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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

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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

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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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$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

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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

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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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$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

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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

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(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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$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

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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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$225

2 BR / 2 BA / Sleeps 4

9 Reviews

$225

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President's Lane

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

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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

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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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$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

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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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$743

3 BR / 4 BA / Sleeps 8

1 / 25

$743

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Ocean Paradise

3 BR / 4 BA / Sleeps 8 | Quick view

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Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing available as well. …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$255

2 BR / 2 BA / Sleeps 4

3 Reviews

$255

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Banana Key

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

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Reviews

(3)

Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just steps from the Gulf …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(3)

Better than the pictures!!!

Left on Jan 11, 2012 for a stay in December 2011

We absolutely loved the apartment and the fantastic walk behind the apartment that lead to Duval Street. If we could retire in Key West, this apartment is perfect. The master bedroom was so private, we barely noticed our two daughters in their room. The only complaint would be that the internet signal was weak and we a few problems with that.

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$743

3 BR / 4 BA / Sleeps 6

1 / 22

$743

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The Water's Edge

3 BR / 4 BA / Sleeps 6 | Quick view

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

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$184

2 BR / 1 BA / Sleeps 4

4 Reviews

$184

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"LAZY LANE" - WEEKLY OR MONTHLY(Truman Annex) - Color and Style Front to Back

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

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Reviews

(4)

***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The spacious living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private deck which features outdoor seating and a Gas BBQ Grill, making your vacation a true …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

261 Lazy Lane- Vacation!!!

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

The condo was clean and had all of the necessary items needed for a 10 day stay (cleaning products, laundry, etc). It was a nice place to stay and would stay there again next time

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$700

4 BR / 3 BA / Sleeps 8

15 Reviews

$700

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Admiral's Lane

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 15 Reviews

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Reviews

(15)

As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere gated waterfront …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

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Reviews

(15)

Excellent experience

Left on May 11, 2010 for a stay in March 2010

Beautiful accommodations, helpful and friendly staff, and excellent experience
overall. Highly recommend both the house and the management company.

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$258

2 BR / 3 BA / Sleeps 6

1 / 11

$258

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Island Brownstone ~ Weekly Rental

2 BR / 3 BA / Sleeps 6 | Quick view

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An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as "Truman Annex", this striking tri-level historic building has all the architectural allure of a 19th century urban brownstone with an unparalleled modern Caribbean reinterpretation. …
  • A/C or climate control
  • Porch
  • Grill
  • Television
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$750

4 BR / 3 BA / Sleeps 8

1 Reviews

$750

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By The Beautiful Sea ~ Weekly Rental

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

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Reviews

(1)

If you've been searching for a private home overlooking the tropical turquoise sea, you've probably found that nearly all water-view vacation rental properties on Key West are hotels, condominiums, or time-shares, and that it's nearly impossible to find a private Key West house that offers both an open …
  • Internet Access
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(1)

Location, view, everything you need!

Left on Jun 23, 2014 for a stay in June 2014

Very convenient to all the local sights and everything needed for a reasonably large group of people. Everyone had their space but also a large living/dining/kitchen for gathering. We enjoyed the week!

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$184

2 BR / 1 BA / Sleeps 4

5 Reviews

$184

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"SEASHORE AT THE SHIPYARD" - Weekly Or Monthly (Truman Annex) Gourmet Kitchen

2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 5 Reviews

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Reviews

(5)

***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are…
  • 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

Details

Reviews

(5)

Too small - bad/uncomfortable/inadequate seating in living room

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

Condo well-kept but too small for 4 people. Really feel that rental should specify actual square footage of a unit. It was clean and satisfactory, located in a quiet enclave. But not a good value for the money, actually. Swimming pool was old/too small and the concrete - stained - and pool area very unkempt. It was a real turn-off.

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$184

2 BR / 1 BA / Sleeps 4

4 Reviews

$184

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"SHIPYARD" - WEEKLY OR MONTHLY (Truman Annex) - A Short Stroll to Sunset!

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

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Reviews

(4)

***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The Shipyard 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 magnificent development…
  • 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

(4)

Great Get away

Left on Nov 29, 2013 for a stay in November 2013

The Shipyard Complex is very nice, clean and easy to get in and out of. The house is close to all the action of Duval, the boat races and if you want to take a walk to the Southern Most that's fairly close too. Great weather, the house is outfitted perfectly with all the comforts of home. No doubt that I'll rent it again next year.

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$472

3 BR / 3 BA / Sleeps 6

1 / 15

$472

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Private Key West Sunset ~ Weekly Rental

3 BR / 3 BA / Sleeps 6 | Quick view

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Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island visitor should…
  • A/C or climate control
  • Balcony or terrace
  • Television
  • Stereo or CD player
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$258

2 BR / 3 BA / Sleeps 6

2 Reviews

$258

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Foundry on the Waterfront ~ Weekly Rental

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

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Reviews

(2)

Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern luxury condominium constructed within an important piece of historic American architecture. Situated along the gateway waterfront to the island…
  • A/C or climate control
  • Porch
  • Grill
  • Television
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Perfect location to stay in Key West

Left on Nov 28, 2011 for a stay in November 2011

This unit was in the perfect location to experience Duval Street and Mallory Square. Close walking distance to everything and yet just far enough away so you do not hear the goings on late at night! The condo was ready when we arrived and spotless. It had everything we needed right down to beach towels and chairs.

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$200

2 BR / 1 BA / Sleeps 4

3 Reviews

$200

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Céad Míle Fáilte - Truman Annex

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

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Reviews

(3)

Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our home across the pond. We know you will enjoy your time in Key West as much as we …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(3)

Great Location

Left on Sep 11, 2010 for a stay in August 2009

The accommodation was very clean, spacious, and with an incredible location close to down town and local grocery shops. Renting this property was a great decision as it comes with access to swimming pool which was great for the kids.

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$300

2 BR / 2 BA / Sleeps 6

9 Reviews

$300

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A Touch of Bermuda in Key West

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

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Reviews

(9)

Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is on the picturesque main entrance …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(9)

warm, convenient and comfortable

Left on Jun 24, 2010 for a stay in May 2010

great location, lovely unit, comfortable, clean, nice pool, and a terrific owner.

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$999,999

2 BR / 2 BA / Sleeps 6

16 Reviews

$999,999

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Rare 2BR/2BA Shipyard Condo Truman Annex Old Town

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 16 Reviews

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Reviews

(16)

This weekly (minimum) condo is in a perfect location for enjoying all the sights of Old Town Key West - a car is not even necessary as you can walk to everything! Fly in to Key West or take the Keys Shuttle from the Miami or Ft. Lauderdale airports. This rare condominium with a second full bath works very nicely …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(16)

Great Location and Reasonably Priced

Left on Jun 07, 2011 for a stay in February 2011

This unit is convenient to restaurants, shopping and Old Town. It's quite comfortable, though some of the appliances and entertainment items are a bit past their prime. The unit is a great location and I fully intend to rent it again.

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$149

1 BR / 1 BA / Sleeps 2

2 Reviews

$149

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"VAN GOGH" Studio For 2

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

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Reviews

(2)

This Peaceful and Cozy Efficiency is the Perfect Place to Rest After an Active Day In Key West! Located in vibrant and diverse Bahama Village, the Vangogh Studio for Two is an economical option for active adult travelers. It is one of the FEW accommodations with a 3 night minimum stay!!! The Galleria is known for …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control

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Reviews

(2)

A clean, quiet place to stay.

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

This rental was perfect for us. It was pretty small, but it was comfortable, stylish, and very convenient to all the best places in Key West. I don't think you will find a nicer, more reasonable rental on Key West. Our concierge, Carlos was phenomenal. Overall, a very good experience!!

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$243

2 BR / 3 BA / Sleeps 6

21 Reviews

$243

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Casa Del Sol, a Key West Vacation (Truman Annex)

2 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 21 Reviews

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Reviews

(21)

Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community is bordered on one …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(21)

Comfortable, cozy & perfectly located - a great place to stay!

Left on Jul 18, 2013 for a stay in June 2013

We stayed for a week in June, and enjoyed it so much that we extended the stay 3 more days. This is a beautiful and cozy rental with quick access to everything in the Keys we wanted to do and see. We had every amenity we needed, to the point that we felt like we were at home. The owners made us feel the same way - as family instead of strangers renting their space. We are already looking …

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$9,999,999

2 BR / 3 BA / Sleeps 6

14 Reviews

$9,999,999

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Foundry Condo 2BR/2.5BA Truman Annex Old Town KW

2 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 14 Reviews

Details

Reviews

(14)

Two bedrooms, two and a half baths, Foundry Condo 121 Front Street in the Truman Annex, is located in the heart of Key West's Old Town. Fly in and take a taxi from the Key West airport or the Keys Shuttle from the Miami or Ft. Lauderdale airports. One reserved vehicle parking space. Available for a week minimum, …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(14)

Best place I have stayed in KW

Left on Jun 07, 2011 for a stay in August 2010

I have stayed all over Key West over the past few years and this was the best. Its located right in Truman annex which is a block from Duval and only a few blocks from Mallory Square. The rooms were awesome, the place was clean, and Dave was very helpful. Oh, and the air was super cold. I will definitely stay there anytime they have an opening.

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$279

2 BR / 1 BA / Sleeps 4

8 Reviews

$279

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Artist Cottage in Truman Annex

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

Details

Reviews

(8)

Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful townhome sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our beautiful beach..great …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(8)

Thank you for the memories!

Left on Sep 12, 2010 for a stay in July 2010

Dear Susan & staff,

We wanted to take this opportunity to thank you for our amazing stay this summer. The artist Cottage was just immaculate and we were very impressed. It was a perfect place for us and our boys for our summer vacation. We've been to Key West before, and this place by far surpasses all the other places we have stayed. Next time we plan a trip to Key West, you can guarantee we …


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