Holiday rentals near Upper Sugarloaf Key
We found 652 holiday rentals — enter your dates for availability
Take a look at private holiday rentals near Upper Sugarloaf Key that can be your home away from home. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, such as air conditioning and Wi-Fi. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Upper Sugarloaf Key
Showing deals for:14 Nov - 21 Nov
Image gallery for A Tropical Luxury Getaway, Your own private resort!!
1010 out of 10 rating
Exceptional
(38 reviews)
A Tropical Luxury Getaway, Your own private resort!!
Summerland Key, FL
8% off
Price is S$28,404
S$28,404
S$4,058 nightly
Includes taxes & fees
Image gallery for Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.68.6 out of 10 rating
Excellent
(49 reviews)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Summerland Key, FL
8% off
Price is S$1,832
S$1,832
S$262 nightly
Includes taxes & fees
Image gallery for Water View Town home
1010 out of 10 rating
Exceptional
(12 reviews)
Water View Town home
Summerland Key, FL
8% off
Price is S$4,445
S$4,445
S$635 nightly
Includes taxes & fees
Image gallery for OCEANIA... water front cottage retreat ~
9.89.8 out of 10 rating
Exceptional
(6 reviews)
OCEANIA... water front cottage retreat ~
Summerland Key, FL
6% off
Price is S$7,423
S$7,423
S$1,060 nightly
Includes taxes & fees
Image gallery for 34’ Catamaran Sailboat
9.49.4 out of 10 rating
Exceptional
(35 reviews)
34’ Catamaran Sailboat
Key West, FL
8% off
Price is S$3,528
S$3,528
S$504 nightly
Includes taxes & fees
Image gallery for 20 MINUTES TO KEY WEST , BOATERS PARADISE
9.49.4 out of 10 rating
Exceptional
(58 reviews)
20 MINUTES TO KEY WEST , BOATERS PARADISE
Summerland Key, FL
8% off
Price is S$2,301
S$2,301
S$329 nightly
Includes taxes & fees
Image gallery for Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
8.88.8 out of 10 rating
Excellent
(86 reviews)
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Summerland Key, FL
8% off
Price is S$3,596
S$3,596
S$514 nightly
Includes taxes & fees
Image gallery for water at your back door
8.88.8 out of 10 rating
Excellent
(34 reviews)
water at your back door
Summerland Key, FL
8% off
Price is S$3,301
S$3,301
S$472 nightly
Includes taxes & fees
Image gallery for Tropical Island Paradise W / Open Water Views!
9.69.6 out of 10 rating
Exceptional
(105 reviews)
Tropical Island Paradise W / Open Water Views!
Summerland Key, FL
8% off
Price is S$2,860
S$2,860
S$409 nightly
Includes taxes & fees
Image gallery for Lower Keys paradise
1010 out of 10 rating
Exceptional
(34 reviews)
Lower Keys paradise
Summerland Key, FL
8% off
Price is S$2,653
S$2,653
S$379 nightly
Includes taxes & fees
Image gallery for Kelly's Kabin - Adorable Private Summerland Key Cottage
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key, FL
23% off
Price is S$2,242
S$2,242
S$320 nightly
Includes taxes & fees
Image gallery for Island Therapy
9.89.8 out of 10 rating
Exceptional
(59 reviews)
Island Therapy
Summerland Key, FL
8% off
Price is S$2,860
S$2,860
S$409 nightly
Includes taxes & fees
Image gallery for Relax by Florida Keys Beaches, just a 7-min drive away
9.89.8 out of 10 rating
Exceptional
(194 reviews)
Relax by Florida Keys Beaches, just a 7-min drive away
Summerland Key, FL
8% off
Price is S$2,662
S$2,662
S$380 nightly
Includes taxes & fees
Image gallery for Emerald Seas - Florida Keys Ocean Front Paradise!
1010 out of 10 rating
Exceptional
(18 reviews)
Emerald Seas - Florida Keys Ocean Front Paradise!
Summerland Key, FL
8% off
Price is S$4,673
S$4,673
S$668 nightly
Includes taxes & fees
Image gallery for Cottage with Pool and Dockage, just minutes to Key West
9.29.2 out of 10 rating
Wonderful
(151 reviews)
Cottage with Pool and Dockage, just minutes to Key West
Summerland Key, FL
8% off
Price is S$1,649
S$1,649
S$236 nightly
Includes taxes & fees
Image gallery for Ocean Front Access - just 30 miles to Key West
8.28.2 out of 10 rating
Very good
(162 reviews)
Ocean Front Access - just 30 miles to Key West
Summerland Key, FL
7% off
Price is S$1,502
S$1,502
S$215 nightly
Includes taxes & fees
Image gallery for Fishermen’s Paradise
9.29.2 out of 10 rating
Wonderful
(97 reviews)
Fishermen’s Paradise
Summerland Key, FL
8% off
Price is S$2,644
S$2,644
S$378 nightly
Includes taxes & fees
Image gallery for Waterfront RV Lot w 35' dock in "Venture Out". Utility hookups & beautiful views
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Waterfront RV Lot w 35' dock in "Venture Out". Utility hookups & beautiful views
Summerland Key, FL
8% off
Price is S$1,096
S$1,096
S$157 nightly
Includes taxes & fees
Image gallery for ATLANTIS...Ocean Front Cottage Retreat!
9.89.8 out of 10 rating
Exceptional
(13 reviews)
ATLANTIS...Ocean Front Cottage Retreat!
Summerland Key, FL
5% off
Price is S$9,986
S$9,986
S$1,427 nightly
Includes taxes & fees
Image gallery for Paradise in the Lower Keys!
8.68.6 out of 10 rating
Excellent
(19 reviews)
Paradise in the Lower Keys!
Summerland Key, FL
5% off
Price is S$3,302
S$3,302
S$472 nightly
Includes taxes & fees
Image gallery for A slice of paradise
9.09.0 out of 10 rating
Wonderful
(96 reviews)
A slice of paradise
Summerland Key, FL
8% off
Price is S$2,349
S$2,349
S$336 nightly
Includes taxes & fees
Image gallery for waterfront cottage near key west, sleeps 6
9.49.4 out of 10 rating
Exceptional
(24 reviews)
waterfront cottage near key west, sleeps 6
Summerland Key, FL
7% off
Price is S$2,702
S$2,702
S$386 nightly
Includes taxes & fees
Image gallery for Crystal Clear Water Getaway!
9.89.8 out of 10 rating
Exceptional
(70 reviews)
Crystal Clear Water Getaway!
Summerland Key, FL
8% off
Price is S$2,671
S$2,671
S$382 nightly
Includes taxes & fees
Image gallery for NAUTILUS...ocean front cottage retreat ~
8.88.8 out of 10 rating
Excellent
(6 reviews)
NAUTILUS...ocean front cottage retreat ~
Summerland Key, FL
8% off
Price is S$6,206
S$6,206
S$887 nightly
Includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Upper Sugarloaf Key
Oasis - Ocean front with pool
Sleeps 12 · 4 bedrooms · 4 bathrooms
9.09.0 out of 10
Wonderfulwonderful
28 reviews(28 reviews)
Private Secluded Ocean View & Pool Near Key West
Sleeps 10 · 4 bedrooms · 2 bathrooms
8.28.2 out of 10
Very goodvery good
94 reviews(94 reviews)
Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!
Sleeps 10 · 4 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
4 Bedroom 3 Bath Water View Home
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Sleeps 6 · 2 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
236 reviews(236 reviews)
One of the very few beach houses with a daily, rental license in the Keys.
Sleeps 12 · 4 bedrooms · 3 bathrooms
8.88.8 out of 10
Excellentexcellent
64 reviews(64 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value