Monthly Rentals in Key West

(32 rentals)
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4 BR | 3 BA | Sleeps 10 | Quick View

1

$614

avg/night

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Key Amenities

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

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny and bright, ...

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Property Type

Key West House

"Perfection in every way"

This home is beautifully appointed, spacious, quiet, comfortable and perfectly located. The pool is a haven on hot afternoons, the upper deck is amazing on warm nights for stargazing and the kitchen has ...

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3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Higg's Beach

$371

avg/night

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Key Amenities

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

About this property

Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district ...

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Property Type

Key West House

"Great home to enjoy Key West!"

Four of us , and our dog, stayed at Lynda’s beautiful home in Casa Marina area. We had a wonderful month there. The location was great and quiet. We spent most of our time enjoying the covered deck ...

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3 BR | 3 BA | Sleeps 6 | Quick View

1

$466

avg/night

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Key Amenities

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

About this property

Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside ...

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Property Type

Key West House

"Perfect pet-friendly vacation cottage"

The house is tucked away on a lane in Old Town within walking distance to everywhere. It is very private with lush plantings and a variety of outdoor spaces to sit. The house is well equipped and the owners ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive to Old Town or take Uber for just $10!A meticulously updated pool home with beautifully lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, ...

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Property Type

Key West House

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Key Amenities

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

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, ...

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Property Type

Key West House

"Perfect place!"

This house is in the perfect location that is quiet and private. It’s literally in the center of old town and just a short walk to everything. It is very comfortable and has a great layout. The cabana ...

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2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 2 miles to Smathers Beach

$267

avg/night

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Key Amenities

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

About this property

Come stay in a premier development in Key West. This would be a great location to stay with a monthly 28 day rental minimum. Yearly rates available. You would be close to everything Key West has to offer and the peaceful serenity of your temporary home in Paradise. Our house offers many amenities to ...

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Property Type

Key West Townhome

"Three months in Paradise"

The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific ...

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Key Amenities

  • Kitchen
  • Pool

About this property

This spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the back yard and the pool!The ...

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Property Type

Key West Condo

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2 BR | 2 BA | Sleeps 7 | Quick View

1

$133

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Located just 10 miles from Key West on beautiful Geiger Key. Cozy and comfortable canal front getaway perfect for the fisherman eager to explore the crystal blue waters of the Keys or the person wanting to experience all that Key West has to offer. Deep water with quick direct access to Atlantic Ocean. ...

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Property Type

Key West Mobile Home

"Awesome Key West Getaway-We'll be back!"

This location is amazing just minutes to downtown Key West and a few minute idle by Boat to the Ocean(we brought our own boat and docked out back!) Had fun Snorkeling in crystal clear water, and even tried ...

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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

$410

avg/night

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Key Amenities

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

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for ...

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Property Type

Key West Cottage

"Island Magic"

Great location! Great people! Very nice place that gave us memories of a lifetime! I’ll be returning soon!

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Overlooking the Historic Key West Bight Seaport, this large 1/1 with King sized bed features a fully equipped kitchen, renovated bathroom, front loading washer/dryer, 4K smart TV, new split unit AC, high speed internet, right in the middle of it all! Steps from the water, just 3 blocks from Duval street, ...

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Property Type

Key West Apartment

"This Space is a true Key West Gem, location can not be beat!"

We have stayed with this host numerous times and can not say enough about them as well as this particular space and location. If you are looking for a true taste of Key West look no further. This building ...

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Key Amenities

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

About this property

The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is ...

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Property Type

Key West House

"Beautiful Paradise"

The owners and property are one of a kind in the Florida Keys. I have stayed in many locations in the Florida Keys and this is one most unique places to stay. We stayed in their other house on the same ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history that befits its esteemed place along one of the most elegant streets in Key West. Unit # 6 is a second floor, 1BR/2BA unit that is entered on the left side of the building. The condo ...

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Property Type

Key West Condo

"Perfect place for a warm-weather couple!"

The location is perfect! Close to Duval Street, Mallory Square and many fabulous shops. We rode our bikes every morning to Higgs Beach to play tennis then enjoyed the white sand and cool morning breeze ...

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$502

avg/night

View Details

Key Amenities

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

About this property

The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just ...

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Property Type

Key West House

"Loved it!!!!"

We thought the accommodations were great, there were some minor things that could have helped but overall we give a glowing review. The pool and outdoor tiki bar were amazing and the owners were wonderful. ...

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Key Amenities

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

About this property

Looking to ​ Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset ...

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Property Type

Key West House

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 30 feet to property 20 yards from ocean, 4 mile white sand be

$669

avg/night

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Key Amenities

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

About this property

Notice: Due to Corona Virus We suggest you purchase "Cancel For Any Reason Insurance". (CFAR) CSA Insurance In the event you purchase the insurance and cancel,It costs a little over 10% of the total trip costs. Great for people with health problems or in this case "Pandemics"Here ...

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Property Type

Key West Condo

"Great Escape"

Love these condos !! Second time to same place!! Great escape from Seattle. Family friendly. Great food.

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Fort Zachary Taylor State Park

Key Amenities

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

About this property

Dog-friendly home in great location with fenced yard, & lanai.Welcome to your own private, dog-friendly oasis in the heart of Key West, just one and a half blocks off Duval St. and within walking distance of a public swimming pool, park, the beach, the Southernmost Point, shops, restaurants, ...

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Property Type

Key West House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports and ...

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Property Type

Key West Townhome

"our vacation at Key West Golf Club"

We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf ...

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Key Amenities

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

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discriminating travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos ...

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Property Type

Key West House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathroom, front loading washer/dryer, 4K smart TV, and one of the best people watching front porches in Key West. Steps from the water, just 3 blocks from Duval street, and surrounded by ...

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Property Type

Key West Studio

"Key West Gem"

We stayed at this property for 6 weeks. The location is awesome! It is steps away from the marina, a short walk to a small beach, and just several blocks from Duval Street. The location is also set in close ...

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Key Amenities

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

About this property

**Available for rent by the month. Although you rent it for a month, you may of course come late and/or leave early. The monthly price will generally be the same as for a comparable unit rented by the day for 10-14 days. It does however give you a lot more options and freedom.Located on a side ...

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Property Type

Key West Townhome

"Beautiful Stay!"

This unit is in a tucked away little oasis one street over from all the action on Duval street. If is a very peaceful and unique spot. The unit itself is exceptionally clean and well appointed. It has ...

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4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 600 yards to Simonton Street Beach

$485

avg/night

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Key Amenities

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

About this property

Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, theatre and entertainment. Unique features include open air kitchen and ...

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Property Type

Key West House

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2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 1 miles to Fort Zachery Taylor State Park

$333

avg/night

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Key Amenities

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

About this property

924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for the guest who wants to feel like a local and enjoy ...

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Property Type

Key West House

"I wish I didn't write this review."

Mainly because it will lessen our chances to get back here. My wife and I used to live in Key West for close to 10 years. We had our house and a couple of rental properties and vacation properties. Then ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Private home located in New Town available for 28 day minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in ...

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Property Type

Key West House

"A Beautiful Private Key West Home"

Staying for an entire month in Key West was a first for my husband and I as we usually vacation weekly each year there. It was also the first time renting a private home. There's nothing negative to write. ...

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Key Amenities

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

About this property

Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious walk ...

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Property Type

Key West Condo

"beautiful ocean view condo"

condo was very clean and on the top floor with vault ceilings. Check in process was seamless as well as checkout.

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Key Amenities

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

About this property

Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an extra large floor plan with a nice ocean view. This property features 2 queen beds in the master bedroom and a king in the guest bedroom. Full size washer/ dryer and 1 assigned private ...

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Property Type

Key West Condo

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3 BR | 3 BA | Sleeps 6 | Quick View

1

$170

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor ...

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Property Type

Key West House

"Soon to be there"

I have not stayed there yet, but will gladly take $5 for this review. I hope is as nice as it its described

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 2 miles to Smarthers Beach and Higgs Beach

$204

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding trim. Open living room and ...

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Property Type

Key West House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

A gorgeous 3 bedroom / 2 bathroom vacation rental home with high vaulted ceilings and french doors that bring the outside in. The backyard features a large covered patio and an in-ground heated swimming pool, perfect for relaxing anytime of the year. New outside table with seating and gas bbq grill ...

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Property Type

Key West House

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2 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park

$391

avg/night

View Details

Key Amenities

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

About this property

[PLEASE ASK ABOUT MY LATE SUMMER SPECIAL PRICE. Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My over sized two bedroom, ...

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Property Type

Key West Condo

"A touch is all you need…"

A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Casa Coastal East – C231 After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its new owners. From new interior design work and furnishings, courtesy of Royal Furniture of Key West, to new closets, drapes and local art, includes works from the gallery of Alan ...

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Property Type

Key West Condo

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Key Amenities

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

About this property

3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Keys to Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk in shower. ...

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Property Type

Key West Condo

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Key Amenities

  • Kid friendly
  • Kitchen
  • Pool

About this property

Beautifully renovated 2 bedroom 2 bath condo at the exclusive 1800 Atlantic Condo's. Each bedroom has a king size bed and plenty of closet space. Both have access to the private balcony that faces the nature preserve in a quiet tranquil location at the property. The unit is located across from the Elevator ...

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Property Type

Key West Condo

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