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Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Vacation Homes of Key West
Listed since May 2010

Vacation Homes of Key West has 41 rentals in Key West

Vacation Homes of Key West offers an exclusive collection of privately owned Key West vacation rentals including houses, cottages, condos, suites, compounds, and estates in Key West, Florida. Most of our properties are located in the historic Old Town neighborhoods and all are close to the beach and the Historic Seaport.
Response Rate:
95%
Languages spoken:
English
Response Time:
Within a few hours
Member on:
FlipKey
Listed since :
May 2010
Flower Power House ~ Weekly Rental1 / 29
(1)Excellent
6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
From
$1,000
Per Night
Reviewed April 18, 2016
This house was a great choice for our group of 3 families traveling together. We each had a separate apartment with its own kitchen and bathroom, but were able to gather for...
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Location Information
Key West, Florida Keys
Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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On Hemingway's Rounds ~ Monthly Rental1 / 14
(1)Excellent
3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
Reviewed March 12, 2016
Very comfortable home, well furnished, very homey. Great location. Management company very responsive to all questions and needs. We loved our stay at On Hemingway's Rounds.
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Key West, Florida Keys
Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 58
(7)Very good
4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
From
$750
Per Night
Reviewed February 20, 2017
If you want to immerse yourself in true Key West charm .. This is a perfect place for you. From the front porch through the front door you enter a world that is rich in Key...
Reviewed August 28, 2016
We stayed at the Heavenly Hideout at Rainbow End. I thought the property was excellent and the location was awesome. It is only one long block from Duval Street which made...
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Key West, Florida Keys
Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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Villa Nouveau Key West ~ Weekly Rental1 / 19
(1)Excellent
4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
From
$850
Per Night
Reviewed September 20, 2015
We loved Villa Nouveau! It's a really well-done small 4 bedroom cottage. Bedrooms are small but nice. King beds in 3 rooms and doubles in the 4th, all very comfortable. Each...
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Key West, Florida Keys
Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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The Meeting Point - Key West ~ Weekly Rental1 / 54
(2)Average
11 Bedrooms, 11 Bathrooms, Sleeps 24 Quick View
From
$2,450
Per Night
Reviewed February 26, 2016
This amazing property had everything depicted on the website. When we arrived, the home was spotless and smelled clean. There were 11 bedrooms each with their own full...
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Key West, Florida Keys
Rental Home - 11 Bedrooms, 11 Bathrooms, Sleeps 24
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5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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Location Information
Key West, Florida Keys
Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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Key West, Florida Keys
Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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Seaport Treasure Estate ~ Monthly Rental1 / 34
(1)Excellent
6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
From
$600
Per Night
Reviewed March 8, 2016
My husband and i were celebrating our 50th wedding anniversary and chose this property because we were looking for the ideal location to entertain our friends and family...
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Key West, Florida Keys
Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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Key West, Florida Keys
Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
From
$750
Per Night
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Location Information
Key West, Florida Keys
Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
From
$480
Per Night
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Key West, Florida Keys
Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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Down Island Digs ~ Weekly Rental1 / 14
(8)Very good
2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
From
$475
Per Night
Reviewed January 24, 2017
We stayed for a week at 508 Bahama St. We were 1 block behind Duval but you would never have known it. The backyard is so peaceful and where we basically lived all week...
Reviewed June 12, 2016
If you want to be near the heart of Duval, but never hear it when you choose to take a break, then this is your place. The backyard garden is amazing with gorgeous landscaping...
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Key West, Florida Keys
Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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Key West, Florida Keys
Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
From
$375
Per Night
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Location Information
Key West, Florida Keys
Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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Vintage Luxury Cottage ~ Weekly Rental1 / 11
(4)Very good
1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
From
$400
Per Night
Reviewed November 7, 2016
This is such a secluded feeling cottage yet it's right in the middle of everything! Closer to Southernmost point but very walkable up Duval to Mallory Square and the wharf...
Reviewed March 10, 2016
We booked this cottage a year ago, planning for three weeks vacation this February 2016 in Key West, Florida. Travelling from Canada in February, we were so excited to immerse...
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Location Information
Key West, Florida Keys
Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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Twice as Nice ~ Weekly Rental1 / 17
(3)Excellent
4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
From
$850
Per Night
Reviewed October 27, 2016
We rented. Other cottages for a family vacation. Both units were better than expected for all that we wanted to do. The rooms were spacious, the pool area was private and...
Reviewed November 4, 2012
House decorated nicely and very well maintained. Great pool and above average accommodations. Close enough to walk to everything at Mallory Square if you like a little exercise...
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Location Information
Key West, Florida Keys
Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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Tropical ~ Tranquility ~ Weekly Rental1 / 14
(6)Very good
4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
From
$1,150
Per Night
Reviewed June 26, 2017
We recently returned from a one week stay at Tropical Tranquility. This was an amazing Key West find! It's close to Duval St and we walked or biked to almost all activities...
Reviewed June 21, 2017
Tropical Tranquility is a wonderful house to rent. I would recommend this house to anyone. It was clean and comfortable. Since we visited KW in June the pool was a welcome...
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Location Information
Key West, Florida Keys
Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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Secret Courtyard Cottage ~ Weekly Rental1 / 9
(6)Very good
2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
From
$350
Per Night
Reviewed June 22, 2016
Everything was as advertised. The location was great and since the cottage sits back a bit from the road it was nice and quit at night. We had one plumbing problem (that could...
Reviewed March 1, 2016
I wanted to keep this little piece of paradise a secret, but I guess I can't. This is much better than a motel, and much cheaper. A wonderful little home equipped with...
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Key West, Florida Keys
Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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Penthouse On Duval ~ Weekly Rental1 / 20
(10)Very good
4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
From
$675
Per Night
Reviewed October 26, 2016
A group of friends and I came down for my bachelor party and couldn't have asked for a better set up. The place is massive, more than enough room for everybody to get either a...
Reviewed July 2, 2015
We stayed at Penthouse on Duval for a week, renting the entire unit (4 Bedrooms and 4 1/2 baths) and it was absolutely as described including the pictures. It was large...
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Location Information
Key West, Florida Keys
Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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Pavilion Villa ~ Weekly Rental1 / 20
(8)Average
4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
From
$850
Per Night
Reviewed May 21, 2016
Stayed with friends and family place need work. A/C in bathroom terrible, none. Kitchen, family room in main house never stayed cool. it says 3 baths 1 is outside beside the...
Reviewed August 17, 2015
When we arrived the main house smelled very musty. I immediately cranked the AC units down to 73 to get some of the air dried out. The King bedroom never lost the musty smell...
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Location Information
Key West, Florida Keys
Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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Property Summary Rating
4.5 of 5
Very good
31 rated properties
  • Excellent
    8
  • Very good
    18
  • Average
    5
  • Poor
    0
  • Terrible
    0
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