This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Sugarloaf Key Vacation Rentals Show this location only Back to top
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Exclusive, Private Neighborhood in Lower Sugarloaf
3BR/2BA
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Sleeps 6
– Sugarloaf Key #22366
$6000 per month 30 night min stay
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Unparalleled Surroundings and 180 Degree Ocean Views.
3BR/2BA
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Sleeps 6
– Sugarloaf Key #271794ha
$11200 per month 28 night min stay
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Sugarloaf Open Water Home with Beach, Dock and Swimming Canal
4BR+/4BA
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Sleeps 8
– Sugarloaf Key #436830
$8000 - $10000 per month 28 night min stay
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Spectacular Waterfront Paradise
3BR/3BA
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Sleeps 8-10
– Sugarloaf Key #207533
$8,000 - $11,000/mo
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Open Water with Pool!
5BR/3BA
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Sleeps 10
– Sugarloaf Key #447003
$9500.00 Per Month US
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Incredible, Peaceful, Florida Keys Getaway Home
3BR+/2BA
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Sleeps 5-7
– Sugarloaf Key #345763
$2,800 - $3,600/wk
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3 Bedroom Island Home Surrounded by Warm Caribbean Water
3BR/2BA
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Sleeps 6
– Sugarloaf Key #80822
$2250/wk - $6500/mo
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Bayside Beauty
3BR+/2BA
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Sleeps 8
– Sugarloaf Key #247141
From $7200.00/mo. to 10500.00/mo.
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Beachfront Home on Sugar Sand Beach,Tropical,Private and Gated
2BR+/2BA
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Sleeps 2-4
– Sugarloaf Key #133509
$2400- $3300/wk
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Ballyhoo Shores - Open Water Oasis
3BR/2BA
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Sleeps 2-6
– Sugarloaf Key #259329
$6000/mo
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Stunning Sunsets Over Crystal Clear Water in a Family Friendly Setting
2BR+/2BA
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Sleeps 4-8
– Sugarloaf Key #430548
from 8000 to $9000/month
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Open Water Luxury 3/3 Pool
3BR+/3BA
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Sleeps 10
– Sugarloaf Key #43380
$6750- $8500/28 nts
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Oceanfront Home-Gated 5 Acres,New Pool and Spa,Tiki Bar,Dock
3BR/2BA
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Sleeps 6
– Sugarloaf Key #246254
$7560 - $8400 per month 28 night min stay
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Beautiful Sugarloaf Open Water Home with Private Pool & Dock
3BR+/2BA
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Sleeps 8
– Sugarloaf Key #213234
$7000- $9000/mo
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Sweet Views with a Pool, Summer Months Available!!!
3BR/0BA
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Sleeps 2-6
– Sugarloaf Key #457467
Monthly
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Waterfront Paradise with Privacy and Sunshine
4BR/2BA
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Sleeps 8
– Sugarloaf Key #116099
$3500/mo
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Beautiful Pool Home in Sugarloaf Key
3BR/2BA
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Sleeps 6
– Sugarloaf Key #460051
Monthly US
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Elegant Open Water, Boat Dock and Sandy Beach
4BR+/3BA
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Sleeps 8-10
– Sugarloaf Key #210791
$5000- $7000/mo
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Call Now for Discounted Summer Rates for Qualified Tenant!
2BR/1BA
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Sleeps 4
– Sugarloaf Key #391130
$1,900 - $2,900/month
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Sugarloaf Paradise:Pool, Private on Canal/Fish/Swim/Boat Backyard
4BR+/3BA
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Sleeps 8-10
– Sugarloaf Key #347987
From $6250- $7500.
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Serenity Abounds in Brand New Waterfront Florida Keys Getaway
3BR+/2BA
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Sleeps 6-8
– Sugarloaf Key #393351
From $1,800.00wk- $5,000.00mo
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Vintage Sugarloaf Shores Home on Open Water Corner Lot
3BR+/2BA
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Sleeps 5-8
– Sugarloaf Key #430064
$4900 per month 28 night min stay
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Bamboo Palms Open Water Home W/ Heated Pool/Hot Tub/Kayaks/Bikes
4BR+/2BA
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Sleeps 2-12
– Sugarloaf Key #373204
From $2200- $3200/wk
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Canal Front Home Weekly and Monthly Rentals
3BR/2BA
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Sleeps 6-10
– Sugarloaf Key #480732
$770 - $1540 per week 7-30 night min stay
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No Longer Available / Spectacular, Huge Open Water Home with Amazing Views!!!
3BR+/2BA
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Sleeps 8
– Sugarloaf Key #439552
N/A N/A
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Tranquillity in Paradise 2
5BR+/3BA
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Sleeps 10-12
– Sugarloaf Key #431470
$4,000 to $10,000
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Monthly Canal Front Ground Level Single Family Rental with Dockage
3BR/3BA
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Sleeps 6
– Sugarloaf Key #437013
from $3500 to $4500/month
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Upscale and Spacious Waterfront Property
2BR/3BA
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Sleeps 4-6
– Sugarloaf Key #370832
From $7100/mo
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Keys Living at its Best
3BR+/3BA
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Sleeps 6-8
– Sugarloaf Key #254600
$1600-$1800/wk - $4500/mo
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Canalfront Home on a Quiet Street, Only Minutes from Key West.
3BR+/3BA
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Sleeps 10
– Sugarloaf Key #334334ha
$1505 per week 7 night min stay
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Spacious Luxury Home with Pool
5BR/5BA
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Sleeps 10
– Sugarloaf Key #368235ha
$6200 per month 31 night min stay
- Waterfront 3BR Beauty-Kayaks-Sun Porch-Easy Ocean Access 3BR/2BA – Sleeps 8 – Sugarloaf Key #276386ha
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Spectacular Waterfront Paradise
3BR/3BA
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Sleeps 12
– Sugarloaf Key #214002ha
$7500 per month
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Beautiful Open Water Home with Heated Pool and Hot Tub
5BR/2BA
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Sleeps 10
– Sugarloaf Key #961105ha
$1517 - $3200 per week
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Exclusive, Private Neighborhood in Lower Sugarloaf
3BR/2BA
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Sleeps 6
– Sugarloaf Key #22366
Overview of Sugarloaf Key Vacation Rentals
A Vacation on the Ocean: Sugarloaf Key house rentals
For those who have the great fortune of spending their vacations in Sugarloaf Key house rentals, there are many ways to enjoy the surrounding waters. Some people enjoy taking kayaking trips with Reelax Charters. Those who decide to spend time in seafaring vessels may enjoy a trip to see the American Shoal Lighthouse, which is an offshore lighthouse. Of course, the water isn't the only thing to love about Sugarloaf. Many people who enjoy this key enjoy spending evenings dining at Mangrove Mama's, a restaurant that serves a number of seafood dishes as well as steaks and pasta dishes.
Privacy is Key
There are a number of benefits to spending a vacation in one of the available Sugarloaf Key house rentals, but one of the best is the amount of privacy that it affords. Instead of having to dress to go down to a hotel restaurant for breakfast, those staying in Lower Keys vacation rentals can enjoy their favorite breakfasts without changing out of their pajamas. Imagine all of the privacy that you enjoy at home, but better. Better because you are on vacation in the gorgeous lower Florida Keys!
Memories, Not Souvenirs
Let's face it, most hotels are the same. The overpriced restaurant. The laundry service prices that can make your head spin. The impersonal room. When staying in Sugarloaf Key beach rentals, you'll have the experience of really living in the Keys, like a local. And instead of taking photos by a standard hotel pool, you'll be taking photos of you and your travel mates really enjoying an authentic experience. Years later, looking back on vacations in Sugarloaf Key beach rentals will be much more memorable than vacations in a bland hotel. Dream of your vacation in one of the Sugarloaf Key beach rentals today and savor the memories tomorrow.