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$208

2 BR / 1 BA / Sleeps 4

TRUMAN @ DUVAL 'Old Town KW' Home Just A Hop-Skip-And-Jump To Duval St. - Key West vacation rentals
1 / 25

$208

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TRUMAN @ DUVAL 'Old Town KW' Home Just A Hop-Skip-And-Jump To Duval St.

Key West cottage
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people watching, it's all…
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$418

3 BR / 4 BA / Sleeps 8

1 / 34

$418

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

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

Details

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

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$127

2 BR / 2 BA / Sleeps 4

2 Reviews

$127

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Angela Cottage: A hideaway in Old Town

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows create a relaxing Key …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Outstanding

Left on Jun 26, 2009 for a stay in March 2009

I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and outdoor dining area is outstanding for any meal. The kitchen is new and all the necessary pots and pans are present.

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$358

2 BR / 5 BA / Sleeps 6

Hyatt Beach Club - Key West vacation rentals
1 / 13

$358

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Hyatt Beach Club

Key West condo
2 BR / 5 BA / Sleeps 6 | Quick view

Details

This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a view of water with …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Housekeeping Optional
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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$179

2 BR / 1 BA / Sleeps 6

Elegantly Furnished Key West Condo - Key West vacation rentals
1 / 24

$179

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Elegantly Furnished Key West Condo

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

Details

Elegantly furnished Key West vacation condo in the historic Truman Annex in the heart of Old Town in Key West. This is the premier gated community in Key West, bordering the Atlantic Ocean. Grounds of the Annex are beautifully landscaped. The Shipyard units are done in the traditional Key West Conch style. This is a …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Patio
  • Pet friendly

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$200

1 BR / 1 BA / Sleeps 6

1 Reviews

$200

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Key West - Capt. Andy

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

Details

Reviews

(1)

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

Details

Reviews

(1)

Worst stay for the highest price ever paid nightly.

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

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

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$180

1 BR / 1 BA / Sleeps 2

16 Reviews

$180

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Key West Garden House

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

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Reviews

(16)

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

Details

Reviews

(16)

Great Experience!

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

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

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$418

3 BR / 3 BA / Sleeps 8

8 Reviews

$418

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

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

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Reviews

(8)

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

Details

Reviews

(8)

Walk to everywhere, but feels very private .

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

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

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

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$289

1 BR / 1 BA / Sleeps 4

1 / 18

$289

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Eyebrow House - Historic Home in Heart of Old Town

Key West B&B
1 BR / 1 BA / Sleeps 4 | Quick view

Details

Eyebrow House is a very spacious one-bedroom suite with a large front porch and palm tree-filled private fenced-in yard overlooking a quiet side street. Our guests enjoy the best of both worlds as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a half block away. You feel like a …
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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$600

2 BR / 2 BA / Sleeps 6

1 / 24

$600

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Garden Home Paradise in Midtown Key West

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

Details

2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered outdoor pavillion with …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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$140

1 BR / 1 BA / Sleeps 4

1 / 13

$140

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Conch Haven Built 1883 Beautiful ! MONTHLY Rental

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

Details

This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping. Due to local zoning laws we can only rent by the …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly

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$300

2 BR / 2 BA / Sleeps 8

12 Reviews

$300

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Pelican Landing Abaco Retreat

Key West condo
2 BR / 2 BA / Sleeps 8 | Quick view
Excellent12 Reviews

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Reviews

(12)

Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront condos have a range of …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(12)

Flawless new year stay

Left on Jan 20, 2012 for a stay in January 2012

Outstanding time wonderful facilities, will bring boat next time

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$183

3 BR / 3 BA / Sleeps 10

1 / 24

$183

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

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

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Cayo Hueso: As you approach the front door to 1120 Curry Lane the transformation starts to happen. The small lush tropical lane, the two wonderfully inviting porches... your journey to the tropics and relaxation has begun! …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$378

2 BR / 2 BA / Sleeps 6

11 Reviews

$378

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"DU PONT HOUSE" Luxury Rental - Private Pool - 1/2 Block To Duval St.

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent11 Reviews

Details

Reviews

(11)

Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and bath are …
  • 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

(11)

Another wonderful stay

Left on Sep 10, 2010 for a stay in August 2010

We love the Dupont House! Pictures don't quite do it justice because it has two-story ceilings because of the second bedroom. It is much more open and roomy than it appears. This is our second stay there and both times it has been perfect. It is current and appropriately (not to mention cutely) decorated... Seriously cute - we have a bunch of pictures of the house and its decorations! The house …

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$198

1 BR / 2 BA / Sleeps 4

29 Reviews

$198

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Andros Suite

Key West house
1 BR / 2 BA / Sleeps 4 | Quick view
Excellent29 Reviews

Details

Reviews

(29)

Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with a colorful Caribbean …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(29)

Andros Suite MADE our Vacation perfect.

Left on Jun 24, 2009 for a stay in May 2009

We are so glad we stayed in the Andros Suite. This place is much better than one of the hotels. It's one block off the main street so is quiet but close enough to walk to everything. The home was great, just the right size. We loved the birds in the courtyard as well as the beautiful plants.

We received great service from Key West Vacation Rentals. This location is central on Duvall, so …

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$117

2 BR / 1 BA / Sleeps 7

3 Reviews

$117

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The Tree House Old Town Built 1883 MONTHLY Rental

Key West house
2 BR / 1 BA / Sleeps 7 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key West has to offer. …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • 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

(3)

Wonderful

Left on Jul 18, 2014 for a stay in December 2013

Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

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$353

3 BR / 2 BA / Sleeps 8

8 Reviews

$353

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Hemmingway's Retreat

Key West house
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent8 Reviews

Details

Reviews

(8)

Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50", 42", and 27" flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home Furnishings. The …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly

    Details

    Reviews

    (8)

    1211 Catherine St.

    Left on May 10, 2010 for a stay in April 2010

    My wife and I spent time in April at 1211 Catherine St., Key West, FL and had a marvelous time. The house is wonderful expecially the private pool. All that Key West has to offer is within easy walking or cycling distance of the house. The house is beautifully furnished and appointed so much so we spent many days just staying home and relaxing around the pool. One of the bicycles provided had to…

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    $188

    1 BR / 1 BA / Sleeps 4

    4 Reviews

    $188

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    HIDEAWAY @ TROPICAL VILLAGE - Cozy Condo For 2 w/ Shared Pool

    Key West cottage
    1 BR / 1 BA / Sleeps 4 | Quick view
    Excellent4 Reviews

    Details

    Reviews

    (4)

    Part of TROPICAL VILLAGE Tropical Hideaway - Lush gardens surround this lovingly restored two-story vacation house. This downstairs rental cottage has one bedroom with full bath and features a living room with queen sleeper-sofa, cable TV, DVD, stereo with CD player, and wireless internet. The bedroom has a queen …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (4)

    Great stay!!!

    Left on Oct 08, 2014 for a stay in October 2014

    Everything was great! The location was perfect - and the private hot tub was the best! Only down side (which wasn't a big deal) was there were ants on the kitchen counter!

    Very nice rental!!!!

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    $288

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $288

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    SOUTHERN CROSS @ TROPICAL VILLAGE - Beautifully Updated Home w/ Shared Pool.

    Key West cottage
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    Part of TROPICAL VILLAGE Southern Cross: Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Tropical Perfection

    Left on Oct 07, 2014 for a stay in October 2014

    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15 minute walk to the Mallory Square. Higgs Beach was a close, great market nearby, and a CVS, you really couldn't have asked for a better location! The trip was epic, relaxing and wild from start to finish. I can't wait to come …

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    $298

    2 BR / 2 BA / Sleeps 6

    15 Reviews

    $298

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    Hidden Treasure

    Key West cottage
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent15 Reviews

    Details

    Reviews

    (15)

    Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high end amenity that you could possibly desire…
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (15)

    Will be going back

    Left on Jul 31, 2012 for a stay in May 2012

    We stayed at Hidden treasure in May 2012. Great place, great management, and actually a lot bigger and more private than I expected. We had four people and two dogs and it wasn't crowded at all. I pretty much think of going back every day. Its within walking distance to everything, including Irish Kevin's which is awesome.

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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

    Key West house
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent8 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
    • Deck
    • Grill
    • Linens Provided
    • 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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    $227

    3 BR / 3 BA / Sleeps 6

    2 Reviews

    $227

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

    Key West house
    3 BR / 3 BA / Sleeps 6 | Quick view
    Excellent2 Reviews

    Details

    Reviews

    (2)

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

    Beautiful and comfortable home

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

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

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    $198

    2 BR / 2 BA / Sleeps 6

    1 / 27

    $198

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    SAINT THOMAS SUITE #302 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $1,448

    11 BR / 9 BA / Sleeps 32

    1 / 33

    $1,448

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    TROPICAL VILLAGE 6 Homes w/ Pvt Pool & BBQ Grill. Great For Large Parties!

    Key West house
    11 BR / 9 BA / Sleeps 32 | Quick view

    Details

    Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. COTTAGE @ TROPICAL VILLAGE POOLSIDE @ TROPICAL VILLAGE SOUTHERN CROSS @ TROPICAL VILLAGE TOON HALL @ TROPICAL VILLAGE RETREAT @ TROPICAL VILLAGE HIDEAWAY @ TROPICAL VILLAGE Located at 706 and…
    • Pet friendly
    • 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

    Key West house
    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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    $167

    3 BR / 3 BA / Sleeps 6

    4 Reviews

    $167

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

    Key West house
    3 BR / 3 BA / Sleeps 6 | Quick view
    Excellent4 Reviews

    Details

    Reviews

    (4)

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

    Details

    Reviews

    (4)

    Perfect in Every Way!

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

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

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

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    $83

    1 BR / 2 BA / Sleeps 4

    6 Reviews

    $83

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    "PARADISE SUITE" Monthly Villa In Gated Complex w/ Pool. Steps to Duval St

    Key West house
    1 BR / 2 BA / Sleeps 4 | Quick view
    Excellent6 Reviews

    Details

    Reviews

    (6)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels lays the Paradise Suite. Paradise Suite (renovated for January 2013) is a bi-level suite with one bedroom upstairs. The …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    Great time in Keys at Esperanza

    Left on Jan 28, 2011 for a stay in October 2009

    Very Nice! Great location for Fantasy Fest and the Parrothead music week that follows. Separate upstairs bedroom and a couch downstairs with its own bathroom was great for a short term friend to stay. Very private with the courtyard and gate. We really liked it...

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    $93

    1 BR / 1 BA / Sleeps 4

    1 / 14

    $93

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    "BOARDWALK LOFT" - Monthly Rental - Newly Renovated Condo w/ Shared Pool.

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

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautiful Getaway Spot w/ Pool! Boardwalk Loft is the perfect getaway spot for families, or for individuals that just need some peace and quiet. The interior exudes elegance from top to bottom. You will fall in love with …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $208

    4294967295 BR / 1 BA / Sleeps 2

    19 Reviews

    $208

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    "HARRISONS HIDEAWAY" Luxury Cottage - Private Hot Tub - Half Block To Duval

    Key West cottage
    1 BA / Sleeps 2 | Quick view
    Excellent19 Reviews

    Details

    Reviews

    (19)

    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this free standing historic cottage at 918-920 Center Street, features a king pillow-top bed, 2 lushly padded swivel chairs and a full kitchen which includes a full stove, refrigerator with ice-maker, microwave, dishwasher and soft mood lighting under …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (19)

    Relaxation

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

    Enjoyed a very relaxing stay in Key West. With access to the pools, hot tub and restaurants, much to chose from.

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    $233

    2 BR / 2 BA / Sleeps 4

    2 Reviews

    $233

    Book

    Pinder House - Monthly Rental

    Key West house
    2 BR / 2 BA / Sleeps 4 | Quick view
    Average2 Reviews

    Details

    Reviews

    (2)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Located at 516 Elizabeth Street, the Pinder House is an address and house of distinction! Previously owned by Theopolis Pinder of the historic Pinder Family, whose roots go back to the 1850’s, this historic Eyebrow home has …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Central heating
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Live in an 1830's house w / 2014 conveniences

    Left on Jan 23, 2014 for a stay in January 2014

    B+ no Choices in cable channels no prkg
    On site , parrot sanctuary adjacent
    Property's remote pool. Access. K

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    $248

    1 BR / 1 BA / Sleeps 2

    1 / 20

    $248

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    "BANANA SPLIT"

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

    Details

    Part of Banana's Foster Guest House This one bedroom apartment is on the 2nd floor of this historic property and accessed through the shared gated courtyard, right beside the shared off street parking on Simonton. Once through the gates, walk around the shared plunge pool and BBQ grill, going upstairs to the large …
    • 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

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    $198

    2 BR / 2 BA / Sleeps 6

    1 / 38

    $198

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    SAINT BARTS SUITE #303 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $186

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $186

    Inquire

    Sunshine Luxury Suite - 2 Free Bicycles & Garage

    Key West condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    My Sunshine Luxury Suite is an upscale property located in Key West, an island paradise. Sunshine Suite provides the luxury and convenience of your own condo home just 90 miles from Havana. Surrounding the resort, you will enjoy lush tropical foliage and amenities such as our tennis court, gym facilities, and heated …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Great Place!

    Left on Oct 28, 2014 for a stay in October 2014

    fabulous condo on a very secure property close to the beaches. Roosevelt Blvd is within walking distance and has a sidewalk large enough for walking and biking along the ocean. The unit is very clean, well stocked with linens, has a fully equipped kitchen and has everything you need and/or forgot. It also has a covered parking spot and bicycles! Perfect layout for two couples each bedroom has…

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    $183

    2 BR / 2 BA / Sleeps 6

    1 / 20

    $183

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    A Low Key Paradise- Monthly rental only

    Key West house
    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 …
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $308

    3 BR / 4 BA / Sleeps 8

    1 / 21

    $308

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    La Dolce Vita - Luxury Monthly Rental Private heated pool

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

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Located in one of Key West's best neighborhoods just a short walk from Higgs and Smathers beaches, La Dolce Vita offers uncommon space and the finest of appointments throughout. Upon entering the gated property complete with…
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $83

    1 BR / 1 BA / Sleeps 6

    1 / 17

    $83

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    Providence Suite - Monthly Rental

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

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in tropical, flowering gardens, the Providence Suite is perfectly located, 1/2 block from Duval Street Downstairs is the living room with Queen sleeper sofa, dining room and fully equipped kitchen. Outdoor table and…
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $198

    2 BR / 2 BA / Sleeps 6

    1 / 26

    $198

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    RUM CAY SUITE #304 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $198

    2 BR / 2 BA / Sleeps 6

    1 / 28

    $198

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    GREAT EXUMA SUITE #406 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $198

    2 BR / 2 BA / Sleeps 6

    1 / 24

    $198

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    PUERTO RICO SUITE #103 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped…
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $100

    1 BR / 1 BA / Sleeps 4

    1 / 23

    $100

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    "FRANGIPANI OASIS" Beautifully Decorated Featured Home w/ Pvt Pool

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

    Details

    ***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This inviting HGTV Featured Home (Bang for Your Buck, 2010) surrounds you with luxury, comfort and history. Originally a Cuban Cigar Maker’s Cottage (circa 1920’s), this vacation home has been updated with no expense spared. …
    • 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

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    $157

    3 BR / 3 BA / Sleeps 8

    1 / 26

    $157

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

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

    Details

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

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    $183

    3 BR / 3 BA / Sleeps 6

    1 Reviews

    $183

    Book

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

    Key West house
    3 BR / 3 BA / Sleeps 6 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a tub and full …
    • Internet Access
    • A/C or climate control
    • Patio
    • Grill
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Club Clark

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

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

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    $508

    3 BR / 3 BA / Sleeps 10

    1 / 32

    $508

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    Conch Republic Cottages - 3 Bed 3 Bath Group Property - Steps from Duval St!

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

    Details

    This nightly group rental consists of 3 separate units. 1) Porchside Paradise 2) Orange Blossom Suite 3) Deckside Suite . Three separate bedrooms with queen sized beds. Two sleeper sofas and two private hot tubs! Located at 510 Petronia St, literally steps from Duval St! Take advantage of the vivid nightlife, …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • Deck
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $198

    2 BR / 2 BA / Sleeps 6

    1 / 25

    $198

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    ISLA MARGARITA SUITE #305 - 2/2 Condo w/ Pool & Hot Tub - Pvt Parking

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

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $778

    4 BR / 5 BA / Sleeps 12

    1 / 30

    $778

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    "HAVANA OASIS" Luxury 2-Home, Group Rental w/ 2 Pvt Pools. Sleeps 12!

    Key West house
    4 BR / 5 BA / Sleeps 12 | Quick view

    Details

    Island Oasis The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island …
    • Internet Access
    • A/C or climate control
    • Patio
    • Grill
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $378

    3 BR / 3 BA / Sleeps 8

    6 Reviews

    $378

    Book

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

    Key West house
    3 BR / 3 BA / Sleeps 8 | Quick view
    Excellent6 Reviews

    Details

    Reviews

    (6)

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

    Details

    Reviews

    (6)

    Fantastic, wonderful experience.

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

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

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    $200

    5 BR / 3 BA / Sleeps 18

    1 / 24

    $200

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    "BAY HARBOR VIEW" - Waterfront Monthly Rental w/ Spectacular Views

    Key West house
    5 BR / 3 BA / Sleeps 18 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of the home, the large …
    • Waterfront
    • Internet Access
    • A/C or climate control
    • Patio
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    PreviousNext property

    $198

    2 BR / 2 BA / Sleeps 6

    1 / 24

    $198

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    TIERRA BOMBA SUITE #403 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

    Details

    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $838

    6 BR / 5 BA / Sleeps 16

    1 / 25

    $838

    Book

    ESCAPE 2 PARADISE - 2 Beautiful 3-Story Homes w/ Pvt Pools. Steps From Duval

    Key West house
    6 BR / 5 BA / Sleeps 16 | Quick view

    Details

    Located in the luxury townhome complex "Echo Gardens," "Escape 2 Paradise" consists of two homes, units #3 and #4 - A Key Escape and Absolutely Paradise - which are right next door to each other. Equipped with two private pools, two private parking spaces, and enough room to sleep 16 people, "Escape 2 Paradise" truly…
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Grill
    • Stereo or CD player
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    PreviousNext property

    $258

    2 BR / 3 BA / Sleeps 7

    18 Reviews

    $258

    Book

    "CASA BONITA @ DUVAL SQUARE" Luxury Duval St. Condo w/ Shared Pool & Balcony

    Key West condo
    2 BR / 3 BA / Sleeps 7 | Quick view
    Excellent18 Reviews

    Details

    Reviews

    (18)

    Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking…
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Deck
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (18)

    One week not enough

    Left on Jul 02, 2009 for a stay in March 2009

    Our Duval St location while not in party central was close enough for our liking.We had access to far more restaurants/bars and night time activities than we could visit or participate in. Our accommodations in Casa Bonita were excellent -especially the master bedroom. The registration process and service were excellent . We appreciated being allowed to leave our baggage in our place well after …

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