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Key West Time
February 23rd
5:11pm · 81°F

Key West Vacation Rental Blog

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Vacation Homes of Key West (VHKW) News. We are on your favorite social networks. Friend Us, Like Us, & follow Us for updates on the latest additions to our vacation rental property inventory, and beautiful pictures of and information about Key West.

Key West Songwriters Fest 2018

It's time to book your stay for The Key West Songwriters Festival. Running from May 9-13th, this is the 23rd year the festival has rocked Key West. For the past 23 year this event has grown to be both a tourist attraction and local favorite. This event is the largest festival of songwriters in the world. With a full schedule featuring five nights of performances and appearances by the best songwriters alive. Get introduced to the faces behind your favorite songs. With countless performances scheduled at venues around key west, this event should not be missed. Why not book a front row seat & stay with VHKW. See the schedule and a list of available vacation rentals below.

This local event attracts some of the best know in the music industry. The event features several performances and informative talks at various venues across town. There is a complete schedule you can see by following the link below.



Available Vacation Rental Homes:

penthouse on duval


Mar 10- Mar 17
Mar 24- Mar 31
Weekly $3900

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Standard Rates: $2900 - $6000 per week

4BR 4BA + (2 1/2 BA) - Sleeps 8
2 Kitchens
Entire 2nd + 3rd floors of the building
Porch overlooks Duval Street in the 700 Block.
Spacious deck in the back.
Perfectly staged on Duval Street Key West, this unique downtown Key West rental received a major renovation to become the  fabulous "Penthouse On Duval." Stroll to South Beach and Mallory Square. Plenty of room to spread out. Enviable Fantasy Fest location!  Mallory Square and the beach.

tropical tranquility


Feb 10- Feb 17
Mar 3- Mar 10
Weekly $6100

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Standard Rates: $3900 - $8575 per week

4BR 3.5BA - Sleeps 8
Heated Oasis Swimming Pool
Private Manicured Pool Garden
Little lane in the Heart of Old Town Key WestFew places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real.

cocos poolside retreat


Feb 24- Mar 17
Weekly $2800
Nightly $450

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Standard Rates: $1750 - $3670 per week

3BR 2.5BA - Sleeps 6-8

The artist-owner of this sun-lit pool-side town-home has created a delightful living space that welcomes you to an authentic tropical life-style in a unique Key West "pool garden compound."


truman treasure

Standard Rates: $2600 - $5600 per week

3BR 2.5BA - Sleeps up to 5
Stroll to the Beach
Truman Annex residence with Ocean View from Bedroom Balconies
Short Walk to all Downtown Old Town Key West Features

Rent this Key West Luxury Home and Experience a Remarkable Piece of American Architectural History. A renovated 'Truman Treasure', in one of the most desirable Ocean Front Old Town Key West locations.


heavenly hideout at rainbows end


Feb 24- Mar 10
Mar 17- Mar 29
Weekly $4800

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Standard Rates: $3500 - $6700 per week

4BR 4BA - Sleeps 8
Famous Mile 0 Location
1 block off Duval Street.
Custom Interior Design
Private Heated Pool starting August 1, 2017
Sun deck on ground level

Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout Key West penthouse, you’re spot on, and you can do exactly that.


dancing palms villa


Mar 3- Mar 24
Weekly $2675

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Standard Rates: $1850 - $3475 per week

2BR 2BA - Sleeps 4
Manicured Tropical Swimming Pool Garden
Shared Heated Pool
Walk to Duval St. in 3 minutes

I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. This is what you’ll experience as you make your entrance to this beautiful Bahamian ‘eyebrow’ style home, nestled away in private back corner of the small Old Town Key West gated community of Windward Park.






Hurricane Irma Takes Some Trees but Not Key West Spirit

Mother nature is incredibly resilient, and as refreshing rains followed Hurricane Irma, green leaves began to quickly sprout from the trees. At first the skyscape seemed nearly barren with trees down and leaves blown off by the storm. But already the canopy is green and flourishing. Read More

Summertime Things to Do (on the water)

There's nothing better to do in the summer than be out on the water. The surrounding oceans of Key West provide plenty of possible activities to fill everyday for everyone from those who have never seen the ocean to confident boaters and spear-fisherman. The only way you can miss out on your summertime vacation in Key West is if you spend every day on land! Read More

Parks, Picnics, and Playgrounds

A local Key Wester takes you on a tour of some of his favorite public places on the island. This guide will take you to a number of Key West parks, beaches, and points of interest you probably don't know about. If you're someone who enjoys to picnic, exercise, or just relax with a book under a palm tree, be sure to check out some of these spots to spend your day with local knowledge. Read More

Available Properties For The 4th of July, 2017

Key West loves the 4th of July and there is plenty of family fun to be had. At VHKW, we have many privately owned vacation rentals that are perfect to host you own 4th of July celebration. Read More

Vacation Homes of Key West - VHKW Hosts Business After Hours With The Chamber of Commerce

As members of our local Key West Chamber of Commerce, VHKW staff enjoy participating in the regular chamber events. Key West is a unique island community, and gathering face-to-face for a business social, always promises a fun event and an opportunity to build on our commitment to sustain and develop locally owned and operated business with other local merchants. Read More

7 Mellow Ways to Beat the Key West Rainy Day Blues

Just because the sun isn't out now doesn't mean there's nothing to do! These seven suggestions for rainy day activities will keep you off the standard tourist track and let you keep living your vacation to the fullest. Museums, beach walks, and pools are just some of the many ways locals enjoy the rain and you can too. Read More

New Truman Annex Weekly Vacation Rental

Check out the latest addition to our vacation rental inventory. With its 3 bedrooms and fantastic location next to Fort Zachary Taylor state park and beach, this new rental can accommodate families up to 8 people. Read More

New Sunset Key Monthly Rental

We are excited to announce the addition of this beautiful private island vacation rental into our inventory. A 10 minute ferry ride from Key West, this home is perfect for those looking to escape the hustle and bustle but still want access to the action. Read More

Latest Pins On Pinterest

Inside the Hemingway House with a bottle of Hemingway branded rum. Felt like there was a little magic in the air! #keywest #rum #pilar #hemingway #papawouldbeproud #papaspilar #travel #justgo
Went shopping... Going to catch some bigger dinner #MissMarianne #greatloop #keywest #fishing
This white wine sangria with mango and berries is the perfect fruity, summer cocktail / White Sangria Recipe
Getting Around Key West
Key West is a great stop on a cruise! There are so many great things to do in the Conch Republic. Read more on #KeyWest #LoveFL #ConchRepublic #KeyWestFlorida #Cruise #CruisePort
Key West Wrecker's Race on Appledore II - January 28th
Beautiful beach Key West wedding dress idea
2 Things You Should Never Do in Key West and 10 You Should
Make getting to your Key West vacation rental an island hopping adventure with the Key West Express.
Snook's Bayside Restaurant in Key Largo, FL - Stone Crab Claws, suds and sunshine! A great place to stop and eat on the way to Key West.