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Vacation Rentals in Key West, FL

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$175
Per Night
1 / 21
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1 Bedroom, 4 Bathrooms, Sleeps 2
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$199
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1 / 14
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2 Bedrooms, 1 Bathroom, Sleeps 6
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$239
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1 / 9
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Also consider
Tee by the Sea - Luxury 2/3 condo - 7 Bikes FREE
2 Bedrooms, sleeps 6
$250 - $500 / night
Sunshine Luxury Suite - 2 Free Bicycles & Garage
2 Bedrooms, sleeps 6
$186 - $286 / night
Top Of Duval- 6 Bedroom Penthouse
6 Bedrooms, sleeps 16
$1,076 - $1,800 / night
Tropical Paradise on the Atlantic Ocean
2 Bedrooms, sleeps 6
$310 - $360 / night
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$219
Per Night
1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed September 25, 2014
Our place was beautiful. Beds were comfortable, beautifully appointed and more room than we ever imagined! Close to everything! Very clean and all the amenities you need. Check in...
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$233
Per Night
1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed October 17, 2014
My husband and I chose Key West to celebrate our 25th anniversary. Can't say enough about this gorgeous condo. In addition to the cleanliness, ease of reservation, security and...
5 of 5 stars Reviewed July 12, 2014
Checking in was a fast no hassle process. Condo was clean and decorations were wonderful with all the comforts if home . Although we did not use the bikes they are a nice touch...
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$250
Per Night
1 / 15
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed December 31, 2013
Really enjoyed staying at Shelleys Rooftop. Far enough down Duval St. to be away from the crowds but just a walk away to the crowds and popular bars. Spent Christmas with...
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$208
Per Night
1 / 11
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Studio, Sleeps 2
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5 of 5 stars Reviewed November 11, 2014
This place was perfect for what we were looking for: Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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$225
Per Night
1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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2 of 5 stars Reviewed April 15, 2014
We certainly did not get what we thought we were paying for. WiFi was virtually non-existent. The "fully-equipped" kitchen had no serving spoons, only two dish towels, and ants...
5 of 5 stars Reviewed February 10, 2014
I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
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$209
Per Night
1 / 15
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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5 of 5 stars Reviewed November 16, 2014
So glad they just added the pool. The backyard is now an oasis. Location was awesome. And cleanliness was impressive. Only down side was you could hear the people upstairs...
4 of 5 stars Reviewed October 27, 2014
Clean, nicely decorated and close to all the action. The pool and outside area was great! We cooked two meals on the grill poolside which was a nice break from dining out, and...
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$198
Per Night
1 / 10
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Studio, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed August 12, 2014
We rented three units for 5 nites. We had a great week. The staff was very friendy. Everything was clean, Couldn't have ask for a better place to spend our vacation. Cant wait to...
5 of 5 stars Reviewed July 29, 2014
From the minute we stepped off the plane, we were extremely impressed by Key West Vacation Rentals. We flew in on a Saturday morning, and they do not typically do airport pick-ups...
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$348
Per Night
1 / 22
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed October 13, 2014
The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
5 of 5 stars Reviewed July 25, 2014
I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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$250
Per Night
1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed March 22, 2014
A great condo. All the amenities. Covered parking, close to the pool. Easy access to downtown, either by car or taxi. Wonderful communication with the owner. First time for 4 of...
5 of 5 stars Reviewed January 23, 2014
The condo was fantastic. I was clean convenient and would recommend to anyone. This was exactly as described.
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$248
Per Night
1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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4 of 5 stars Reviewed November 11, 2014
We had a great night at sunrise suites. It is not central, so you have to get a taxy to go downtown. Because you have a sunset drink, wine with dinner and one before going...
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$257
Per Night
1 / 26
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed July 31, 2014
Great rental, right in the middle of everything. We arrived and everything was as described. Wifi was a great bonus for teenage son. House clean and tidy with plenty of linen...
4 of 5 stars Reviewed June 14, 2014
Everything about our vacation at Casa del Sol was perfect. The apartment is a perfect size and the rooms were decorated to match the Key West atmosphere, which we loved! The...
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$5,000
Per Month
1 / 22
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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4 of 5 stars Reviewed March 12, 2014
We were at Tobago House for the month of February 2014. It is absolutely wonderful !! I will say that I would have preferred if everything had been tested out before we got...
5 of 5 stars Reviewed January 23, 2014
Tobago House is very nice, close to Duval - quiet street. Nice amenities, pool, hot tub, great outdoor area. Would recommend to anyone. Close walk to everything. Wonderful!
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$1,400
Per Week
1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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4 of 5 stars Reviewed September 18, 2014
Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
5 of 5 stars Reviewed May 12, 2014
Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
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$198
Per Night
1 / 11
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Studio, 1 Bathroom, Sleeps 2
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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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$7,000
Per Month
1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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4 of 5 stars Reviewed January 23, 2014
B+ no Choices in cable channels no prkg On site , parrot sanctuary adjacent Property's remote pool. Access. K
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$6,800
Per Month
1 / 20
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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4 of 5 stars Reviewed February 3, 2011
We spent the month of March at Villa azul in 2008. It was amazing. We discovered Key West in a way I never thought possible...some of our best moments were spent in the oasis...
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$188
Per Night
1 / 18
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Studio, 1 Bathroom, Sleeps 4
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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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$188
Per Night
1 / 16
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Studio, 1 Bathroom, Sleeps 4
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4 of 5 stars Reviewed September 4, 2014
My girlfriend and I spent 5 days at Papa's Hideaway and absolutely loved it. The place was a quiet refuge from the hustle and bustle of Key West. Most of the fun things to do...
5 of 5 stars Reviewed June 25, 2014
Small bathroom but a great property. Pool was nice and privacy of location was excellent. A block an a half from Duvall Street, 3 blocks from Southern Most Point. Would stay...
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$288
Per Night
1 / 21
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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3 of 5 stars Reviewed November 5, 2014
The home was perfect, loved the porch. Everything we needed for a great home away from home vacation was supplied. The only draw back was the shared pool with other rental units...
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...
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$378
Per Night
1 / 37
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3 Bedrooms, 3 Bathrooms, Sleeps 10
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4 of 5 stars Reviewed July 30, 2014
Lovely we'll maintained, self catering, semi-detached apartments which allows privacy yet accommodates large extended family barbecues and mingling. We hired 3 of the apartments...
5 of 5 stars Reviewed July 28, 2014
Pictures online are great and the property was perfect for 3 families traveling together. We tried not to be in rooms during the day since we were busy with excursions but the...
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From
$3,800
Per Month
1 / 27
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2 Bedrooms, 3 Bathrooms, Sleeps 4
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From
$290
Per Night
1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed November 2, 2014
This two bedroom condo has everything! Beautiful views, beautiful decor, incredibly clean and comfortable and equipped with everything you could want. We stayed for four days and...
5 of 5 stars Reviewed June 23, 2014
We had a wonderful stay at the Atlantic Sunrise condo. The condo was tastefully decorated and well appointed. It was roomy and very comfortable for the four of us. The fine...
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$138
Per Night
1 / 14
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Studio, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed October 17, 2014
We had an excellent experience staying in this studio for our honeymoon. Only drawback was the lack of kitchen equipment which made it difficult to cook a full meal for...
4 of 5 stars Reviewed September 24, 2014
It was a great location out of the way but by everything. Also the room was very secluded to the back of the property for a nice romantic time.
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$258
Per Night
1 / 22
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed November 10, 2014
My husband and I have rented this unit twice now and it is the perfect place. The rental company is wonderful to work with try to get you in to the unit early if possible. This...
4 of 5 stars Reviewed August 5, 2014
Nice condo right on duval st. Good location for a more quiet stay.Cvs right around the corner Rooms where nice. Hot tub on patio is a plus. Only negative comment is I wish we...
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$138
Per Night
1 / 11
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Studio, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed August 28, 2014
This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin to...
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$138
Per Night
1 / 14
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Studio, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed August 5, 2014
The room was a nice size for two friends. It was not fancy, but clean and well equipped. Another plus was the front porch where we sat and people watched while having coffee or a...
4 of 5 stars Reviewed July 25, 2014
The Egret Studio is very close to the Southernmost Point and next door to a Cuban cafe, so I had coffee there every morning. The studio is very clean, well appointed and we were...
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$138
Per Night
1 / 12
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Studio, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed October 29, 2014
We have stayed in this lodging five times. It is very clean and service is excellent and friendly. The location is secluded and especially quiet.
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$408
Per Night
1 / 20
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed July 29, 2014
This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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$408
Per Night
1 / 22
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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5 of 5 stars Reviewed July 1, 2014
We took our family of 6 to Toon Hall and were greeted by 2 Cadillac SUV's at the airport to check us in and take us to our home. Toon Hall was very spacious and comfortable...
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$178
Per Night
1 / 19
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1 Bedroom, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed November 14, 2014
I booked our condo through VRBO based on location and price. What a great find. Perfect location to Old Town activity and only a mi,e leasurely walk to Mallory Square and the...
4 of 5 stars Reviewed October 8, 2014
Everything was great! The location was perfect - and the private hot tub was the best! Only down side (which wasn't a big deal) was there were ants on the kitchen counter! Very...
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$258
Per Night
1 / 18
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2 Bedrooms, 1 Bathroom, Sleeps 6
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4 of 5 stars Reviewed July 21, 2014
Very nice place, beds were super comfy. Close to Duval but quiet. This place does have a parking spot, but we were not told about it until I called.
5 of 5 stars Reviewed March 24, 2014
Excellent accommodations! Slept five adults comfortably, but the one bathroom was a little rough at times. We're all friends so no big deal! Especially enjoyed the hot tub and...
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$178
Per Night
1 / 14
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1 Bedroom, 1 Bathroom, Sleeps 4
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4 of 5 stars Reviewed April 24, 2014
The suite was very clean and well taken care of. The pool was terrific. There is a nice fairly private deck to sit under some magnificent trees. We rented bicycles which made it...
4 of 5 stars Reviewed April 6, 2014
The location a few blocks off Duval and not right on Olivia street was great. By not right on Olivia street I mean you walk through a tiny parking lot, past the pool, down a short...
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$1,300
Per Week
1 / 13
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2 Bedrooms, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed October 24, 2014
I visit Key West often (twice a year if I can). Over the past couple years, I've been booking exclusively with Key West Vacation Rentals. They have wonderful properties available...
5 of 5 stars Reviewed June 5, 2014
We rented this 1st floor condo for two weeks & thoroughly loved it. Location was perfect - tranquil yet within walking distance to Duval Street, dining & the excitement of...
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$4,500
Per Month
1 / 22
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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4 of 5 stars Reviewed August 31, 2009
HAd all you needed. Space was limited and you had to walk to the pools. Clean and great location. PArking left much to be desired. But in Key West you take what you get!!
5 of 5 stars Reviewed July 13, 2009
Good times, great location! I'll be back!
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$128
Per Night
1 / 14
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Studio, 1 Bathroom, Sleeps 2
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5 of 5 stars Reviewed October 24, 2012
We loved this place. We travel with out camper but thought staying in old town would be a good choice. We were right. We stored the camper and parked the van (one of the few...
5 of 5 stars Reviewed April 20, 2012
This little efficiency apartment was just perfect for the two of us. The parking spot on-site let us leave our rental car there, and get around easily. We had coffee every...
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$178
Per Night
1 / 9
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1 Bedroom, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed September 2, 2014
I stayed here this past Labor Day weekend for a friend's bachelorette party. There were 10 of us, and the Heron Hideaway as well as the three other one-bedroom condos in the area...
5 of 5 stars Reviewed May 1, 2014
My husband and I spent 10 nights at Heron Hideaway in celebration of our 20th anniversary. Every thing that we needed was provided in this very clean and ideally located home...
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$268
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1 / 25
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed August 21, 2014
I have stayed in this location once before. They have upgraded the flooring and it looks great. The pool is quiet and relaxing. The unit sits back from Duval Street so there is...
5 of 5 stars Reviewed August 18, 2014
Positioned right with ammeneties, beaches, and bars close by. Short stroll to any need. Place was very clean and with 2 bedrooms, 2.5 baths , pull out beds was very...
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  • Suitable for children (72)
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Book Online(231)

Suitability

  • Wheelchair access (22)
  • Elder access (109)
  • Suitable for children (72)
  • Pet friendly (103)
  • Smoking allowed (4)

Amenities

  • Air Conditioning (454)
  • Internet (410)
  • Other outdoor space (400)
  • All pools (328)
  • Grill (288)
  • View all amenities
Key West Vacation Rentals

Great deals on vacation rentals make Key West a favorite beach getaway spot for all types of travelers. It’s a laid-back beach town with a twist of eccentricity—along with a diverse dining scene and, of course, famous (one might even say infamous) nightlife. From luxury beach houses to budget cottages, you’ll find it in Key West… and our Key West vacation rental reviews will help you book with confidence.

Where to rent in Key West, Florida

Vacation rentals in Key West can be found all over town. Renting in Old Town (the historic district) will put you in the center of the action—steps from restaurants, bars, boutiques, souvenir shops and major attractions. Live like a local and catch an ocean breeze on your verandah (a typical feature of “conch” architecture). Or how about a modern apartment rental near Duval Square? If you’re craving privacy and relaxation, though, consider a Key West vacation rental away from the center of town—enjoy oceanfront views away from the hustle and bustle. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

Key West Bars and Restaurants

Forget paying a premium for mediocre room service in a hotel—book a vacation rental home in Key West and put that money toward excellent meals in restaurants. (Or, if you’re patterning your vacation after Ernest Hemingway, your bar tab.) Be sure to try the conch fritters. And we recommend trying as many different versions of key lime pie as possible—after all, you do want to find the best key lime pie in Key West, right? Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

Sightseeing and Activities in Key West

Now that you’ve found a great vacation house in Key West, what are you going to do with yourself during your vacation? Beach bums will naturally gravitate toward, well, the beach (try Smathers Beach or Fort Taylor Beach)… but there are plenty of other options if you want a more cerebral or active vacation. Hemingway’s house (complete with seven-toed cats descended from his own beloved pets) is a must-see for any literature buff, and you’ll find plenty of secondhand bookstores in town too. Historians will want to explore Henry Truman’s Little White House (located right on Front Street), as well as Fort Zachary Taylor Historic State Park. And definitely don’t leave town without taking in at least one sunset in Mallory Square. Not surprisingly, many of the best things to do in Key West take place out on the water. If you’re new to saltwater fishing, try a fishing charter excursion. A local captain can take you to the best spots for tarpon, marlon, tuna and grouper. Rent a Jet Ski and tour the coastline, or take a charter sunset cruise. Feel like a bit of gambling? You’ll find plenty of casino cruises in Key West as well. They’ll take you out to international waters, where you’re free to hit the slot machines.