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$838

6 BR / 5 BA / Sleeps 16

ESCAPE 2 PARADISE - 2 Beautiful 3-Story Homes w/ Pvt Pools. Steps From Duval - Key West vacation rentals
1 / 25

$838

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

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
  • Patio
  • Grill
  • Stereo or CD player
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$598

4 BR / 5 BA / Sleeps 10

1 / 35

$598

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"SIMONTON COURT COTTAGES" 4 Units in 1! Sleeps up to 10 Only 1 Block To Duval

4 BR / 5 BA / Sleeps 10 | Quick view

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"Simonton Court Cottages" consists of the 4 nightly units "Audubon House," "Truman Efficiency," "Monroe Efficiency," and "Mallory Efficiency." In total, this group rental sleeps 8 - 10 comfortably. Perfect for cost-conscious, larger, groups who are looking for great a location. Take advantage of this fantastic …
  • A/C or climate control
  • Microwave
  • Refrigerator
  • Toaster
  • 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

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

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Reviews

(2)

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

Details

Reviews

(2)

Outstanding

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

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

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$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
  • A/C or climate control
  • Grill
  • Linens Provided
  • Satellite or cable TV
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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

Details

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
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$66

1 BR / 1 BA / Sleeps 4

1 Reviews

$66

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Artist cottage with hot tub

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

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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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$117

2 BR / 2 BA / Sleeps 6

1 / 17

$117

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Amazing Grace

2 BR / 2 BA / Sleeps 6 | Quick view

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***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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$150

3 BR / 3 BA / Sleeps 8

1 / 25

$150

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

3 BR / 3 BA / Sleeps 8 | Quick view

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Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath that runs along the Atlantic side of the island; very close (less …
  • Internet Access
  • A/C or climate control
  • Linens Provided
  • Dishwasher
  • Microwave
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$200

2 BR / 2 BA / Sleeps 4

1 / 12

$200

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

2 BR / 2 BA / Sleeps 4 | Quick view

Details

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

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$183

2 BR / 2 BA / Sleeps 6

1 / 20

$183

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A Low Key Paradise

2 BR / 2 BA / Sleeps 6 | Quick view

Details

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

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$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

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CAT ISLAND SUITE #205 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

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Reviews

(1)

Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many amenities, the …
  • 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

Details

Reviews

(1)

Aweful

Left on Nov 11, 2014 for a stay in October 2014

Avoid this place at all costs . It is horrible ….. I would rather have stayed in my car. The apartment was disgusting . Furniture looked like it was from the early 80's and was dirty.

The walls are mirrored and broken, fixed with tape. The smoke alarms are missing but the wires are hanging out of the walls. I would never stay there again. I do have to say the girl at the front desk was nice …

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$468

4 BR / 2 BA / Sleeps 12

1 Reviews

$468

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"SEAPORT SUITE" - Great Party House w/ Hot Tub! 1 Min Walk to Sloppy Joe's

4 BR / 2 BA / Sleeps 12 | Quick view
“ Poor ” 1 Reviews

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Reviews

(1)

Seaport Suite is available for daily or weekly vacation rentals and located on the second floor of 219 Simonton in Old Town Key West. The location is as close to perfect as you can get, being one block off Duval Street and within walking distance to every single thing you could possibly want to do. With four bedrooms …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Seaport Suite not the place to stay

Left on Dec 02, 2014 for a stay in November 2014

Rental agents were very helpful can't complain about them or the maintenance staff. The property was not in the best shape. washer dryer didn''t work , had to have it replaced. One bathroom did not drain properly so when showering you could also take a bath. Ants all over the kitchen and bathrooms. Not impressed for the price I paid.

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$300

3 BR / 2 BA / Sleeps 8

1 / 23

$300

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Oceanside Key West's Best Luxury Penthouse Condo

3 BR / 2 BA / Sleeps 8 | Quick view

Details

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

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$180

1 BR / 1 BA / Sleeps 2

16 Reviews

$180

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Key West Garden House

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 16 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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$83

1 BR / 1 BA / Sleeps 6

1 / 17

$83

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Providence Suite - Monthly Rental

1 BR / 1 BA / Sleeps 6 | Quick view

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***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
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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.

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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$140

1 BR / 1 BA / Sleeps 4

1 / 12

$140

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Conch Haven Built 1883 Beautiful ! MONTHLY Rental

1 BR / 1 BA / Sleeps 4 | Quick view

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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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$167

2 BR / 2 BA / Sleeps 6

8 Reviews

$167

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

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

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Reviews

(8)

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

Details

Reviews

(8)

Always love 625

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

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

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$300

3 BR / 2 BA / Sleeps 8

12 Reviews

$300

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Key West - Libra

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 12 Reviews

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Reviews

(12)

Come stay aboard our FABULOUS houseboat Libra! Docked in one of Key West's most exclusive yacht club marinas, our guests have free access to a host of "members only" amenities including a swimming pool, private beach, tiki bar, fitness facility, sauna, clubhouse, onsite restaurant, free parking and much more! This …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(12)

Fantastic time

Left on Mar 28, 2013 for a stay in October 2012

We all had a great time. It was far away from everything yet close to everything at the same time. Restaurant had excellent food and pool was great. On the downside the boat was not cleaned when we got there and the hammock I so looked forward to was not there. All n all it was a great time n we rented it again this year. Hope it's clean n ready this year when we get there

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$138

4294967295 BR / 1 BA / Sleeps 2

1 Reviews

$138

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"DECKSIDE SUITE" Studio w/ Shared Hot Tub Steps To Duval St

1 BA / Sleeps 2 | Quick view
“ Terrible ” 1 Reviews

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Reviews

(1)

Part of Conch Republic Cottages Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get the most bang for their buck. You have everything you need in this cozy, studio-style unit, including a fully-stocked kitchen, cable TV, free wireless internet, and a…
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Rats Rats and Rats

Left on Jan 21, 2015 for a stay in January 2015

this is a very small unit... in need of a total make over. and yes there are rats all over the deck and in the walls. We could hear them at night and in the moring we saw 4 run across the deck.... Management (Key West Vacation Rentas)was not concerned simply saying there are rats everwhere in Key West.. It appears that one side of the unit is rented to locals and they helped entertain us by …

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$227

3 BR / 3 BA / Sleeps 6

2 Reviews

$227

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

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

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Reviews

(2)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Beautiful and comfortable home

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

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

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$167

3 BR / 3 BA / Sleeps 6

4 Reviews

$167

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

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

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Reviews

(4)

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

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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$600

2 BR / 2 BA / Sleeps 6

1 / 24

$600

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Garden Home Paradise in Midtown Key West

2 BR / 2 BA / Sleeps 6 | Quick view

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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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$467

5 BR / 5 BA / Sleeps 14

1 / 40

$467

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"SHARK KEY CHATEAU" Incredible 3-Story Mansion w/ Private Beach, Pool, & Spa

5 BR / 5 BA / Sleeps 14 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Shark Key Chateau is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. Shark Key Chateau is designed in true keys …
  • Private Beach
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$300

3 BR / 2 BA / Sleeps 8

10 Reviews

$300

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Key West - MV Coconuts

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

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Reviews

(10)

The M/V Coconuts is a completely unique home with 360 degree water views, it also happens to be a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat. It really is a very comfortable home, with proper living area, bedrooms and large sundecks. There is over 1100 sq ft of indoor …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(10)

awesome stay in Key West

Left on Apr 04, 2013 for a stay in September 2012

Great large space to share with friends, yet you all have privacy with multiple floors and decks. The beds could use some new mattresses and sheets, but otherwise it was much better than a b & b. The marina is just outside of town and provides a safe quiet stay. The club house has great food and services. During our stay, our a/C went out and our host worked into the wee hours of the morning …

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$188

1 BR / 1 BA / Sleeps 4

1 Reviews

$188

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"ORANGE BLOSSOM SUITE" Cute Condo w/ Loft Half Block To Duval. Shared Hot Tub

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

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Reviews

(1)

Part of Conch Republic Cottages Welcome to sweet paradise! Located at 510 Petronia, the 'Orange Blossom Suite' is in close proximity to all the fun-filled action of Duval St, however, it is private enough to not hear any of it! 'Orange Blossom Suite' shares a huge back patio with one other suite (also managed by Key…
  • Deck
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Basically acceptable accommodations -- pleasant and helpful staff.

Left on Feb 15, 2015 for a stay in February 2015

Although the house was small, it was clean and comfortable, except for a few small details. The bathtub faucets were not easy to turn off (not sure of the positions for "off")and the guide on the wall was not clear. One chair needs to be replaced (it was lopsided). Kitchen could have been better equipped.

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$378

3 BR / 3 BA / Sleeps 8

6 Reviews

$378

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

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

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Reviews

(6)

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

Details

Reviews

(6)

Fantastic, wonderful experience.

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

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

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$200

1 BR / 1 BA / Sleeps 6

1 / 23

$200

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Key West - Capt. Andy

1 BR / 1 BA / Sleeps 6 | Quick view

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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

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$217

5 BR / 3 BA / Sleeps 18

1 / 24

$217

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

5 BR / 3 BA / Sleeps 18 | Quick view

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***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
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$158

1 BR / 1 BA / Sleeps 4

37 Reviews

$158

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"DUVAL CORNER" - Cute Condo Just off Duval St! Full Kitchen & Great Porch!

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 37 Reviews

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Reviews

(37)

Formerly Amelia St Hideaway With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(37)

50th Birthday vacation

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

We had a great time at the Amelia House,me my husband,my brother, and sister inlaw. It was very clean and in a great lacation. The hot tub was very nice after a long day in Key West. The staff was also great, they even had a bottle of bubbly for me. I would stay there again!!

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$388

2 BR / 3 BA / Sleeps 6

1 / 34

$388

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

2 BR / 3 BA / Sleeps 6 | Quick view

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

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$157

3 BR / 3 BA / Sleeps 8

1 / 26

$157

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

3 BR / 3 BA / Sleeps 8 | Quick view

Details

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

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$128

4294967295 BR / 1 BA / Sleeps 2

5 Reviews

$128

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"CORAL COVE" Affordable Old Town Efficiency - Patio and BBQ Grill

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

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Reviews

(5)

This wonderful unit that has been completely remodeled in July 2013 has a private entrance in to the quaint efficiency on the back side of the complex. Featuring hardwood floors, Dade County Pine walls and a high-end, fully stocked kitchenette, this secluded hideaway offers the finest of appointments and one of the…
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(5)

Great Value.

Left on Aug 17, 2013 for a stay in August 2013

Very Small but a great value if it will only be one or two staying. Not a bad location either. My wife and I rent from Key West vacation rentals every year and they are a pleasure to work with. No surprises!

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$888

5 BR / 4 BA / Sleeps 12

1 / 32

$888

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"ABBEY ROAD" Great for Big Parties! - 4 Luxury Units - 4 Private Hot Tubs

5 BR / 4 BA / Sleeps 12 | Quick view

Details

Abbey Road - Gated Compound, Sleeps up to 12! Lennon's Lodge (Sleeps 6 with 8 person hot tub), McCartney's Manor (Sleeps 2 with 2 person hot tub), Starr's Suite (Sleeps 2 with 2 person hot tub) and Harrison's Hideaway (Sleeps 2 with 2 person hot tub) and will accommodate up to 12 persons for the ultimate in …
  • 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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$408

3 BR / 2 BA / Sleeps 10

13 Reviews

$408

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

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

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Reviews

(13)

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

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Reviews

(13)

Enjoyed our Stay

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

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

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$350

3 BR / 2 BA / Sleeps 6

1 / 19

$350

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KEY WEST LIVIN' BEAUTIFUL 50' Yacht 3 Bed , 2 bath, WIFI, Flatscreen,Sleeps 6

3 BR / 2 BA / Sleeps 6 | Quick view

Details

BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach , Heated Infinity -Edge …
  • Waterfront
  • Ocean or water views
  • Sauna
  • Internet Access
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • 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

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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$268

2 BR / 2 BA / Sleeps 6

1 / 31

$268

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THE COTTAGE @ TROPICAL VILLAGE - Spacious Home w/ Shared Pool. Close To Beach

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Part of TROPICAL VILLAGE Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a …
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$233

2 BR / 2 BA / Sleeps 4

1 Reviews

$233

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Pinder House - Monthly Rental

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

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Reviews

(1)

***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

(1)

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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$408

2 BR / 2 BA / Sleeps 6

9 Reviews

$408

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HELEN'S HIDEAWAY - Gated, Unique, 2 BR House W/ Private Heated Pool

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

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Reviews

(9)

This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise reflects his passion for …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(9)

Quiet, private, unique concept, but big price for significant di

Left on Sep 12, 2013 for a stay in September 2013

Truly a hideaway! Very private-locked behind a wooden fence. Location-excellent! Fun detached bedroom w/a wall of sliders that open to the private pool. Outdoor hot/cold shower well placed amidst foliage for privacy. Sufficiently equipped kitchen, but outdated & narrow - two large people may have trouble passing each another. 3 flat screens. Lg bathroom in main bldg recently redone with huge walk…

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$748

4 BR / 4 BA / Sleeps 16

1 / 30

$748

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Palm Gardens - Great for Groups!

4 BR / 4 BA / Sleeps 16 | Quick view

Details

The Condos are tied together in a lushly landscaped garden setting with a spa pool in the rear. Booking all 4 condos gives you a great alternative to booking a single house as you are offered privacy and closeness at the same time. Call to book your Island Paradise while there is still time! Palm Gardens is …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$408

3 BR / 2 BA / Sleeps 10

2 Reviews

$408

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

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

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Reviews

(2)

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

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Reviews

(2)

Best vacation ever!

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

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

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$190

3 BR / 3 BA / Sleeps 6

1 Reviews

$190

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

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

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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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$268

2 BR / 2 BA / Sleeps 6

1 Reviews

$268

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

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

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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

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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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$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

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"GRENADA SUITE #209" - 2/2 Condo w/ Pool & Hot Tub - Pvt Parking

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

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Reviews

(1)

*** 1 Private, covered parking spot is included when you rent this particular vacation condo Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let …
  • 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

Details

Reviews

(1)

Too Expensive for outdated rental property

Left on Dec 31, 2014 for a stay in December 2014

The unit was very old, the cot mattress were outdated. The patio door was not locking properly, the main door was not locking properly. It was very outdated one and didnt expect his kind of property for the amount we spent.

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$200

2 BR / 1 BA / Sleeps 4

4 Reviews

$200

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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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$788

5 BR / 4 BA / Sleeps 12

1 / 24

$788

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"SOUTHERN PALMS" Historical Hideaway - Bahama Village - 2 Hot Tubs & Pvt Pool

5 BR / 4 BA / Sleeps 12 | Quick view

Details

Located at 729 Whitehead St, "Southern Palms" is the group property consisting of the following homes Coconut Palm formerly Island Oasis Traveler's Palm formerly Palm Isle Royal Palm formerly Little Palm which can all be booked individually. All together, these three units have 5 separate bedrooms, 3 …
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$588

4 BR / 4 BA / Sleeps 10

46 Reviews

$588

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"KEY WEST HIDEAWAY" Sleeps Up To 10 - Private Patio - Half Block To Duval!

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 46 Reviews

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Reviews

(46)

Two Queen bedrooms upstairs (each with a private bath) and two Queen bedrooms downstairs (each with a private bath) gives sleeping privacy and convenience for up to 8. Each bedroom has flat screen TVs, air-conditioning and ceiling fan. The two upstairs bedrooms have showers, the two downstairs bedrooms have …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(46)

Second time, won't be the last time.

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

This was the second year in a row that we rented the house. We absolute love staying here. We don't usually get to relax on vacations, however when we come here that is all we do and the house has all the comfort and ammenities to allow us to relax. Will be back to Key West often (live in Dallas) and will always rent this property.

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$188

1 BR / 2 BA / Sleeps 4

21 Reviews

$188

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"THE AUDUBON HOUSE" Customer Favorite! Great Location 1 Block To Duval

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

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Reviews

(21)

AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a living room. The dining …
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(21)

Nice, but

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

The home was nice and well maintained. It had all the amenities it said it did, but the pool was away a bit and across the street and was very small with little if any sun, so we ended up not using it at all and going to the beach. This house is in the area where the roosters wake you up early in the morning. Too early for vacation. The master bedroom is tight -- the bed is cramped and closet …

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$198

2 BR / 2 BA / Sleeps 6

1 / 25

$198

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SAINT MARTIN SUITE #207 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many amenities, the …
  • 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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