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$1,048

6 BR / 6 BA / Sleeps 22

1 / 33

$1,048

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

6 BR / 6 BA / Sleeps 22 | Quick view

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Papa's Hideaway is a Guesthouse property comprised of Garden of Eden , Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls , Islands in the Stream Minimum Stay: Please contact Key West Vacation Rentals regarding minimum stays and special rates. Minimum stay requirements apply on weekends (at least…
  • Internet Access
  • 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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$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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$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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$83

1 BR / 1 BA / Sleeps 6

Providence Suite - Monthly Rental - Key West vacation rentals
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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$200

2 BR / 2 BA / Sleeps 4

30 night Minimum Stay Heart of Historic downtown  2 bedroom 2 1/2 Bathroom - Key West vacation rentals
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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$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

Details

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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$838

6 BR / 5 BA / Sleeps 16

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

Details

"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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$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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$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

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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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$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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$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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$388

2 BR / 3 BA / Sleeps 6

1 / 34

$388

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

2 BR / 3 BA / Sleeps 6 | Quick view

Details

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

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$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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$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

Details

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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$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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$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

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
  • 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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$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
  • Patio
  • 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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$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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$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

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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$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

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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$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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$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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$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

Details

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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$1,448

11 BR / 9 BA / Sleeps 32

1 / 32

$1,448

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

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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$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

Details

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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$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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$188

1 BR / 1 BA / Sleeps 4

23 Reviews

$188

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"VERDE SUITE" - Quiet & Affordable 'Old Town' Cottage - Shared Pool

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 23 Reviews

Details

Reviews

(23)

The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen …
  • 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

(23)

Verde Suite relaxation

Left on Jun 25, 2009 for a stay in April 2009

Glorius week in a great little suite with almost everything you would want. The only thing missing was the availability of authorized parking although there are parking spaces adjacent to the complex that remained vacant the entire week
Everything else ranks high. Cleanliness, secluded, close to everything in Old Town.

Would I do it again? In a heartbeat....as a matter of fact I am planning a …

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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

Details

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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$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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$184

2 BR / 1 BA / Sleeps 4

4 Reviews

$184

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

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

Details

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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$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

Details

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

Details

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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$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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$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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$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

Details

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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$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

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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$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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$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

Details

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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$638

5 BR / 4 BA / Sleeps 16

14 Reviews

$638

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ALMOST SOUTHERNMOST RETREAT Pvt Pool & Hot Tub -1/2 Block to Duval -Sleeps 16

5 BR / 4 BA / Sleeps 16 | Quick view
“ Excellent ” 14 Reviews

Details

Reviews

(14)

Almost Southernmost Retreat is made up of Part of ALMOST SOUTHERNMOST and Part of ALMOST SOUTHERNMOST TOOon the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the front …
  • Hot Tub/Jacuzzi
  • 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

(14)

Perfect for a large group!

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

We rented the Retreat and love it. We had 11 people (26-29yrs old) at one point and everyone had plenty of room. The location is perfect and having parking spots is a huge plus. Check-in and check-out was painless. Overall I would highly recommend this rental for a large group looking to be close to the action.

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$188

1 BR / 1 BA / Sleeps 4

47 Reviews

$188

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Osprey’s Nest

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 47 Reviews

Details

Reviews

(47)

Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have been saved to create …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(47)

Perfect

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

The location is great! Close to everything yet far enough away that you have privacy. The rental was tastefully decorated and clean. Loved everything about it!! Will definitely keep in my Rolodex for future plans!!

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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

Details

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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$268

2 BR / 2 BA / Sleeps 6

47 Reviews

$268

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"FAMILY HOUSE" Stunning 'Old Town' Home - 1 Block To Duval - Private Hot Tub

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

Details

Reviews

(47)

Inside, you will find all of the comforts of home and This two-story 1880's Cigar Maker's Cottage has been completely renovated and has a living room with 42' flat screen TV/DVD, Queen sleeper sofa, kitchen with dishwasher, dining room and bath (with outdoor shower) on the ground floor. Upstairs in the loft style …
  • 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

(47)

They thought through every little detail to make it feel more we

Left on Jun 24, 2009 for a stay in May 2007

We used this cabin for four of us to rendevous from the far reaches of the
United States and found the cabin to be comfortable, tastefully decorated, and
even included many amenities you normally find only at home. There were
tons of clean towels, boxes of tissues everywhere, plenty of cooking utensils,
an outdoor grill, phone, TV, stereo. We did have an issue with the stereo
when we …

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$338

3 BR / 2 BA / Sleeps 8

8 Reviews

$338

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"CASA KEY WEST @ DUVAL SQUARE" Extra Large Condo Located On Duval St.

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

Details

Reviews

(8)

Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe), This development extends from Duval Street to Simonton Street and is in the heart of historic Old Town. It is comprised of residential units upstairs and …
  • Shared outdoor pool (unheated)
  • 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

(8)

Beautiful Condo, Relaxing Community

Left on Apr 02, 2013 for a stay in March 2013

Had a great two-night stay with my all-adult family of 5. The condo has three full bedrooms so it was very comfortable for our group. The condo also features 2 completely windowed living areas (one upstairs, one downstairs) with stunning views of the harbor. The patio gets lots of sun for reading and sunbathing. We spent evenings cooking in the open kitchen and on the patio grilling.

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$248

2 BR / 1 BA / Sleeps 6

8 Reviews

$248

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"POOLSIDE SUITE" - A Few Steps To Duval St! Pvt Parking & Shared Pool!

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby bars, shops, and fine …
  • 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

(8)

Nice Vacation Rental, kinda expensive

Left on Jun 25, 2009 for a stay in August 2008

This was a beautiful suite, it was well stocked and clean. We were pleasantly surprised when we walked in and saw how much room there was and how much stuff there was in the kitchen. One bathroom was not ideal but it was workable. The biggest problem was the pool, it was absolutely the grossest pool I've ever seen. It was a horrible mossy green color that you could not see the bottom of the pool…

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$258

2 BR / 1 BA / Sleeps 6

7 Reviews

$258

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WINDWARD ISLE - Half Block To Duval St.- Private Hot Tub - Private Parking

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

One half of the group unit Tradewinds and Opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side or direction from …
  • Hot Tub/Jacuzzi
  • 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

(7)

Absolute Heaven

Left on Jun 25, 2009 for a stay in July 2006

We traveled with a family of 5 and no problem whatsoever being comfortable. We have stayed with Naomi for almost 12 years and have recommended her properties to EVERYONE we come in contact with! All of her properties sail far above most others on the Island. This house was perfect. Perfect location, perfect size, perfect everything. Only wished I owned it!!
Thanks

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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

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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$418

3 BR / 4 BA / Sleeps 8

50 Reviews

$418

Book

TROPICAL RETREAT- Upscale Home w/ Private Pool & BBQ Grill 1/2 Block To Duval

3 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 50 Reviews

Details

Reviews

(50)

Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting nightlife, music, bars and …
  • 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

(50)

Perfect place to stay with a family

Left on Jun 24, 2009 for a stay in July 2007

It was truly a perfect place with the pool, patio, location, and was laid out just great. We had 8 people (4 adults & 4 teenagers) and had more than enuff room for everyone. Can't imagine anyone would be dissappointed. Also had a large enuff secure driveway that we could park our full size rental van inside behind a lockable gate (i.e. no parking problems).

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$978

5 BR / 7 BA / Sleeps 20

1 Reviews

$978

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OLD TOWN GARDEN VILLAS- Sleeps 20. Great For Large Gatherings! 1 Blk To Duval

5 BR / 7 BA / Sleeps 20 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

The location is set on Center Street, which is located ½ block off Duval Street. These Villas are a favorite of our guests who like to relax in the quiet, beautiful garden area. Your party can book 1 to 5 of these Villas for a relaxing vacation. Old Town Garden Villas is comprised of the following individual …
  • 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

(1)

Quiet and relaxing in a perfect location!

Left on Feb 11, 2015 for a stay in February 2015

I stayed here with a group of friends and we reserved all five of the villas for 14 people. Each villa had one bedroom and most had one and a half bath with a small kitchen that was fully equipped. There is a large bed that will sleep two and a sofa bed in each unit. We were able to walk everywhere during our stay. The location is just north of Truman and a block from Duval Street but it could …

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$198

2 BR / 2 BA / Sleeps 6

1 / 24

$198

Book

GRAND CAYMAN SUITE #309 - 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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