Key West Monthly Vacation Rentals
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February 23rd
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Key West ~ Monthly Vacation Rentals

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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 inquires and pending reservation. 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


seaport treasure estate

Standard Rates: $18000 - $26000 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!


elegant key west tree house

Standard Rates: $3800 - $5750 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.


island village cottage
New

Standard Rates: $3300 - $5500 per month

2BR 1BA - Sleeps 2-4
Ground to Roof Designer Renovation
High-End Amenities
Original Artwork
Private Bricked Porch
Tropical Landscaping

Enchanting as can be, this impeccably renovated Key West shot-gun cottage is imaginatively decorated to detail - achieving an authentic colorful Caribbean ambience with calming feng shui elements. Situated in the Heart of Old Town neighborhood, it is just a stroll away from the famous docks lined with restaurants, bars, and shops amidst the schooner yachts and fishing boats.


cabana boheme
New

Standard Rates: $3950 - $9500 per month

3BR 3BA
Small Gated Garden Compound
Shared Pool w/ Trickling Waterfall
Newly Constructed in Traditional Design
Private Covered Parking
On Block Off Duval St.

Center to the common gardens, a brick path winds through a hidden courtyard, leading to an alluring pool with trickling waterfall. This is what creates the "ah ... feeling." So relaxing yet only a  block from boho Upper Duval St., in Old Town Key West.

 


sunset sonnet luxury villa
New

Standard Rates: $10000 - $17000 per month

2BR 2.5BA - Sleeps 6
Private Tropical Resort Island
w/Luxury Amenities
Expansive Wrap-Around Porches
w/Pool-Garden Views
Private Rooftop Viewing Deck
Oasis Swimming Pool
Crescent white sandy beaches

'Turquoise waters surrounding the land, with crowning sunsets in a pastel sky …' Private luxury villa blends airy contemporary island design with access to high end Sunset Key resort amenities. The crowning glory is a private roof top deck where you can steal away and savor the famous Key West sunsets.


bella grand premier

Standard Rates: $12000 - $21500 per month

5BR + Den 5BA - Sleeps 12
Extraordinary swimming pool gardens
Famous Elizabeth St. in Historic Seaport Neighborhood
Stroll to Duval Street

Refined and Elegant. Displaying a perfected cosmopolitan flair, the designer has artfully intertwined a look-back into architectural history with a sophisticated contemporary Caribbean charm. Situated on renowned Elizabeth Street, in the historic seaport neighborhood of Old Town, this home is steeped in a colorful lore and seafaring history – so much so, it is sometimes referred to as “the pirate house.”


little red pool garden cottage
New

Standard Rates: $4000 - $5950 per month

2 BR 1 BA
Private Pool
Idyllic Pool-Garden Island Cottage
Close to the Beach on a Lane
Quiet Neighborhood
Sleeps 2 - 4

‘Heads Up’ to all of you incurable romantics who are looking for the perfect Old Town Key West garden cottage retreat close to the beach. Dream worthy and authentic, it’s a little bit like ‘Little Red Riding Hood’s cottage merges with a ‘Fantasy Island’s’ private pool garden,’ and the two are seamlessly blended.


key west sunset sojourn
New
special rates available

March ~ $15000

view all specials


Standard Rates: $10000 - $17000 per month

2BR + Office 3BA - Sleeps 6
Private Tropical Resort Island
Roof Top Viewing Deck
White Sandy Beaches
Oasis Swimming Pool

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. 


hidden story book cottage

Standard Rates: $3200 - $4450 per month

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

As I stand on the front porch of this little Hidden Story-Book Cottage in the Old Town Key West, I could swear I’m in a neighborhood in the Bahamas on Green Turtle Cay. But as diminutive as it is, impressive interior upgrades that give it a proportionately larger and luxurious feel.


island elegance
New

Standard Rates: $5400 - $9500 per month

3BR 3BA - Sleeps 6
Timeless Historic Features
Split-bedroom Design
Spacious Front Porch
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore

Channeling the island spirit in oft-missed mid-town, this home makes a classical curbside statement. Timeless craftsman-colonial architecture, lush mature tropical landscaping.Here you live away from the hubbub, yet close enough to beaches and Old Town. With many places to place a hammock, you may even find yourself making a new daily island ritual of swinging, reading, and sipping wine.


butterfly garden

Standard Rates: $3200 - $4200 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 Butteryfly Garden flat provides you with two private entrances off the large gated meditatiion 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.


avant garde key west luxury home

Standard Rates: $4950 - $9500 per month

2BR 2.5BA
Sleeps 4
Premier Heart of Old Town neighborhood
Classic architecture / upscale minimalist interior renovation
Private Heated Pool

Extraordinary upscale renovation. Traditional Key West architecture is flawlessly melded with a minimalist contemporary interior. Exotic and calming, this unique home is offers all the best features of classic and modern island living.


belle maison du port

Standard Rates: $13000 - $25000 per month

3BR 3.5BA
Victorian Home + Private Guest Cottage
Available to rent separate from the estate from May through October
Gated and Grand
Large Private Heated Pool
Premier Historic Seaport location. Steps from the 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. Comprised of a stunningly renovated 2 – Story Victorian home, plus an adjoining one-bedroom guest cottage, and large private resort-style swimming pool.


tropical sun garden retreat

Standard Rates: $4600 - $6550 per month

2BR 2BA - Sleeps 2-4
Private deck and garden
Plus Shared Manicured Swimming Pool Garden
Peaceful Setting

Small pets (under 35 pounds) considered - Restrictions Apply

Everyone dreams of a charming Key West cottage tucked away in a tropical sun garden where flowers and trees flourish around an outdoor living porch all year round.


the qm ~ quartermaster house key west

Standard Rates: $6000 - $10000 per month

3BR 2BA - Sleeps 6-7
Private Back Deck and garden
Shared Pool
Special Resort Amenities Gratis

Born in 1925, the Key West Quartermaster House may have found its way from the Bahamas, ‘lock stock and barrel’, during one of the most colorful points in Key West maritime history. Located in the Historic Seaport Neighborhood, today it offers all the comforts of home plus gratis resort amenities.


on hemingways rounds

Standard Rates: $4500 - $9300 per month

3BR 2BA - Sleeps 6
Private Spa Garden with Pool & Waterfall
1/2 block off Duval St.

On Hemingway's Rounds, is an inspired renovation of a classic 1930's ‘American Bungalow’ redone Key West style.  While the street side remains true to the original casual arts-and-crafts form, the interior now boasts an elegant simplicity that meets even the most discerning of modern tastes.

 


ultimate key west beach house  sunset key ~ vip

Standard Rates: $18000 - $26000 per month

5BR + Den 6BA - Sleeps 10-12
Private Tropical Resort Island
Front Line Ocean Views
White Sandy Beaches
Custom Fantasy Swimming Pool w/ Waterfalls

Sit back, relax, and choose your favorite mesmerizing view from one of the magnificent private decks on this private island property, 500 yards from the ''main island' of Key West.  Unhurried sunrise, serene sunset, warm turquoise waters, and white sandy beaches – from any direction, it’s divine.


governors retreat

Standard Rates: $5000 - $6600 per month

2BR 2BA - Sleeps 4
Serene setting - Large Lap Pool
Manicured Gardens
Old Town Meadows neighborhood
Easy Stroll to Historic Seaport

A luxury cottage in an idyllic retreat settng where you have the use of a manicured garden and swimming pool.  Perfectly Renovated and Immaculate Neighborhood.


mediterranean caribbean villa

Standard Rates: $5500 - $9000 per month

2BR 2.5BA - Sleeps 4
Free-form heated pool - large sun deck
Manicured Tropical Gardens
Close to Higgs Beach and stylish White St.Gallery neighborhood

Tucked behind a breathtaking tropical garden wall and located along one of Key West's most desirable residential streets, this spectacular home reflects a dynamic blend of contemporary Mediterranean and Caribbean architectural design.

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