Islamorada Vacation Rentals

(91 rentals)
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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

$275

avg/night

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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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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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Luxury Oceanfront Home, Views, Pool, Sandy Beach

4 BR | 4.5 BA | Sleeps 8 | Quick View

1
Owner special: Oceanfront, Beach & Pool Available August 14-28th Enjoy Summer Fun at FALL DISCOUNTED RATES!

$636

avg/night

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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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Bayside Paradise in the Heart of Islamorada *Private Boat Dockage Upon Request*

$623

avg/night

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Key Amenities

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

About this property

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and ...

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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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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....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 405 - Gorgeous Remodeled 2 Bedroom Condo with Ocean Views

$108

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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Beacon Reef Condominium 205

2 BR | 2 BA | Sleeps 4 | Quick View

$167

avg/night

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Key Amenities

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

About this property

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

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Property Type

Islamorada Apartment

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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

"Beautiful Location"
Reviewed July 23, 2021

Loved this location! We visited Anne's beach and Bahia Honda beaches and nothing compared to Jerry's private beach. Quiet and beautiful sunsets. Apartment was very clean. Highly recommend!

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Waterfront Paradise with Free Dockage - Contact us to price your stay!!

1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 12 miles to Founders Park

$150

avg/night

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Key Amenities

  • Air Conditioning
  • Rentals by Owner

About this property

Secluded Waterfront Studio with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this listing. ...

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Property Type

Islamorada Apartment

"Little piece of paradise!"
Reviewed July 26, 2020

We stayed two weeks in the beautiful apartment and it was the best vacation ever! Chris is a wonderful host, very friendly and a wealth of information about the area! We will be back next year!

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

$260

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

"Fun time in Tollgate"
Reviewed May 14, 2021

Just got back from spending the month of April at Bill and Tiffany’s Piece of Paradise. It was everything we had hoped it would be.I brought my 28 foot center console and the home was setup perfectly ...

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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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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

$457

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 REVIEWS HERE YET BUT MANY AT OUR DIRECT SITE (SEE "LINKS" TAB ON THE LEFT) AND 12 YEARS ON VRBO PROPERTY #186650. If you are seeking an Islamorada rental for ...

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Property Type

Islamorada Villa

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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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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

$557

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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Five Bedroom Pool home with Boat Slip in Marina..... Your Florida Keys Getaway!

$243

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to paradise! This home is a new listing. If you are looking for a large beautiful home with a pool in a peaceful setting and in an absolutely perfect location for your stay in Islamorada, you have found it! We are located in Venetian shores off Snake Creek with a boat slip for your use in the ...

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Property Type

Islamorada House

"Great family vacation!"
Reviewed August 12, 2020

Clean, well maintain, upgraded spacious home for the family. Great location. Planning next vacation already. Thanks!

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Oceanviews

2 BR | 1 BA | Sleeps 4 | Quick View

1

$149

avg/night

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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 Access Master Bedroom with King size bed Second bedroom with full size bed Inflatable full size bed available One full bath with bath tub Living room with sofa, sofa chair, accent chair, ...

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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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Pool Home - Fisherman's Dream! Ask about our Winter Getaways

$187

avg/night

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Key Amenities

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

About this property

This beautifully furnished waterfront home with ocean views will thrill the most ardent diver or fisherman and his family. You will love the luxury of a heated pool, magnificent view, and protected deep water dockage for multiple boats. It is located on a large harbor with multiple sailing yachts and ...

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Property Type

Islamorada House

"Unforgettable family vacation"
Reviewed January 3, 2019

My husband and I rented this house this past month, along with our 7 adult kids/significant others. (9 of us in total) We absolutely loved it. The house itself was perfect. Very clean, and up to date. Had ...

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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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Southern Diversion Islamorada

5 BR | 3.5 BA | Sleeps 17 | Quick View

1

$1360

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

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

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Property Type

Islamorada Estate

"Great stay"
Reviewed July 26, 2021

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

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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

$241

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • 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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Dream Home in the Keys

5 BR | 3 BA | Sleeps 12 | Quick View

4

$530

avg/night

View Details

Key Amenities

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

About this property

Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large bedrooms ...

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Property Type

Islamorada House

"Amazing Family Vacation! Beautiful and affordable home in amazing location."
Reviewed January 24, 2021

This was our first family trip to the FL keys and we had the most amazing time! Bridget was so helpful, especially since we booked prior to covid and decided to take our planned trip. She answered all my ...

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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

$450

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 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

$150

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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Bay Harbor 116D

3 BR | 2.5 BA | Sleeps 6 | Quick View

$400

avg/night

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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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Bay Harbor 110C​

2 BR | 2 BA | Sleeps 4 | Quick View

1

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

$266

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 Harbour #202

2 BR | 2 BA | Sleeps 4 | Quick View

$290

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This Condo is located on Lower Matecumbe Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Bay Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a second floor location make it easy to enjoy your stunning view ...

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Property Type

Islamorada Condo

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EXECUTIVE BAY ISLAMORADA - 2 & 3 BDR WATERFRONT TOWNHOMES

$167

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

"Perfect get away"
Reviewed May 16, 2021

Beautifully decorated, everything you would need was there. Quality dishes, pots and pan in an upscale kitchen. Safe and quiet location. Relaxing to sit in the sun and watch the boats. Tennis court in ...

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Escape to a private island where the ocean and boat dock are 20 feet away

$203

avg/night

View Details

Key Amenities

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

About this property

Enjoy the sunrise from the balacoy or from in the condo through 50 ft of glass sliding doors. You can also see the sunset from our walkway on bayside. We have a full kitchen from dishwasher to microwave, washer/dryer, even beach towels. We have wifi, cable TV, and a Master Bath with whirlpool tub, ...

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Property Type

Islamorada Condo

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Apartment with beach access.

1 BR | 1 BA | Sleeps 2 | Quick View

4

$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

"Our second trip was as good as the first!"
Reviewed June 28, 2021

We returned for a 2 week stay in June and had a wonderful time fishing, and relaxing. There was plenty of dock space, and the apartment was clean and well equipped. The bed was very comfortable, air conditioning, ...

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

$294

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

$571

avg/night

View Details

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

$111

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

$159

avg/night

View Details

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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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
  • 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 CONDO WITH MARINA,POOL AND BEACH

$129

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

"Nice condo for the price. Crossed Florida Keys off our bucket list."
Reviewed June 21, 2021

This was our first visit to the Florida Keys. Our Moon Bay condo was very nice for the rate. Next time, we'll be sure to rent a condo with a balcony. Not all rentals in this resort have them, and we missed ...

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Sunshine Place - Ground Level Unit with Ocean Views.

$201

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

$141

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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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

$1286

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

$99

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

$161

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

$500 DISCOUNT for LAST MINUTE BOOKING JULY, AUGUST, or SEPTEMBER 2021Minimum 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 ...

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Property Type

Islamorada Condo

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

$73

avg/night

View Details

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

$107

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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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

$147

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

$126

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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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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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 #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

$119

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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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!