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$103

3 BR / 2 BA / Sleeps 6

First Breath - Key West vacation rentals
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$103

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First Breath

3 BR / 2 BA / Sleeps 6 | Quick view

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FIRST BREATH: 3-bedroom 2-bath Conch home with pool in Old Town. Fenced and landscaped for the ultimate privacy. Back gate opens onto Elgin Lane.2 bedrooms upstairs, 1 with queen and 1 with twins, share the full bath. Downstairs is the 3rd bedroom with king bed and bath ensuite. Well-stocked kitchen. Dine inside…
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$261

3 BR / 3 BA / Sleeps 6

12 Reviews

$261

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Alluring Porches

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 12 Reviews

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Reviews

(12)

ALLURING PORCHES – This 2 bedroom 3 bath townhome with den in Truman Annex is the tranquil escape you’ve been looking for. 50% larger than similar homes in the area. First level is the kitchen with all you need, dining room, oversized living room with high-end electronics, den that doubles as extra living space …
  • Shared outdoor pool (unheated)
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(12)

A home away from home.

Left on Oct 01, 2009 for a stay in September 2009

The service we received was mostly good. The only problem we had is when we arrived on a Sunday afternoon when the office was closed the staff failed to provide us with a lock box code so that we could get the keys to the property. We had to call the emergency number to get the code.
The home itself was very nice. Equipt with everything we could want or need. The location is great, being able…

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$400

3 BR / 3 BA / Sleeps 6

Eliza's Jewel is a charming property close to White Street. - Key West vacation rentals
1 / 19

$400

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Eliza's Jewel is a charming property close to White Street.

3 BR / 3 BA / Sleeps 6 | Quick view

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30 DAY MINIMUM Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West. Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved historical architecture with …
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$220

3 BR / 3 BA / Sleeps 8

10 Reviews

$220

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Coral Villa

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 10 Reviews

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Reviews

(10)

CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas, Smathers Beach and the airport.Fully equipped kitchen, HDTVs, WIFI and off-street parking for 2 vehicles.First …
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(10)

It was a good place to stay for the price.

Left on Jan 19, 2013 for a stay in January 2013

We enjoyed our stay at Coral Villa. It was comfortable, clean, roomy, and well furnished. The only drawback was the daytime street noise. The pool area had plenty of seating and the convenience of a nearby bathroom. Each of the 3 couples had their own private bath. My husband and I took the bedroom with the twin beds and simply put them together.

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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

3 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 3 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 …
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(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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$173

3 BR / 4 BA / Sleeps 8

3 Reviews

$173

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Casa Alegria - a Bahamian style conch house

3 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

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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…
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(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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$193

3 BR / 4 BA / Sleeps 6

2 Reviews

$193

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Packer Retreat: A beautifully renovated "Conch" house

3 BR / 4 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

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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 …
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(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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$286

3 BR / 2 BA / Sleeps 6

22 Reviews

$286

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Key West Casa

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 22 Reviews

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Reviews

(22)

KEY WEST CASA: One of only a few 3 bedroom 2 bath condos in the Shipyard complex in Truman Annex. Enter the fully stocked kitchen to the living room to the French doors that open onto the back porch. The downstairs bedroom is just to your left and offers 2 twin beds next to the bathroom.Upstairs is the front …
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(22)

Absolutely Fantastic!

Left on Nov 06, 2008 for a stay in July 2008

This house was perfect for our group of five. It was beautiful and well kept. All the amenities of home. Walking distance to all Duval Street activities and the beach. Great deck out back. Couldn't ask for anything more. I will definitely stay at this house again when I go back to Key West.

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$580

3 BR / 3 BA / Sleeps 6

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$580

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Tucked away near the Southernmost Point, Louisa's Hideaway is it!

3 BR / 3 BA / Sleeps 6 | Quick view

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Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the gate to the palm tree lined path that leads to …
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$310

3 BR / 2 BA / Sleeps 7

17 Reviews

$310

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Duval Courtyard

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 17 Reviews

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Reviews

(17)

DUVAL COURTYARD - 3 bedroom 2 bath townhome has plenty of space, a fabulous location and all the amenities you could wish for. The main living area flows from kitchen to dining area to French doors that open to a balcony where you can sit and people watch. Master bedroom has bath ensuite along with its own balcony…
  • Shared outdoor pool (unheated)
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(17)

Christmas in Paradise

Left on Nov 06, 2008 for a stay in December 2006

A wonderful Christmas experience. No snow, no cold, just a relaxing time. Condo was roomy and aesthetically lovely. Loved the balcony overlooking the courtyard. Convenient location to everything in Old Town. Used the kitchen quite abit. Mini washer and dryer not great but a minor complaint. Would easily stay here again.

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$470

3 BR / 2 BA / Sleeps 6

38 Reviews

$470

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Coconut Cabana: A restored Old Town home with charm & tropical ambience

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 38 Reviews

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Reviews

(38)

An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story historic home is …
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(38)

Coconut Cabana - Go Nuts!

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

We loved Coconut Cabana! This house was perfect for a "sibling celebration" of my brother's 50th birthday. The house was darling, well equiped and the entire rental process was smooth sailing. There is no place like Key West and this house just off Duval was just where we needed to be. We would highly recommend!

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$450

3 BR / 3 BA / Sleeps 6

34 Reviews

$450

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Villa Paradiso: A unique mid-town paradise

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 34 Reviews

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Reviews

(34)

This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached pavillion with an ornate…
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(34)

The 3 couples loved this home.

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

We chose the Villa because it advertised 3 bedrooms and 3 baths. I would advertise it as 2.5 bedrooms. However, the space worked out very well for the 6 of us. The home is graciously appointed and easy to live in. The small pool area was a perfect gathering spot. There were other decks and seating areas when each of us choses a bit more privacy. The Villa was within walking distance of the …

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$465

3 BR / 2 BA / Sleeps 8

78 Reviews

$465

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Bahama Dreaming

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 78 Reviews

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Reviews

(78)

BAHAMA DREAMING: 3-bedroom Conch cottage with outdoor dining and private pool, fenced and landscaped, off-street parking, 1/2 block from Duval Street. Downstairs has 2 bedrooms (queen and 2 twins), living room with sleeper sofa and full bathroom, kitchen and covered back porch. A couple steps down to the 12'x18' …
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(78)

cozy, clean home

Left on Nov 06, 2008 for a stay in March 2008

Decent, small home with all of the necessary amenities and
close to town. We have rented many places in and around
Florida. This was a smaller home. The front bedroom faced the
road and was quite bright and loud early in the morning.

There was a lot of construction noise around, so, we
had to turn up our music when in the pool. The pool was
beautiful but there were no pool toys. They …

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$540

3 BR / 2 BA / Sleeps 6

1 / 18

$540

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Casa de Cuba:Beautiful home loaded with style and elegance

3 BR / 2 BA / Sleeps 6 | Quick view

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Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored and used as …
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$133

3 BR / 2 BA / Sleeps 6

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$133

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"SEMINARY ST HIDEAWAY" 3 Bd 2 Bth Home w/ Private Pool

3 BR / 2 BA / Sleeps 6 | Quick view

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***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This newly renovated 3 bedroom "home away from home" sits right smack in the middle of the Key West island and is a short distance to everywhere you will want to go during your vacation! Located on Seminary St, in a quiet …
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$370

3 BR / 2 BA / Sleeps 6

42 Reviews

$370

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

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 42 Reviews

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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). An outdoor …
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(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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$625

3 BR / 4 BA / Sleeps 8

22 Reviews

$625

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Bahama House

3 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 22 Reviews

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Reviews

(22)

BAHAMA HOUSE: Conveniently located in the heart of Old Town 1/2 block from shops, restaurants and nightlife on Duval Street. 3 bedrooms with private baths on 3 floors. Main level with gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors to the deck and private pool. Master bedroom …
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(22)

Beautiful house / bad management company / horrible owner

Left on Sep 03, 2009 for a stay in August 2009

The house was just what we wanted! PERFECT!!!!

However, the management company told us we could park in the empty spot that no one was using and take a spot on the side. The first night we were there, the OWNER of the house, who should NOT have my phone number called me while we were at dinner screaming at me and saying the two other cars were going to be towed. Then your management company…

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$249

3 BR / 2 BA / Sleeps 8

10 Reviews

$249

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Steps to Duval, Old Town Charm -Grand Bahama Suite

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 10 Reviews

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Reviews

(10)

Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable charm found only in …
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(10)

Amazing location!!!

Left on Nov 05, 2013 for a stay in August 2013

Location was wonderful one block block of Duval street, 3 of us shared the rental each had their own bedroom and there were 2 baths, and we 3 grown men having the 2nd bath was very valuable. The backyard area while not being the most beautiful thing in the world was still a great place to sit out and have a few drinks with friends old and new, our upstairs neighbors were great people and we …

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$625

3 BR / 3 BA / Sleeps 8

23 Reviews

$625

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Duval Penthouse

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 23 Reviews

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Reviews

(23)

DUVAL PENTHOUSE: Fabulous location, beautiful furnishings and plenty of space, suited to the casual lifestyle here in Key West. 2nd and 3rd story of the building; 3 bedrooms 2.5 bathrooms and an open floor plan. Living room, kitchen and master suite on the 2nd floor; French doors open from living room to the …
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(23)

Great houses in a great location.

Left on Apr 22, 2010 for a stay in April 2010

Great houses that are in a great location. The houses are beautifly done and the Duval Condo is really incredible. Be aware that it is on Duval and is very loud at night, but if you are comfortable with that it is a great place to stay. A great house for entertaining.

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$180

3 BR / 3 BA / Sleeps 6

1 / 24

$180

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FAN-tastic Getaway

3 BR / 3 BA / Sleeps 6 | Quick view

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FAN-tastic GETAWAY: Formerly owned by actress and fan dancer, Sally Rand.60" Smart TV and surround sound in living room; Dade County pine walls, wine cellar and every conceivable culinary tool in kitchen.1st floor master suite with Smart TV, WIFI, and bathroom ensuite with indoor shower and outdoor private shower…
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$107

3 BR / 3 BA / Sleeps 6

1 Reviews

$107

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Island Breeze

3 BR / 3 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

ISLAND BREEZE: Located in the exclusive Sanctuary within the Key West Golf Club, this is a spacious home with 3 bedrooms and a sleeper sofa. Enter an open floor plan of kitchen, dining room, half-bath and living room, with French doors leading outside to the private deck. Upstairs offers the Master bedroom with …
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(1)

My Key West Seclusion!

Left on Apr 06, 2013 for a stay in December 2012

I try to avoid the winter in the northeast as much as possible and this house in the sanctuary made my life a lot easier this year. The home is beautiful and I would recommend this home to everyone and anyone. It has all the amenities you need. Thank you at Home In Key West!

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$150

3 BR / 2 BA / Sleeps 8

1 / 8

$150

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30 night minimum stay requirement. Manatee Manor

3 BR / 2 BA / Sleeps 8 | Quick view

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Just 10 miles from Old Town you’ll find a seaside neighborhood that recalls Lower Keys life in the good old days, when you would go fishing in the morning, have lunch and a beer (or two) at Geiger Key Marina, fish some more in the afternoon then cook some of the catch out on your deck with a few cold ones. And while…
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$150

3 BR / 3 BA / Sleeps 8

1 / 25

$150

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Higgs Beach Hacienda - 3 Bed 2.5 Bath Monthly Rental Near Beach. Huge Yard!

3 BR / 3 BA / Sleeps 8 | Quick view

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Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath that runs along the Atlantic side of the island; very close (less …
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$572

3 BR / 4 BA / Sleeps 8

1 Reviews

$572

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Easy Livin'

3 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

EASY LIVIN' : Private home with pool in Truman Annex, a gated community in historic Old Town, in walking distance of anything you'll want to do during your visit.Bricked yard with outdoor living space and tranquil pool; custom built by the owners with family gatherings in mind. 3 bedrooms, sleeper sofa and 4 baths…
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(1)

Great Experience

Left on Jun 15, 2012 for a stay in May 2012

This house was beautiful. The pictures don't do it justice. It's the perfect house for families. The location couldn't be better - walking distance to everything.

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$183

3 BR / 2 BA / Sleeps 6

1 / 13

$183

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On Hemingway's Rounds ~ Monthly Rental

3 BR / 2 BA / Sleeps 6 | Quick view

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Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s …
  • Housekeeping Optional
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$175

3 BR / 3 BA / Sleeps 6

1 / 17

$175

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Mediterranean Caribbean Villa ~ Monthly Rental

3 BR / 3 BA / Sleeps 6 | Quick view

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Tucked behind a breathtaking tropical garden wall this spectacular Mediterranean Caribbean vacation rental home reflects a dynamic blend of contemporary Mediterranean with Caribbean architectural design. Located along one of Key West's most desirable residential streets this "Casa el Paradiso" most …
  • Housekeeping Optional
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$288

3 BR / 2 BA / Sleeps 6

1 / 10

$288

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Southernmost Retreat- 1 Block from Duval

3 BR / 2 BA / Sleeps 6 | Quick view

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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…
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  • Outdoor Dining Area
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  • Porch
  • Pet friendly - ask
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$227

3 BR / 3 BA / Sleeps 6

2 Reviews

$227

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"VILLA AZUL" Luxurious Monthly Home w/ Pvt Pool, Deck & Gorgeous Interior.

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks …
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  • Fitness Room
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(2)

Beautiful and comfortable home

Left on Jan 27, 2011 for a stay in December 2008

Villa azul is a wonderfully decorated and appointed home in the historic Old Town section of Key West. The home and grounds were beautiful, serene, private and cozy. It is hard to imagine that this property would not exceed anyone's expectations.

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$167

3 BR / 3 BA / Sleeps 6

4 Reviews

$167

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"TOBAGO GRANDE" Monthly Rental Home w/ Private Pool Just 1 Block To Duval

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

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Reviews

(4)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors, cathedral ceilings …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(4)

Perfect in Every Way!

Left on Nov 14, 2013 for a stay in October 2013

I stayed at Tobago house for the month of October and loved it! This was my 2nd stay - my best friend rented the house for 6 weeks in the spring of 2012 - and it was even better than I remembered. The house is well appointed with all the things one needs to set up house for a few days or for several weeks.

The location is prime and provides easy access to Duval street and all the shops and …

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$600

3 BR / 3 BA / Sleeps 6

9 Reviews

$600

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Kemp House

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort and contemporary …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(9)

very lovely

Left on Feb 09, 2009 for a stay in November 2008

Beautiful house. Near everything. Comfortable and well kept.

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$232

3 BR / 3 BA / Sleeps 6

1 / 21

$232

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Blackbeard's Treasure - MONTHLY Rental (30 night min.)

3 BR / 3 BA / Sleeps 6 | Quick view

Details

Save 3% off published rates if you pay by cash/check. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

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$175

3 BR / 2 BA / Sleeps 8

1 / 16

$175

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Island Elegance ~ Near The Beach ~ Monthly Rental

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this island home is a fabulous…
  • Housekeeping Optional
  • A/C or climate control
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$450

3 BR / 2 BA / Sleeps 6

8 Reviews

$450

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3 Bedroom Oceanfront Condo Key West

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 8 Reviews

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Reviews

(8)

Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at your fingertips. Sorry …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children

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Reviews

(8)

Beautiful oceanfront condo

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

We just rented this unit - it was wonderful!!! Beautiful kitchen,
recently remolded. Large family room. Bedrooms nice sizes. Unit
has a complete wrap around deck with ocean views. About 3 minute walk to Smathers beach. Really nice pool & 15 person hot tub. If you are
a beach person this unit is for you!! Only negative - not that close
to the down town area(5 minute car ride) - however unit …

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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

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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    $378

    3 BR / 3 BA / Sleeps 8

    6 Reviews

    $378

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    "ALMOST SOUTHERNMOST TOO" - Private Pool - Half Block To Duval St! Sleeps 8

    3 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 6 Reviews

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    Reviews

    (6)

    Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of shotgun architecture …
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    Fantastic, wonderful experience.

    Left on Nov 23, 2011 for a stay in November 2011

    Great location, in the center of KeyWest. Parked the car and walked,biked,trollied everywhere. Beautiful color scheme, every room was vibrant with a South Florida palat. Fantastic new kitchen and pool. Spent many hours on the pool patio with a 6-toe cat from the Hemmingway house. Just an all around wonderful experience. We will return to this house again in 2013...Thanks for making this a …

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    $300

    3 BR / 2 BA / Sleeps 8

    1 / 23

    $300

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    Oceanside Key West's Best Luxury Penthouse Condo

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    WOW Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool Direct Oceanfront 1490 Sq Ft Condo, 3 Bedrooms, 2 Baths, (Sleeps 6) Oceanside Marina is one of the newest and one of the most prestigious communities offering breath taking water views and large, open units. The amenities are rounded out …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - elevator access
    • Wheelchair accessible

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    $190

    3 BR / 3 BA / Sleeps 6

    1 Reviews

    $190

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    "CLUB CLARK" Gorgeous 3 Bd 3 Bth Home w/ Pvt Pool. Close to Dante's!

    3 BR / 3 BA / Sleeps 6 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a tub and full …
    • 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

    (1)

    Club Clark

    Left on Apr 10, 2014 for a stay in March 2014

    The place was really nice and the staff was very easy to work with. It was a very good vacation and would definitely like to stay there again.

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    $157

    3 BR / 3 BA / Sleeps 8

    1 / 26

    $157

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    "BEACH CLUB BREEZE" Monthly Rental - Two Story Home w/ Sun Deck & BBQ Grill

    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** This well-manicured, "home away from home" is two stories of wonderful! It has 3 bedrooms, 3 baths and has a colorful, comfortable style. The traditional white picket fence greets you when you arrive. Though, it's only a …
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $408

    3 BR / 2 BA / Sleeps 10

    13 Reviews

    $408

    Book

    "POOLSIDE PARADISE" Amazing Home 1/2 Block to Duval w/ Pool and Pvt Parking

    3 BR / 2 BA / Sleeps 10 | Quick view
    “ Excellent ” 13 Reviews

    Details

    Reviews

    (13)

    POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living room. The bath with …
    • Internet Access
    • A/C or climate control
    • Deck
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (13)

    Enjoyed our Stay

    Left on Oct 14, 2011 for a stay in September 2011

    The place was perfect for our group. My husband and I traveled with my parents and another couple. It worked out great because the parents stayed with us and our friends had their own little apartment which gave us all our privacy if needed. The location was pretty nice as well. We were one block off Duval. Even though we were down on the end closest to SouthernMost everything was within …

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    $408

    3 BR / 2 BA / Sleeps 10

    2 Reviews

    $408

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    "TOON HALL @ TROPICAL VILLAGE" - Great For Large Groups. Close to ATL Ocean!

    3 BR / 2 BA / Sleeps 10 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Best vacation ever!

    Left on Jul 01, 2014 for a stay in June 2014

    We took our family of 6 to Toon Hall and were greeted by 2 Cadillac SUV's at the airport to check us in and take us to our home. Toon Hall was very spacious and comfortable, perfectly situated blocks from the beach and Duvall Street. We were able to chill and grill at home by our pool or walk into town for a night of fun.We also loved the privacy and security the fenced yard offered.

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    $87

    3 BR / 3 BA / Sleeps 6

    4 Reviews

    $87

    Inquire

    Sunset Lake

    3 BR / 3 BA / Sleeps 6 | Quick view
    “ Excellent ” 4 Reviews

    Details

    Reviews

    (4)

    SUNSET LAKE -- Discover paradise and empty yourself of worries & hurries. Set at the end of a quiet lane, amid tropical landscaping, this 3-bedroom 3-bath townhome exudes an ambiance of peace and tranquility. The spacious interior overlooks the 15th and 17th holes on the Rees Jones designed golf course. Nature …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Grill
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (4)

    A Great Place to Reelax

    Left on Mar 10, 2011 for a stay in February 2011

    48 Spoonbill is in our view one of the best houses at the Golf Club. `With 3 bedrooms and 3 baths it's roomy and comfortable. With three screened porches and one open porch it has places to read, relax or watch the passing parade of birds, iguanas or golfers at any time of the day over two fairways and a small lake. The furnishings are excellent including completely up-to-date TV and …

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    $180

    3 BR / 3 BA / Sleeps 6

    1 / 27

    $180

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    Heliconia House

    3 BR / 3 BA / Sleeps 6 | Quick view

    Details

    HELICONIA HOUSE (monthly rental): Pristine 3 bedroom private home is a true island escape.Located in a quiet Old Town residential neighborhood. Only two short blocks to Duval Street . An open living room and dining room to dine or relax. Luxurious king bed with bath ensuite. Glass doors open to a private deck. …
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Parking
    • Grill
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $117

    3 BR / 3 BA / Sleeps 6

    1 Reviews

    $117

    Inquire

    Ecco Domani

    3 BR / 3 BA / Sleeps 6 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    ECCO DOMANI: A beautiful 3 story home with private pool and off street parking. Centrally located just off Simonton Street, you are 1 block to Duval Street, walking distance to galleries, shopping and restaurants. Living, dining and well-equipped kitchen, in an open floor plan on 1st level. On the 2nd floor is the …
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Parking
    • Grill
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Exceeded our expectations

    Left on Aug 09, 2014 for a stay in June 2014

    We loved this house!

    Super location - just one block off Duval - and also near to the beach; we went to the Southernmost beach a lot.

    We thought that the house is bigger then it looks in the photographs. We were expecting a small little conch cottage whereas we got a nice size 3 storey house. The bedrooms in particular were very roomy and of course the main bathroom with the jacuzzi bath, …

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    $338

    3 BR / 2 BA / Sleeps 8

    8 Reviews

    $338

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    "CASA KEY WEST @ DUVAL SQUARE" Extra Large Condo Located On Duval St.

    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 8 Reviews

    Details

    Reviews

    (8)

    Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe), This development extends from Duval Street to Simonton Street and is in the heart of historic Old Town. It is comprised of residential units upstairs and …
    • Shared outdoor pool (unheated)
    • 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

    (8)

    Beautiful Condo, Relaxing Community

    Left on Apr 02, 2013 for a stay in March 2013

    Had a great two-night stay with my all-adult family of 5. The condo has three full bedrooms so it was very comfortable for our group. The condo also features 2 completely windowed living areas (one upstairs, one downstairs) with stunning views of the harbor. The patio gets lots of sun for reading and sunbathing. We spent evenings cooking in the open kitchen and on the patio grilling.

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    $200

    3 BR / 3 BA / Sleeps 7

    1 / 16

    $200

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    Luxurious Manor ~ Monthly Rental

    3 BR / 3 BA / Sleeps 7 | Quick view

    Details

    Live in the lap of luxury in this stunningly renovated Key West classic "Eyebrow House." An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist / sailor to execute his plans to create this Luxurious …
    • A/C or climate control
    • Parking
    • Satellite or cable TV
    • Stereo or CD player
    • Telephone
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $408

    3 BR / 2 BA / Sleeps 6

    31 Reviews

    $408

    Book

    "CASA SERENDIPITY" - World Class Comfort in Lush, Tropical Paradise

    3 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 31 Reviews

    Details

    Reviews

    (31)

    Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and one full bath …
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (31)

    Very quaint

    Left on Jun 24, 2009 for a stay in March 2008

    Loved the house, nicely decorated and well kept. Lots of room except you
    need to watch your head going down the stairs - low clearance. Nice wrap
    around porch and yard with small pool (too cold for me but the kids loved it).
    The walk to town (Duval St area) was longer than expected especially since the
    house is across from the cemetary (above ground).

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    $418

    3 BR / 4 BA / Sleeps 8

    50 Reviews

    $418

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    TROPICAL RETREAT- Upscale Home w/ Private Pool & BBQ Grill 1/2 Block To Duval

    3 BR / 4 BA / Sleeps 8 | Quick view
    “ Excellent ” 50 Reviews

    Details

    Reviews

    (50)

    Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting nightlife, music, bars and …
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (50)

    Perfect place to stay with a family

    Left on Jun 24, 2009 for a stay in July 2007

    It was truly a perfect place with the pool, patio, location, and was laid out just great. We had 8 people (4 adults & 4 teenagers) and had more than enuff room for everyone. Can't imagine anyone would be dissappointed. Also had a large enuff secure driveway that we could park our full size rental van inside behind a lockable gate (i.e. no parking problems).

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    $743

    3 BR / 4 BA / Sleeps 6

    1 / 22

    $743

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    The Water's Edge

    3 BR / 4 BA / Sleeps 6 | Quick view

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    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable three-bedroom, four-bath lies …
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area

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    $418

    3 BR / 3 BA / Sleeps 8

    8 Reviews

    $418

    Book

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

    3 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 8 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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    $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

    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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