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October 6th
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Key West ~ Monthly Vacation Rentals

Your Search Results:
Below are Monthly Rentals with no specified number of bedrooms

Key West monthly vacation rentals must be rented for at least a month, but not for more than six months. Monthly rentals are designed for guests who want to experience living in Key West, settle in and enjoy the comforts of a home away from home.

Monthly rentals are furnished and decorated to provide the experience of a well-appointed local. Interior designs reflect the unique tastes of property owners. Some are luxuriously stylized, and some are furnished more simply. All are set with the essential amenities and conveniences of home, including internet, TV, linens, and kitchenware. Read our property descriptions to learn the details.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquiries and pending reservations. Please contact our office to be sure of availability. info@vhkw.com or 305-294-7358 ext. 1

There are no properties available that fit all of your search options. Please contact our office if you would like assistance. info@vhkw.com or 305-294-7358 ext. 1


elegant key west tree house
special rates available

2BR 1BA

Oct 5- Nov 30

Monthly $4200

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Standard Rates: $3750 - $7350 per month

2BR 1BA
Overlooks large historic Meditation Garden
Quiet living
One Set of Stairs
Close to Higgs Beach

Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building. Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road in the exclusive Old Town Casa Marina neighborhood. With a wide wooden covered porch spanning the front of the house, every room still has the original casement windows providing a fabulous look-down view of different garden scenes.

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designer octagon house of key west
special rates available

4BR 4BA



Monthly
$20,000

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Standard Rates: $25000 - $40000 per month

4BR 4.5BA - Sleeps 8
Famous Iconic Victorian Estate
Extraordinary Designer Home
Expansive Resort-Style Gardens
Large Swimming Pool
Wrap-around Verandahs

Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic designer octagon Victorian house is often feaured in notable architectural publilcations. Purchased and restored by superstar designer Angelo Donghia in 1976, and purchased in 1981 by famous designer Calvin Klein, it raised the bar on historic home renovation in Key West. Today is stands as a phenomenal paradise home with luxury designer decor and 5-Star amenities. Truly an amazing historic and top-of-the-line place to stay in Key West.

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casa bella petite le bleu
New

Standard Rates: $6000 - $15000 per month

2BR 2BA - Sleeps 4
Award Winning Historic Cottage
Gorgeous Interior Re-design
Swimming Pool

First impressions are everything. And its love at first glance with this Old Town Key West cottage. The 2BR 2BA Casa Bella Petite le Bleu is a luxurious charming pool-garden home. Situated on the quiet upper end of famous Elizabeth Street, this stylish house is filled with authentic charm. 

The impressive renovation of this 18th Century wooden cottage earned it the coveted Historic Florida Keys Foundation Preservation Award. It provides off-street bricked parking with a Tesla charging station.

An ideal cottage for 2 to 4 people, if more people decide to join you in Key West - No Problem! Right across the street is the extraordinary 5BR 5.5 BA  Bella Grand Premier Estate.

 

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the blue llama estate compound
New

Standard Rates: $28000 - $53800 per month

7BR 7.5BA - Sleeps up to 14
2 heated swimming pools
Premier Street in Center of Old Town
2-Story Guest House + 2-Story Main House and separate 2BR cottage

5-Star rental compound Ideal for extended families or a group of friends.Revel in luxuy while you relax, unwind, and reconnect with plenty of room to spread out. Property includes: two private swimming pool gardens and enjoy three fully equipped upscale kitchens. Grill on a unique secluded BBQ porch, workout in a private home gym, and at your fingertips is a Steinway piano! Three off-street parking spaces.Off-the-beaten path yet just three streets from mid-Duval St.

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debonair victorian estate
New

Standard Rates: $22000 - $35000 per month

5BR 5.5BA - Sleeps 10
Heated Swimming Pool
Private Parking
Stunning New Re-Design
Hisotric Seaport Neighborhood

An exceptional degree of refinement was reserved for the sophisticated redesign of this turn-of-the-19th-century 5BR 5.5BA Debonair Victorian Estate. Key West Victorian house. Displaying a perfected cosmopolitan tropical style, the designer has artfully intertwined a romantic look-back into architectural history with a 5-Star elegant contemporary Caribbean charm.

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sunset serenade

Standard Rates: $8950 - $19500 per month

2BR + Office 2.5 BA
Sleeps 4 - 6
Private Roof Top Viewing Deck
White Sandy Beaches
Garden Oasis Swimming Pool
Private Tropical Resort Island

You’re one click closer to a private island paradise. Sunset Serenade can put you right there.  Here you’re softly serenaded with the sounds of the surrounding sea and rustling fronds of the palm trees, while you chill-out on your own private rooftop deck to enjoy the changing colors of the tropical sky.

 

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little digs key west
special rates available

1BR !BA



Monthly $3500

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Standard Rates: $3000 - $5500 per month

1 BR 1 BA
Sleeps 2 - 3
Luxury Interior Upgrades
Solares Hill Neighborhood
Center of Old Town
5 Minute Walk to Duval Street

Diminutive in size but huge in style, Little Digs Key West, authenticates how ‘big things’ really do happen in small spaces. Spacious design. A complete luxury makeover of this 1933 historic cottage. It sits in proud harmony with other historic residential cottages, on a narrow one-way lane in the middle of Old Town Key West. 

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bella grand premier estate

Standard Rates: $22000 - $38800 per month

5BR 5.5BA - Sleeps 10
Grand Luxury Estate on 7,500 Sq Ft Lot
2-Story Guest House + 2-Story Main House
Deluxe Zen-Garden Pool with Pool Bridges
Steinway Upright Piano
Premier Street in Center of Old Town
Gated and Private
5-Star Quality Experience

Deluxe Old Town Key West estate with a new twist on history. Premier custom design reflects the historic neighborhood, while reinventing the Key West luxury lifestyle. Zen-garden swimming pool, trickling tiled waterfalls and a spa. Wide stone bridges built over the pool sleekly connect the houses together. A remarkable home to experience with family and friends. 

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seaport hideaway
New
special rates available

2BR 1.5BA



Monthly $4500

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Standard Rates: $4750 - $8850 per month

2BR 1.5BA
Sleeps 2 - 4
Limited Edition 2-Story Condo
2 Streets from Historic Seaport
Private Porches and Courtyard Garden
Hidden from View in Heritage Building

Magic happened when this Key West wooden heritage building was redesigned. Now offers limited-edition condominiums. A case in point is this 2BR 1.5BA Seaport Hideaway. Architecturally intriguing. Epic historic atrium stairwell. Masterfully tucked away on Fleming Street. A special residence ideally located 2 short blocks from the docks, at the Key West Historic Seaport neighborhood.

 

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villa corazon
New

Standard Rates: $8000 - $16000 per month

3BR 3BA
Private garden with heart-shaped pool
Luxury renovation with upscale furnishings
Private Guest Cottage in Garden
Casa Marina Neighborhood
Close to Higgs Beach

There’s lots to love about the luxurious 3BR 4BA Villa Corazonit even has a heart shaped pool. Experience ultimate resort style living in this private home retreat. A perfect pairing of a renovated Key West gingerbread cottage with an elegant free-standing cottage that are seamlessly joined with a tropical pool-garden.The interior is a harmonious sweet spot between modern aesthetics and laid-back Caribbean. 

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hidden story book cottage
special rates available

1BR 1BA

Oct 25 - Nov 30

Rental $3900

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Standard Rates: $3200 - $5700 per month

1 BR 1 BA
Sleeps 2 - 3
Free-Standing Story-Book Cottage
Gorgeous Interior Upgrades
On a Hidden Walking Path
5 Minute Walk to Duval Street

Tucked away down a short walking path in the Center of Old Town Key West, this precious 1BR 1BA Hidden Story-Book Cottage is completely hidden from the street. Comfortable as it is adorable, it even offers a fenced in yard. Perfect for one or two people, here you can set up home and live as a local for a month or more - or settle in to work remotely.

 

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the grand marshall
New

Standard Rates: $11700 - $32800 per month

5BR 4.5 BA - Sleeps 10
2 Heated Swimming Pools
2 Upscale Renovated Houses w/ Fenced Backyards that border each other.
1/2 Block from the Hemingway House & Museum
1 block off Duval Street

If you plan to stay with your family or friends, but treasure your own place to retreat,The Grand Marshall offers the perfect layout. A back-to-back combination of 2 upscale renovated and beautifully decorated historic homes. Around the corner from the Hemingway Home and Museum, one block off Duval St. Settle in for a month or more and become thoroughly relaxed and ‘islandized.’

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key west poolside loft
New
special rates available

2BR 2BA



Monthly $4150

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Standard Rates: $4500 - $8400 per month

2BR 2BA - Sleeps 4
Overlooks Tropical Swimming Pool Garden
Shared Heated Pool w/ Caribbean Cabana
Truman Annex Neighborhood
Gates lead to Ft. Zachary Taylor Beach, Truman Waterfront, and Downtown Old Town Key West

You know that adage … An unexpected turn can lead to hidden treasures. If there were ever a place that meets that description, it's this 2BR 2BA Key West Poolside Loft. Cleverly tucked away, here you’re in a unique loft-style Key West cottage, with a private deck and beautiful down-look poolside view.

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private island key west beach house  sunset key ~ vip
New

Standard Rates: $18000 - $31000 per month

3BR 4BA Sleeps 6
Epic View from the Pool to the Beach
Private Tropical Resort Island
Garden Connects with White Sandy Beaches

Epic views from the house, to the pool, to the beach. Grand traditional beach house on the private island of Sunset Key. Far enough away that life slows down. White sandy beaches, turquoise ocean, palm trees rustling, birds twittering - peacefulness. 5-Star Resort amenities at your service.

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governors retreat

Standard Rates: $6500 - $19000 per month

3BR 2.5BA - Sleeps 6
Upscale renovation of Historic Home on Picturesque Lane
Private Swimming Pool w/ Sun Deck
1st & 2nd FL Covered Porches
Expansive Porch Room off Master BR
Off-Street Parking
1 Block Off Duval

Governor's Retreat is situated on a less-traveled lane that exudes sought after charm and character. Pictorial 1900’s historic home with upscale renovations and amenities. Exquisite and imaginative décor. Private pool and deck in fenced tropical garden. Multiple sitting porches in the front and back of the house. A block from the Hemingway Home and Museum.  

 

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seaport treasure estate

Standard Rates: $17000 - $31750 per month

6BR 6.5BA - Sleeps 12
Luxurious Estate ~ 2 Houses plus Guest Cottage = Private Residential Resort
Gated and Grand
Premier Historic Seaport location! Steps from the boardwalk.

A whole vacation experience for the entire family. Rent this estate and live in luxury in the most requested Historic Seaport location in Key West. Three historic dwellings are seamlessly joined to become one private luxury Key West rental estate. A combination of unique design elements impart that elusive je ne sais quoi of island architectural history. Rent the best of Key West!

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butterfly garden
special rates available

1BR !BA



Monthly $3600

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Standard Rates: $3300 - $5750 per month

1BR 1BA - Sleeps 1-2
Historic meditation garden.
Quiet Living Exclusive Casa Marina neighborhood.
Close to Higgs Beach

Completely hidden from the street, this historic Butterfly Garden flat provides you with two private entrances off the large gated meditation garden. A private covered sitting porch outside your front door beckons you to sit in the freshness of the garden and watch for the butterflies.

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key west sunset sojourn
New

Standard Rates: $12750 - $180000 per month

3BR + Media Room 4BA
Sleeps 6
Private Swimming Pool w/ fenced gardens
Private porches off each BR
Private Roof-Top Lookout Deck
White Sandy Beaches
Private Tropical Resort Island

Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – a sojourn on a private island surrounded by sparkling turquoise waters and balmy breezes. 

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on hemingways rounds
New

Standard Rates: $5200 - $13800 per month

2BR 2BA - Sleeps 4
Beautifully Renovated 1920 Bungalow
Private Swimming Pool & Sun Deck
Upscale Amenities
On Famous Whitehead St.
1 Block off Duval Street

On Hemingway's Rounds, is an inspired renovation of a classic circa 1920 American Bungalow redone Key West style. Private swimming pool garden and deck in the fenced back yard. Historic front porch with comfy chairs to relax and watch Key west go by. Interior design is imaginative and elegant. Less than one block from the Hemingway Home and Museum. 

 

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island cosmopolitan cottage

Standard Rates: $5300 - $14000 per month

3 BR 2 BA
Sleeps 4 - 6
Historic Cottage
Upscale Renovation and Interior Design
Large Lap-Swimming Pool
Quiet Neighborhood close to White St.
Easy walk to Higgs Beach

An upscale renovation with elegant furnishings, this heritage cottage has all the luxuries you could want and still enjoy the ambiance of staying in an historic Key West property. Mixing a dash of contemporary style with selected cottage pieces, the designer created a unique island style cosmopolitan hide-away in the White Street Gallery district of Old Town Key West. 

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island elegance
special rates available

3BR 3BA



Monthly $5900

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Standard Rates: $5000 - $12800 per month

3BR 3BA - Sleeps 6
NEW Swimming Pool Garden with Spacious Deck installed Fall 2021
Timeless Historic Features
Split-bedroom Design
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore

Channeling the island spirit in oft-missed mid-town, this pool-garden home makes an enviable Key West hideaway. Timeless craftsman-colonial architecture. New swimming pool with spacious sun deck. Lush mature tropical landscaping.

Here you live removed from the hubbub, yet close enough to beaches and Old Town. With a luxuious outdoor poolside living room, you may even find yourself making new island rituals of reading, and sipping Cuban coffee or your favorite cocktail on the deck.

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island interlude
special rates available

2BR 2.5BA

Dec 1 - Dec 31

Monthly $5250

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Standard Rates: $3950 - $8950 per month

2BR 2.5BA - Sleeps 4
Upscale Town home in gated bricked pool-garden courtyard
Shared Dipping pool with waterfall
Around the corner from trendy Petronia Street where you find Blue Heaven
Short Street from entrance to Fort Zachary Taylor Beach

Aspirational, luxurious, well appointed, and whimsical, are four attributes that make this courtyard townhome a lovely place to call home in Key West. Aptly named, Island Interlude, this 2-story property is situated around the corner from one of the most popular transitional urban scenes of Key West. 

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belle maison du port

Standard Rates: $13000 - $29650 per month

3BR 3.5BA
Victorian Home + Private Guest Cottage
Situated in Private Gated Estate
Available from May through October
Large Private Heated Pool
Premier location - Hidden But Only Steps from Historic Seaport Boardwalk!

Extraordinary French Caribbean style Victorian home, Belle Maison du Port (Fine Harbor House), is available as a monthly vacation rental from May through November. Situated on the grounds of the Seaport Treasure Estate. It is comprised of a stunningly renovated 2–Story Victorian home, plus an adjoining one-bedroom guest cottage. Large private resort-style swimming pool with spacious sunning deck..

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key west island village cottage

Standard Rates: $4050 - $10350 per month

2BR 1.5 BA - Sleeps 2-6
Award Winning Historic Cottage
Private Dipping Pool in Tropical Garden
Great For Small Family
Historic Seaport Neighborhood
5 Minute Walk to Seaport Docks

Story-book charm, originally built in 1860, a restoration won it the coveted Star Award by the Historic Florida Keys Foundation, in 1995. Situated on famous Southard St., in the Historic Seaport neighborhood, its unique character has so captured lovers of Key West homes and gardens, that it’s been featured in two books - Mary Emmerling’s American Country Cottages, 1993, and again in Key West Gardens and Their Stories, Frawley-Holler, 2000.

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