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$208

2 BR / 1 BA / Sleeps 4

TRUMAN @ DUVAL 'Old Town KW' Home Just A Hop-Skip-And-Jump To Duval St. - Key West vacation rentals
1 / 25

$208

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TRUMAN @ DUVAL 'Old Town KW' Home Just A Hop-Skip-And-Jump To Duval St.

Key West cottage
2 BR / 1 BA / Sleeps 4 | Quick view

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Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people watching, it's all…
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$179

2 BR / 3 BA / Sleeps 4

2 Reviews

$179

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Olivia Cottage: A charming Old Town house near Key West's historic cemetery

Key West house
2 BR / 3 BA / Sleeps 4 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our town, the Oliva …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Stepping Into a Picture

Left on Jul 21, 2011 for a stay in June 2011

I stayed in Olivia Cottage five weeks and loved every minute. After looking at pictures on the internet, I felt like I was stepping into the pictures. It's exactly as shown. The patio/pool area is just the most relaxing place. Everything I needed was provided and the staff at KW Vacation Rentals were most friendly and helpful. I had one problem with the smoke detectors and it was repaired quickly…

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$127

2 BR / 2 BA / Sleeps 4

2 Reviews

$127

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Angela Cottage: A hideaway in Old Town

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows create a relaxing Key …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Outstanding

Left on Jun 26, 2009 for a stay in March 2009

I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and outdoor dining area is outstanding for any meal. The kitchen is new and all the necessary pots and pans are present.

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$358

2 BR / 5 BA / Sleeps 6

Hyatt Beach Club - Key West vacation rentals
1 / 13

$358

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Hyatt Beach Club

Key West condo
2 BR / 5 BA / Sleeps 6 | Quick view

Details

This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a view of water with …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Housekeeping Optional
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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$179

2 BR / 1 BA / Sleeps 6

Elegantly Furnished Key West Condo - Key West vacation rentals
1 / 24

$179

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Elegantly Furnished Key West Condo

Key West condo
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Elegantly furnished Key West vacation condo in the historic Truman Annex in the heart of Old Town in Key West. This is the premier gated community in Key West, bordering the Atlantic Ocean. Grounds of the Annex are beautifully landscaped. The Shipyard units are done in the traditional Key West Conch style. This is a …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Patio
  • Pet friendly

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$113

2 BR / 2 BA / Sleeps 6

Mango Menagerie:  A treasury of island colors and Key West charm - Key West vacation rentals
1 / 17

$113

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Mango Menagerie: A treasury of island colors and Key West charm

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

30 DAY MINIMUM RENTAL Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm. Located in the heart of Old Town, this home is located just one block from the ever popular Cuban restaurant El Siboney and one block from the local's favorite Flaming Buoy restaurant. The property is …
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$100

2 BR / 1 BA / Sleeps 4

1 / 28

$100

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Angelfish Cottage | Summer slow lane | Bring a friend or two

Key West house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Historic Old Town Classic Conch Cottage This monthly vacation home is located in the heart of Historic Old Town Key West Florida on a very private, quiet lane. Restaurants & bars, marinas and shopping are all within walking distance. 6 blocks from the center of Duval St. and 6 blocks from the historic seaport. Your …
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Parking
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$236

2 BR / 2 BA / Sleeps 4

3 Reviews

$236

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"SOUTHERN WIND" Immaculate Home w/ BBQ Grill & Shared Pool. Seconds To Duval

Key West condo
2 BR / 2 BA / Sleeps 4 | Quick view
Very Good3 Reviews

Details

Reviews

(3)

***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** This recently renovated two bedroom/two bathroom vacation dream home offers an open floor plan with the best of appointments throughout including hardwood floors, marble counter tops and impeccable style. The first floor of …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Convenient

Left on Jan 11, 2014 for a stay in January 2014

Southern Winds is a stand alone 2 story, 2 BR, 2 bath ( only 1 bathroom on 2nd floor), condo in a private, gated 14 unit complex. Nicely decorated and offered all supplies and appliances needed for the kitchen. There was very little interaction with other guests; a very quiet complex. The location is very good, just more than one block from the intersection of Duval and Truman Streets.

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$229

2 BR / 2 BA / Sleeps 6

6 Reviews

$229

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1/2 Block to Duval, World of its own -Nassau Suite

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent6 Reviews

Details

Reviews

(6)

The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an endless party, The …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(6)

Wish I had found this place 15 years ago.

Left on Jan 06, 2014 for a stay in December 2013

Stayed in the Nassau the week of Christmas thru New Years. Came down with two other couples. The pictures do not do this place justice. Plenty of room for all. Having two bathrooms was also a plus. Very close to Duval street, and anywhere you really would want to go is in walking distance, minus the beach, but is a short/cheap taxi ride away. Our unit had 90% new furniture, and matresses. …

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$270

2 BR / 1 BA / Sleeps 4

43 Reviews

$270

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Key Lime Calypso: A cottage in the heart of Bahama Village

Key West house
2 BR / 1 BA / Sleeps 4 | Quick view
Very Good43 Reviews

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Reviews

(43)

The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this two bedroom cottage…
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(43)

Lovely cottage and great location

Left on Jun 18, 2009 for a stay in September 2008

The cottage was a great "get away from it", but yet was right in the heart of the main area Key West, just off Duval St. As the property was centrally located along Duval St, it was also quiet and peaceful. The private pool was great to have and the garden had a lovely sunny aspect, but there was enough shade to get out of the sun if you wanted too. The pool was welcome as the main beaches on the…

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$217

2 BR / 2 BA / Sleeps 6

1 / 12

$217

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Historic Hideaway Olivia Retreat Key West

Key West cottage
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Look no further you have found a beautiful 2 bedroom 2 bath "Shot-Gun" house in the heart of Old Town Key West, just 4 blocks from Famous Duval Street. This great property is very spacious and will accommodate up to 6 guests comfortably. There is a Fully equipped kitchen with a full size dining table in the …
  • Washing Machine
  • Outdoor Dining Area
  • A/C or climate control
  • Patio
  • Books
  • Suitable for children
  • Suitable for the elderly - ask

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$400

2 BR / 2 BA / Sleeps 4

49 Reviews

$400

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Valhalla

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent49 Reviews

Details

Reviews

(49)

This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special residence isn't …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(49)

Wonderful Home

Left on Oct 17, 2008 for a stay in October 2008

We participated in a fund raiser for epilepsy in Houston and won the week at the house in an auction. We had never been to Key West and could not have been happier with the house and the island. It was beautiful, well furnished and very comfortable. It was also very close to both the beach and the clubs. We had a great week and will come back and rent from Historic Hideaways again.

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$127

2 BR / 2 BA / Sleeps 4

1 / 11

$127

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South Street Cottage: Bright & sunny in the Casa Marina district

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view

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30 DAY MINIMUM RENTAL A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A large open kitchen, skylights, light tile floors and …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$199

2 BR / 1 BA / Sleeps 6

18 Reviews

$199

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Center of It All - Paradise Island Suite

Key West condo
2 BR / 1 BA / Sleeps 6 | Quick view
Excellent18 Reviews

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Reviews

(18)

Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West vacation memorable…
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly

Details

Reviews

(18)

Great Locaction!!

Left on Nov 08, 2013 for a stay in October 2013

Great location! loved the apartment, will definitely rent there rent it again. If I had to complain about 1 thing, the beds where awful!!!
But I was told there changing all the furniture so the place is perfect! loved it!

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$400

2 BR / 2 BA / Sleeps 4

2 Reviews

$400

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Quilted Giraffe

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(2)

Relaxing respite

Left on Mar 05, 2010 for a stay in February 2010

The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A parking spot in the front yard would be recommended. The location was excellent for walking anywhere. The service was good once we met Bill. Prior to him, Corey and Libby both seemed disorganized and inattentive to our …

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$290

2 BR / 2 BA / Sleeps 5

14 Reviews

$290

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Beach Club #204 - Unique Oceanfront living

Key West condo
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent14 Reviews

Details

Reviews

(14)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This is one of the most elegant and colorful 2 bedroom units in the Key West Beach Club. It …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(14)

Great Time

Left on Jun 18, 2009 for a stay in May 2008

I just wish I had the money to buy a condo at The Beach Club. It's the second time I've stayed there and each time was perfect.

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$270

2 BR / 2 BA / Sleeps 6

21 Reviews

$270

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Vista Fresco : Oceanside condominiums with resort-style amenities

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent21 Reviews

Details

Reviews

(21)

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees. Plan a picnic or …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(21)

The appart was fantastic but it was impossible to use the pool.

Left on Aug 12, 2009 for a stay in July 2009

If there wasn't any pool at this condo, we'd never rent it. Unfortunatly, the pool
was broken and it was impossible to use it. We arrived on thurdays and friday,
the pool was broke. We ask to know when it would be repare, they told us it
would be the next monday but when we left on thursday night, the pool was
still broke... This point realy desapoint us.

For the condo, everything was …

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$310

2 BR / 1 BA / Sleeps 4

4 Reviews

Details

Reviews

(4)

THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite is furnished with a full kitchen, contemporary living room with comfortable furniture, new ultra comfortable mattresses with premium …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Outstanding place!

Left on Dec 17, 2014 for a stay in December 2014

This is a great place to stay that puts you in the heart of Key West and has off-street parking! The unit has been completely remodeled including a full kitchen but still maintains the areas unique charm. Everything you could ask is right there within walking distance including all of Duval Streets goodness but still maintains the option for a level of seclusion.

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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

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Beach Club #201 - Unique Oceanfront living

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent15 Reviews

Details

Reviews

(15)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This 2 bedroom, 2 bath unit features a huge oceanfront balcony accessed from both the living/…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

Key West Wedding Vacation

Left on Jun 18, 2009 for a stay in June 2008

We loved staying at the condo.. It fit 5 of us very comfortably. We were down for a wedding. The view was great, the securty made me feel safe. We used the pool almost daily and actually had a couple of friends over for a cookout by the pool. I would stay with Rent Key West Vacations again and would recommend it to a friend.

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$378

2 BR / 2 BA / Sleeps 6

13 Reviews

$378

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PASSOVER COTTAGE - Adorable, Historic Home w/ Caribbean Attitude and Pvt Pool

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent13 Reviews

Details

Reviews

(13)

This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom which has a two twin…
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

Loved it! Great neighbours!

Left on Aug 22, 2011 for a stay in August 2011

We had a great time in Key West! This is a great little hidden cottage. Almost downtown, but with a feeling of total seclusion. I would recommend this location for a family up to six or two couples. Lots of room and well maintained. Good job Key West Vacation Rentals! We will be back!

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$378

2 BR / 2 BA / Sleeps 6

11 Reviews

$378

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"DU PONT HOUSE" Luxury Rental - Private Pool - 1/2 Block To Duval St.

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent11 Reviews

Details

Reviews

(11)

Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and bath are …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(11)

Another wonderful stay

Left on Sep 10, 2010 for a stay in August 2010

We love the Dupont House! Pictures don't quite do it justice because it has two-story ceilings because of the second bedroom. It is much more open and roomy than it appears. This is our second stay there and both times it has been perfect. It is current and appropriately (not to mention cutely) decorated... Seriously cute - we have a bunch of pictures of the house and its decorations! The house …

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$209

2 BR / 2 BA / Sleeps 5

14 Reviews

$209

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Best Location, 1/2 Block to Duval, Bimini Suite

Key West condo
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent14 Reviews

Details

Reviews

(14)

Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire, bedding, decor and …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly

Details

Reviews

(14)

location! location! location!

Left on Apr 24, 2014 for a stay in April 2014

The location was perfect for going out in Key west! I stayed with 3 other friends and there was plenty of space. The place was clean the bathrooms were nice. The only thing that was a bit of a pain was the parking. its just a driveway you share with the rest of the guests. So one night/ eve I was out and had to go back and move the car so another guest could leave. Aside form that the place was …

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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

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Beach Club #104 - Unique oceanfront living with breathtaking views

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent15 Reviews

Details

Reviews

(15)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. The huge oceanfront balcony can be accessed from both the living/dining area and master …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

Good facility overall, but lots of rules for teeneagers

Left on Apr 16, 2011 for a stay in March 2011

Beach Club #104 is nicely and recently decorated. Everything was in good working order (TVs, washer/dryer, kitchen appliances). The cleaning service could have done a better job. There are a number of loose floor tiles which could be dangerous for older renters. The public areas are well kept, but there are some rather draconian rules -- the owners are not particularly friendly and I have to …

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$300

2 BR / 2 BA / Sleeps 8

12 Reviews

$300

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Pelican Landing Abaco Retreat

Key West condo
2 BR / 2 BA / Sleeps 8 | Quick view
Excellent12 Reviews

Details

Reviews

(12)

Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront condos have a range of …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(12)

Flawless new year stay

Left on Jan 20, 2012 for a stay in January 2012

Outstanding time wonderful facilities, will bring boat next time

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$320

2 BR / 2 BA / Sleeps 4

37 Reviews

$320

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Catherine House: A charming Old Town Key West cottage

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent37 Reviews

Details

Reviews

(37)

This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably sleep four and …
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(37)

Cozy spot in perfect location

Left on Jun 18, 2009 for a stay in March 2009

Catherine House is truely a shotgun house -- long and narrow -- but has been renovated into a cozy and lovely little two-bedroom. The beds are large and comfy, with two full baths perfect for two couples. The kitchen is basic, but open to the living area and more than sufficient for vacation meals. The pool is more like a tub, but is fine for toddlers and tired parents who want to dip their …

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$350

2 BR / 3 BA / Sleeps 4

3 Reviews

$350

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City Island View ~ Weekly Rental

Key West house
2 BR / 3 BA / Sleeps 4 | Quick view
Average3 Reviews

Details

Reviews

(3)

Perched just above the fun and frolic of Duval Street at the City Island View vacation rental suite, you're sure to capture the "island beat" that stirs this tiny tropical island of Key West, Florida. This extraordinary Key West vacation rental features the original 2nd floor front porch that spans the …
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Not worth the price

Left on Nov 04, 2011 for a stay in July 2011

My husband and I were so excited to stay at City Island View during our Florida vacation last July. We'd looked and looked for a hotel or home in Key West that would meet our standards for cleanliness, convenience to downtown Key West attractions, and Key West charm. We finally found the City Island View condo, and it sounded perfect for what we wanted. The price was high, but based on the photos…

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$600

2 BR / 2 BA / Sleeps 6

1 / 24

$600

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Garden Home Paradise in Midtown Key West

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view

Details

2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered outdoor pavillion with …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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$290

2 BR / 2 BA / Sleeps 5

9 Reviews

$290

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Beach Club #112 - Unique Oceanfront living

Key West condo
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent9 Reviews

Details

Reviews

(9)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This comfortable 2 bedroom unit features a huge oceanfront balcony accessed from both the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(9)

Fabulous view

Left on Jun 19, 2009 for a stay in May 2009

This unit was just lovely, the view off the terrace was amazing. We had the pool (one of 2) to ourselves everyday. We never heard any of our neighbors. Although the beach was not manicured, the unit was very close to 2 beaches, if you want to sit in the sand.
We could see cruise ships and parasailing right off the pation. I can't say enough, it was GREAT.

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$230

2 BR / 2 BA / Sleeps 5

2 Reviews

$230

Inquire

Royal Palm

Key West house
2 BR / 2 BA / Sleeps 5 | Quick view
Very Good2 Reviews

Details

Reviews

(2)

There's no better way to experience "Island Time"-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse offers privacy and …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for the elderly - ask

Details

Reviews

(2)

Really Great Experience

Left on Mar 15, 2013 for a stay in February 2013

Had a great time. Historic Hideaways was very helpful. Our place was central to everything, very clean. Perfect for our needs.

Thank you.

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$290

2 BR / 2 BA / Sleeps 6

18 Reviews

$290

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Beach Club #103 - Unique oceanfront living with breathtaking views

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent18 Reviews

Details

Reviews

(18)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This spacious 2 bedroom unit features a large oceanfront balcony accessed from both the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(18)

Great Location

Left on Jun 27, 2009 for a stay in April 2009

We are very satisfied with Rent Key West Vacations. The staff was very helpful. We stayed at Key West Beach Club. We were extremely pleased with the Condo we rented, very comfortable, beautiful views of the ocean, it was better than we expected. The kitchen was nicely equipped. We could have used a better vacuum and the washer & dryer combo was very noisy. The pool and grill area were …

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$215

2 BR / 2 BA / Sleeps 6

1 / 4

$215

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Key West Hyatt Windward Pointe

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping. This unit rents …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$357

2 BR / 2 BA / Sleeps 5

12 Reviews

$357

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Potter`s Cottage: Historic Old Town - Private Pool - Steps from Duval Street

Key West house
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent12 Reviews

Details

Reviews

(12)

Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for up to 5 guests (please see our calendar). Potter’s Cottage is located in the heart of Old Town – Key West’s …
  • Shared outdoor pool (unheated)
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(12)

Found what we were looking for

Left on May 05, 2011 for a stay in April 2011

Cute cottage with a great master bedroom loft suite, well appointed throughout, furnishings look new. The private pool and really cool poolside seating area were perfect for sun or shade. Location couldn't have been better. Near the sights, near the Southernmost Beach, and a block off Duval - convenience without the noise. Nice touch with the gift basket at check in.

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$300

2 BR / 2 BA / Sleeps 6

4 Reviews

$300

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1800 Atlantic Condominiums Key West C327

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
Average4 Reviews

Details

Reviews

(4)

Fabulous spacious two bedroom condominiums, directly on the Atlantic Ocean in Key West Florida. The Condo is fully equipped with a full size Kitchen. There is also a full size washer & dryer for your convenience. All rooms have a color cable TV and the unit has high There is an extensive private balcony that can …
    • Suitable for children - ask
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (4)

    Key West

    Left on Oct 31, 2010 for a stay in October 2010

    The explanation & photos on the internet were not all true. I booked this condo expecting to be able to use the beach. But the beach was not accessible. The security guard said that the last time the beach was nice was about 5-6 yrs ago. So, we had to drive downtown to a park and pay to use the public beach. There's alot of traffic 24/7. There were workers on-site re-doing the hallway walls so …

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    $320

    2 BR / 2 BA / Sleeps 4

    30 Reviews

    $320

    Inquire

    Havana Lane: A classic conch cottage with rustic charm

    Key West house
    2 BR / 2 BA / Sleeps 4 | Quick view
    Excellent30 Reviews

    Details

    Reviews

    (30)

    Thoughtfully restored, Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery, this classic conch cottage embodies the essence of rustic charm while offering modern amenities and style. Centrally …
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (30)

    Gorgeous surroundings, comfortable Key West home

    Left on Jun 18, 2009 for a stay in April 2009

    As soon as we unlocked the gate to the high wooden fence surrounding 1
    Havana Lane, we knew we had picked a gem of a place to stay for Spring Break.
    My husband and I came to Key West with our 15 year-old daughter and her
    friend. The home was perfect for us four, and we enjoyed being there almost
    as much as going out and about the island. We called the yard our "Secret
    Garden." It was so lush…

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    $270

    2 BR / 1 BA / Sleeps 4

    2 Reviews

    $270

    Inquire

    Pete's West Cottage steps from Duval

    Key West cottage
    2 BR / 1 BA / Sleeps 4 | Quick view
    Average2 Reviews

    Details

    Reviews

    (2)

    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Patio
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Nice but could use some sprucing up

    Left on Oct 13, 2014 for a stay in October 2014

    Nice place. Quiet location. I would have thought someone might clean the pool during our stay since the iguanas in the trees used it for their bathroom quite frequently

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    $288

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $288

    Book

    SOUTHERN CROSS @ TROPICAL VILLAGE - Beautifully Updated Home w/ Shared Pool.

    Key West cottage
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    Part of TROPICAL VILLAGE Southern Cross: Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Tropical Perfection

    Left on Oct 07, 2014 for a stay in October 2014

    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15 minute walk to the Mallory Square. Higgs Beach was a close, great market nearby, and a CVS, you really couldn't have asked for a better location! The trip was epic, relaxing and wild from start to finish. I can't wait to come …

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    $133

    2 BR / 2 BA / Sleeps 4

    1 / 11

    $133

    Inquire

    30 night minimum stay requirement. The Pearl in Paradise - 2 Bedroom House w

    Key West house
    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical district. Close to downtown and the beaches. Perfect for two couples looking for Old Town and peace and quiet. This home offers a two bedroom, two bathroom and was nicely remodeled with hardwood …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Patio
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $150

    2 BR / 1 BA / Sleeps 4

    1 / 15

    $150

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    "ISLAND RENDEZVOUS" Gorgeous Old Town Home w/ Private Pool

    Key West house
    2 BR / 1 BA / Sleeps 4 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** This exclusive home in the heart of the island offers optimum privacy while having an airy and open floor plan and the best of appointments throughout. Whether enjoying the heated pool flanked by meticulously maintained …
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $83

    2 BR / 2 BA / Sleeps 6

    1 / 30

    $83

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    "HOWE STREET HIDEAWAY" Newly Renovated 2 Bed Two Bath Home.

    Key West house
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The neighborhood is complete with conch style homes, little lanes, corner gardens and yes our famous Key West Roosters watching their chicks. Featuring a classic front porch for greeting the neighbors as they go about their day…
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $83

    2 BR / 2 BA / Sleeps 6

    1 / 24

    $83

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    "SALT POND HIDEAWAY" 2/2 Condo w/ Huge Shared Pool & Hot Tub. Close to Beach!

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right across the …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Patio
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $83

    2 BR / 2 BA / Sleeps 4

    1 / 23

    $83

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    Playa Royale - Monthly Rental

    Key West condo
    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Playa Royale is located on South Roosevelt Blvd., directly across from Key West's largest beach (Smathers) on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the pool, tennis courts …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Sauna
    • Internet Access
    • A/C or climate control
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $167

    2 BR / 2 BA / Sleeps 6

    8 Reviews

    $167

    Book

    "CASA 625" Monthly Rental w/ Private Pool. Beautiful Interior

    Key West house
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent8 Reviews

    Details

    Reviews

    (8)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to detail! Sit on the …
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (8)

    Always love 625

    Left on Jan 27, 2011 for a stay in November 2010

    This is a nice property I have stayed at multiple times. If it were my house, I would enhance it by making the master suite upstairs private (not wide open to the rest of the house) and I would put a TV in the master that's a reasonablt size (there was a 17" or so TV in a beautiful MBR!). Put the small TV downstairs in the BR there and get a new flatscreen that fits the property and the MBR.

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    $117

    2 BR / 2 BA / Sleeps 6

    1 / 17

    $117

    Book

    Amazing Grace

    Key West house
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Amazing Grace is nestled in the middle of the island on Seidenberg Avenue that dead ends into Salt Run Canal that divides Key West in half. With 2 bedrooms, 2 bathrooms, off street parking and a hot tub you may find that you …
    • Dishwasher
    • Microwave
    • Refrigerator
    • Toaster
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $133

    2 BR / 2 BA / Sleeps 4

    1 / 30

    $133

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    "ROYAL OASIS" - Beautiful 2/2 Monthly Rental w/ Private Heated Pool

    Key West house
    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautifully decorated with abstract art throughout, this 2 bed 2 bath monthly rental is the perfect "get away" spot for individuals looking to fully immerse themselves in Key West culture. This house is located in on Royal St. …
    • Internet Access
    • A/C or climate control
    • Deck
    • Linens Provided
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    PreviousNext property

    $83

    2 BR / 2 BA / Sleeps 6

    1 / 29

    $83

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    "SEASIDE HIDEAWAY" Beautiful Key West Condo w/ Shared Pool & Tennis Courts

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    ***Due to licensing restrictions, this property requires minimum stay of 28 nights*** This condominium is located right near the entrance of Key West and offers unparalleled seclusion and privacy. Although it is on the opposite side of the island from world famous Duval St, it is only about a 10 minute drive away. …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $198

    2 BR / 2 BA / Sleeps 6

    1 / 27

    $198

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    SAINT THOMAS SUITE #302 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $270

    2 BR / 1 BA / Sleeps 4

    1 / 13

    $270

    Inquire

    Pete's East Cottage: Cypress east cottage steps from Duval

    Key West cottage
    2 BR / 1 BA / Sleeps 4 | Quick view

    Details

    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Patio
    • Linens Provided
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    PreviousNext property

    $198

    2 BR / 2 BA / Sleeps 6

    1 / 22

    $198

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    SAMANA CAY SUITE #405 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    PreviousNext property

    $198

    2 BR / 2 BA / Sleeps 6

    1 / 38

    $198

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    SAINT BARTS SUITE #303 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    PreviousNext property

    $233

    2 BR / 2 BA / Sleeps 4

    2 Reviews

    $233

    Book

    Pinder House - Monthly Rental

    Key West house
    2 BR / 2 BA / Sleeps 4 | Quick view
    Average2 Reviews

    Details

    Reviews

    (2)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Located at 516 Elizabeth Street, the Pinder House is an address and house of distinction! Previously owned by Theopolis Pinder of the historic Pinder Family, whose roots go back to the 1850’s, this historic Eyebrow home has …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Central heating
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Live in an 1830's house w / 2014 conveniences

    Left on Jan 23, 2014 for a stay in January 2014

    B+ no Choices in cable channels no prkg
    On site , parrot sanctuary adjacent
    Property's remote pool. Access. K

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