Holiday rentals near Upper Sugarloaf Key
We found 645 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:26 Sept - 3 Oct
Image gallery for A Tropical Luxury Getaway, Your own private resort!!
1010 out of 10 rating
Exceptional
(36 reviews)
A Tropical Luxury Getaway, Your own private resort!!
Summerland Key, FL
8% off
Price is NZ$33,628
NZ$33,628
NZ$4,804 per night
includes taxes & fees
Image gallery for WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
1010 out of 10 rating
Exceptional
(9 reviews)
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
Summerland Key, FL
8% off
Price is NZ$7,461
NZ$7,461
NZ$1,066 per night
includes taxes & fees
Image gallery for Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock
9.89.8 out of 10 rating
Exceptional
(234 reviews)
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock
Summerland Key, FL
7% off
Price is NZ$5,211
NZ$5,211
NZ$744 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 NZ$5,012
NZ$5,012
NZ$716 per night
includes taxes & fees
Image gallery for ISLAND PARADISE
1010 out of 10 rating
Exceptional
(32 reviews)
ISLAND PARADISE
Summerland Key, FL
7% off
Price is NZ$2,538
NZ$2,538
NZ$363 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 NZ$4,255
NZ$4,255
NZ$608 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 NZ$3,281
NZ$3,281
NZ$469 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
8% off
Price is NZ$3,418
NZ$3,418
NZ$488 per night
includes taxes & fees
Image gallery for 2 Bedroom 2 Bathroom Home with Private Pool Walking Distance to a Water View
9.09.0 out of 10 rating
Wonderful
(26 reviews)
2 Bedroom 2 Bathroom Home with Private Pool Walking Distance to a Water View
Summerland Key, FL
8% off
Price is NZ$5,027
NZ$5,027
NZ$718 per night
includes taxes & fees
Image gallery for Emerald Seas - Florida Keys Ocean Front Paradise!
1010 out of 10 rating
Exceptional
(17 reviews)
Emerald Seas - Florida Keys Ocean Front Paradise!
Summerland Key, FL
8% off
Price is NZ$5,795
NZ$5,795
NZ$828 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 NZ$2,966
NZ$2,966
NZ$424 per night
includes taxes & fees
Image gallery for Private Secluded Ocean View & Pool Near Key West
8.28.2 out of 10 rating
Very good
(92 reviews)
Private Secluded Ocean View & Pool Near Key West
Summerland Key, FL
7% off
Price is NZ$7,600
NZ$7,600
NZ$1,086 per night
includes taxes & fees
Image gallery for Waterfront home with numerous amenities on popular Cudjoe Key!
9.49.4 out of 10 rating
Exceptional
(18 reviews)
Waterfront home with numerous amenities on popular Cudjoe Key!
Summerland Key, FL
15% off
Price is NZ$2,952
NZ$2,952
NZ$422 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
(193 reviews)
Relax by Florida Keys Beaches, just a 7-min drive away
Summerland Key, FL
8% off
Price is NZ$3,432
NZ$3,432
NZ$490 per night
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 NZ$8,136
NZ$8,136
NZ$1,162 per night
includes taxes & fees
Image gallery for Fishermen’s Paradise
9.29.2 out of 10 rating
Wonderful
(95 reviews)
Fishermen’s Paradise
Summerland Key, FL
8% off
Price is NZ$3,409
NZ$3,409
NZ$487 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 NZ$4,257
NZ$4,257
NZ$608 per night
includes taxes & fees
Image gallery for waterfront cottage near key west, sleeps 6
9.49.4 out of 10 rating
Exceptional
(22 reviews)
waterfront cottage near key west, sleeps 6
Summerland Key, FL
7% off
Price is NZ$3,482
NZ$3,482
NZ$497 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
8% off
Price is NZ$3,031
NZ$3,031
NZ$433 per night
includes taxes & fees
Image gallery for Tropical Island Paradise W / Open Water Views!
9.69.6 out of 10 rating
Exceptional
(102 reviews)
Tropical Island Paradise W / Open Water Views!
Summerland Key, FL
8% off
Price is NZ$3,566
NZ$3,566
NZ$509 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 NZ$12,709
NZ$12,709
NZ$1,816 per night
includes taxes & fees
Image gallery for Enjoy Caribbean weather in the USA. Openings in July-Open lobster season!
9.49.4 out of 10 rating
Exceptional
(139 reviews)
Enjoy Caribbean weather in the USA. Openings in July-Open lobster season!
Summerland Key, FL
15% off
Price is NZ$2,324
NZ$2,324
NZ$332 per night
includes taxes & fees
Image gallery for Comfortable Waterfront Vacation Rental
9.49.4 out of 10 rating
Exceptional
(157 reviews)
Comfortable Waterfront Vacation Rental
Summerland Key, FL
5% off
Price is NZ$2,626
NZ$2,626
NZ$375 per night
includes taxes & fees
Image gallery for 35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
9.89.8 out of 10 rating
Exceptional
(129 reviews)
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Summerland Key, FL
7% off
Price is NZ$4,031
NZ$4,031
NZ$576 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Upper Sugarloaf Key
Waterfront Home
Sleeps 4 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
164 reviews(164 reviews)
Grand Opening! New Construction at Venture Out! 3 night minimum stay!
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
4 reviews(4 reviews)
Blue Wahoo-Perfect Keys Getaway
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
3 night minimum! Spectacular Ocean Views!
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.48.4 out of 10
Very goodvery good
23 reviews(23 reviews)
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Sleeps 2 · 1 bedroom · 1 bathroom
8.88.8 out of 10
Excellentexcellent
159 reviews(159 reviews)
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Top rated rentals - Upper Sugarloaf Key
Cute cottage
1010 out of 10
Exceptionalexceptional
57 reviews(57 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