Vacation Rentals in Islamorada

(93 rentals)
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1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 1 miles to Anne's Beach

$200

avg/night

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Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

Secluded Waterfront Apartment 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 ...

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Property Type

Islamorada Apartment

"Little piece of paradise!"

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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3 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 3 miles to Anne's Beach State Park

$310

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your ...

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Property Type

Islamorada House

"Absolutely Amazing!"

This house was everything we had hoped for. We arrived at night and upon waking in the morning we were amazed at the 180 degree gulf view. There is a huge amount of waterfront with a sea wall all the ...

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3 BR | 3 BA | Sleeps 6 | Quick View

last minute deal
LAST MINUTE DEAL 2/29 - 3/25: March renter has cancelled. This luxury unit just reduced to $4,000++ per week. Includes large lift.

Distance to beach: 2 miles to Anne's Beach State Park

$571

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

This stunning top floor end unit in Bay Harbour has stunning ocean and harbor views and includes a 50ft. boat slip and a 25,000# lift. BAY HARBOUR ALLOWS 7-DAY RENTALS. The interior design is spectacular. Coffered ceilings in the living area, top of the line Miele and Thermador appliances, custom kitchen ...

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Property Type

Islamorada Condo

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DEAL

2 BR | 2 BA | Sleeps 4 | Quick View

4

$357

avg/night

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Key Amenities

  • Air conditioning
  • 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

"Bay Harbor 303"

The condo was lovely! Thoroughly furnished. Updated amenities. Beautiful grounds. On-site staff. Friendly and helpful. Highly recommended

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3 BR | 2.5 BA | Sleeps 8 | Quick View

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

$640

avg/night

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Key Amenities

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

About this property

Save $500-600 compared to VRBO by avoiding VRBO's $500-600 booking fee!Welcome to Anglers Reef, a very special community of vacation homes. And to Anglers Reef 140's OceanFRONT location with its unique UNOBSTRUCTED OCEAN VIEWS FROM EVERY ROOM and spacious wraparound decks!Boat slip ...

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Property Type

Islamorada House

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$930

avg/night

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Key Amenities

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

About this property

Welcome to the “Sailfish House” at Tarpon Point!Soak up the sun and take in the spectacular views at this opulent 4 bedroom, 4 bath home located in the private community of Tarpon Point. Accommodating up to eight adults, this impressive home makes it easy to both entertain and unwind with ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"A month in heaven"

My wife and I spent the month of Dec. 2022 at this property in Islamorada (HEAVEN) in the Keys. The property has a pool, a canal and a boat dock that can handle any boat.Let me start of saying that ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$462

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Mother Ocean!This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Beautiful Oceanfront Condo"

Plantation by the Sea is an older condo complex that is beautifully maintained. The condo is located at MM 87.5 just off of U.S. 1 in the heart of Islamorada. Restaurants of various types can be found within ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community ...

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Property Type

Islamorada House

"OUTSTANDING ON SO MANY LEVELS"

The magic began with the excellent, attentive, and kind correspondence with the owners. So excited for us to enjoy their home. Upon arrival, the magic continued. The photos you see are exactly what ...

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5 BR | 5 BA | Sleeps 10 | Quick View

$600

avg/night

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Key Amenities

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

About this property

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

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Property Type

Islamorada House

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$500

avg/night

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Key Amenities

  • Air conditioning
  • 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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2 BR | 2 BA | Sleeps 4 | Quick View

1

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

$327

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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, ...

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Property Type

Islamorada Condo

"Couldn't have picked a better place to kick off the new year!"

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

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4 BR | 4.5 BA | Sleeps 8 | Quick View

1

Distance to beach: 0.5 miles to White Marlin Beach

$771

avg/night

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Key Amenities

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

About this property

Bring your boat and Jet SkisNestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, double jet ski lift, and two floors facing ...

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Property Type

Islamorada House

"Fabulous location, off the beaten path, clean, owner available for questions and very responsive."

We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has ...

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3 BR | 2.5 BA | Sleeps 8 | Quick View

1

$650

avg/night

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Key Amenities

  • Air conditioning
  • 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

"A rental that exceeded expectation"

A well maintained home in a perfect quiet setting. The owner Patrick was outstanding to work with and made sure that all was in order. He is an excellent communicator. Welcome bottles of wine greeted us. ...

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2 BR | 2 BA | Sleeps 4 | Quick View

13

Distance to beach: 5 miles to Anne's Beach

$325

avg/night

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Key Amenities

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

About this property

The "Nest" villa (one of 7 privately owned condo residences) sits on a 1 acre lot located on Islamorda's beautiful Florida Bay. Stunning water views and unforgettable sunsets are guarenteed. The property is filled with mature tropical landscaping along a tree lined private gravel driveway ...

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Property Type

Islamorada Villa

"Beautiful place!!"

Couldn't have been any better. Perfect location, comfortable beds, great views! The deck right out the door was our favorite place to be. Highly recommend the Nest

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3 BR | 2 BA | Sleeps 6 | Quick View

9

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Islamorada House

"Perfect, quiet, and secluded"

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

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 100 feet to Front door

$185

avg/night

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Key Amenities

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

About this property

MINIMUM STAY: 30 daysSpacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip.Walk out your front door and go boating.You’ll ...

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Property Type

Islamorada Condo

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4 BR | 4 BA | Sleeps 10 | Quick View

3

Distance to beach: 2 miles to Founders Park

$650

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"You found it"

If you’re looking for a well kept beautiful home, right on the water positioned right between the Gulf and Atlantic, great pool and hot tub YOU FOUND IT. Communication is great and owner is so helpful. ...

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3 BR | 2.5 BA | Sleeps 6 | Quick View

$500

avg/night

View Details

Key Amenities

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

About this property

Beautiful views from this condo!Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.We are new owners of this condo that has never been in the rental pool. (that is why few reviews)Complete remodel with no expense spared!The location is quiet with the most beautiful ...

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Property Type

Islamorada Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Anne's Beach State Park

$333

avg/night

View Details

Key Amenities

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

About this property

This 3-bedroom condo couldn't be any closer to the ocean. Located on the 4th floor at Palms of Islamorada this unit takes full advantage of the waterfront setting. There are two bedrooms with open water views overlooking the blue waters with Alligator lighthouse off in the distance. Both of these ...

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Property Type

Islamorada Condo

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$500

avg/night

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Key Amenities

  • Air conditioning
  • 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

"We love this house!"

2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights ...

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Key Amenities

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

About this property

See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries.Escape to the ultimate paradise at our stunning oceanside estate in the Florida Keys. This majestic property ...

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Property Type

Islamorada House

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Key Amenities

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

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house ...

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Property Type

Islamorada House

"4 years"

This was our 4th year on Tollgate and somehow it gets better. Tiff and Bill go above and beyond in accommodating us. The updates look fabulous, love the painting in the dining room. Our dog Max has made ...

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$832

avg/night

View Details

Key Amenities

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

About this property

Introducing the "Bonefish House" at Tarpon Point!This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed ...

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Property Type

Islamorada House

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2 BR | 2 BA | Sleeps 4 | Quick View

owner special
Owner special: June, July, August, and September. $5000.00 per month

$200

avg/night

View Details

Key Amenities

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

About this property

Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the 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 Condo

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3 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach State Park

$552

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

See why we have ALL 5-star reviews! Located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries.As soon as you step foot in this stunning two-floor home, you're greeted by a gorgeous yet highly comfortable modern open-floor plan living area. ...

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Property Type

Islamorada House

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Key Amenities

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

About this property

COMING SOON - Beautiful new home on Florida Bay with sandy beach, large pool, beautiful views and sunsets all year round. Private suites are offered for 2-4 people each with king bed, private bath and mini kitchen facilities. Estimated availability February 2024. Monthly bookings only - no pets please. ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner

About this property

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

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Property Type

Islamorada Apartment

"Island beauty at it’s finest"

This is a wonderful rental to enjoy what Islamorada is all about.The post card sunsets and the relaxing sounds of the waves. Definitely laid back, but all of the amenities that you need. The host’s are ...

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4 BR | 4.5 BA | Sleeps 8 | Quick View

6
owner special
Owner special: April 6-13 ($6000/wk) and April 20-27 ($4800/wk) still available as are summer weeks. Inquire now!

$863

avg/night

View Details

Key Amenities

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

About this property

‘The Beach House’ at Tarpon Point in Islamorada- DIRECT RENTAL WITH NO ADDITIONAL FEES‘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 ...

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Property Type

Islamorada House

"The perfect location"

This house was amazing! Great location, the dock location and ease of access was perfect for kids that love fishing. The house was clean and gorgeous! Amazing views from the balcony. Great family vacation ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner

About this property

This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers ...

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Property Type

Islamorada Condo

"Location"

We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.

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1 BR | 1 BA | Sleeps 2 | Quick View

5

$150

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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

"Perfect rental for one couple"

This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under ...

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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.3 miles to Anne's Beach

$144

avg/night

View Details

Key Amenities

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

About this property

Enjoy this modern lagoon front ground level one bedroom condo/apartment with exclusive use of the backyard, pool, dock and carport. Located on the Gulf side of Lower Matecumbe (Islamorada MM 73.5) minutes from the Channel 2 and Channel 5 Bridges offering immediate access to Ocean side. Dockage available ...

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Property Type

Islamorada Condo

"A month in paradise!"

After staying in St. Pete Beach for a month, we decided to go south and visit the Florida keys. We found Bill and Carolyn's place on Florida Rentals and decided to give it a go. What a wonderful experience!The ...

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6 BR | 4 BA | Sleeps 12 | Quick View

3

Distance to beach: 0.5 miles to Port Antigua Private Beach

$421

avg/night

View Details

Key Amenities

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

About this property

This recently renovated property enjoys 6 bedrooms, 4 bathrooms and separate kitchens, living rooms and laundry facilities. It shares an ocean facing veranda with 2 dual gas grills and multiple seating and lounging areas. It has ample offstreet parking for vehicles and trailers. The Admiral on the Cove ...

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Property Type

Islamorada Townhome

"A Spectacular Spot"

We enjoyed our stay at this beautifully furnished and well stocked house. George and Bonnie responded quickly to any questions that we had. The separate living areas allowed us to enjoy family and friends ...

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach State Park

$389

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

This updated Port Antigua home with 85 ft. of concrete dock is ready for a new family to enjoy. The open floor plan and vaulted ceilings make this house feel so welcoming! French doors with side lights let in the natural light and open to the lanai where you can enjoy your morning coffee or a cocktail ...

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Property Type

Islamorada House

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3 BR | 3 BA | Sleeps 6 | Quick View

$560

avg/night

View Details

Key Amenities

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

About this property

Welcome to “At The Sandbar!”This newly built oceanside villa in Islamorada is a wonderful choice for those seeking a serene retreat and an opportunity to immerse themselves in the relaxed nature of the Florida Keys. Situated within the Peaceful Palms community on Windley Key, this three-bedroom, ...

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Property Type

Islamorada Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to the "Keys Life Cottage!"This beautifully updated and spacious two bedroom, one bath home is tucked away on a large landscaped lot in the heart of Islamorada and within walking or biking distance to Islamorada's famed Arts and Cultural district and to some of the most renowned ...

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Property Type

Islamorada Cottage

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Great Home Away From Home!"

Perfect location! Our family had a great week and we will definitely come back. Condo is well furnished, clean and plenty of space. Kitchen is well stocked with essentials. Pool was very refreshing. The ...

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3 BR | 2 BA | Sleeps 6 | Quick View

11

Distance to beach: 4 miles to Anne's Beach

$325

avg/night

View Details

Key Amenities

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

About this property

Enjoy the sunrise from the balcony 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

"Spacious, awesome condo with amazing views."

The condo was very spacious, meticulously clean and well supplied with cooking utensils and supplies. This was probably one of the nicest places we have stayed in the many years we have been going to the ...

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2 BR | 2 BA | Sleeps 4 | Quick View

6

Distance to beach: 0.9 miles to Founders Park

$127

avg/night

View Details

Key Amenities

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

About this property

Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom ...

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Property Type

Islamorada Condo

"Perfect!"

Sharon’s condo was absolutely gorgeous! It was super clean upon arrival and had everything we could have needed for our 3 month stay (linens, dishes, pots & pans, cleaning supplies, etc). The interior ...

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4 BR | 4 BA | Sleeps 8 | Quick View

$833

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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 ...

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Property Type

Islamorada House

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2 BR | 2 BA | Sleeps 4 | Quick View

1

$265

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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 an amazing sunset and a glass ...

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Property Type

Islamorada Condo

"Fantatic"

Fantastic host. fantastic location, fatastic accomodations! Looking forward to returning in 2022. Thank you Susan

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Key Amenities

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

About this property

4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family-friendly and a fisherman's dream. Our home sleeps 8 with every comfort you would want while on vacation in the keys...Large ...

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Property Type

Islamorada House

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Key Amenities

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

About this property

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

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Property Type

Islamorada Townhome

"Lazy Daz Beac House"

Excellent couple to work with. Great communication. The rental was beautiful and clean. We had a problem with the rental and they communicated with us and together we solved the problem. They went over ...

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Key Amenities

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

About this property

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

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Property Type

Islamorada House

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Key Amenities

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

About this property

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

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Property Type

Islamorada Condo

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1 BR | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 5 miles to Founders Park

$97

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Half Duplex HomeAre you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and manatees ...

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Property Type

Islamorada House

"Wonderful stay in the Keys!"

The screened in area and the outdoor space make this rental perfect! We kayaked on the canal, and walked around the neighborhood daily. We watched boats and manatees from the screened in porch. Lee (the ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$250

avg/night

View Details

Key Amenities

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

About this property

MM 87.7 . 2 Bedroom & 2 Bath. Rented 28 days minimum Experience the epitome of oceanfront luxury in this exquisite paradise! Delight in fishing the pristine waters of the Keys with the convenience of your own 30ft slip in a secure marina. Unwind in the comfort of your spacious condo that boasts ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Escape to paradise and experience the ultimate vacation getaway at our stunning 4-bedroom, 3-bathroom canal home in the heart of Islamorada. Nestled along the crystal-clear waters of the Florida Keys, this exceptional rental offers a perfect blend of comfort, convenience, and natural beauty.Key Features:Spacious ...

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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°

Find Your Ultimate Vacation with Islamorada Vacation Rentals


Islamorada is a small village located south of mainland Florida along the state’s gorgeous tropical keys. In fact, Islamorada vacation rentals and the village in which they reside encapsulate six of the Florida Keys and is known as one of the most beautiful vacation destinations throughout Florida. 

Plus, Islamorada is often called the “Sport Fishing Capital of the World,” making it a great place to visit for those who enjoy fishing for sport or recreation. 

Due to its separation from mainland Florida, Islamorada is made up mostly of white-sand beaches and clear waters, which offer plenty of opportunity for some peaceful R & R as well as all of the oceanside water sports you could imagine. 

Swim with the dolphins, take a snorkeling excursion, ride the waves on your surfboard, or simply relax on the beach with a good book; whatever you choose to do, you’re sure to have an incredible experience in Islamorada. 

In a village as unique and special as Islamorada, the best way to get the most out of your vacation is to browse Islamorada vacation rentals instead of opting for a hotel.

Hotels are crowded and impersonal, but your Islamorada home rental will be a one-of-a-kind space completely dedicated to you and your family. Plus, you’ll be able to live the life of a local and enjoy the unique architecture of the Florida Keys from a new perspective in your Islamorada rental home.

How to Get the Most out of Your Islamorada Vacation


As a tropical location, Islamorada sees steady rainfall throughout the year as well as relatively high levels of humidity, especially in the summer months. The rainiest seasons tend to be early summer and early autumn, making springtime and late autumn the best times of year to visit Islamorada in order to enjoy the best possible weather. 

Since the Florida Keys are separated from mainland Florida by several miles of ocean, most tourists will access the islands by air instead of by car, even if they’re already Florida residents. 

The Florida Keys/Marathon International Airport is the easiest way to access the city, and vacationers can reach Islamorada from the airport within a 40-minute drive by way of the Overseas Highway.

Best Activities Nearby Islamorada House Rentals


You can’t get much closer to ocean wildlife than on the Florida Keys, which is why Islamorada’s Wild Dolphin Tours are so wildly popular. 
Get to know the resident dolphins of the Florida coast by swimming alongside them and experience many other incredible types of aquatic creatures from a close range, all guided by locals who know the waters of the Florida Keys inside and out. 

With Wild Dolphin Tours in Islamorada, you can also opt to take a snorkeling excursion along the scenic coral reefs surrounding the islands with the Snorkel & Sandbar Boat Tours. 

These excursions include Alligator Reef, Florida Bay, and Cheeca Rocks, some of Florida's most stunning and highly sought-after coral reefs. Book a three-hour, four-hour, or private tour to create a one-of-a-kind experience for you and your family. 

There’s plenty more natural beauty to see in Islamorada apart from the expansive ocean views. Nature lovers will enjoy a trip to the Lignumvitae Key Botanical State Park, a unique botanical experience that features a variety of local plant life and even some opportunities to view Florida Keys wildlife. 
The park is open from 8 a.m. to 4 p.m. Thursday through Monday, and the entrance fee is $2.50 per person, with self-guided tour brochures available to get the most out of your visit. 

Looking to take in a bit of local history as you enjoy the gorgeous scenery? Pay a visit to Indian Key Historic State Park, the site of the original Dade County seat in 1836. 
In 1840, a group of local natives led by leader Chakaika raided the settlement and burned the town to the ground, leaving only one building behind. You can visit the remaining town building and learn more about the area’s unique history any day of the week between 8 a.m. and sunset, and the entrance fee is $2.50 per visitor.

Islamorada, FL, Annual Events


Island Fest is one of the most anticipated annual events in Islamorada. Taking place early each April, Island Fest features an art show and competition, unique food vendors, live music, a classic car show, and more. Plus, local food vendors go head-to-head to earn the sought-after People’s Choice Award for the best food of the festival. 
Another popular Islamorada event more heavily focused on the local art scene is the Morada Way Art Walk, a monthly event that showcases local art in a variety of mediums, including photography, painting, ceramics, and printmaking. The Morada Way Art Walk also features live musical acts and delicious dining options and is free to enter.

Best Food and Drink near Islamorada Rentals


If you’re looking to enjoy a fine meal with an unforgettable view of the ocean, there are many incredible options to suit your needs in Islamorada. Locals and visitors alike love Lorelei Restaurant & Cabana Bar, a fun semi-casual joint that serves a variety of fresh seafood entrees and boasts a full bar with unique cocktails to try. 

Islamorada also features the Islamorada Brewery & Distillery, the only establishment of its kind on the Florida Keys. Experience all that Islamorada has to offer with an incredible locally brewed beer in the beer garden, a refreshing hand-crafted cocktail, and delicious eats from local food trucks.


FAQ

How many vacation rentals are there in/around Islamorada?

There are 93 Islamorada vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

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

There are vacation rentals available in Islamorada for as low as $97 per night with an average price per night of $389.

Can I rent a house in Islamorada?

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

Do any vacation rentals in Islamorada have a pool?

Yes there are 39 vacation rentals with a pool in Islamorada on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Islamorada vacation rentals on the ocean?

There are 39 oceanfront rentals in Islamorada available on FloridaRentals.com. Use our filters to search and book yours today!