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Holiday Rentals with Pools in Sugarloaf Key and nearby

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$428
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1 / 31
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Sugarloaf Key
4 Bedrooms, 4 Bathrooms, Sleeps 8
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The following rentals are within 15 kilometres of Sugarloaf Key, Florida Keys, Florida.

From
$289
Per Night
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1 / 24
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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From
$7,065
Per Month
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1 / 8
Summerland Key, FL
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
From
$423
Per Night
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1 / 8
Summerland Key, FL
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
4 Bedrooms, 2 Bathrooms, Sleeps 8 Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open.. This is a spacious oceanfront 4/2 home with a heated pool/spa and breathtaking open water views! It is located on beautiful Ramrod Key 110 ft concrete... View all property information
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5 of 5 stars Reviewed 10 November 2014
This oceanfront home in Ramrod Key is beautiful! It is clean and well kept. The owner ensures that you are comfortable in your home away from home. The view is gorgeous. The...
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From
$166
Per Night
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1 / 24
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is a very cute 24x32 two bedroom, two bathroom home located on mile marker 23 just 19 miles from the entrance to key west. The house has a very nice fully equipped kitchen. All the floors are tile with the exception of the master bedroom which is bamboo. The master bedroom comes with its... View all property information
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5 of 5 stars Reviewed 13 May 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
$423
Per Night
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1 / 22
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach, heated dipping pool and hot tub. This has been a popular honeymoon and anniversary celebration home for over 10 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even have to get out of... View all property information
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5 of 5 stars Reviewed 15 January 2015
A lovely waterfront home facing south on Cudjoe Bay. Outside you have palms, a dock, hot tub, pool, hammock, bikes, kayaks, adirondack chairs, deck, umbrella table, flowers...
5 of 5 stars Reviewed 11 January 2015
In October I contacted owner of this property and I was glad it's was available! We were absolute in love with place from the moment we saw it! It has everything you've ever need...
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From
$608
Per Night
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1 / 32
Cudjoe Key
5 Bedrooms, 3 Bathrooms, Sleeps 12
Details Reviews (34) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Great for groups with up to 12 adults and 2 children, White Ibis Inn is one property with a Main House and Guest House, with a total of 5 bedrooms, 3 baths, 2 kitchens and 1 laundry room. There's plenty of room for play, peace, and parking. The property is situated on Cudjoe Key, MM21, about a 20... View all property information
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5 of 5 stars Reviewed 8 February 2015
This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group...
5 of 5 stars Reviewed 4 November 2014
The White Ibis was perfect. The location at Cudjoe Key is close enough to Key West to go to dinner, but far away enough that the property is huge and private. The layout was great...
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From
$835
Per Night
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1 / 6
Little Torch Key
6 Bedrooms, 4 Bathrooms, Sleeps 12
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Private Home, 6 Bedrooms + Convertible Bed(s), 4 Baths (Sleeps 10-16) Unique Property that has its own private boat basin and boat ramp. Dockage, shopping, scuba diving, off shore fishing, back county fishing, lobstering and privacy. This classic Florida Keys compound is located on Pine Channel,... View all property information
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5 of 5 stars Reviewed 17 March 2014
We had a great time and a relaxing vacation. The house is great lots of room in main house and the guest house has 2 bedrooms, 1 bathroom kitchen and living room. You are supplied...
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From
$4,881
Per Week
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1 / 22
Cudjoe Key
4 Bedrooms, 3 Bathrooms, Sleeps 12
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautiful four thousand plus square foot home located on Cudjoe Key. Private beach and 30 foot swimming pool with 10 foot waterfall hot tub. Huge master suite overlooking the ocean. The house comes with BBQ grill and single and double kayaks. Spectacular views can be enjoyed from the screened... View all property information
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5 of 5 stars Reviewed 6 January 2014
We are 3 families, 5 adults and 3 teenagers. The 4 bedrooms are each very private and quiet. There are 2 master bedrooms each with ensuite bathrooms; 1 upstairs and 1 downstairs...
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From
$4,368
Per Week
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1 / 20
Cudjoe Key
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Designed as the ultimate vacation rental. Five Bedroom/Three Bath Oceanview Home with Heated Pool and Hot Tub. Panoramic Ocean Views. Sleeps 10+. Located on Cudjoe Key. Includes private boat dock, private beach, kayaks, and bikes. Weber BBQ grill, Lot's of lounge chairs and two hammocks.... View all property information
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5 of 5 stars Reviewed 29 July 2014
We rented this home for a week in July for a quiet family getaway. This was my first time renting a home in the keys, I have done so many times in the Smokey Mountains but never...
5 of 5 stars Reviewed 4 March 2014
We had a great experience at Fandango! The house looks exactly like online photos. The kitchen is well equipped, house is very clean, lots of bath and beach towels and a good...
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From
$642
Per Night
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1 / 34
Cudjoe Key
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Unwind and take a deep breath, you have finally found your tropical paradise vacation home. This 4 vacation home is the perfect getaway from the hustle and bustle of everyday life. Only 20 minutes from Key West! If you are ready to kick off your shoes and sit by the pool or grab that fishing pole... View all property information
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5 of 5 stars Reviewed 17 March 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 18 February 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
$450
Per Night
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1 / 27
Cudjoe Key
3 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (16) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Cudjoe Key (20 minutes from Key West) three bedroom, 2 bath new home with master suite having a double sink, handmade tiles, super comfy king sized bed and walk-in closet. Two king size and one queen size bedded rooms give gorgeous, comfortable quarters to each guest decorated in Ralph Lauren and... View all property information
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5 of 5 stars Reviewed 29 April 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 6 January 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
$642
Per Week
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1 / 12
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Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Cute and Cozy Mobile Home located in gated community of Venture Out MM 23 in the Florida Keys. Fully equipped kitchen, new refrigerator, self cleaning oven, free internet, Cable, 50 inch flat screen TV in living room 2 queen size beds 1 queen size sofa bed 1 bathroom gas grill washer & dryer... View all property information
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4 of 5 stars Reviewed 4 September 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 21 August 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
$175
Per Night
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1 / 8
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two... View all property information
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From
$925
Per Week
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1 / 17
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Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Tropical, Affordable Rental in Gated Community, Wi-Fi & Gas Grill Colorful tropical vacation home. The living room nicely decorated with tropical flare, has a flat screen TV with DVD, Directv W/DVR,two sofas, one is a queen size sleeper and comfortable bamboo chair. Dining area conveniently... View all property information
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From
$1,285
Per Night
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1 / 9
Summerland Key, FL
7 Bedrooms, 5 Bathrooms, Sleeps 14
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located 25 miles from Key West, this unique estate property has it all. Dockage, sandy beach, shopping, scuba diving, off shore fishing, back country tarpon fishing, lobstering and privacy. This newly constructed estate just completed in July 2009 is located on 1 acre adjacent to wild life reserve... View all property information
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From
$523
Per Night
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1 / 8
Little Torch Key
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This Florida Style home was built in 1965 and wonderful surprises await you on the inside. The ground level house is painted in bright tropical colors to give you that that old island feel. This spacious 2,000 square foot house has plenty of room to spread out. On one side are 2 king size master... View all property information
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From
$1,010
Per Night
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1 / 24
Cudjoe Key
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
3 Bedrooms, 3 Bathrooms, Sleeps 8 L’Anquesa – The Angel’s Key Luxury Amenities Include: Total renovation completed January 2014 2 master bedrooms suites with king beds, ensuite baths, flatscreen TVs and surround sound with incredible panoramic views 1 Guest room with 2 Queen Beds... View all property information
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From
$257
Per Night
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1 / 12
Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Monthly, 28 day minimum inquiries please! Luxury waterfront monthly vacations Villa Torchwood Cay on Little Torch Key. Spectacular Key West Style - spectacular boating/pool home Direct ocean access from 100 ft private deep water Dock, Hideaway heated In- Ground Pool, Hot Tub Spa, Lush... View all property information
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From
$642
Per Night
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1 / 24
Cudjoe Key
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This 5 bedroom 3 bath house with pool on ocean front property on Highway, located just 20 miles away from the famous Key west complete with WiFi. This lovely home has it's own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill,... View all property information
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Suitability

  • Wheelchair access (1)
  • Elder access (4)
  • Suitable for children (2)
  • Pet friendly (7)
  • Smoking allowed (0)

Amenities

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