Vacation Rentals & House Rentals in Sugarloaf Key

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163 house rentals

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Pool, Hot Tub, D

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$179

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$5,699

Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

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$179

Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D

Sugarloaf Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

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$179

Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

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$179

Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private

Sugarloaf Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

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$179

Great rentals within 20 miles that match your search

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$113

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

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$571

The Mermaids House, Historic Old Town Key West

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

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$327

Harbor Walk Hideaways

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

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$1,296

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

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$788

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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$619

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

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$485

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 2 hours 7 minutes

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$342

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$107

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

“Wonderful” 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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$133

Artist Cottage

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Key West, Spring 2012” In a word,our stay with you was ”wonderful”. We have been to Key West on several occasions and have loved every visit. Staying in Truman annexe was even more special. We all felt like we were at home with everything we needed. You must feel blessed to live in that part of the world. We will be looking for a job for our 19 year old son,Tom. He wants to come and work over in Key West. We have just arrived home and everything seems grey, and much colder than Key West. Depending on finances( the pound-dollar rate is not too good just now) we hope to come back soon. We will definitely be giving you a call.I would recommend your accommodation and company to future holiday makers. Love and blessings John,Jayne,Jack and Tom

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$378

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

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$2,053

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$1,482

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$1,140

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$1,140

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 1 hour 58 minutes

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$319

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$1,997

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$485

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$343

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$172

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$1,939

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$456

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

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$798

Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$257

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$770

Truman Annex-Steps to Famous Duval Street

Key West townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 38 minutes

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$392

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$165

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$446

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$140

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$154

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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$514

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$266

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rentals in Sugarloaf Key

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