Holiday rentals near Upper Sugarloaf Key
We found 655 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 £15,819
£15,819
£2,260 per night
includes taxes & fees
Image gallery for Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
9.89.8 out of 10 rating
Exceptional
(236 reviews)
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Summerland Key, FL
7% off
Price is £2,950
£2,950
£421 per night
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
7% off
Price is £1,004
£1,004
£143 per night
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 £2,792
£2,792
£399 per night
includes taxes & fees
Image gallery for Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
9.89.8 out of 10 rating
Exceptional
(71 reviews)
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Summerland Key, FL
7% off
Price is £4,877
£4,877
£697 per night
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
5% off
Price is £4,469
£4,469
£638 per night
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 £2,099
£2,099
£300 per night
includes taxes & fees
Image gallery for Tropical Island Paradise W / Open Water Views!
9.69.6 out of 10 rating
Exceptional
(104 reviews)
Tropical Island Paradise W / Open Water Views!
Summerland Key, FL
8% off
Price is £1,694
£1,694
£242 per night
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
7% off
Price is £2,138
£2,138
£305 per night
includes taxes & fees
Image gallery for 20 MINUTES TO KEY WEST , BOATERS PARADISE
9.49.4 out of 10 rating
Exceptional
(57 reviews)
20 MINUTES TO KEY WEST , BOATERS PARADISE
Summerland Key, FL
8% off
Price is £1,376
£1,376
£197 per night
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 £1,962
£1,962
£280 per night
includes taxes & fees
Image gallery for Lower Keys paradise
1010 out of 10 rating
Exceptional
(34 reviews)
Lower Keys paradise
Summerland Key, FL
7% off
Price is £1,572
£1,572
£225 per night
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 £1,343
£1,343
£192 per night
includes taxes & fees
Image gallery for Island Therapy
9.89.8 out of 10 rating
Exceptional
(58 reviews)
Island Therapy
Summerland Key, FL
8% off
Price is £1,694
£1,694
£242 per night
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 £4,002
£4,002
£572 per night
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 £1,588
£1,588
£227 per night
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
7% off
Price is £990
£990
£141 per night
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 £901
£901
£129 per night
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 £650
£650
£93 per night
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
7% off
Price is £1,577
£1,577
£225 per night
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 £5,747
£5,747
£821 per night
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 £1,601
£1,601
£229 per night
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 £1,980
£1,980
£283 per night
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
7% off
Price is £1,406
£1,406
£201 per night
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)
Top rated rentals - Upper Sugarloaf Key
Paradise
1010 out of 10
Exceptionalexceptional
194 reviews(194 reviews)
Excellent
1010 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
Ideal place for our family trip with everything required for a comfortable stay.
1010 out of 10
Exceptionalexceptional
195 reviews(195 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, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value