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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

Details

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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$418

3 BR / 4 BA / Sleeps 8

1 / 34

$418

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"ALEXANDRIA'S SECRET" Luxurious Home w/ Private Pool - 1/2 Block to Duval St

Key West house
3 BR / 4 BA / Sleeps 8 | Quick view

Details

Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost city has to offer- …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Linens Provided
  • 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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$110

1 BR / 2 BA / Sleeps 2

2 Reviews

$110

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Newton Street Hideaway: A secluded one bedroom

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

Details

Reviews

(2)

30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale for an extended stay …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

A Second Home

Left on Jun 17, 2011 for a stay in May 2011

We have stayed at the Newton Street Hideaway for several years, and, as soon as we open the door, it's just like coming home! It's fun to spot the improvements made by the owners since our previous visit (this time there were new rugs in the kitchen, and stools at the breakfast bar) The house is situated in the quiet residential area known as The Meadows, on the far side of White Street, but it …

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$700

3 BR / 3 BA / Sleeps 7

1 Reviews

$700

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Secret Villa II Newly Listed and Available - Sleeps 6 - Private Pool - Parking

Key West house
3 BR / 3 BA / Sleeps 7 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

We are excited to announce the owner of our most popular luxury vacation rental "SECRET VILLA" is now offering the mirror image as a vacation rental! Available NOW...."SECRET VILLA II"! Location, Location, Location....This amazing property is situated on a quiet and peaceful lane away from traffic and noise. The …
  • Parking
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wedding moon with friends

Left on Jan 18, 2015 for a stay in January 2015

Made a long weekend with friends even better. This place is in a great location just a block or two off Duvall street. The house is outstanding and has a great private heated pool. Also has a great little porch and court yard for mornings and evenings for a drink or two. The house has two nice bedrooms upstairs with private baths and one downstairs with its own bath. Great place to visit with …

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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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$193

3 BR / 4 BA / Sleeps 6

2 Reviews

$193

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Packer Retreat: A beautifully renovated "Conch" house

Key West house
3 BR / 4 BA / Sleeps 6 | Quick view
Very Good2 Reviews

Details

Reviews

(2)

30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district. Designed to bring the outdoors in, this home features a bright living room with cathedral ceilings & tall French doors opening to the pool & garden area. Nicely decorated …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great house needs updating

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

Packer retreat is a great house. So great I am renting it in 2010. The layout and outdoor space is unusually large for Key West. And the home is very private and quiet. the location is within walking distance to Duval and White streets.

The home is beautifully decorated but needs to be "freshened" up. The sofas and carpets are dirty. the kitchen has very little equipment (1 pan, no serving…

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$178

2 BR / 1 BA / Sleeps 6

1 / 24

$178

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Elegantly Furnished Key West Condo

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

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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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$1,071

3 BR / 3 BA / Sleeps 6

1 / 7

$1,071

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HISTORIC RESTORED 'EYEBROW' HOME.

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

This Historic home was built in 1895 and lovingly restored in 2001.This is one of only two eyebrow style homes in Key West that have a front dormer in the roof for architectural appeal. Although this home is an historic treasure, it is fully equipped with all modern conveniences including a heated pool, spa, steam …
  • Parking

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$113

2 BR / 2 BA / Sleeps 6

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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$173

3 BR / 2 BA / Sleeps 6

3 Reviews

$173

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Elizabeth Retreat: A three bedroom historic home in Old Town

Key West house
3 BR / 2 BA / Sleeps 6 | Quick view
Very Good3 Reviews

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Reviews

(3)

30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly restored eyebrow 3 …
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

A month in Key West

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

We had an absolutely delightful time! We have been renting homes in the Keys for years and found this to be our best experience yet. The folks at Rent Key West were so helpful - really stayed on top of everything and went out of their way to accomodate our schedule on check in and check out. The house was absolutely lovely and clearly well cared for. We liked it so much, we are coming back …

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$83

1 BR / 1 BA / Sleeps 2

1 Reviews

$83

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Southard Square Hideaway Old Town, Pool, Parking Too!

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view
Very Good1 Reviews

Details

Reviews

(1)

A surprise awaits you inside the gates of the Southard Square village. Nestled in the heart of Historic Key West, you will be only 4 blocks from world famous Duval Street and 3 blocks away from the scenic Historic Seaport of Key West. Please see our video!! When you arrive, park your car in your dedicated parking …
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • Washing Machine
  • A/C or climate control
  • Parking
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great location...Relax and enjoy!

Left on Apr 27, 2014 for a stay in January 2014

Very nice condo with huge pool area. Very clean and neat. We loved the location! We would love to go back again some day. The only negative was the living room furniture. It seem really inexpensive and quite uncomfortable...it did looked nice. No table in condo...only counter with two small bar stools. Wish it had a small table with 4 chairs. Condo manager Carlos was wonderful.

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$83

1 BR / 1 BA / Sleeps 2

2 Reviews

$83

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The Studio at the Sailmaker`s House Sleeps 2 Historic Old Town

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Gorgeous studio apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. The open concept floor plan maximizes the space in this airy tree top studio. Comfortable Queen size bed will…
  • Wireless Internet
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Linens Provided
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

great place, great location, great stay!

Left on Sep 02, 2014 for a stay in July 2014

I really enjoyed my stay at the sailmaker's studio. The staff as well as the owner were very easy to work with and very helpful. My small dog was with me and he enjoyed it too. It is just blocks away from the wharf and restaurants, shops, grocery stores, sailing/boating trips are also just short walks away. It has all the typical amenities you could want: 2 balconies (1 is shared with another apt…

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$357

2 BR / 5 BA / Sleeps 6

1 / 13

$357

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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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$270

2 BR / 1 BA / Sleeps 4

2 Reviews

$270

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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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$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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$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

Details

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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$183

3 BR / 3 BA / Sleeps 6

3 Reviews

$183

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South Street Serentiy-Great Location, Private Pool, Parking, Steps to the Beach

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

This light and airy 3 bedroom, 2.5 bath home has a wrap around deck and expansive French doors that lead from every ground floor room to an outdoor space. Enter the private gate and you will be in a tropical paradise, surrounded by lush palms, fiery bougainvillea, and tropical ambiance. Here you can be part of the …
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • Washing Machine
  • Parking
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Best location, great rental for families~

Left on Apr 29, 2014 for a stay in January 2014

We loved the location, walking distance to everything. The house had everything you could need. There was confusion on the temperature of the pool, which wasn't discovered for nearly two weeks into the rental month, but was quickly readjusted. There were a few leaks that must be repaired by now, as the management company responded quickly. It was quiet and in a nice neighborhood with respectful …

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$235

2 BR / 2 BA / Sleeps 4

3 Reviews

$235

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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

Details

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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$103

1 BR / 1 BA / Sleeps 4

1 / 16

$103

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Topsail Cottage Key West ~ Monthly Rental

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

Details

Island living is made easy in this tropical one bedroom, 2-story Key West cottage. A classic-contemporary Key West style, this attractive rental home is designed with a graceful spiral stair case that connects the 1st and 2nd floors and a romantic gingerbread Juliet-style 2nd floor balcony overlooking a private …
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$418

3 BR / 3 BA / Sleeps 8

8 Reviews

$418

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"CASA MARGARITA" Amazing Location w/ Pvt Pool & Huge Deck. Pvt Parking

Key West house
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent8 Reviews

Details

Reviews

(8)

Casa Margarita is located on the 300 block Margaret Street in one of Old Town Key West’s most desirable locations. This 3 bedroom/3 bathroom home features a large backyard with lush tropical landscaping placed for an ultimate privacy that is rarely seen in Old Town. The heated pool is flanked by a large covered …
  • Internet Access
  • A/C or climate control
  • Grill
  • Linens Provided
  • Microwave
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Walk to everywhere, but feels very private .

Left on Nov 30, 2013 for a stay in November 2013

My family including our havanese puppy (Reggie)just finished a great week stay in key west. Casa Margarita is within a hundred yards of every restaurant of the harbor .Many places are within crawling distance like harpoon harry's,( 3 doors down)or Pepe's (6 doors down).

You wont hear any noise even the traffic out front is quiet as its on a quiet street ( margaret ave )in a residential …

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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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$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

Details

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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$200

1 BR / 1 BA / Sleeps 6

1 Reviews

$200

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Key West - Capt. Andy

Key West house
1 BR / 1 BA / Sleeps 6 | Quick view
Terrible1 Reviews

Details

Reviews

(1)

Have you ever wondered what it would be like to live on a boat? Well now you can try out the liveaboard experience on board Capt Andy, a 43 ft fishing boat in Key West! This is the perfect rental for a group of boat loving friends looking for a budget friendly rental in Key West. Featuring a full galley kitchen, …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Worst stay for the highest price ever paid nightly.

Left on Feb 22, 2015 for a stay in February 2015

I worked for the airline for 13 years and travelled the world. After the taxes, cleaning fee and exchange, this was the highest price I paid for a nightly stay of $410.77cad. This marina is in the middle of a seedy area, surrounded by low income housing. There's no lock box so you have to get a hold of the captain and wait when you get there. We were not advised that the boat was under …

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$245

1 BR / 1 BA / Sleeps 2

1 / 12

Details

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

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$245

1 BR / 1 BA / Sleeps 2

1 / 12

Details

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
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$270

2 BR / 2 BA / Sleeps 6

21 Reviews

$270

Inquire

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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$240

1 BR / 1 BA / Sleeps 2

48 Reviews

$240

Inquire

Ann Street Tranquility: A cozy and peaceful cottage

Key West cottage
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent48 Reviews

Details

Reviews

(48)

This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath …
  • 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

(48)

Ann Street

Left on Jun 18, 2009 for a stay in May 2007

We enjoyed the cottage. The interior was beautiful and very clean. Very nicely decorated with higher end accessories. The location was absolutely perfect. The only improvement that could be made was the entrance and pool area was not well manicured. It was very overgrown and jungle like. We would not hesitate to return.

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$288

3 BR / 2 BA / Sleeps 6

1 / 10

$288

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Southernmost Retreat- 1 Block from Duval

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

Details

Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in the center of the Old…
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Porch
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$290

2 BR / 2 BA / Sleeps 5

14 Reviews

$290

Inquire

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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$370

3 BR / 2 BA / Sleeps 6

42 Reviews

$370

Inquire

Whitehead House: A unique two story home beside the Audubon House

Key West house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent42 Reviews

Details

Reviews

(42)

Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed "prohibition fence" in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1 space for normal-…
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(42)

Hidden Jewel

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

This house is fantastic! The location is awesome - right in the middle of everything!!! Everything you would want was there. House was clean, pool was excellent and off street parking is great! The 2 bedrooms and bathroom downstairs are small, but for the amount of time you really need them, they are fine. I would certainly recommend this house and plan to rent it again.

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$173

3 BR / 4 BA / Sleeps 8

3 Reviews

$173

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Casa Alegria - a Bahamian style conch house

Key West house
3 BR / 4 BA / Sleeps 8 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

30 DAY MINIMUM RENTAL Welcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off-street parking on either side (a rarity in Old Town!) as well as an easy place to park bicycles. You can park…
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

paradise

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

We were fortunate enough to stay in this immaculate and welcoming retreat. We loved swimming in the pool and riding the bikes around town. We could not have asked for a more perfect place to make our vacation more fabulous!!!! Love...love...love!

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$220

1 BR / 1 BA / Sleeps 4

49 Reviews

$220

Inquire

Colony Poolside: A charming bungalow near the historic cemetery

Key West cabin
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent49 Reviews

Details

Reviews

(49)

Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dining area, full kitchen and a spacious bedroom with a king size bed. There is a nice private deck …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(49)

Disappointing

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

After viewing pictures of this cottage on line I was impressed with the layout, decor and proximity to the pool. So, I was looking forward to our stay there.
Disappointed is the only word I can use to describe how I felt when we arrived and actually saw this space in person.
The pool area and the surrounding grounds were not maintained.
The deck patio furniture was filthy and the deck itself …

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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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$220

0 BR / 1 BA / Sleeps 2

43 Reviews

$220

Inquire

Bali Hideaway: A studio cottage that's perfect for two

Key West cottage
0 BR / 1 BA / Sleeps 2 | Quick view
Excellent43 Reviews

Details

Reviews

(43)

Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull…
  • 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

(43)

great place for two!

Left on Jun 18, 2009 for a stay in July 2007

You don't know your only a block off the "main drag". No noise; serene and absolutely beautiful grounds made our stay better than a condo I rented a couple of years before. Absolutely loved the place!!

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$83

1 BR / 1 BA / Sleeps 2

1 / 23

$83

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Harbour Lights Studio in the Historic Sailmaker`s House

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

Details

Gorgeous studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. You will be living the Key West Life to it's fullest in this highly desired walking neighborhood in Old …
  • Wireless Internet
  • Washing Machine
  • A/C or climate control
  • Parking
  • Linens Provided
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$418

3 BR / 3 BA / Sleeps 8

1 / 36

$418

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ABSOLUTELY PARADISE - Luxury Home w/ Pvt Pool Just 1 Block To Duval St

Key West house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

Absolutely Paradise! That's what you will think the moment that you arrive at this luxurious, tropical retreat. Located in the heart of Old Town Key West, this beautiful home will entice, entertain, and excite even the most discriminating traveler. This spacious (almost 2000 sq ft) three story, 3 bedroom, 2.5 bath …
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$490

4 BR / 4 BA / Sleeps 8

40 Reviews

$490

Inquire

Louisa House: A comfortable four bedroom vacation hideaway

Key West house
4 BR / 4 BA / Sleeps 8 | Quick view
Excellent40 Reviews

Details

Reviews

(40)

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable vacation hideaway. …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(40)

Great House, Family Friendly

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

This is the second time I have stayed at this house and we have loved it both times. The house is within walking distance to everything we needed and wanted to do and offered many amentities. The pool area is very nice and the house is very spacious. The only downfall is I wish the pool area had more than 2 lounge chairs and that the trees were cut back a little more so some sunshine could …

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$180

1 BR / 1 BA / Sleeps 2

16 Reviews

$180

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Key West Garden House

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent16 Reviews

Details

Reviews

(16)

Experiance the laid back life of the tropics in this light and airy 1 bedroom, 1 bath private home. Located on a quiet lane in the heart of Old Town, The Key West Garden House features a large covered back porch, outdoor living and dining area, gas barbeque and heated pool in a lush tropical setting. The yard is …
  • Internet Access
  • Washing Machine
  • Outdoor Dining Area
  • Grill
  • Satellite or cable TV
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(16)

Great Experience!

Left on Jul 23, 2013 for a stay in May 2013

We stayed at the Garden House with our maltese in May. Susan was terrific and her place felt like a home away from home in the Keys. It is such an adorable historic house, we just loved it.
I hope to go back soon and stay at the Garden House again.
Maureen B.

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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

Inquire

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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$250

3 BR / 3 BA / Sleeps 8

1 / 23

$250

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To The Nines ~ A Penthouse-Villa ~ Monthly Rental

Key West house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

"Who says you can't have your cake and eat it too?" Well here's the proof you can ... and it's To the Nines -Key West vacation rental. When you rent this totally unique vacation rental, you will have the "best of both worlds" ... a penthouse and a pool courtyard villa, all wrapped up …
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $700

    3 BR / 3 BA / Sleeps 7

    7 Reviews

    $700

    Inquire

    Secret Villa - a Key West Hidden Gem in Historic Old Town

    Key West house
    3 BR / 3 BA / Sleeps 7 | Quick view
    Excellent7 Reviews

    Details

    Reviews

    (7)

    This is the SECRET VILLA! Designer decorated. Picture the azure, crystal water of the Florida Keys, peaceful colors, and all the comforts of a high end 5 Star Resort. Staying at Secret Villa provides you with an experience in Paradise. Location, Location, Location....This amazing property is situated on a quiet and …
    • Parking
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (7)

    Secret Villa - Fabulous

    Left on Apr 26, 2014 for a stay in April 2014

    Wonderful location - quiet, tucked away yet only two blocks from Duval. The house is beautifully decorated -outdoor deck and pool area is superb. Have stayed in a number of luxury Key West vacation rentals over the years and this is by far the best. Carlos was a wonderful host and it was so good to meet Jim, the actual property owner.

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    $183

    3 BR / 3 BA / Sleeps 10

    1 / 24

    $183

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    "CAYO HUESO HIDEAWAY' - Luxury Monthly Rental - Pvt Pool & Pvt Hot Tub

    Key West house
    3 BR / 3 BA / Sleeps 10 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Cayo Hueso: As you approach the front door to 1120 Curry Lane the transformation starts to happen. The small lush tropical lane, the two wonderfully inviting porches... your journey to the tropics and relaxation has begun! …
    • Hot Tub/Jacuzzi
    • 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

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    $490

    3 BR / 3 BA / Sleeps 6

    6 Reviews

    $490

    Inquire

    Sleeps up to 6: Southard Comfort Historic Old Town Private Pool

    Key West house
    3 BR / 3 BA / Sleeps 6 | Quick view
    Excellent6 Reviews

    Details

    Reviews

    (6)

    “Southard Comfort”, True Island Living in Downtown Historic Old Town Key West Two story, 3 bedroom, 2.5 bath plus outdoor shower. Nancy & Carl welcome you to their Key West vacation home! This established rental is a dazzling property, and we are committed to continuing its reputation of excellence. …
    • Shared outdoor pool (unheated)
    • Wireless Internet
    • Washing Machine
    • 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

    (6)

    Fiftieth Bday Party

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

    Fantastic house and location! Three couples and we all have been to EYW annually over the last 25 years...we have rented almost every large home in EYW and this is one of the best! Great spot,nice pool kitchen was really bigger than needed...outdoor shower is always a favorite and off street parking for a rental car or in our case six bikes....

    Would definitely return to this house....

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    $150

    4 BR / 3 BA / Sleeps 8

    1 Reviews

    $150

    Inquire

    Large 4 Bedroom W/ Pool! `Seabreeze` Luxury Vacation Rental in the Sanctuary

    Key West house
    4 BR / 3 BA / Sleeps 8 | Quick view
    Very Good1 Reviews

    Details

    Reviews

    (1)

    A warm color scheme and meticulous design details lend an elegant tropical ambience to this spacious four bedroom, 3 bath home located in the "Sanctuary" on the Key West Golf Club. Key West Golf Club legend Rees Jones masterfully designed this 18 hole, 6500 yard course to be a challenge to players of all abilities. …
    • Internet Access
    • 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

    (1)

    Awesome Month!!!

    Left on May 01, 2014 for a stay in February 2014

    We rented Seabreeze for a month! It was in the Golf Course a gated community. It was a great home away from home. Very comfortable, stocked well. Had a few glitches with the pool. [the pool company not sweeping the pool} a lot of vegetation so many leaves and such in pool. Gym [we were told it was included and they tried charging us, took a few days to get key] But, I will say everything worked …

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    $240

    1 BR / 2 BA / Sleeps 2

    47 Reviews

    $240

    Inquire

    Ann Street Cottage: A bright and airy home near Duval Street

    Key West cottage
    1 BR / 2 BA / Sleeps 2 | Quick view
    Excellent47 Reviews

    Details

    Reviews

    (47)

    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll …
    • 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

    (47)

    Nice

    Left on Jun 18, 2009 for a stay in July 2006

    My husband and I stayed at the ann street cottage. It is a nice cozy house. Nice size bedroom, and a equipped kitchen to make your own dinners. We went shopping for groceries and made a nice dinner every night--saved a ton on eating out. The cottage was quiet, and clean--there is also a nice private outdoor back patio area. There is also a nice community pool. Only drawback was that the tv …

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