Cheap Vacation Rentals in Islamorada

(23 rentals)
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2 BR | 1.5 BA | Sleeps 6 | Quick View

$97

avg/night

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Key Amenities

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

About this property

Beautiful area of island on ocean

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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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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

"Great vacation"

We have never stayed in the Florida Keys before so this was a new adventure that we will definitely do again. The weather was a perfect 80 degrees. Nothing but chill time. We would start the day in the ...

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2 BR | 2 BA | Sleeps 4 | Quick View

6

Distance to beach: 0.9 miles to Founders Park

$117

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

"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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Key Amenities

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

About this property

SPECIAL SUMMER SALE RATES MAY-JULY!! SEE SPECIAL POSTED RATES MAY-JULY! Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of the world, Islamorada. ...

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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
  • 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

"Wonderful"

I highly recommend this vacation spot. Not only is the condo very nice the whole property is set up for your every need. The owner and property manager are very nice and accommodating. I was amazed by the ...

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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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$133

avg/night

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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Experience total seclusion in this ten-unit oceanfront complex called Port of Call, nestled between the mansions of Millionaire's Row in Islamorada on the Atlantic Ocean, Mile Marker 88.Outdoor facilities include a heated pool; chickee hut with common area barbecue grills, and a small sand beach. ...

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Property Type

Islamorada Townhome

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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. Brand new King sized bed frame 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 brand new pull out sofa. Condo ...

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Property Type

Islamorada Condo

"Perfect Pool With A View!!"

We stayed here in Nov. Weather was great.Condo is located 5 mins.from Founders Park.Check out Founders Park online. Owners can give you more info about securing a pass for entry. Condo is close to shopping, ...

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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.3 miles to Anne's Beach

$146

avg/night

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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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1 BR | 1 BA | Sleeps 2 | Quick View

5

$150

avg/night

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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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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

Gorgeous updated 2 bedroom, 2 bathroom condo with large modern kitchen in an oceanfront gated building with oceanfront pool, fishing dock, gym, sauna, barbecue grills and so much more, and the best part is YOU'RE IN THE FLORIDA KEYS!

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Property Type

Islamorada Condo

"Jan Feb 2023"

Great condo, pool, and neighbors. Highly recommend. The pool is heated. Ocean view is great. Community room. Has exercise room and sauna.

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Founders Park

$158

avg/night

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Key Amenities

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

About this property

Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condominium (CHC) . Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally decorated in Tropical Modern style. A 30' Boat Slip ...

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Property Type

Islamorada Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 100 feet to Front door

$160

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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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, bright, clean apartment!"

The location of this apartment is amazing. You are right on the ocean with a very private beach directly out your front door. We spent many days on the lounge chairs enjoying the view and listening to ...

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Key Amenities

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

About this property

Enjoy breathtaking sunsets on the private beach while staying in this beautifully remodeled corner unit. The unit was completely gutted in 2021 and features 2 bedrooms plus a built out loft and 3 full bathrooms.The unit has a huge master with a king bed plus a bathroom/walk-in closet and ...

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Property Type

Islamorada Townhome

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2 BR | 2 BA | Sleeps 4 | Quick View

$175

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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3 BR | 2 BA | Sleeps 6 | Quick View

21
owner special
Owner special: APRIL 20-27 CANCELLATION SPECIAL!! 30% off .... $975 For that Week!!

$192

avg/night

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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 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, pickleball, heated pool, private beach, and dockage for ...

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Property Type

Islamorada Condo

"Top of the Keys"

Perfect location. Everything is close by. Even trips south and even to Key West are no big deal we drove in from North Carolina and we went everywhere. What a great property too our guests who wanted to ...

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2 BR | 2 BA | Sleeps 4 | Quick View

1

$193

avg/night

View Details

Key Amenities

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

About this property

Tropically furnished condominium with amazing views of the Gulf of Mexico, located 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, ...

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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
  • 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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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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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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Islamorada Vacation Rentals