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$70

2 BR / 2 BA / Sleeps 4

Bogey's Retreat - Key West vacation rentals
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$70

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Bogey's Retreat

2 BR / 2 BA / Sleeps 4 | Quick view

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BOGEY'S RETREAT: Ideal for a golfer, it is located at Key West Golf Club. 2 pools nearby. $50 security deposit for Association gym card use. Stainless kitchen appliances, new beds and furnishings. HDTVs, DVD/Blu-Ray, Bose sound and WIFI.Rear bedroom looks at the golf course, front bedroom has French doors …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Grill
  • Television
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$70

2 BR / 2 BA / Sleeps 6

2 Reviews

$70

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Wind Swept

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

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Reviews

(2)

WIND SWEPT: Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States.This lovely 2 bedroom 1.5 bath townhome is freshly painted and newly furnished. Enter the open and airy living space which includes kitchen…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(2)

Wind Swept

Left on Dec 12, 2013 for a stay in October 2013

The house was great Loved being on the golf course very quite area great pool Security was very nice and helpful The staff: At home was great Libby is the best

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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

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

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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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$113

2 BR / 2 BA / Sleeps 6

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

$113

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

2 BR / 2 BA / Sleeps 6 | Quick view

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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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$270

2 BR / 1 BA / Sleeps 4

Pete's East Cottage: Cypress east cottage steps from Duval - Key West vacation rentals
1 / 13

$270

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

2 BR / 1 BA / Sleeps 4 | Quick view

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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

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$113

2 BR / 2 BA / Sleeps 4

South Street Cottage: Bright & sunny in the Casa Marina district - Key West vacation rentals
1 / 11

$113

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

2 BR / 2 BA / Sleeps 4 | Quick view

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

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$225

2 BR / 3 BA / Sleeps 6

47 Reviews

$225

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Duval Sea Turtle

2 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 47 Reviews

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Reviews

(47)

DUVAL SEA TURTLE: This townhome has 2 bedrooms and 2.5 baths with a balcony off the master bedroom and the living room.Covered, gated parking space, WIFI, 3 TVs, free long distance calls King mattress, washer/dryer, and living room furniture new in March 2014.There is a community pool area to relax in the refreshing…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(47)

Very Nice !

Left on Nov 07, 2008 for a stay in June 2008

We had a good time. The Sea Turtle

was really nice. We rented a car but

we really didn't use it much we could

walk to all the main attractions.

It was wonderful. The fireworks on the

4th were great!!

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$320

2 BR / 2 BA / Sleeps 4

36 Reviews

$320

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Catherine House: A charming Old Town Key West cottage

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 36 Reviews

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Reviews

(36)

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

Details

Reviews

(36)

Cozy spot in perfect location

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

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

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$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

2 BR / 3 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

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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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$260

2 BR / 3 BA / Sleeps 4

1 / 28

$260

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"THE FOREVER AFTER HOUSE" KW Golf Club Home on 18th Fairway w/ Pvt Pool, Spa

2 BR / 3 BA / Sleeps 4 | Quick view

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Luxury living on the 18th tee! Arguably the most beautiful home on the Key West golf course, meticulously created by Key West's premier interior designer. The best location to enjoy the peace and quiet with your special friends and family. BBQ on your spacious deck by the private pool. Ready access to the Key West…
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$265

2 BR / 2 BA / Sleeps 4

34 Reviews

$265

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Leeward Isle Key West Retreat

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 34 Reviews

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Reviews

(34)

LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of Old Town. 2-bedroom 2-bath townhome remodeled from top to bottom. Decorated with Key West flair, this is truly a unique property. Flatscreen TVs, stereo, CD player and …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(34)

Family getaway

Left on Nov 07, 2008 for a stay in July 2007

The property and the condo was perfect. Very close to Duval St. and ample parking both on lot and street. On property staff not friendly and rental staff a bit stuffy as friends were discouraged to visiting. When they say no more than 4 people staying at one time they mean it. Although the unit has ample space for more people and isn't this a vacation. A bit pricey but the unit has everything…

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$70

2 BR / 2 BA / Sleeps 6

1 / 32

$70

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A Little Slice of Paradise

2 BR / 2 BA / Sleeps 6 | Quick view

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A LITTLE SLICE OF PARADISE (monthly rental): Secluded community, steps from the golf course, minutes from the beach, airport and some of the locals' favorite restaurants. 2 bedrooms, 1 full bath upstairs; open floor plan downstairs with sleeper sofa for guests, half bath, and screened porch. WIFI, HDTVs, fully-…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Television
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

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Beach Club #104 - Unique oceanfront living with breathtaking views

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

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

Details

Reviews

(15)

Good facility overall, but lots of rules for teeneagers

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

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

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$270

2 BR / 1 BA / Sleeps 4

1 Reviews

$270

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Pete's West Cottage steps from Duval

2 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

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

(1)

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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$290

2 BR / 2 BA / Sleeps 5

14 Reviews

$290

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Beach Club #204 - Unique Oceanfront living

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 14 Reviews

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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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$320

2 BR / 2 BA / Sleeps 4

30 Reviews

$320

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Havana Lane: A classic conch cottage with rustic charm

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 30 Reviews

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Reviews

(30)

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

Details

Reviews

(30)

Gorgeous surroundings, comfortable Key West home

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

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

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$290

2 BR / 2 BA / Sleeps 6

18 Reviews

$290

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Beach Club #103 - Unique oceanfront living with breathtaking views

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 18 Reviews

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Reviews

(18)

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

Details

Reviews

(18)

Great Location

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

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

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$209

2 BR / 2 BA / Sleeps 5

11 Reviews

$209

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

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 11 Reviews

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Reviews

(11)

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

Details

Reviews

(11)

location! location! location!

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

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

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$229

2 BR / 2 BA / Sleeps 8

5 Reviews

$229

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

2 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 5 Reviews

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Reviews

(5)

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

(5)

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

2 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 43 Reviews

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Reviews

(43)

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

Details

Reviews

(43)

Lovely cottage and great location

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

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

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$265

2 BR / 2 BA / Sleeps 4

32 Reviews

$265

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Conch Wind

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 32 Reviews

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Reviews

(32)

CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dining area with an open kitchen. A separate private deck just off the dining area complete with BBQ grill and laundry closet. Guest bedroom on the main level with 2 twin beds …
  • Shared outdoor pool (unheated)
  • Internet Access
  • 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

Details

Reviews

(32)

key west

Left on Feb 18, 2010 for a stay in January 2010

location was perfect.
The only problem was our front door key was a little hard to get to work, other than that, perfect.
Gary&Vicki

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$400

2 BR / 2 BA / Sleeps 4

10 Reviews

$400

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Casa Camilla

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the property is beautifully …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(10)

absolutely gorgeous!

Left on Dec 07, 2011 for a stay in November 2011

The house is absolutely beautiful and in a great location; easy to get to Duval street. Very quiet neighborhood. The house had everything except internet access and a heated pool/jacuzzi.

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$270

2 BR / 2 BA / Sleeps 6

21 Reviews

$270

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Vista Fresco : Oceanside condominiums with resort-style amenities

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 21 Reviews

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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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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

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Beach Club #201 - Unique Oceanfront living

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

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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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$290

2 BR / 2 BA / Sleeps 6

9 Reviews

$290

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Beach Club #112 - Unique Oceanfront living

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

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

Details

Reviews

(9)

Fabulous view

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

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

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$167

2 BR / 2 BA / Sleeps 4

1 / 30

$167

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

2 BR / 2 BA / Sleeps 4 | Quick view

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

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$367

2 BR / 2 BA / Sleeps 4

1 / 32

$367

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Steam Plant - Luxurious 2/2 Condo w/ Amazing Views & Private Hot Tub

2 BR / 2 BA / Sleeps 4 | Quick view

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Key West regulars know that one of the best parts of downtown is actually a few blocks of the main street at the Historic Key West Seaport. The Seaport is a big part of the heart of Key West where dingy captains, commercial fisherman, sports anglers, pleasure seeking vessels, and those that admire it all come together…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$117

2 BR / 2 BA / Sleeps 6

1 / 17

$117

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Amazing Grace

2 BR / 2 BA / Sleeps 6 | Quick view

Details

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

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$230

2 BR / 2 BA / Sleeps 5

2 Reviews

$230

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Royal Palm

2 BR / 2 BA / Sleeps 5 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

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

Details

Reviews

(2)

Really Great Experience

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

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

Thank you.

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$167

2 BR / 2 BA / Sleeps 6

8 Reviews

$167

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

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

Details

Reviews

(8)

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

Details

Reviews

(8)

Always love 625

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

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

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$200

2 BR / 2 BA / Sleeps 4

1 / 12

$200

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30 night Minimum Stay Heart of Historic downtown 2 bedroom 2 1/2 Bathroom

2 BR / 2 BA / Sleeps 4 | Quick view

Details

This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities include one …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

2 BR / 2 BA / Sleeps 4

8 Reviews

$198

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"Shipyard Perch" Weekly or Monthly (Truman Annex) - Gourmet Appointed Kitchen

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The Shipyard’s Perch is a great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Wonderful trip!

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

Something to do every day, perfect location, nice condo.

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$150

2 BR / 1 BA / Sleeps 4

1 / 15

$150

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

2 BR / 1 BA / Sleeps 4 | Quick view

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

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$400

2 BR / 2 BA / Sleeps 4

2 Reviews

$400

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Quilted Giraffe

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 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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$83

2 BR / 2 BA / Sleeps 6

1 / 30

$83

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

2 BR / 2 BA / Sleeps 6 | Quick view

Details

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

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$215

2 BR / 1 BA / Sleeps 6

1 / 6

$215

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The Banyan Resort at Key West

2 BR / 1 BA / Sleeps 6 | Quick view

Details

Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge yourself at this …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$255

2 BR / 2 BA / Sleeps 5

10 Reviews

$255

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Havana Hideaway

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships, cruise ships, pleasure …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(10)

Week in Paradise

Left on Jan 16, 2013 for a stay in December 2012

This was one of the greatest stays that we have had. Condo was within walking distance to everything block to most. Very nice place to stay. Easy check in and check out process. This place has a great view from pool. We were here in December with about 80 degree temps each day so we shut down the air and had the doors open most of the time the only draw back to this is the chickens will wake…

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$400

2 BR / 2 BA / Sleeps 8

1 / 6

$400

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Hyatt Sunset Harbor Key West, FL

2 BR / 2 BA / Sleeps 8 | Quick view

Details

Please note. This is a timeshare rental and I have only 1 week allotted to me. Please do not request any dates other than available week of March 8th through the 15th. This Hyatt property is a 2 floor--2 Bedroom Caribbean furnished condo type unit situated right in the heart of Key West facing the famous sunset. …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Balcony or terrace
  • Parking
  • Grill
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

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$286

2 BR / 2 BA / Sleeps 4

20 Reviews

$286

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Foundry's Corner

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 20 Reviews

Details

Reviews

(20)

Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious Truman Annex gated community only a block from Duval and the Historic Seaport. While the impressive brick structure that houses this residence was built around 1845 as …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(20)

Awesome Hideaway

Left on Nov 19, 2008 for a stay in October 2008

I was absolutely thrilled with this property, the townhouse was well appointed and beyond comfortable. The location cant be beat as its just a minutes walk to the north end of Duval St. and all its bars and restaurants. We were there for Fantasy Fest and having a secluded, quiet place to come back to away from all the madness that is FF was quite wonderful. I suppose if I had to rate this …

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$199

2 BR / 1 BA / Sleeps 6

15 Reviews

$199

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Center of It All - Paradise Island Suite

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

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 children - ask
  • Suitable for the elderly

Details

Reviews

(15)

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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$250

2 BR / 2 BA / Sleeps 6

25 Reviews

$250

Inquire

Duval Street Suite

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 25 Reviews

Details

Reviews

(25)

Everybody knows it's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and expansive Bahamian-style …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating

Details

Reviews

(25)

Beth was great!

Left on Apr 06, 2011 for a stay in March 2011

It was a great location. Any problems we had Beth got it taken care of very quick...even one of the tvs went out and they replaced that day. It could use internet was the only thing we missed.

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$308

2 BR / 2 BA / Sleeps 6

13 Reviews

$308

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"GARDEN OF EDEN" - Papa's Hideaway Historic Inn's 2 BR/2 Bath Cottage

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 13 Reviews

Details

Reviews

(13)

Located at Papa's Hideaway , the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best attractions. The …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

Great Cottage Property

Left on Nov 22, 2013 for a stay in November 2013

I spent a long weekend at this property with my wife and another couple. The property was clean, well maintained, quiet (although only a short walk to Duval) and very private. The landscaping, outdoor seating and pool were also nice added features. We would definitely stay again.

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$388

2 BR / 3 BA / Sleeps 6

1 / 34

$388

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"HAVANA HIDEAWAY" - Beautiful Home w/ Pvt Pool Just Steps To Duval

2 BR / 3 BA / Sleeps 6 | Quick view

Details

The Beach Boys on one of their many trips to Key West (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in the best conch …
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$185

2 BR / 1 BA / Sleeps 4

21 Reviews

$185

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Shipyard

2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 21 Reviews

Details

Reviews

(21)

This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket fences give the …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(21)

Great for Boat Races!

Left on Nov 13, 2008 for a stay in November 2008

Great location for walking to watch the races and Duval Street. Quaint,clean, and spacious. Small bathroom and kitchen that need an update, but otherwise a great place! I stayed in a gated complex so the added security was a plus and I felt safe at all times. I would certainly stay again without hesitation!

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$183

2 BR / 2 BA / Sleeps 6

1 / 20

$183

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A Low Key Paradise

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your family member …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$250

2 BR / 2 BA / Sleeps 6

34 Reviews

$250

Inquire

Duval Square

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 34 Reviews

Details

Reviews

(34)

The rooftop community of Duval Square is a prime perch from which to launch the best tropical vacation ever. The townhomes cluster on the second story above their namesake square. Winding pathways bordered by swaying palm and colorful plantings arranged in terracotta pots define the layout. Best of all, the small …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(34)

Barbecue

Left on Aug 14, 2008 for a stay in February 2008

The vacation week was good, except for the use of the barbecue. When we had stayed there before we had used the barbecue every other night (and gone out for dinner the other nights). We have a 6 yr. old and the deal we made with him was the above (as you know 6 yr. olds couldn't care less about eating out) and prefer barbecues and staying in. (ours does anyway). This February we were told that we…

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$133

2 BR / 2 BA / Sleeps 6

2 Reviews

$133

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"PARADISE PALMS" Tropical Key West Home w/ BBQ Grill & Pvt Patio

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

Details

Reviews

(2)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The master bedroom features a king-size bed, flat screen television, en suite bathroom and french doors leading you out to the private side deck. The second bedroom features a queen-size bed and flat screen television. The …
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great house, nice location

Left on Mar 03, 2014 for a stay in February 2014

great house, nice location. Would be perfect if there was a pool. Fantastic private outdoor shower. We were there for a month and for the money, it should have included a cleaning half way through our stay. It was spotless when we checked in. We just we not up for housework during our vacation. I would recommend it.

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$216

2 BR / 2 BA / Sleeps 6

1 / 17

$216

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Key West Bluewater Retreat

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It offers a private patio, …
    • Pet friendly - ask
    • Suitable for children

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    $400

    2 BR / 2 BA / Sleeps 4

    47 Reviews

    $400

    Inquire

    Valhalla

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Excellent ” 47 Reviews

    Details

    Reviews

    (47)

    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

    (47)

    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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    $225

    2 BR / 2 BA / Sleeps 4

    9 Reviews

    $225

    Inquire

    President's Lane

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Excellent ” 9 Reviews

    Details

    Reviews

    (9)

    If any residence deserves the location-location-location mantra, it's this two-bedroom, two-bath townhouse in Truman Annex. The first "location" is the island of Key West, a world-class vacation destination. The second is Truman Annex, a premiere gated waterfront community named for President Harry Truman. The third "…
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Central heating
    • Suitable for the elderly - ask

    Details

    Reviews

    (9)

    great location

    Left on Aug 16, 2008 for a stay in April 2008

    The location of the townhouse in Truman annex was perfect for us. I walked to the Fort Zachary beautiful beach every morning for yoga on the beach and sunbathing and snorkeling. We were able to walk to town and most everywhere we wanted to go. The house was clean,beautifully appointed and comfortable for two couples. We would definitely stay here again.

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