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$778

4 BR / 5 BA / Sleeps 12

1 / 30

$778

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

4 BR / 5 BA / Sleeps 12 | Quick view

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

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

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$470

4 BR / 2 BA / Sleeps 8

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

$470

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Pete's Cottages: Twin Cypress cottages steps from Duval

4 BR / 2 BA / Sleeps 8 | Quick view

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This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$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
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  • Wheelchair accessible - 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

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***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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$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

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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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$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…
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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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$858

6 BR / 6 BA / Sleeps 24

1 / 25

$858

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"SOUTHERNMOST SANCTUARY" - 3 Pvt Hot Tubs - BBQ Grill - Sleeps 24

6 BR / 6 BA / Sleeps 24 | Quick view

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Southernmost Sanctuary Suites are comprised of the following homes Egret Suite Heron Suite Ibis Suite Osprey Suite Pelican Suite Seagull Suite which can all be booked individually. Minimum Stay: Please contact Key West Vacation Rentals regarding minimum stays and special rates. …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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

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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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$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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$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 …
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  • Suitable for children - ask
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$1,028

5 BR / 6 BA / Sleeps 14

1 / 42

$1,028

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"BANANA'S FOSTER" 5 / 5.5 Guest House 1 Block to Duval St! Pvt Pool & Parking

5 BR / 6 BA / Sleeps 14 | Quick view

Details

When rented as a group, Banana’s Foster includes- Sweet Caroline - Banana Split - Key Lime Cottage Creme Brûlée All together this grouping has 5 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic…
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  • Deck
  • Grill
  • Linens Provided
  • 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 Big Groups! 4 Condos 4 Hot Tubs 1 Pool. Sleeps 16!

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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$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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$490

4 BR / 4 BA / Sleeps 8

39 Reviews

$490

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Louisa House: A comfortable four bedroom vacation hideaway

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

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Reviews

(39)

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable vacation hideaway. …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(39)

Great House, Family Friendly

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

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

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$850

4 BR / 4 BA / Sleeps 8

15 Reviews

$850

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

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

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Reviews

(15)

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

Details

Reviews

(15)

The coolest house ever!

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

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

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$750

4 BR / 4 BA / Sleeps 8

27 Reviews

$750

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

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

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Reviews

(27)

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor plan with living and dining room, …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(27)

What a lovely property

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

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

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$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

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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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$588

4 BR / 4 BA / Sleeps 10

47 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 ” 47 Reviews

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Reviews

(47)

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

(47)

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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$1,200

7 BR / 6 BA / Sleeps 18

1 Reviews

$1,200

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Suite Dreams in Key West

7 BR / 6 BA / Sleeps 18 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented together are as follows: …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Perfect stay

Left on Feb 16, 2014 for a stay in January 2014

So our stay was Friday - Tuesday in January … We rented the Hemingway suite then added additional rooms … Love Love Love this place !! can not say enough about the owners / and their property manager Vicki …. Highly recommend this place , it has everything you need .. Full property, private pool , Patio, Bbq, fully stocked kitchen , an on "your honor" store , washer dryer … going to …

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$498

4 BR / 2 BA / Sleeps 12

3 Reviews

$498

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"TRADEWINDS" Private Parking - Two Private Hot Tubs - 1/2 Block To Duval!

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

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Reviews

(3)

Tradewinds is comprised of the Leeward Isle and Windward Isle Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your party can …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Very Nice accommodations. Hot tubs were great!

Left on Mar 20, 2014 for a stay in March 2014

Very close to activities. Good parking area and cmfortable homes.

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$1,000

5 BR / 4 BA / Sleeps 12

19 Reviews

$1,000

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DREAMING ON DUVAL- Luxury 5 Bed & Private Pool- As seen on HGTV House Hunters

5 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 19 Reviews

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Reviews

(19)

Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to offer and accommodates …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(19)

Fabulous...

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

Dreaming in Duval is a beautiful, spacious home. The home is very well equipt,and accomodated 10 people easily.
The location was perfect, we could walk to everything.
Dean and Paul were both great and very helpful.
One of our best vacations ever, we are already planning a return trip.

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$650

4 BR / 3 BA / Sleeps 10

1 Reviews

$650

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Amanda's Dream Suites ~ Weekly Rental

4 BR / 3 BA / Sleeps 10 | Quick view
“ Average ” 1 Reviews

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Reviews

(1)

Originally built in 1938, Amanda's Dream Suites vacation rental is a charming large wooden home offering two full stories with deep porches which overlook the garden and pool. An exterior stair case on one end of the building join the first and second floor. A renovation of the home in the early 1990's …
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Linens Provided
  • Television
  • Stereo or CD player
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Comfortable but over priced, tired and in need of updating.

Left on Mar 16, 2014 for a stay in March 2014

Management company was very inattentive to advertised included amenities. No beach towels to use or forks in the kitchen for three days after three requests. An added note this property is in the direct flight path of the airport so it can be deafening at times.

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$400

5 BR / 4 BA / Sleeps 12

1 / 22

$400

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Bella Grand Premier ~ Monthly Rental

5 BR / 4 BA / Sleeps 12 | Quick view

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Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated contemporary Caribbean …
  • Shared outdoor pool (unheated)
  • Housekeeping Optional
  • A/C or climate control
  • Porch
  • Garden
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$700

4 BR / 4 BA / Sleeps 8

2 Reviews

$700

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Hermitage South

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

Details

Reviews

(2)

The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage South to be a one-of-a-…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(2)

Family Vacation in Key West

Left on Aug 11, 2012 for a stay in July 2012

The staff at Historic Hideaways was absolutely wonderful in assisting with the long distance scheduling of this vacation. In addition they were very responsive to any question related to the property both before arrival and during our stay.

The home was exactly as described...Clean...and stocked with all the items needed for a home away from home vacation rental. This home was close to …

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$600

5 BR / 6 BA / Sleeps 12

1 / 42

$600

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Ultimate Key West Beach House - Sunset Key~ VIP~ Monthly Rental

5 BR / 6 BA / Sleeps 12 | Quick view

Details

Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property …
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$600

6 BR / 7 BA / Sleeps 12

1 / 31

$600

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Seaport Treasure Estate ~ Monthly Rental

6 BR / 7 BA / Sleeps 12 | Quick view

Details

While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly …
  • Housekeeping Optional
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$167

4 BR / 3 BA / Sleeps 10

1 / 31

$167

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30 night minimum stay requirement. Key Haven Retreat - 4 Bedroom House with

4 BR / 3 BA / Sleeps 10 | Quick view

Details

This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar area where you can …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$700

4 BR / 3 BA / Sleeps 10

9 Reviews

$700

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Truman House

4 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located on an upscale and …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(9)

Extremely comfortable house in a great neighborhood

Left on May 13, 2011 for a stay in February 2011

The Truman house is an extremely comfortable house in a great neighborhood. We rented the house two years in a row for three months. We loved the huge heated pool and the privacy afforded by the landscaping. The location gives you the opportunity to enjoy some of the best restaurants in Key West, all within walking distance. While only a few blocks from Duval Street, you are far enough away to …

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$700

4 BR / 3 BA / Sleeps 8

15 Reviews

$700

Inquire

Admiral's Lane

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

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Reviews

(15)

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

Details

Reviews

(15)

Excellent experience

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

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

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$800

4 BR / 3 BA / Sleeps 10

4 Reviews

$800

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Villa Deja vu Key West ~ Weekly Rental

4 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get that sense that you’ve been there before? When I first visited this vacation rental house, it happened to me. My mind sparked, the place seemed wonderfully familiar, and I felt an…
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Perfectly Private in Key West

Left on Jun 05, 2012 for a stay in June 2012

We just returned from a wonderful trip to Key West and a much anticipated visit with my daughter and her boyfriend. We were also very fortunate to have stayed at a wonderful rental called Villa Deja Vu. From the minute we walked into Villa Deja Vu it was like entering a sweet, happy and quiet place. Every inch of the resident was beautifully decorated in perfect Key West fashion and the most …

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$800

4 BR / 4 BA / Sleeps 10

9 Reviews

$800

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Amelia's Hideaway ~ Weekly Rental

4 BR / 4 BA / Sleeps 10 | Quick view
“ Very Good ” 9 Reviews

Details

Reviews

(9)

"In-the-know" travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval, and …
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Stereo or CD player
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(9)

Hidden Gem

Left on May 10, 2011 for a stay in April 2011

My husband and I rented this property with two other couples for a weeklong get away. The house is located at the end of what is now a dead-end street. Standing outside looking at the front of the house you would never guess what is behind the gates - thus the title "hideaway" is very appropriate. The description of this property as well as the pictures on the web site were exactly as we found …

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$800

4 BR / 3 BA / Sleeps 10

6 Reviews

$800

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Pavilion Villa ~ Weekly Rental

4 BR / 3 BA / Sleeps 10 | Quick view
“ Very Good ” 6 Reviews

Details

Reviews

(6)

A Private Tropical Paradise... is the feeling you get when you enter the pavilion of this extraordinary award winning villa just a half block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select private homes…
  • Housekeeping Optional
  • A/C or climate control
  • Parking
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Great Stay!

Left on Jan 12, 2011 for a stay in April 2010

We stayed here with a big group in April, and had the time of our lives. GREAT PLACE!

We got there early, and the maid was still cleaning when we walked in. She was hesitant to let us leave our bags there because of liability reasons, which we totally understood. She let us leave them there anyway, and all was well. :)

There are actually 3 bedrooms available, but you can make it 5. My …

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$572

4 BR / 2 BA / Sleeps 8

2 Reviews

$572

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OLD TOWN KEY WEST - Historic & Charming - Main

4 BR / 2 BA / Sleeps 8 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends. The house can comfortably accommodate a maximum of eight (8) guests - (1) queen bed, (1) full …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

February visit to Key West

Left on May 21, 2010 for a stay in February 2010

Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

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$1,200

6 BR / 5 BA / Sleeps 12

1 Reviews

$1,200

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Island Rendezvous ~ Weekly Rental

6 BR / 5 BA / Sleeps 12 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in the heart of Old Town Key West. Here you will enjoy a completely private retreat with an atmosphere of wonderfully unchanged Caribbean charm. By combining Pavilion Villa and Down Island Digs it won&#…
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Perfect for a large family

Left on Jun 15, 2014 for a stay in June 2014

We had 14 people (5 couples and 4 children) and this place was absolutely perfect. The location could not be better. It's a block away from duval, but very quiet (aside from the garbage trucks once a week, and the expected key west roosters). It was very private and very comfortable. With our 14 people, it didn't feel crowded, everyone had plenty of room, and we all got to hang out together …

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$700

4 BR / 4 BA / Sleeps 8

2 Reviews

$700

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Key West Wabi Sabi ~ Weekly Rental

4 BR / 4 BA / Sleeps 8 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof. True to its name, …
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great house - PRIME location

Left on Dec 28, 2014 for a stay in December 2014

We stayed here for a week over Christmas with 4 adult kids and had the best time ever. The accommodations were great for 6 of us and we couldn't ask for a better location! Across the street from the market, 1/2 block off Duval and easy walk to the best bars, the marina, and the beach. The back patio and pool were a bonus. Would never stay anywhere else when we come back to Key West!

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$800

4 BR / 4 BA / Sleeps 10

5 Reviews

$800

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Key West Spa Villa ~ Weekly Rental

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

Have you ever outgrown a favorite small space, and dreamed about transforming it into something larger and even better?  Wishing you could somehow magically gain enough room to expand it so it offered twice the space, while keeping all its original charm?  Well … that’s exactly what happened …
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Deck
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(5)

Great house and location!

Left on Jan 08, 2012 for a stay in November 2011

We wanted a rental that was located close to everything on Duval St. and that is what we got. It is only a couple of streets away from South Beach and the beautiful sunsets Key West has to offer. The house was fully furnished so the only thing u need are some groceries. It also has a small but deep dipping pool which was nice when you needed to cool off or just have a soak. The house has been …

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$1,200

7 BR / 5 BA / Sleeps 14

3 Reviews

$1,200

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Classic Key West Estate ~ Weekly Rental

7 BR / 5 BA / Sleeps 14 | Quick view
“ Average ” 3 Reviews

Details

Reviews

(3)

Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once authentic and magnificent. If you have ever had the opportunity to stroll the residential streets of the Historic Seaport of Old Town of Key West, you have experienced first hand the …
  • Shared outdoor pool (unheated)
  • Housekeeping Optional
  • A/C or climate control
  • Porch
  • Garden
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

bad area

Left on Jun 25, 2012 for a stay in June 2012

house is spacious with large rooms. pool is small but enough to get wet. i was attacked out front on the street by a strange man and police were called. do not walk this street alone. house keeping walk in on you without knocking which made me uncomfortable too. also exchange the 3 keys face to face and get a signed receipt.

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$600

4 BR / 3 BA / Sleeps 8

1 / 15

$600

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Fantasy Resort Villa ~ Weekly Rental

4 BR / 3 BA / Sleeps 8 | Quick view

Details

This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in Old Town Key West. …
  • A/C or climate control
  • Linens Provided
  • Stereo or CD player
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$800

4 BR / 4 BA / Sleeps 8

1 / 18

$800

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Villa Nouveau Key West ~ Weekly Rental

4 BR / 4 BA / Sleeps 8 | Quick view

Details

Sometimes a Key West cottage that at first glance appears predictable from the outside, is full of abundant surprises when you walk inside. Villa Nouveau Key West vacation rental has an interesting story that attests to this truth. Once a prosaic 'shot-gun' style cottage, a modern redesign has thoughtfully …
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Stereo or CD player
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$800

4 BR / 4 BA / Sleeps 10

1 Reviews

$800

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Twice as Nice ~ Weekly Rental

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

In this case... "Two is definitely better than One"! A rare set of early 1900's "twin-cigar maker's cottages" perched on the southern end of famous Duval Street. The Twice As Nice  vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to…
  • Shared outdoor pool (unheated)
  • Housekeeping Optional
  • A/C or climate control
  • Deck
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Exactly as described - very nice!

Left on Nov 04, 2012 for a stay in October 2012

House decorated nicely and very well maintained. Great pool and above average accommodations. Close enough to walk to everything at Mallory Square if you like a little exercise. Lots of things to do very close by and you can definitely walk to the beach if you like. Right in the heart of things but not too close so you can still get a good nights sleep!

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$675

4 BR / 4 BA / Sleeps 8

3 Reviews

$675

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Heavenly Hideout at Rainbow's End ~ Weekly Rental

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

Details

Reviews

(3)

Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This …
  • Housekeeping Optional
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Perfect stay

Left on Jun 09, 2013 for a stay in June 2013

The staff is fantastic. After we booked the house we received the welcome packet with all our questioned answered. This was a perfect house for me and my family. The rooms were very comfortable. Each room had a bathroom. The kitchen was fully stocked with plates, cups, utensils, etc. The location is amazing. Just a block away from Duval. We walked everywhere. We will stay here again.

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$1,350

9 BR / 7 BA / Sleeps 22

1 / 39

$1,350

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Family Reunion ~ Weekly Rental

9 BR / 7 BA / Sleeps 22 | Quick view

Details

Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key West vacation rental compound, with large private swimming pool in spacious landscaped tropical garden setting, could be the perfect place. Family Reunion Key West vacation rental includes: The Flower …
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Linens Provided
  • Stereo or CD player
  • Telephone
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$283

4 BR / 3 BA / Sleeps 8

1 / 16

$283

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Key West~Indies ~ Monthly Rental

4 BR / 3 BA / Sleeps 8 | Quick view

Details

When I first toured this special Key West ~ Indies vacation house, I was struck by the refreshingly authentic blend of its multi-cultural exterior design and interior decor, and felt as if I could be standing in a villa in the British Virgin Islands (BVI). It's not surprising the home embodies this "savoir …
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Parking
  • Garden
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$675

4 BR / 4 BA / Sleeps 8

6 Reviews

$675

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Penthouse On Duval ~ Weekly Rental

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the  fabulous Penthouse on Duval. This unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched just above the fun and frolic of the…
  • Housekeeping Optional
  • A/C or climate control
  • Deck
  • Satellite or cable TV
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Amazing Remodeled Units and Location on Duval

Left on Aug 31, 2011 for a stay in May 2011

I strongly recommend this property for those planning on enjoying themselves on Duval street. We rented both units for a group of eight and felt like it was an MTV Real World house. Both units were completely remodeled in high quality with unique features. The master bathroom in one unit had a rain shower-head above the bathtub with no enclosure. The balcony overlooking Duval made for some …

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$1,150

5 BR / 4 BA / Sleeps 10

2 Reviews

$1,150

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The Caroline House Estate ~ Weekly Rental

5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West Victorian house…
  • Internet Access
  • A/C or climate control
  • Grill
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great Family Vacation for 12!!!

Left on Mar 28, 2014 for a stay in February 2014

The Caroline House can do no wrong. Each room is painted a cheerful color and casually decorated. The kitchen is fully stocked with dishes, wine glasses, martini glasses and anything you could ask for to host an evening dinner. We spent many mornings in the pool and hot tub (my kids favorite part) before heading out to Duval St. Duval is a short 2 block walk. There are tons of restaurants to …

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$1,150

4 BR / 4 BA / Sleeps 8

1 Reviews

$1,150

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Tropical ~ Tranquility ~ Weekly Rental

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

Details

Reviews

(1)

Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and completely hidden from view …
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Stereo or CD player
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Girl get-away

Left on Apr 12, 2012 for a stay in February 2012

Wonderful place. As nice as photos in ads. Pool has sun all day, am and pm! Plenty of bathroom space. Lovely kitchen. We managed a week without a car. Not too far to walk to all the fun night spots. Beach walk took 5 minutes!

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$1,525

7 BR / 7 BA / Sleeps 16

6 Reviews

$1,525

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Grande Dame Key West - 'The Watson House' ~ Weekly Rental

7 BR / 7 BA / Sleeps 16 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and modern …
  • Housekeeping Optional
  • A/C or climate control
  • Porch
  • Garden
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

One of the best vacations I've taken.

Left on Oct 17, 2011 for a stay in October 2011

There were a total of 16 people staying in the main house and the cottage. We were there celebrating a friends 50th birthday. The houses were wonderful!! They were clean andthe amenities were great!! The kitchens saved us from having to go out every morning to eat. We put the food in the main house kitchen and had our beer and liquor in the cottage refrigerator. :) The 3 washers and dryers …

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$2,325

11 BR / 11 BA / Sleeps 24

1 Reviews

$2,325

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The Meeting Point - Key West ~ Weekly Rental

11 BR / 11 BA / Sleeps 24 | Quick view
“ Poor ” 1 Reviews

Details

Reviews

(1)

The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. Situated in the heart of Old Town, there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West, both in …
  • Housekeeping Optional
  • A/C or climate control
  • Balcony or terrace
  • Garden
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Not up to standars

Left on Apr 09, 2015 for a stay in March 2015

Not well mantained

Low quality furniture, and kitchen equipment, silver and tableware very cheap, plastic glases and cups. For 23 people very small dinning are. Not clean. For the price we paid it was a disappointment.

Good thing: excelent location and good parking space.

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