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Cottages in Key West, FL

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From
$178
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
19 photos Details Reviews (1) Make Inquiry
From
$138
Per Night
Studio, 1 Bathroom, Sleeps 4
14 photos Details Reviews (3) Make Inquiry
From
$188
Per Night
Studio, 1 Bathroom, Sleeps 2
12 photos Details Reviews (14) Make Inquiry
From
$118
Per Night
Studio, 1 Bathroom, Sleeps 2
7 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 17, 2014
This unit was perfect for our needs. It's just a small studio cottage, but has a nice porch and access to the large "shared" (and I put it in quotations because we had the pool...
4 of 5 stars Reviewed July 28, 2014
This rental was almost exactly how I imagined it to be when I booked it. It was small, yet quiet with an adjacent pool that was large enough for my float and warm enough for me...
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From
$178
Per Night
Studio, 1 Bathroom, Sleeps 2
12 photos Details Reviews (35) Make Inquiry
5 of 5 stars Reviewed May 16, 2014
Heaven in the middle of Key West. Beautifully decorated, clean, perfect pool & hot tub, Amazing! Staff is very attentive and replenishes towels, changes garbage, maintains the...
5 of 5 stars Reviewed March 31, 2014
We stayed with our yorkie, love love it. Very clean (although the bed was a bit uncomfortable) very clean staff was very friendly and helpful.five stars in our book we will stay...
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From
$198
Per Night
Studio, 1 Bathroom, Sleeps 2
11 photos Details Reviews (19) Make Inquiry
5 of 5 stars Reviewed September 2, 2014
Really enjoyed this place. Pics are accurate as this place looks in great condition. Loved the patio/hot tub area, also the use of the pool just across the street and grill...
5 of 5 stars Reviewed March 12, 2014
We absolutely loved Harrison's Hideaway. It was in the perfect location - 1/2 block off of Duval, a very short bike ride to the beach. It was immaculate, too - must have been...
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From
$378
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (12) Make Inquiry
3 of 5 stars Reviewed August 12, 2014
Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking. Cons - across...
5 of 5 stars Reviewed July 27, 2014
Stayed at Passover Cottage for my wife's 50th birthday with friends and family. The property was well-maintained and clean. Location was perfect, close enough to the activities...
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From
$468
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 12
36 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed July 29, 2014
Tradewinds was the perfect place for 6 cousins to stay as we gathered in KW to send my sister's ashes off into her beloved warm ocean. The accommodations were perfect for the 6...
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From
$208
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
12 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed October 13, 2014
The location of our rental was fabulous. We were in walking distance of everything Key West had to offer. Having the front porch open would have made the stay even better.
4 of 5 stars Reviewed September 29, 2014
Great place to stay! Located right on Duval Street. Two rooms with double beds and a pull out bed-couch. A/C nice and cold when you need to get out of the summer heat in the...
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From
$338
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
16 photos Details Reviews (41) Make Inquiry
4 of 5 stars Reviewed June 30, 2014
Great house pretty much right off Duval. Very close to great restaurants, bars, and shops, and a very short walk to the beach. Plenty of room for three couples and one child. Not...
5 of 5 stars Reviewed April 23, 2014
From the moment we received our key to the time we turned it in to go home. Everyone involved made our stay perfect.
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From
$258
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
23 photos Details Reviews (15) Make Inquiry
5 of 5 stars Reviewed July 1, 2014
Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
5 of 5 stars Reviewed February 4, 2014
We have stayed at this property on previous visits to Key West- it is a great location- close to everything and has plenty of space. Easy to cook at home if you don't want to go...
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From
$178
Per Night
Studio, 1 Bathroom, Sleeps 2
10 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed June 30, 2014
The unit was clean and in a great location. Maintenance was attentive and cleaning staff also. The only trouble we had was virtually ever night some giant vehicle was running...
5 of 5 stars Reviewed April 4, 2014
The place we stayed at was small inside, but big on the outside space. The courtyard was beautiful and added another dimension to the space. Like a living room in the tropics!
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From
$158
Per Night
Studio, 1 Bathroom, Sleeps 2
Booking
10 photos Details Reviews (15) Make Inquiry
5 of 5 stars Reviewed July 16, 2014
Excellent location just off Duval street but still very quiet and private feeling. The unit was small but had all the amenities we needed. The private hot tub and the pool and...
5 of 5 stars Reviewed May 29, 2014
I had stayed at Little Havana Suite numerous years ago and loved it. I knew I wanted to stay in the property again... I ended up traveling solo as my other half got stuck working...
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From
$288
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed October 8, 2014
Papa's Hideaway is the PERFECT place for a group vacation. Everyone has their own room with kitchen and bathroom but there is plenty of space for everyone to gather and eat, drink...
5 of 5 stars Reviewed August 26, 2014
Great southernmost location near the point and near Anna's which has great Cuban coffee and food. Lush tropical grounds and pool with lots of shade. The rooms were nice and...
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From
$258
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
20 photos Details Reviews (34) Make Inquiry
4 of 5 stars Reviewed June 5, 2014
This house is the perfect little hideaway. Close enough to Duval and all the action but far enough away that you can shut out the world and just relax. The hot tub is very...
5 of 5 stars Reviewed March 27, 2014
Leeward Isle is a great place to stay for a trip to Key West. It is within walking distance to all the hot spots and to the beautiful sunsets at Mallory Square, yet far enough...
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From
$298
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
17 photos Details Reviews (19) Make Inquiry
5 of 5 stars Reviewed October 15, 2014
Lennon Lodge has it all - 1 block from Duval in a top of the line apt. with its own hot tub and shared pool. Two very comfortable king bedrooms with shared bathroom , large...
5 of 5 stars Reviewed October 7, 2014
We LOVED Lennon's Lodge. Our trip could not have been made any easier by Key West Vacations. They were very accommodating! My ONLY suggestion is that they place a sign on the...
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From
$188
Per Night
Studio, 1 Bathroom, Sleeps 4
18 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed August 8, 2014
I stayed at Papa's hideaway for 11 nights. I spent some of the time with girlfriends and the last few days by myself. Torrents of spring was perfect for both parts of my trip...
4 of 5 stars Reviewed February 10, 2014
I stayed in unit number 1 for 7 nights and I didn't want to leave!! The property is safe and secure and is perfectly hidden but still a walk to all you need. There is a bbq on...
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From
$138
Per Night
Studio, 1 Bathroom, Sleeps 4
Booking
16 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed July 28, 2014
Located right by the Southernmost Hotel and a block off Duval this was a great stepping off point for fun in Key West. Cuban market on the corner for café con leche each morning...
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From
$268
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed October 7, 2014
The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15 minute...
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From
$408
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
Booking
29 photos Details Reviews (49) Make Inquiry
5 of 5 stars Reviewed July 24, 2014
Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
5 of 5 stars Reviewed May 9, 2014
We rented the Tropical Retreat for our parents during our wedding in Key West. They were extremely happy with everything that this house had to offer. Some of the comments I heard...
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From
$110
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
54 photos Details Reviews (1) Make Inquiry
From
$500
Per Night
Studio, 1 Bathroom, Sleeps 2
Booking
11 photos Details Make Inquiry
From
$6,500
Per Month
3 Bedrooms, 3 Bathrooms, Sleeps 10
24 photos Details Make Inquiry
From
$248
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
11 photos Details Make Inquiry
From
$268
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details Make Inquiry
From
$238
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
18 photos Details Make Inquiry
From
$188
Per Night
Studio, 1 Bathroom, Sleeps 2
10 photos Details Make Inquiry
From
$138
Per Night
Studio, 1 Bathroom, Sleeps 4
Booking
12 photos Details Make Inquiry
From
$138
Per Night
Studio, 1 Bathroom, Sleeps 4
10 photos Details Make Inquiry
From
$138
Per Night
Studio, 1 Bathroom, Sleeps 2
12 photos Details Make Inquiry
From
$188
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
15 photos Details Make Inquiry
From
$1,448
Per Night
11 Bedrooms, 9 Bathrooms, Sleeps 32
24 photos Details Make Inquiry
From
$508
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 10
19 photos Details Make Inquiry
From
$298
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
9 photos Details Reviews (13) Make Inquiry
4 of 5 stars Reviewed September 11, 2014
Great location for walking and biking all around Key West. Close to restaurants and attractions. Limited Parking.
5 of 5 stars Reviewed May 22, 2014
Great location 2 blocks off Duval. Bright, airy, tropical decor. Clean, lots of amenities. Pool was great. Onsite parking. Perfect size for our group of 5 women. Would...
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From
$228
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 6
Bookings
10 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed July 12, 2014
My friend and I stayed at the Bonaire Suite and it was perfect! Cute bungalow style with plenty of room and amenities. So close to Duval, but you couldn't hear the roar, which...
5 of 5 stars Reviewed June 12, 2014
Perfect location! Half block from Duval street. Very cozy and well equipped and lovely pool area. I highly recommend this place.
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From
$288
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
10 photos Details Make Inquiry
From
$225
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
13 photos Details Reviews (18) Make Inquiry
5 of 5 stars Reviewed January 1, 2014
We love staying at the Atlantis House. We stayed in the Master Suite, which was beautiful and comfortable. Kayla and Capt. Steve made us feel very welcomed and at home. We...
5 of 5 stars Reviewed December 3, 2013
This is a great property to stay in Key West. Steve & Kayla are superb hosts, very attentive to every need you may have. Location short bike trip to old town & very close to the...
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From
$215
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
25 photos Details Reviews (41) Make Inquiry
5 of 5 stars Reviewed October 7, 2014
we spent 3 nights here in September , only wish we had stayed for the week . the place was the villa was located just off Duval street but very quite. the rental had everything...
5 of 5 stars Reviewed July 7, 2014
I'm currently sitting by the pool at Ann Street gardens, this place is heaven! The cottage provides you with everything you could ask for. Pictures do not give it justice. Ann...
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From
$100
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
20 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed September 2, 2014
My husband and I stayed in lovely Namaste from May 15th through Aug 15th and were enchanted the entire time. The house is lovely, even better than the fabulous pictures. It is...
5 of 5 stars Reviewed April 30, 2013
The Namaste Cottage was an amazing place to stay during our time in Key West. We spent two weeks at Namaste and were constantly reminded of how central it is to all of the great...
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2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details Make Inquiry
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Suitability

  • Wheelchair access (2)
  • Elder access (9)
  • Suitable for children (5)
  • Pet friendly (13)
  • Smoking allowed (0)

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  • Other outdoor space (25)
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Book Online(36)

Suitability

  • Wheelchair access (2)
  • Elder access (9)
  • Suitable for children (5)
  • Pet friendly (13)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (25)
  • Air Conditioning (24)
  • Grill (24)
  • Internet (23)
  • All pools (18)
  • View all amenities