Islamorada Condo Rentals

(31 rentals)
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3 BR | 2.5 BA | Sleeps 6 | Quick View

$556

avg/night

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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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$457

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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3 BR | 2 BA | Sleeps 6 | Quick View

owner special
Owner special: $2,800 / week for spring dates! Ocean view Islamorada condo with FREE boat slip up to 30'!!!

$438

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
  • 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 | 3 BA | Sleeps 6 | Quick View

4

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

$576

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 from every room 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, ...

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Property Type

Islamorada Condo

"Best place to stay in Islamorada"

We have stayed at Bay Harbour before, but this was our first time renting this unit and it was absolutely perfect. The location and water views are wonderful, and the inside of the unit is beautifully decorated. ...

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3 BR | 2.5 BA | Sleeps 6 | Quick View

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

$514

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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2 BR | 2 BA | Sleeps 4 | Quick View

4

$358

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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2 BR | 2 BA | Sleeps 4 | Quick View

2

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

$333

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

"Fantastic views"

This 5th floor condo did not disappoint. The double balcony offered great views of the bay, and a spiral staircase up to the private roof top was another great place to watch the spectacular sunsets. The ...

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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 | 2 BA | Sleeps 4 | Quick View

Distance to beach: 100 feet to Front door

$160

avg/night

View Details

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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3 BR | 2 BA | Sleeps 6 | Quick View

1

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

"Excellent Oceanfront Rental"

This unit far exceed our expectations. Beautiful decor, ocean views, pool, clubhouse, all were top notch. Management team very responsive, had an issue with door lock and was immediately resolved. Great ...

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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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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

5

Distance to beach: 5 miles to Anne's Beach

$318

avg/night

View Details

Key Amenities

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

About this property

Enjoy the sunrise from the balcony or from the condo through 50' of glass sliding doors. You can also view the sunset from our walkway on bayside. We have a full kitchen, dishwasher to microwave, washer/dryer, even beach towels. We have wifi,cable TV in living area and all bedrooms, master bath ...

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Property Type

Islamorada Condo

"Great Time"

Well equipped condo with great sunrises. Our grandson enjoyed fishing from the dock. Convienent to Marathon and Islamorada restaurants. Can't wait to go back A hidden gem

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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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2 BR | 2 BA | Sleeps 4 | Quick View

1

$194

avg/night

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

6

Distance to beach: 0.9 miles to Founders Park

$117

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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3 BR | 2 BA | Sleeps 6 | Quick View

11

Distance to beach: 4 miles to Anne's Beach

$327

avg/night

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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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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

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 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 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
  • 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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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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Key Amenities

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

About this property

Mile Marker 81.6 — Conch VillaConch Villa, aptly named for the famous large snails that inspired the Keys to be called the ‘Conch Republic,’ is located in the heart of Islamorada. The 3-bedroom villa is rented separately, and is tastefully furnished with modern styles and amenities. ...

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Property Type

Islamorada Condo

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Key Amenities

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

About this property

I have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you ...

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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

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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2 BR | 1.5 BA | Sleeps 6 | Quick View

$97

avg/night

View Details

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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Key Amenities

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

About this property

3 Beds/2 bath townhouse in Islamorada, Florida Keys. Ground Floor features a full kitchen, full bath, living room with large tv, dining room with views of the tennis court, outdoor patio with BBQ and additional dining table. Second Floor features a large full bath, 1 king size bed, 1 queen size bed, 2 ...

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Property Type

Islamorada Condo

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1 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Founders Park

$260

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Founders Park

$158

avg/night

View Details

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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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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