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$99

3 BR / 2 BA / Sleeps 8

7 Reviews

$99

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Family Friendly Executive Bay**Discounts Available**

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 7 Reviews

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(7)

Beautiful three bedroom bay side townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, …
  • Shared outdoor pool (unheated)
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  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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(7)

Wonderful

Left on Jul 20, 2013 for a stay in June 2013

This rental by far was one of the best rentals we have stayed at. The location and the house were perfect! The house is very large and everything you can imagine has been supplied. The pool, community center, tennis courts and complex in general were beautiful and well maintained. Really good experience!

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$99

2 BR / 2 BA / Sleeps 8

1 Reviews

$99

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Newly Renovated Executive Bay Townhouse**Discounts Available**

2 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Beautiful two bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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(1)

Great condo, perfect location!

Left on Jan 02, 2015 for a stay in December 2014

I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and very friendly. The location was close to everything. The property management service was excellent. We had a wonderful family vacation and will definitely be returning next year!

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$145

2 BR / 2 BA / Sleeps 6

11 Reviews

$145

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Ocean Pointe Two Bedroom Ocean Views

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 11 Reviews

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Reviews

(11)

Beautiful, newly remodeled 2 bedroom, 2 bathroom condo in sunny Tavernier Key (North Florida Keys), with a king bed in the master bedroom and 2 twin beds in the second bedroom, featuring flat screen TVs, a private balcony with chairs, cable TV, and complementary amenities. Ocean Pointe Suites at Key Largo is an all-…
  • Ocean or water views
  • Shared outdoor pool (unheated)
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(11)

Typical Florida Keys experience

Left on Jan 01, 2014 for a stay in December 2013

The Florida Keys are laid back and most of the structures look like something out of a Popeye movie. Ocean Point Suites is no better and no worse than the competition. Finding the reservation desk is a bit confusing, but the receptionist was friendly and helpful.

We had two apartments, both pleasant enough, both with a view of the sea (and some swamp) and dozens of cats running around behind …

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$400

3 BR / 3 BA / Sleeps 6

Eliza's Jewel is a charming property close to White Street. - Florida Keys vacation rentals
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$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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$490

4 BR / 4 BA / Sleeps 8

39 Reviews

$490

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Louisa House: A comfortable four bedroom vacation hideaway

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 39 Reviews

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Reviews

(39)

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable vacation hideaway. …
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(39)

Great House, Family Friendly

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

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

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$470

4 BR / 2 BA / Sleeps 8

Pete's Cottages: Twin Cypress cottages steps from Duval - Florida Keys vacation rentals
1 / 28

$470

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Pete's Cottages: Twin Cypress cottages steps from Duval

4 BR / 2 BA / Sleeps 8 | 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
  • Deck
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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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$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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(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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$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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(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 …
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(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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$1,048

6 BR / 6 BA / Sleeps 22

1 / 33

$1,048

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"PAPA'S HIDEAWAY - NIGHTLY GROUP UNIT" Guesthouse - Sleeps up to 22!

6 BR / 6 BA / Sleeps 22 | Quick view

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Papa's Hideaway is a Guesthouse property comprised of Garden of Eden , Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls , Islands in the Stream Minimum Stay: Please contact Key West Vacation Rentals regarding minimum stays and special rates. Minimum stay requirements apply on weekends (at least…
  • Internet Access
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  • Balcony or terrace
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$133

3 BR / 2 BA / Sleeps 6

1 / 25

$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 …
  • Internet Access
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  • Satellite or cable TV
  • Pet friendly
  • Suitable for children - ask
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$270

2 BR / 1 BA / Sleeps 4

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

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 …
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$220

0 BR / 1 BA / Sleeps 2

42 Reviews

$220

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

0 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 42 Reviews

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Reviews

(42)

Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
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  • Suitable for children - ask
  • Suitable for the elderly - ask
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(42)

great place for two!

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

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

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$580

3 BR / 3 BA / Sleeps 6

1 / 12

$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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$240

1 BR / 2 BA / Sleeps 2

47 Reviews

$240

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

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

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Reviews

(47)

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
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  • Suitable for children - ask
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(47)

Nice

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

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

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$110

1 BR / 2 BA / Sleeps 2

2 Reviews

$110

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Newton Street Hideaway: A secluded one bedroom

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

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(2)

30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale for an extended stay …
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(2)

A Second Home

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

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

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$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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(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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$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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(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 …
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(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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$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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$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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$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…
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$220

1 BR / 1 BA / Sleeps 4

49 Reviews

$220

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Colony Poolside: A charming bungalow near the historic cemetery

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 49 Reviews

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Reviews

(49)

Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The bungalow features an one level open space living/dining area, full kitchen and a spacious bedroom with a king size bed. There is a nice private deck …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
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  • Suitable for children - ask
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(49)

Disappointing

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

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

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$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 …
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(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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$113

2 BR / 2 BA / Sleeps 6

1 / 17

$113

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

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 …
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  • Suitable for children - ask
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$500

4 BR / 3 BA / Sleeps 8

9 Reviews

$500

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Private Beachfront Paradise

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen. The covered patio is huge at 60X15. The second floor…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
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  • Suitable for the elderly
  • Wheelchair accessible

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(9)

Great House and Great Property Owner

Left on Dec 06, 2013 for a stay in November 2013

My family and I had the pleasure of staying at this home during Thanksgiving week. Not only did the house beat our expectations, but the communication with the owner was also fantastic. She was so helpful with every inquiry we had and went well above what we expected to make sure our time in Islamorada was as well as it could be.

The house itself was extremely clean, beautiful and very …

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$750

4 BR / 4 BA / Sleeps 8

27 Reviews

$750

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Southard Street Queen Conch - A Historic compound with large sunny pool

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 27 Reviews

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Reviews

(27)

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor plan with living and dining room, …
  • Internet Access
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(27)

What a lovely property

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

This is a great home in a great location. All of the rooms are wonderfully furnished and clean. The backporch and sun deck are truly amazing and relaxing. I especially enjoyed the privacy of the pool and backyard for relaxing and resting. I would stay here again over and over again.

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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

Details

Reviews

(14)

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

Details

Reviews

(14)

Great Time

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

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

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$370

3 BR / 2 BA / Sleeps 6

42 Reviews

$370

Inquire

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

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

Details

Reviews

(42)

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

Details

Reviews

(42)

Hidden Jewel

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

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

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$240

1 BR / 1 BA / Sleeps 2

48 Reviews

$240

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Ann Street Tranquility: A cozy and peaceful cottage

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 48 Reviews

Details

Reviews

(48)

This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(48)

Ann Street

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

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

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$320

2 BR / 2 BA / Sleeps 4

30 Reviews

$320

Inquire

Havana Lane: A classic conch cottage with rustic charm

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

Details

Reviews

(30)

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

Details

Reviews

(30)

Gorgeous surroundings, comfortable Key West home

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

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

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$290

2 BR / 2 BA / Sleeps 6

18 Reviews

$290

Inquire

Beach Club #103 - Unique oceanfront living with breathtaking views

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

Details

Reviews

(18)

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

Details

Reviews

(18)

Great Location

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

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

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$143

2 BR / 2 BA / Sleeps 4

1 / 16

$143

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Tropical condo with spectacular ocean view

2 BR / 2 BA / Sleeps 4 | Quick view

Details

14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area, full kitchen, washer/dryer, central heat/airconditioning and a private patio or balcony. This unit has a great corner view of the ocean! The kitchen is equipped with stove, refrigerator, dishwasher, utensils, cookware…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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

Details

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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$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

Details

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 …
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$243

3 BR / 3 BA / Sleeps 6

11 Reviews

$243

Inquire

Bay Harbour A-304- 7 night minimum

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 11 Reviews

Details

Reviews

(11)

Brilliant views of Sandy Cove Yacht Basin and the Atlantic Ocean, combined with 50ft of deep-water dockage (uses 50amp) complete this 3BD/2.5BA Bay Harbour Condos penthouse. This spacious unit features updated furnishings, a full kitchen with stainless steel appliances and granite countertops, a spacious screened …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

Details

Reviews

(11)

Excellent. Very nice unit

Left on Aug 23, 2011 for a stay in July 2011

We thorough enjoyed our stat in this unit. It was spotless, had a nice view, and very convenient. We would definitely ask for the same unit next time.

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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

Inquire

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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$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

Details

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

Inquire

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

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

Details

Reviews

(43)

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

Details

Reviews

(43)

Lovely cottage and great location

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

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

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$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

Details

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 …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(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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$850

4 BR / 4 BA / Sleeps 8

15 Reviews

$850

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Villa Tropicale: A lush, secluded estate in the Casa Marina District

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of mature palms, birds of …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

The coolest house ever!

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

I would highly recommend this property to anyone looking for a place to stay in Key West with a group of friends. It offers the best of both worlds....You could never leave the property and have a wonderful time or a quick cab ride and you're at Duval Street. Our group ventured off on a day trip to the Dry Tortugas, which was set up by the properties conceier service...and that was awesome...…

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$149

2 BR / 2 BA / Sleeps 4

1 / 1

$149

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Moon Bay Condo A-206

2 BR / 2 BA / Sleeps 4 | Quick view

Details

A beautifully decorated condo located at mm 104. This unit has 2 bedrooms and 1.5 baths and its own deeded boat slip. This condo in conveniently located close to the main land. This is a perfect condo for fishermen, divers, or just a Key's getaway. Amenities include heated pool, jacuzzi, tennis courts, sauna, and game…
  • Shared outdoor pool (unheated)
  • Sauna
  • Internet Access
  • A/C or climate control
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$270

2 BR / 2 BA / Sleeps 6

21 Reviews

$270

Inquire

Vista Fresco : Oceanside condominiums with resort-style amenities

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

Details

Reviews

(21)

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

Details

Reviews

(21)

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

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

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

For the condo, everything was …

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$77

2 BR / 2 BA / Sleeps 4

1 / 21

$77

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Executive Bay Club A-1

2 BR / 2 BA / Sleeps 4 | Quick view

Details

N/A
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Dishwasher
  • Microwave
  • Toaster
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$258

2 BR / 3 BA / Sleeps 6

3 Reviews

$258

Book

Islamorada Luxury Waterfront Condo with Boat Slip

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

Details

Reviews

(3)

Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(3)

Wonderful stay at Bay Harbour

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

This condo exceeded our expectations. It was truly a home away from home. It has all the amenities you will need to have a great vacation. The kitchen is fully furnished, the condo is spacious, and the little extras like bikes, tennis rackets, and baseball gloves are an added bonus.

Our family was happy to see a manatee and calf in the water right outside the condo!

Pool was very …

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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

Inquire

Beach Club #201 - Unique Oceanfront living

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. 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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$190

2 BR / 3 BA / Sleeps 4

1 Reviews

$190

Inquire

Futura Townhome 731

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

Details

Reviews

(1)

Enjoy the spectacular view of the Florida Bay from this beautiful townhome. There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the property. Make your self at home in our home away from home. Boat dockage …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Most awesome vacation in Islamorda Florida!!

Left on Jul 14, 2010 for a stay in June 2010

Futura - The price is right. The location is perfect. The townhouse is very comfortable, beautifuly decorated, with a most awesome view of Florida Bay. The marina, dock, and boat ramp are all at the same location and are well maintained. The pool, tennis courts, basketball, and volley ball court are an added bonus.
In addition, Freewheeler Realty has been providing our vacation services for over …

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$214

2 BR / 3 BA / Sleeps 6

1 / 24

$214

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LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

2 BR / 3 BA / Sleeps 6 | Quick view

Details

This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set along quaint streets …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

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$66

1 BR / 1 BA / Sleeps 4

1 Reviews

$66

Book

Artist cottage with hot tub

1 BR / 1 BA / Sleeps 4 | Quick view
“ Poor ” 1 Reviews

Details

Reviews

(1)

The artist cottage is mainly used as a residence for visiting artist that are in town doing shows at my gallery. The cottage is very quiet and secluded with lots of privacy,situated amongst 100 year old trees and lush tropical foliage. The cottage was built in 1913 and is a true piece of old key west. The property is…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wonderful little cottage, not so wonderful owner

Left on Apr 07, 2014 for a stay in June 2013

First, let me say that I intended not to review this property simply because I didn't want to leave a negative review but today I got a letter in the mail that made me change my mind.The cottage was great, clean,neat,location great, and a great place for our little dogs, who were welcome. First there was no washing machine which didn't seem a problem because David assured us that our laundry …

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