This precious 2 bedroom cottage with its coral shutters will charm you from the moment you walk in the front gate. The front porch is private, for some quiet time reading a book. Inside, you'll see that "Casita Coralina" reflects… | $1,900 More Info |
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In the heart of Old Town, just a half block from the Historic Seaport Harbor, is a very exclusive and unique residence: Two homes and a guest house set on an over-sized corner lot surrounding a spacious courtyard and pool;… | $14,000 More Info |
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Located on the south side of Sugarloaf Key, "Bonefish Hideaway" is a home that is perfect for the family that wants to be away from it all, yet close enough to Key West for the occasional night on the town.… | $3,600 More Info |
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On a quiet street just a couple blocks from Old Town is "Ceilo Tropicale", a stunning home completely hidden from view by large hedges. This beautiful enclave is perfect if you wish to have a quiet retreat away from the… | $8,000 More Info |
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This charming conch cottage is located on 404 Aronovitz Lane, a little cul-de-sac just off Angela Street half a block from Duval. You couldn?t be much closer to the nightlife and attractions on Duval Street (Cowboy Bill?s is just around… | ContactOwner More Info |
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Sunset Dreams has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world with a… | $3,600 More Info |
This charming home has just been completely renovated, from its gingerbread on the front porch to the restored Dade County Pine inside. All of the furnishings are brand new and of the highest quality. The location is ideal, just 5… | $4,000 More Info |
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The Coral House is a historic home situated in the heart of Old Town, near the Historic Seaport. You'll be just steps from everything Key West has to offer, and yet you'll have the peace and quiet of being on… | $7,850 More Info |
The M/V Coconuts is a completely unique home with 360 degree water views, located at 6000 Peninsular Avenue. It also happens to be a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat.… | ContactOwner More Info |
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Just outside of town, sits a gulfside neighborhood straight out of the Old Key West, with pickup trucks in the carports, not BMW's. You can fish all morning, have lunch and a beer (or two) at Babalu's, fish some more… | $1,400 More Info |
Located right on the ocean in the middle of Old Town, Truman Annex is the most exclusive gated community in Key West, and the villas of Mills Place are among the most desirable homes in the Annex. Tucked in the… | $2,200 More Info |
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Recently, our friends Barry and Trish were visiting us in Key West where we manage 50 vacation homes. They asked if we might be interested in managing their home “Xanadu” in Mismaloya. We were intrigued after seeing the photos, but… | $5,000 More Info |
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A little over two years ago, we started a complete renovation of this lakeside home to do better justice to its gorgeous lakeside setting. First we gutted the interior and stripped the house right down to the studs. Then we… | $1,800 More Info |
Location: Key West Golf Club, Key West, Key West Area, Florida Keys, Florida, USA (Smathers Beach and Old Town are both just minutes away) "La Provence" is a bright and airy private home located in The Sanctuary, a quiet gated… | $3,100 More Info |
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The Meadows is one of the nicest neighborhoods in the Old Town area, but this exquisitely detailed home on Petronia Street truly stands out. As you turn onto this quiet little one-way lane, you will immediately see this stately new… | $6,000 More Info |
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What if you could stay right on the dock in Old Town but with the quiet and solitude of an exclusive gated community? The Green Parrot (oldest blues bar in America) is just two blocks away, and yet the peace… | $1,950 More Info |
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Located on a quiet little alley not far from the Southernmost Point in the Uptown part of Key West, you will find Koi House, a unique and very private residential compound with its own meandering pond filled with Koi fish,… | $11,000 More Info |
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Your spacious oceanfront balcony will be a front row seat for a panorama of azure blue ocean and sky. With direct views of the ocean from the living room, master bedroom and your own private balcony, you will never want… | ContactOwner More Info |
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Choosing a vacation home is always a challenge. It sometimes seems like the owners have decorated the home with the best that the discount stores had to offer, and then let it ride for as many years as possible. Well,… | $4,800 More Info |
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This beautiful private home has everything you could want in a vacation home. It has been meticulously furnished and maintained inside and out, and is located in 'The Sanctuary', a lush enclave set within the private gated community of the… | $5,000 More Info |
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This gracious home has everything you would want for your stay in Old Town Key West. Its central location in historic Old Town at White Street and Truman Avenue means you will be just steps from the White Street art… | $7,700 More Info |
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In the Historic Seaport area of Old Town, there is a house that is very attractive from the street, beautifully maintained with carefully tended landscaping. However, nothing will prepare you for what is inside. As you walk in, you will… | $8,000 More Info |
Located on a quiet little alley not far from the Southernmost Point in the Uptown part of Key West, you will find Koi House, a unique and very private residential compound with its own meandering pond filled with Koi fish,… | $9,000 More Info |
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Half a block from the Historic Seaport on William Street is a home that was recently recognized by the Historic Florida Key Foundation for excellence in preservation: the Ceramic Star is worn proudly on the front door. Attention to detail… | $6,000 More Info |
Conch Casa Grande might well be the largest home available for vacation rental in the Truman Annex, which is appealing to anyone who wants to have some elbow room during their stay in American Paradise. But what really sets this… | $9,000 More Info |
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Located in the Truman Annex, a gated community with some of the most impressive homes in Key West, this meticulously furnished estate stands out from all the rest in every way. ?Noona?s Mansion by-the-Sea? is nestled in a quiet cul-de-sac… | $10,000 More Info |
'Casa Paradiso ” is an elegant two-story town home located at the Key West Golf Club, just across the street from the community's large resort style pool. This peaceful gated neighborhood is a quiet oasis that will provide some respite… | $2,000 More Info |
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CONCH-by-the-POOL is a private two-story town home just steps away from the resort-style pool in the gated community known as the Key West Golf Club. The neighborhood is a quiet oasis that will provide some respite from the madcap activities… | $2,200 More Info |
Poolside Retreat is a private two-story town home nestled in the lush tropical landscaping that surrounds the gorgeous resort-style private pool in the Key West Country Club. The back yard gate is just steps from the pool's edge. The neighborhood… | $3,300 More Info |
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If you are going to spend time in America's Tropical Paradise, why not make the most of it? This beautiful private home has everything you could want in a vacation home. It has been meticulously maintained inside and out,… | $4,400 More Info |
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Imagine waking up every morning to the sun rising over the azure blue Atlantic Ocean. That's what you will experience with this beautifully furnished three bedroom condo right on the ocean at Oceanside Marina. With direct views of the ocean… | $1,600 More Info |
On a quiet lane just 3 blocks from Smathers Beach is a very special home we've named "Hidden Treasure" because it is literally hidden behind a sheltered front entrance with a five foot high louvered fence. Once you've opened the… | $4,400 More Info |
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You will never find this perfect little cottage (or its sister cottages, 'Conch Casita 1' and Conch Casita 2') without directions, even though it is right in the middle of Old Town. Located on 720 Elizabeth Street, a quiet one-way… | n/a More Info |
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"Sunset Dreams 2" has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world with… | $3,000 More Info |
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Private Cottage, 1.5 Bedrooms, 1 Bath, (Sleeps 2-3) This wonderful little cottage is the sister to "Conch Casita 3" and is right next door. Located on 720 Elizabeth Street, a quiet one-way lane, this home is set 100 feet back… | n/a More Info |
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You will never find this perfect little cottage (or its sister, "Conch Casita 2") without directions, even though it is right in the middle of Old Town. Located on 720 Elizabeth Street, a quiet one-way lane, this home is set… | n/a More Info |
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Directly facing the Gulf of Mexico right next to Mallory Square, this beautiful penthouse condo in the Truman Annex is the perfect place to spend your stay in Key West. With panoramic views of the water and cruise ships as… | n/a More Info |
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This beautiful penthouse condo is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of your condo, and two… | n/a More Info |
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In the Meadows, a neighborhood with some of the nicest homes in town, this exquisitely detailed home on 1314 Petronia Street is a hidden gem. As you come down this quiet little one-way lane, the lush landscaping that screens the… | n/a More Info |
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f ever a home was a precious jewel, it is this immaculate restoration located on 320 Elizabeth Street just two blocks from the Historic Seaport. When you enter through the front gate, you'll be struck by the privacy of the… | n/a More Info |
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This beautiful town home is to be found in the Truman Annex, Key West's most exclusive gated community. You'll be just around the block from Mallory Square, Duval Street and all the attractions Key West has to offer, yet you'll… | n/a More Info |
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There is nothing else like this home in all of Key West: Card-only access to your assigned spaces in the parking garage, a private elevator that opens into your own 3000 square foot condo, window walls throughout the home, private… | n/a More Info |
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Imagine a traditional conch home stunningly restored, then decorated in a post-modern style with vivid colors and sophisticated decor. Every room is adorned with colorful art and has been furnished with unique pieces that are themselves works of art. This… | n/a More Info |
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This gracious home has everything you would want for your stay in Old Town Key West. Its central location in historic Old Town at White Street and Truman Avenue means you will be just steps from the White Street art… | n/a More Info |
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In the Historic Seaport area of Old Town, there is a house that is very attractive from the street, beautifully maintained with carefully tended landscaping. However, nothing will prepare you for what is inside. As you walk in, you will… | n/a More Info |
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If you're going to spend time in America's Tropical Paradise, why not make the most of it? This beautiful private home has everything you want in a vacation home. It's been meticulously furnished and maintained inside and out, and is… | n/a More Info |
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If you are going to spend time in America's Tropical Paradise, why not make the most of it? This beautiful private home has everything you could want in a vacation home. It has been meticulously furnished and maintained inside and… | n/a More Info |
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In the heart of Old Town, just a half block from the Historic Seaport Harbor, is a very exclusive and unique residence: two homes and a guest house on an oversized corner lot surrounding a spacious courtyard and pool; ideal… | n/a More Info |
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This beautiful 5 bedroom home is located directly on the water at Garrison Bight, with direct access to Florida Bay. "Paradise @ The Bight" has everything you'll need while you're in Key West: luxurious accommodations, a dramatic water view from… | n/a More Info |
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“Fat Nancy's Villa” is a two-story town home located at the Key West Golf Club, just a block from the community's large resort style pool on Kingfisher Lane, a quiet cul-de-sac. This peaceful gated neighborhood is an oasis that will… | $2,500 More Info |
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In the Sanctuary at the Key West Golf Club, just 3 miles from Old Town, is a unique residence: two separate homes flanking a spacious deck and pool; ideal for a large group that wants to be close, but not… | $6,600 More Info |
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Solares Hill is the highest point in Key West, and one its nicest neighborhoods. “Southernmost Comfort Cottage” is in the middle of this community, on 623 Grinnell Street between Southard and Angela. It’s a wonderful street, with virtually no traffic… | $5,000 More Info |
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