. Newly refurnished and refurbished, this condo ...

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Property Type

Islamorada Condo

"Couldn't have picked a better place to kick off the new year!"
Reviewed January 4, 2021

Great location with lots of fishing, great restaurants, beautiful sunsets and only 90 minutes to Key West. Highly recommend!

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Bay Harbor 116D

3 BR | 1 BA | Sleeps 6 | Quick View

$414

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.

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Property Type

Islamorada Condo

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Martin Family Fish Camp - Private Bayfront Peninsula with 2 Houses & Dockage

4 BR | 3 BA | Sleeps 12 | Quick View

1

Distance to beach: 5 miles to Founder's

$543

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

MINIMUM STAY: 7 Nights SATURDAY TO SATURDAY The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each home offers two private bedrooms. Between the two homes there is sleeping for 10 in beds plus an additional 2 on the sleeper sofa for ...

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Property Type

Islamorada House

"Awesome"
Reviewed July 11, 2019

We stayed for a month at Blue Water Retreat and had an awesome time with family and friends. The ocean views were magnificent. The pool was a big hit with the kids. We even had our dog with us. Hope to ...

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

$130

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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A jewel in the crown of the Florida Keys! 119 Anglers Way

$342

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

VR-237 - 2-bedroom home rental in the heart of Islamorada, Florida Keys! A jewel in the crown of the Florida Keys…Welcome to Anglers Reef!  A charming, oceanfront gated community in the heart of Islamorada, the sportfishing capital of the world!  Delightful Key West-style architecture ...

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Property Type

Islamorada House

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

$156

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet 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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FISH WHISTLE - Stunning Bayfront Home Directly on Snake Creek. Dock, Pool&More!

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 2 miles to Founder's Park

$533

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool

About this property

MINIMUM STAY: 28 DAYS Fish Whistle is an amazing privately owned estate located directly on Snake Creek in Islamorada. It offers spectacular views and easy access to the Atlantic Ocean or Florida Bay for either sport fishing or diving/snorkeling activities. This home comfortably sleeps 8 people in ...

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Property Type

Islamorada House

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PALMS #317 - 1 Bedroom Condo in Oceanfront Complex in Islamorada

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$92

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool

About this property

MINIMUM RENTAL: 1 Month The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful sunshine. ...

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Property Type

Islamorada Condo

"Great condo!"
Reviewed October 19, 2020

This was a great location to watch beautiful sunrises. The facilities were as described. The condo was super clean and up to date.

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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
  • Pet Friendly

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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Ocean Sunrise Villa

3 BR | 2 BA | Sleeps 6 | Quick View

$667

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private Pool

About this property

Miles Marker 82.6 – Open Oceanfront Top shelf views from this oceanfront home in Islamorada, Florida Keys. Spend every morning watching world famous Islamorada sunrises from the living room or out on the pool or terrace. Spend warm summer days in the sun-warmed ocean front pool, or go for a walk ...

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Property Type

Islamorada Villa

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Sea Ranch

4 BR | 3 BA | Sleeps 8 | Quick View

$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

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Antigua Place - Charming vacation home located in Port Antigua.

$187

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

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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DIRECT OCEANFRONT POOL HOME W/ Deep Water dock, Huge Heated Pool INQUIRE WITHIN!

$400

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!!OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated ...

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Property Type

Islamorada House

"Truly the best stay we have had in the Keys in over 15 years. Gorgeous views and awesome location!!"
Reviewed January 31, 2019

We have been renting in the Keys since 2005 and have booked many homes from Key Largo to Marathon and this one surpassed them all. The views are amazing, pool was big and warm, beds comfortable and the ...

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BEACON REEF 306 - 2 Bedroom Condo with Gorgeous Views of the Ocean and Complex

$143

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 1 Month Enjoy a relaxing summer and fall here in the Keys at this immaculate and charming two bedroom and two bath condo with screened balcony overlooking views of the tropical complex and of course the beautiful ocean. While the owners attend to their other property "up north" ...

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Property Type

Islamorada Condo

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

$263

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

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

$127

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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Island Living with Gulf Views

2 BR | 2 BA | Sleeps 4 | Quick View

LAST MINUTE DEAL 1/16 - 1/30: DISCOUNT - $100.00 Off Weekly Rate

$197

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Tropically furnished, privately owned condominium at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. Enjoy your morning coffee watching the boats go out. Relax with a amazing sunset and a glass ...

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Property Type

Islamorada Condo

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DEAL
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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Little Bay Cottage- Gated Bayfront Property Shared with 2 Other Rental Units

$393

avg/night

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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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Ishmaels

7 BR | 4 BA | Sleeps 14 | Quick View

$600

avg/night

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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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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

$136

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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Little Bay - Entire Compound in Islamorada w/Gorgeous Bay Views and Boat Basin

6 BR | 6 BA | Sleeps 18 | Quick View

Distance to beach: 5 miles to Founder's Park

$1250

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

MINIMUM RENTAL: 7 NIGHTS This is a lush tropical setting in a gated compound located directly on Florida Bay. Protected dockage in the "Little Bay" will keep your 30' boat (or smaller) safe. There’s a “sunning” area with lounge chairs on the peninsula so you can capture ...

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Property Type

Islamorada Estate

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Sunshine Place - Ground Level Unit with Ocean Views.

$224

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

Minimum Rental: 7 Days"Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people ...

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Property Type

Islamorada House

"Wonderful!"
Reviewed April 23, 2019

Beautiful view; lots of privacy; an exceptional experience! The home was immaculate and had a “well-supplied” kitchen. We genuinely enjoyed our stay, We loved getting up in the morning and having ...

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BAYSIDE CONDO WITH MARINA,POOL AND BEACH

$172

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for your ...

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Property Type

Islamorada Condo

"Exceptional experience"
Reviewed November 23, 2020

The location is perfect. We really enjoyed the pool. It wasn't very busy at all. The beach area is amazing. But the best part of this rental is the property owners response to help out with anything. Recommendations ...

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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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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 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!