Islamorada Vacation Rentals

(93 rentals)
Boater's Dream Home

4 BR | 4.5 BA | Sleeps 12 | Quick View

Distance to beach: 0.5 miles to White Marlin Beach

$500

avg/night

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Key Amenities

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

About this property

Bring your boat and Jet SkisNestled on a canal less than 2 minutes to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. 80' dock with fish cleaning table, double jet ski lift, and two floors facing the canal and a private sanctuary. 1st floor: 2 bed/2.5 bath, full ...

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Property Type

Islamorada House

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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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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

"Solitude Oasis"
Reviewed March 6, 2021

During this pandemic Jerry’s rental was the perfect place to decompress and seek solitude. The studio was squeaky clean , the views were amazing , my husband loved the hammock Jerry was a wealth of information ...

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

$280

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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sea oats beach

5 BR | 5 BA | Sleeps 14 | Quick View

$562

avg/night

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

$331

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

"Truly enjoyed our stay!"
Reviewed April 13, 2021

Thank you Bill and Tiffany for providing such great accommodations. We had so much fun and wish we could've stayed longer. Everything imaginable is provided in the house and if not, all you need to do ...

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MATECUMBE FL KEYS OCEAN SIDE JUNE 12-19 SLEEPS 4

$171

avg/night

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Key Amenities

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

About this property

1BEDROOM, 1 BATH, QUEEN SLEEPER, UNIT #101, Large One Bedroom 1st Floor With Ocean View, THE BEST UNIT IN RESORT ! Beautiful Oceanfront Matecumbe Resort. The resort is very casual... so expect to make your own umbrella drink. Great for fishing and diving with Alligator Reef a short boat ride off shore. ...

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Property Type

Islamorada Apartment

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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

$533

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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Waterfront Paradise on Canal W/New Pool

$395

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

Distance to beach: 5 miles to Anne's Beach

$275

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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BEAUTIFUL 3 BEDROOM VACATION HOME LOCATED ON DEEP CANAL W/OCEAN & BAY ACCESS

3 BR | 3 BA | Sleeps 8 | Quick View

2

Distance to beach: 1 miles to founders park

$585

avg/night

View Details

Key Amenities

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

About this property

Located on the peaceful upper Keys, in Islamorada, licensed to rent weekly this home is situated in the quiet residential neighborhood of Venetian Shores MM 86. Immediate access to ocean and Bay side off of Snake Creek. Islamorada is just 75 miles from Miami and 86 miles from Key West. The average temperature ...

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Property Type

Islamorada House

"Great house... Great location!"
Reviewed April 22, 2019

The house we rented was GREAT! It was on a canal- had a pool and was in a great location of Islamorada. It was clean when we arrived. The pool was clean as well. It has all the amenities anyone would need ...

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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

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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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Luxury Oceanfront Home, New Rental, Views, Pool

4 BR | 4.5 BA | Sleeps 8 | Quick View

1
Owner special: May 1-8 Now $4,900/wk Discounted $1000 off

$845

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

"The Perfect Escape"
Reviewed April 1, 2021

We could not have been happier at this exquisite home. It was clean, in a great location, and the pool was awesome! The marina across the street is within walking distance and they have food, shopping, ...

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

$124

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

3 BR | 2.5 BA | Sleeps 8 | Quick View

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

$514

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. WE ARE BRAND NEW TO THIS SITE SO NO REVIEW HERE YET BUT MANY AT OUR DIRECT SITE (SEE LINKS TAB HERE) AND 12 YEARS ON VRBO PROPERTY #186650. If you are seeking an Islamorada rental for your vacation, Anglers ...

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Property Type

Islamorada Villa

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PALMS 405 - Gorgeous Remodeled 2 Bedroom Condo with Ocean Views

$124

avg/night

View Details

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

$257

avg/night

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Key Amenities

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

About this property

ALERT: BRAND NEW POOL JUST COMPLETED AND INSTALLED....This listing is for BOTH sides of the duplex the whole house can be rented through here so that you can Enjoy the keys life in style living in this beautifully furnished 4 Bedroom (2 on each side), 2 Bath (1 on each side) , 2 kitchens (1 on each ...

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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

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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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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

avg/night

View Details

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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Island Conch Cottage

2 BR | 1.5 BA | Sleeps 4 | Quick View

6

Distance to beach: 0.5 miles to Anne Beach

$126

avg/night

View Details

Key Amenities

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

$406

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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Apartment with beach access.

1 BR | 1 BA | Sleeps 2 | Quick View

3

$143

avg/night

View Details

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

"A Private Tranquil Retreat"
Reviewed March 27, 2021

We had a wonderful time at 202 Sunset. The setting was just what we were looking for PRIVATE and TRANQUIL. The apartment was spacious. We spent each morning walking the path across the highway along Route ...

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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

$317

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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Ocean Harbor M31

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Founder's Park

$283

avg/night

View Details

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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Blue Heaven Coastal Cottage

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach

$217

avg/night

View Details

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

4 BR | 4 BA | Sleeps 8 | Quick View

$633

avg/night

View Details

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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Bay Harbor 116D

3 BR | 2.5 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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EXECUTIVE BAY ISLAMORADA - 2 & 3 BDR WATERFRONT TOWNHOMES

$170

avg/night

View Details

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

$124

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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Flamingo Cottage - Adorable 2 bedroom, 2 bath cozy cottage with pool.

$133

avg/night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 DaysFlamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like feeling ...

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Property Type

Islamorada House

"Lovely little home on a quiet street"
Reviewed August 29, 2020

I rented this so I could have a quiet place to swim and relax before undergoing major surgery. The pool area is a perfect oasis with the occasional visiting birds and squirrels. The house is comfortable ...

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Brand New Waterfront Home with Pool and Dock

$450

avg/night

View Details

Key Amenities

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

About this property

This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast. ...

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Property Type

Islamorada House

"Sunshine Getaway"
Reviewed March 18, 2021

We usually book 2 months in the lower keys but this year we booked our first month on Islamorada in the upper Keys ....what a perfect house and location and the pool was larger than most which added to ...

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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

$183

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

$102

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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Ishmaels

7 BR | 4 BA | Sleeps 14 | Quick View

$633

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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Sea Ranch

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"
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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Island Living with Gulf Views

2 BR | 2 BA | Sleeps 4 | Quick View

LAST MINUTE DEAL 4/24 - 5/8: 10% Off Weekly Rate !!

$178

avg/night

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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
Maison 202

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

$12,500-$15,000 Weekly***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, Poolside… A world-class oceanfront residence, located ...

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Property Type

Islamorada Condo

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

$136

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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Maison 101

4 BR | 4 BA | Sleeps 8 | Quick View

$2143

avg/night

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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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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

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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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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
  • 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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My Paradise - Oceanfront beach house with protected dockage.

$298

avg/night

View Details

Key Amenities

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

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Property Type

Islamorada House

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Antigua Place - Charming vacation home located in Port Antigua.

$187

avg/night

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

$429

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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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

$142

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

$400

avg/night

View Details

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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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!