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$200

3 BR / 3 BA / Sleeps 7

Luxurious Manor ~ Monthly Rental - Key West vacation rentals
1 / 16

$200

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Luxurious Manor ~ Monthly Rental

Key West house
3 BR / 3 BA / Sleeps 7 | Quick view

Details

Live in the lap of luxury in this stunningly renovated Key West classic "Eyebrow House." An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist / sailor to execute his plans to create this Luxurious …
  • A/C or climate control
  • Parking
  • Satellite or cable TV
  • Stereo or CD player
  • Telephone
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$400

2 BR / 2 BA / Sleeps 4

49 Reviews

$400

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Valhalla

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 49 Reviews

Details

Reviews

(49)

This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special residence isn't …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(49)

Wonderful Home

Left on Oct 17, 2008 for a stay in October 2008

We participated in a fund raiser for epilepsy in Houston and won the week at the house in an auction. We had never been to Key West and could not have been happier with the house and the island. It was beautiful, well furnished and very comfortable. It was also very close to both the beach and the clubs. We had a great week and will come back and rent from Historic Hideaways again.

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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

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

Details

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

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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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$350

2 BR / 3 BA / Sleeps 4

3 Reviews

$350

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City Island View ~ Weekly Rental

Key West house
2 BR / 3 BA / Sleeps 4 | Quick view
“ Average ” 3 Reviews

Details

Reviews

(3)

Perched just above the fun and frolic of Duval Street at the City Island View vacation rental suite, you're sure to capture the "island beat" that stirs this tiny tropical island of Key West, Florida. This extraordinary Key West vacation rental features the original 2nd floor front porch that spans the …
  • Housekeeping Optional
  • A/C or climate control
  • Satellite or cable TV
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Not worth the price

Left on Nov 04, 2011 for a stay in July 2011

My husband and I were so excited to stay at City Island View during our Florida vacation last July. We'd looked and looked for a hotel or home in Key West that would meet our standards for cleanliness, convenience to downtown Key West attractions, and Key West charm. We finally found the City Island View condo, and it sounded perfect for what we wanted. The price was high, but based on the photos…

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$550

2 BR / 2 BA / Sleeps 4

7 Reviews

$550

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Key West Dreamin' ~ Weekly Rental

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 7 Reviews

Details

Reviews

(7)

Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one that links us to …
  • Shared outdoor pool (unheated)
  • Housekeeping Optional
  • A/C or climate control
  • Garden
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(7)

Perfect week in Key West!!!

Left on Jun 25, 2011 for a stay in June 2011

My two sisters and I spent a week in Key West, starting Memorial Day Weekend, for my sister's 60th birthday. We could not have been more pleased with Key West Dreamin'!!! The house and location are perfect. I cannot say enough about the cleanliness of this house - VERY clean and well kept. Pictures on the website are very true to the property. Kitchen had everything we needed. LOVED the …

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$600

6 BR / 7 BA / Sleeps 12

Seaport Treasure Estate ~ Monthly Rental - Key West vacation rentals
1 / 31

$600

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Seaport Treasure Estate ~ Monthly Rental

Key West house
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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$133

2 BR / 5 BA / Sleeps 4

1 / 14

$133

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Buoy's Backyard

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

Details

MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has 2 buildings …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - over five
  • Wheelchair accessible

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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

Key West 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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$172

1 BR / 1 BA / Sleeps 2

21 Reviews

$172

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Key West Seashell Cottage-1 block to Duval, spa

Key West house
1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 21 Reviews

Details

Reviews

(21)

Forget that "been there, done that" hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and "Sunset Celebration". The original local artwork throughout…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(21)

Great rental at a great price!

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

My husband and I went here for a summer vacation and really enjoyed staying here. The location is very close to Duval Street, restaurants, shops, and other activities but still on a quiet, private street. The house is bigger than it looks in the pictures, is well kept and very clean. The furniture is comfortable. The bed was a little harder than I am used to but my husband liked it :) Everything …

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$175

2 BR / 2 BA / Sleeps 5

8 Reviews

$175

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Sunrise at Seaside Condo 2 Bedroom

Key West condo
2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers Beach. Plenty of …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(8)

OK

Left on Feb 14, 2014 for a stay in February 2014

when we arrived the condo smelled cigarette smoke, there was no notation if there is wi-fi and if there was no code was provided until we called the following day.

i know this is Key West where smoking is allowed everywhere. when i looked at the ad smoking was not mentioned. i just assumed that the condo would be smelling great since the rent was top notched. it is about 4 miles to the heart of …

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$185

2 BR / 1 BA / Sleeps 4

21 Reviews

$185

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Shipyard

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

Details

Reviews

(21)

This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket fences give the …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(21)

Great for Boat Races!

Left on Nov 13, 2008 for a stay in November 2008

Great location for walking to watch the races and Duval Street. Quaint,clean, and spacious. Small bathroom and kitchen that need an update, but otherwise a great place! I stayed in a gated complex so the added security was a plus and I felt safe at all times. I would certainly stay again without hesitation!

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$400

2 BR / 2 BA / Sleeps 4

11 Reviews

$400

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Casa Camilla

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 11 Reviews

Details

Reviews

(11)

You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the property is beautifully …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(11)

absolutely gorgeous!

Left on Dec 07, 2011 for a stay in November 2011

The house is absolutely beautiful and in a great location; easy to get to Duval street. Very quiet neighborhood. The house had everything except internet access and a heated pool/jacuzzi.

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$83

2 BR / 2 BA / Sleeps 4

1 / 23

$83

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Playa Royale - Monthly Rental

Key West condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Playa Royale is located on South Roosevelt Blvd., directly across from Key West's largest beach (Smathers) on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the pool, tennis courts …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$183

3 BR / 3 BA / Sleeps 10

1 / 24

$183

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

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

Details

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

Key West house
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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$167

3 BR / 3 BA / Sleeps 6

4 Reviews

$167

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

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

Details

Reviews

(4)

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

Details

Reviews

(4)

Perfect in Every Way!

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

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

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

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$83

2 BR / 2 BA / Sleeps 6

1 / 29

$83

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"SEASIDE HIDEAWAY" Beautiful Key West Condo w/ Shared Pool & Tennis Courts

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

Details

***Due to licensing restrictions, this property requires minimum stay of 28 nights*** This condominium is located right near the entrance of Key West and offers unparalleled seclusion and privacy. Although it is on the opposite side of the island from world famous Duval St, it is only about a 10 minute drive away. …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$117

2 BR / 2 BA / Sleeps 6

1 / 17

$117

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Amazing Grace

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

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Amazing Grace is nestled in the middle of the island on Seidenberg Avenue that dead ends into Salt Run Canal that divides Key West in half. With 2 bedrooms, 2 bathrooms, off street parking and a hot tub you may find that you …
  • Dishwasher
  • Microwave
  • Refrigerator
  • Toaster
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$178

4294967295 BR / 1 BA / Sleeps 4

4 Reviews

$178

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"SUN ALSO RISES" - Papa`s Hideaway Historic Inn - Studio (2nd Flr)

Key West house
1 BA / Sleeps 4 | Quick view
“ Very Good ” 4 Reviews

Details

Reviews

(4)

Papa's Hideaway is a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value. This studio is located on the second floor and offers a king-size bed, queen-size sleeper sofa, kitchenette, beautiful …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

really nice grounds

Left on Feb 13, 2014 for a stay in January 2014

pool area and grounds were very nice...room was clean but needed some TLC..screen was broken on sliding door..no way to lock the door...kitchenette lacked anything but bare bones...coffee filters would have been nice...decent basic room..but no frills

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$167

2 BR / 2 BA / Sleeps 6

8 Reviews

$167

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

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

Details

Reviews

(8)

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

Details

Reviews

(8)

Always love 625

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

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

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$93

1 BR / 1 BA / Sleeps 4

1 / 14

$93

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

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

Details

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

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$157

3 BR / 3 BA / Sleeps 8

1 / 26

$157

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

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

Details

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

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$308

3 BR / 4 BA / Sleeps 8

1 / 21

$308

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La Dolce Vita - Luxury Monthly Rental Private heated pool

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

Details

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

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$150

2 BR / 1 BA / Sleeps 4

1 / 15

$150

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"ISLAND RENDEZVOUS" Gorgeous Old Town Home w/ Private Pool

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

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** This exclusive home in the heart of the island offers optimum privacy while having an airy and open floor plan and the best of appointments throughout. Whether enjoying the heated pool flanked by meticulously maintained …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$183

3 BR / 3 BA / Sleeps 8

1 / 21

$183

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Blackbeard's Treasure - MONTHLY Rental (30 night min.)

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

Details

SPRING SPECIALS! 10% off MAY & JUNE 2015! Please see Specials Page for terms, rules and limitations. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water…
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

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$83

2 BR / 2 BA / Sleeps 6

1 / 24

$83

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"SALT POND HIDEAWAY" 2/2 Condo w/ Huge Shared Pool & Hot Tub. Close to Beach!

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

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right across the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$83

1 BR / 2 BA / Sleeps 4

6 Reviews

$83

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

Key West house
1 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

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

Details

Reviews

(6)

Great time in Keys at Esperanza

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

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

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$286

2 BR / 2 BA / Sleeps 5

10 Reviews

$286

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Havana Hideaway

Key West condo
2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships, cruise ships, pleasure …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(10)

Week in Paradise

Left on Jan 16, 2013 for a stay in December 2012

This was one of the greatest stays that we have had. Condo was within walking distance to everything block to most. Very nice place to stay. Easy check in and check out process. This place has a great view from pool. We were here in December with about 80 degree temps each day so we shut down the air and had the doors open most of the time the only draw back to this is the chickens will wake…

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$229

2 BR / 2 BA / Sleeps 6

5 Reviews

$229

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1/2 Block to Duval, World of its own -Nassau Suite

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an endless party, The …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(5)

Wish I had found this place 15 years ago.

Left on Jan 06, 2014 for a stay in December 2013

Stayed in the Nassau the week of Christmas thru New Years. Came down with two other couples. The pictures do not do this place justice. Plenty of room for all. Having two bathrooms was also a plus. Very close to Duval street, and anywhere you really would want to go is in walking distance, minus the beach, but is a short/cheap taxi ride away. Our unit had 90% new furniture, and matresses. …

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$700

4 BR / 4 BA / Sleeps 8

2 Reviews

$700

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Hermitage South

Key West house
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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$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

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BONAIRE SUITE #210 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Average ” 1 Reviews

Details

Reviews

(1)

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

Details

Reviews

(1)

Our trip

Left on Feb 19, 2015 for a stay in February 2015

When we got into the condo we had ants on the counter. The next day went to the office to let them know, they had someone come and spray. The sofa bed's mattress needed to be replaced. Last year rented a condo in the same build, it was nicer. Had beach chair to take to the beach nice touch.

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$700

3 BR / 3 BA / Sleeps 7

7 Reviews

$700

Inquire

Secret Villa - a Key West Hidden Gem in Historic Old Town

Key West house
3 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

Location, Location, Location....This amazing property is situated on a quiet and peaceful lane away from traffic and noise. The secret location is also just a few blocks from everything Key West has to offer; fine dining, nightlife, shopping, museums. Private Pool, lush tropical gardens, fine furnishings all add up to…
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(7)

Secret Villa - Fabulous

Left on Apr 26, 2014 for a stay in April 2014

Wonderful location - quiet, tucked away yet only two blocks from Duval. The house is beautifully decorated -outdoor deck and pool area is superb. Have stayed in a number of luxury Key West vacation rentals over the years and this is by far the best. Carlos was a wonderful host and it was so good to meet Jim, the actual property owner.

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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

Key West condo
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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$286

2 BR / 2 BA / Sleeps 4

20 Reviews

$286

Inquire

Foundry's Corner

Key West house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 20 Reviews

Details

Reviews

(20)

Thoroughly Key West and designed for easy living, this three-story town home is located in the Foundry, part of the residences within the prestigious Truman Annex gated community only a block from Duval and the Historic Seaport. While the impressive brick structure that houses this residence was built around 1845 as …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(20)

Awesome Hideaway

Left on Nov 19, 2008 for a stay in October 2008

I was absolutely thrilled with this property, the townhouse was well appointed and beyond comfortable. The location cant be beat as its just a minutes walk to the north end of Duval St. and all its bars and restaurants. We were there for Fantasy Fest and having a secluded, quiet place to come back to away from all the madness that is FF was quite wonderful. I suppose if I had to rate this …

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$117

2 BR / 1 BA / Sleeps 7

3 Reviews

$117

Inquire

The Tree House Old Town Built 1883 MONTHLY Rental

Key West house
2 BR / 1 BA / Sleeps 7 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key West has to offer. …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Wonderful

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

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

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$140

1 BR / 1 BA / Sleeps 4

1 / 13

$140

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Conch Haven Built 1883 Beautiful ! MONTHLY Rental

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

Details

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

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$350

3 BR / 2 BA / Sleeps 8

12 Reviews

$350

Inquire

Key West - Libra

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

Details

Reviews

(12)

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

Details

Reviews

(12)

Fantastic time

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

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

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$66

1 BR / 1 BA / Sleeps 4

1 Reviews

$66

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Artist cottage with hot tub

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

Details

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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$325

2 BR / 3 BA / Sleeps 4

34 Reviews

$325

Inquire

The Mermaids House, Old Town Key West

Key West house
2 BR / 3 BA / Sleeps 4 | Quick view
“ Excellent ” 34 Reviews

Details

Reviews

(34)

Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga or meditation on the …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Smoking allowed - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(34)

Excellent choice for Key West!

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

This is a great place to stay for seeing Key West! All the amenities you need for 2-4 people; has all the comforts of home and just 1 block off of Duval St. It's very well decorated, many original historic features, clean, and has a great backyard patio for outdoor dining, relaxing in the hammock, or just enjoying time there. Bikes are available for discovering the beaches, the Hemingway House …

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$185

2 BR / 2 BA / Sleeps 6

1 Reviews

$185

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Penthouse Condo in Key West Florida

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Average ” 1 Reviews

Details

Reviews

(1)

Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the beautiful pool and …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Noisy inconsiderate poorly behave guests

Left on Sep 03, 2013 for a stay in September 2013

Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day they were all over the pool and parking and once again kept me up until 4:29 PM. By Sunday I was a wreck, very tired and could not stop yawning with a severe headache and not for having a hang over but from lack of …

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$217

2 BR / 2 BA / Sleeps 6

1 / 12

$217

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Historic Hideaway Olivia Retreat Key West

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

Details

Look no further you have found a beautiful 2 bedroom 2 bath "Shot-Gun" house in the heart of Old Town Key West, just 4 blocks from Famous Duval Street. This great property is very spacious and will accommodate up to 6 guests comfortably. There is a Fully equipped kitchen with a full size dining table in the …
  • Washing Machine
  • Outdoor Dining Area
  • A/C or climate control
  • Patio
  • Books
  • Suitable for children
  • Suitable for the elderly - ask

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$83

2 BR / 2 BA / Sleeps 6

1 / 30

$83

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"HOWE STREET HIDEAWAY" Newly Renovated 2 Bed Two Bath Home.

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

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The neighborhood is complete with conch style homes, little lanes, corner gardens and yes our famous Key West Roosters watching their chicks. Featuring a classic front porch for greeting the neighbors as they go about their day…
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

2 BR / 2 BA / Sleeps 6

1 / 26

$198

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

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

Details

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

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$198

2 BR / 2 BA / Sleeps 6

1 / 27

$198

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

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

Details

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

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$100

1 BR / 1 BA / Sleeps 4

1 / 23

$100

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

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

Details

***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This inviting HGTV Featured Home (Bang for Your Buck, 2010) surrounds you with luxury, comfort and history. Originally a Cuban Cigar Maker’s Cottage (circa 1920’s), this vacation home has been updated with no expense spared. …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$149

1 BR / 1 BA / Sleeps 4

10 Reviews

$149

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Your Condo by the Beach with Ocean View

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

Details

Reviews

(10)

The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen size sleeper sofa in the living area. It accommodates 2-4 people. This property is rented by the week from Saturday to Saturday, it is not a hotel; it is a privately owned condo facing the …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

Details

Reviews

(10)

The View

Left on Jan 14, 2011 for a stay in June 2010

The wonderful view made the hot, tropical, June climate worth it. It was so nice to relax on the balcony and enjoy the view. Apartment was very nice to come home to after a day of fun in the sun! Location a big plus. Use of bikes and bus line helped with getting around. Can't wait to return!!!

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$250

2 BR / 2 BA / Sleeps 6

35 Reviews

$250

Inquire

Duval Square

Key West house
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 35 Reviews

Details

Reviews

(35)

The rooftop community of Duval Square is a prime perch from which to launch the best tropical vacation ever. The townhomes cluster on the second story above their namesake square. Winding pathways bordered by swaying palm and colorful plantings arranged in terracotta pots define the layout. Best of all, the small …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(35)

Barbecue

Left on Aug 14, 2008 for a stay in February 2008

The vacation week was good, except for the use of the barbecue. When we had stayed there before we had used the barbecue every other night (and gone out for dinner the other nights). We have a 6 yr. old and the deal we made with him was the above (as you know 6 yr. olds couldn't care less about eating out) and prefer barbecues and staying in. (ours does anyway). This February we were told that we…

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$215

1 BR / 2 BA / Sleeps 4

1 / 6

$215

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Coconut Beach

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

Details

This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a "closet kitchen", a king bed…
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$350

3 BR / 2 BA / Sleeps 8

12 Reviews

$350

Inquire

Key West - MV Coconuts

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

Details

Reviews

(12)

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

Details

Reviews

(12)

awesome stay in Key West

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

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

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$600

3 BR / 3 BA / Sleeps 6

9 Reviews

$600

Inquire

Kemp House

Key West house
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort and contemporary …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(9)

very lovely

Left on Feb 09, 2009 for a stay in November 2008

Beautiful house. Near everything. Comfortable and well kept.

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