Cheap Vacation Rentals in Islamorada

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

1

Distance to beach: 5 miles to Founders Park

$79

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

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 7 | Quick View

3

Distance to beach: 0.9 miles to Founders Park

$83

avg/night

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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

"I found my winter getaway"

From the moment we walked through the door of Unit111, we knew we would be back. The unit is warm and comfortable, all the essentials needed are supplied. All furniture is current and comfortable. Location ...

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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$86

avg/night

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Key Amenities

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

About this property

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

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Property Type

Islamorada Condo

"Great condo!"

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

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Key Amenities

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

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

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Property Type

Islamorada Condo

"Awesome!!"

Stayed at Futura Yatch resort for a week. Stayed in 106 and an amazing condo! No problems at all! Loved the location and pool was awesome! Thanks Rick and Carey! Will be back!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Located at Mile Maker 87 Bayside. This gated condo complex offers a large heated pool, club house, Jacuzzi, two tennis court, large Bayside beach. This townhouse (sleeps 8) has just been totally renovated with beautiful tropical furniture, all new kitchen, small garden patio with hammock, living room ...

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Property Type

Islamorada House

"Winter stay Executive Bay Club"

Our unit at Executive Bay Club was just what the doctor ordered. We liked the Tommy Bahamma furnishings in the unit. All the snowbirds here were very friendly and amenities and location in Islamorada ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

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

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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Key Amenities

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

About this property

Large two bedroom, two bath, two balcony condo. King sized bed in master bedroom with a peekaboo ocean view from balcony and a large walk in closet. Guest bedroom also has a king sized bed and balcony with peekaboo views of the ocean. Living room features a pull out sofa. Condo is located next to the ...

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Property Type

Islamorada Condo

"This condo has everything!"

Beautifully decorated, well stocked kitchen, lovely bathrooms, gorgeous bedrooms with very comfortable beds, large TV, and tropical views from the balconies! We enjoyed a leisurely walk to restaurants. ...

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2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 7 miles to Founders

$118

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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"

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

2Bed / 2 baths Sleeps 5. 2 adults max. Brand New -manufactured homeOcean view from property. Steps away from the beautiful turquoise Atlantic Ocean, Jetty, covered Pavilion, fish-cleaning table, sandbars where people can hang out. Gorgeous sunrises and sunsets. Bayside close by also. World class ...

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Property Type

Islamorada Mobile Home

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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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2 BR | 3 BA | Sleeps 6 | Quick View

2

$133

avg/night

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Key Amenities

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

About this property

This is a cute cottage all remodeled white tiled, waterfront in the secluded neighborhood of Plantation Key Colony The house offer two bedrooms one with a king size bed and the second with two full beds A complete remodeled kitchen galley type with all appliances and many kitchen gadgets, spices and ...

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Property Type

Islamorada Cottage

"Review for your home"

Mercy and Jose’ have a beautiful home that we have been able to rent for 4 months during the months of Jan- April! They take great care of their home and they respond very quickly if you need to reach ...

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2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$138

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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"

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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Key Amenities

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

About this property

Minimum Rental: 28 Days "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 everything - restaurants, ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

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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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!"

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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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Key Amenities

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

About this property

Minimum Rental: 28 Days"Beacon Reef 310" is located in one of the most desirable condominium complexes in the Upper Keys. New owners are in the process of remodeling the kitchen and adding new furnishings. NEW PHOTOS will be posted once the removations have been completed. This condo ...

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Property Type

Islamorada Condo

"Great stay."

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront

About this property

MINIMUM STAY: 28 DAYS “Beacon Reef 301” is a fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, clean, spacious 2 bedroom 2 bath condo has all the comforts ...

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Property Type

Islamorada Condo

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$162

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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

"Awesome place and owner"

What a great place. From the location to the boat slips with water and electricity. Just as described. Love the bait freezer addition. Glen is amazing to work with. Made sure everything was perfect for ...

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to Anne's Beach

$164

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

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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2 BR | 2 BA | Sleeps 4 | Quick View

$167

avg/night

View Details

Key Amenities

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

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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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

"Easy to Work With"

Although we had to cancel our trip due to a medical issue, Jerry was extremely helpful during the booking process. He answered all of my many questions and offered suggestions and activities. Based on how ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Minimum Rental: 1 Month This like-new 2 bedroom/2 bath condo has fabulous ocean views and was totally remodeled/updated very recently. You'll love the sparkling new natural stone counter-top kitchen with stainless steel appliances, induction cook top and microwave. The interior is bright, fresh and ...

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Property Type

Islamorada Condo

"Paradise"

We just loved staying in this beautiful condo for a month. This place has everything you need to enjoy your stay. Just bring clothes.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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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Key Amenities

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

About this property

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

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Property Type

Islamorada Condo

"a wonderful place."

beacon reef #503 was a great condo. We really enjoyed our month stay . The grounds were so well maintained and also the condo.We already booked for next year ! Cant wait till then. Lauren Mccrae

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1 BR | 1 BA | Sleeps 2 | Quick View

4

$178

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

"Our second trip was as good as the first!"

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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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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 ...

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Property Type

Islamorada Townhome

"Amazing !"

We recently stayed at Beacon reef in January of 2022 .What a wonderful time we had! The condo was excellent, modern ,clean , just beautiful ! The grounds, immaculate .The exercize room was top notch.It ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Pool

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 2 bedrooms ...

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Property Type

Islamorada Condo

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Islamorada Vacation Rentals