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Vacation Rentals in Sugarloaf Key, FL and nearby

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All 66 Rentals in the Sugarloaf Key Area
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From
$300
Per Night
1 / 20
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Sugarloaf Key
3 Bedrooms, 4 Bathrooms, Sleeps 6
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From
$130
Per Night
1 / 25
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Sugarloaf Key
3 Bedrooms, 4 Bathrooms, Sleeps 6
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$333
Per Night
1 / 31
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Sugarloaf Key
4 Bedrooms, 4 Bathrooms, Sleeps 8
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The following rentals are within 10 miles of Sugarloaf Key, Florida Keys, Florida.

From
$500
Per Night
1 / 21
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Summerland Key, FL
4 Bedrooms, 3 Bathrooms, Sleeps 10
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5 of 5 stars Reviewed January 6, 2013
We were at Windswept for Christmas week 2012. Relaxing and exciting at the same time. Beautiful home right on the water. Location is perfect. Morning sunrises, gentle ocean...
5 of 5 stars Reviewed January 3, 2013
Perfect house for extended family group including a toddler. The house had everything you could ask for, lots of places to sit and relax, plastic kayaks, fishing poles, bicycles...
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From
$500
Per Week
1 / 12
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Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
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4 of 5 stars Reviewed September 3, 2014
Overall was a great week, had a small issue but the owner quickly resolved it and the stay was awesome. Would recommend venture out to anyone
3 of 5 stars Reviewed August 21, 2014
This is an older trailer that could use some updating. It is not perfect by far but it is definitely doable for the price. The doors do not lock at all and I was not really...
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From
$115
Per Night
1 / 17
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Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 5
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From
$107
Per Night
1 / 8
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$250
Per Night
1 / 18
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Cudjoe Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$130
Per Night
1 / 54
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Cudjoe Key
3 Bedrooms, 1 Bathroom, Sleeps 6
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From
$250
Per Night
1 / 19
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Cudjoe Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$107
Per Night
1 / 11
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Ramrod Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
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From
$236
Per Night
1 / 23
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Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed August 7, 2014
This home is clean, very comfortable and well equipped. It has a charming island decor that really lends to the atmosphere and everything is well planned. You can enjoy a drink...
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$129
Per Night
1 / 24
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
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5 of 5 stars Reviewed May 12, 2014
The house is cute and right on the water. There has been a nice strong sea breeze all week. It is quiet in May and safe being a gated community. We are close to Key West without...
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From
$285
Per Night
1 / 30
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Summerland Key, FL
2 Bedrooms, 3 Bathrooms, Sleeps 10
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From
$200
Per Night
1 / 15
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Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed January 10, 2013
Stayed at Little Sleeves End and loved it. Went with friends and have to say the location and views were incredible. The house was very nice and well equiped. Bring your boat and...
5 of 5 stars Reviewed April 7, 2012
This is a wonderfully cute waterfront house in a great neighborhood. The house sits high so the views are just beautiful. There is an outdoor shower which is a little slice of...
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$225
Per Night
1 / 24
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed October 25, 2014
Awesome Cudjoe Key get a way. Good sized personal dock behind the house for my boat and great Atlantic Ocean access, was in deep water in about 10-15 minutes. Good fishing off the...
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From
$136
Per Night
1 / 9
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed November 10, 2014
We had a wonderful stay at Venture Out. It was very peaceful and enjoyable. The internet was fast and the cable TV had plenty of channels. The appliances and furniture are modern...
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From
$184
Per Night
1 / 24
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Ramrod Key
1 Bedroom, 1 Bathroom, Sleeps 2
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5 of 5 stars Reviewed August 12, 2014
Most perfect place to stay in the keys. Judy and Tom are the best at providing anything you need and know everything you need to know about the area
5 of 5 stars Reviewed July 7, 2014
The stay, in short, was a dream come true. For a honeymoon--or any holiday, for that matter--the spot was romantic, charming, impeccably clean, cozy, and incredibly comfortable...
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From
$107
Per Night
1 / 10
Cudjoe Key
1 Bedroom, 1 Bathroom, Sleeps 4
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4 of 5 stars Reviewed May 27, 2014
My family and I loved it. We had a great time. We don't have a boat or anything so we just fished off the back area. The kids fished while my wife and I had drinks in the sun...
4 of 5 stars Reviewed November 15, 2013
I really liked the Ventue Out Experience, Nice clean, quaint, charming, Island Condo Style unit…Located in an VERY upscale RV park, on the water… 30 mins to Key West.. …ONE BAD...
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From
$100
Per Night
1 / 11
Cudjoe Key
1 Bedroom, 6 Bathrooms, Sleeps 6
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4 of 5 stars Reviewed April 23, 2014
The unit was nice and clean. Everything worked good. The screen porch was very popular.. I did not have a chance to have my boat there but the dock area was in good shape. The...
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From
$118
Per Night
1 / 12
Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
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4 of 5 stars Reviewed November 23, 2013
Two bedrooms, living room, full kitchen and bathroom was enough to accommodate five people. Place is quiet, but not very close to public beaches. For the end of October there are...
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From
$500
Per Night
1 / 34
Cudjoe Key
4 Bedrooms, 3 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed March 16, 2014
This home is just as described--bright, sunny, clean, and has fabulous ocean views. Close to anything you could possibly want to do in Key West or Marathon. There was lots to do...
3 of 5 stars Reviewed February 17, 2014
The location at the water front is fantastic with a marvelous sunrise and shallow water in the bay. That is hardly found any better anywhere at the Keys. The kayaks were very...
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From
$213
Per Night
1 / 11
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$186
Per Night
1 / 10
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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4 of 5 stars Reviewed October 27, 2014
Enjoyed our stay. Lots to see and do! The view was breathtaking and the resort was in a great location. The pools and hot tub were very convenient. We would definitely visit again!
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From
$171
Per Night
1 / 11
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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1 of 5 stars Reviewed July 9, 2014
we are a working family and so when we take a vacation we want to really relax. we spent 1500 dollars plus a 450 dollar deposit for this small double wide trailer it was nicely...
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From
$121
Per Night
1 / 10
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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1 of 5 stars Reviewed September 18, 2014
Upon entering the house, floors were dirty. Cabinets had roach feces all through out and live roaches in the oven drawer and in cabinets. Did not cook food in the home the last...
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From
$100
Per Night
1 / 3
Cudjoe Key
Studio, Sleeps 4
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From
$86
Per Night
1 / 7
Cudjoe Key
Studio, 1 Bathroom, Sleeps 6
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From
$136
Per Night
1 / 11
Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
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From
$114
Per Night
1 / 7
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$129
Per Night
1 / 8
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
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From
$93
Per Night
1 / 9
Cudjoe Key
1 Bedroom, 1 Bathroom, Sleeps 4
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From
$121
Per Night
1 / 9
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$171
Per Night
1 / 11
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
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From
$100
Per Night
1 / 10
Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
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From
$157
Per Night
1 / 10
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$350
Per Night
1 / 27
Cudjoe Key
3 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (16) Make Inquiry Similar Properties
5 of 5 stars Reviewed April 28, 2014
Heron's Roost is a lovely home with truly comfy beds as promised. It is very quiet and has a large yard you can roam. We were visited by herons, iguana & small lizards (in the...
5 of 5 stars Reviewed January 5, 2014
We have just finished our stay at this house. The house is quite nice, but what makes this property super-special is the grounds, pool, and the AMAZING view. Found the owner...
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From
$3,450
Per Week
1 / 12
Cudjoe Key
6 Bedrooms, 4 Bathrooms, Sleeps 12
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5 of 5 stars Reviewed July 11, 2014
The house was clean and in good shape. The kitchen was well stocked with cooking and eating utensils. The beach was gravel, and it was clean with no grass or sand. There were...
5 of 5 stars Reviewed May 27, 2014
This property was very clean, spacious and perfect for our large party. Every morning you would find me on the lanai, enjoying the Cudjoe Bay view, with my computer on my lap...
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From
$329
Per Night
1 / 12
Cudjoe Key
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (4) Make Inquiry Similar Properties
5 of 5 stars Reviewed January 26, 2013
All we can say is WOW! We stayed here two weeks. Beautiful sunrises, ocean view, birds to watch and Iggy the resident Iguana. Perfect property for two couples or a small...
4 of 5 stars Reviewed February 2, 2012
Our extended family including grandparents, teenagers and a dog stayed at this house for one week in early January. Although we had some unseasonably cool weather at first, we had...
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From
$179
Per Night
1 / 8
Summerland Key, FL
3 Bedrooms, 2 Bathrooms, Sleeps 8
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4 of 5 stars Reviewed April 2, 2012
The home and pool were clean, comfortable and nicely furnished. Kitchen is simply furnished and could use a variety of serving dishes and sharp knives. You will need to purchase...
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Suitability

  • Wheelchair access (2)
  • Elder access (10)
  • Suitable for children (21)
  • Pet friendly (25)
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Amenities

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  • Internet (46)
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Book Online(21)

Suitability

  • Wheelchair access (2)
  • Elder access (10)
  • Suitable for children (21)
  • Pet friendly (25)
  • Smoking allowed (0)

Amenities

  • Grill (52)
  • Internet (46)
  • Air Conditioning (44)
  • Other outdoor space (42)
  • Washer/Dryer (41)
  • View all amenities