Holiday rentals near Upper Sugarloaf Key
We found 635 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:15 Aug - 22 Aug
Image gallery for Water View Town Home
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Water View Town Home
Summerland Key, FL
8% off
Price is AU$4,662
AU$4,662
AU$666 per night
includes taxes & fees
Image gallery for 2 Bedroom 2.5 Bath Luxury Townhome in the Keys
9.69.6 out of 10 rating
Exceptional
(35 reviews)
2 Bedroom 2.5 Bath Luxury Townhome in the Keys
Summerland Key, FL
8% off
Price is AU$4,662
AU$4,662
AU$666 per night
includes taxes & fees
Image gallery for ISLAND PARADISE
1010 out of 10 rating
Exceptional
(32 reviews)
ISLAND PARADISE
Summerland Key, FL
8% off
Price is AU$2,996
AU$2,996
AU$428 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 AU$4,662
AU$4,662
AU$666 per night
includes taxes & fees
Image gallery for A slice of paradise
9.09.0 out of 10 rating
Wonderful
(95 reviews)
A slice of paradise
Summerland Key, FL
8% off
Price is AU$2,867
AU$2,867
AU$410 per night
includes taxes & fees
Image gallery for Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bike, 3 Kayak, WiFi, large pool
9.49.4 out of 10 rating
Exceptional
(93 reviews)
Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bike, 3 Kayak, WiFi, large pool
Summerland Key, FL
7% off
Price is AU$3,030
AU$3,030
AU$433 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 AU$4,032
AU$4,032
AU$576 per night
includes taxes & fees
Image gallery for Kelly's Kabin - Adorable Private Summerland Key Cottage
9.89.8 out of 10 rating
Exceptional
(112 reviews)
Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key, FL
22% off
Price is AU$2,348
AU$2,348
AU$335 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 AU$3,227
AU$3,227
AU$461 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 AU$4,030
AU$4,030
AU$576 per night
includes taxes & fees
Image gallery for Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.89.8 out of 10 rating
Exceptional
(231 reviews)
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Summerland Key, FL
8% off
Price is AU$5,369
AU$5,369
AU$767 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 AU$7,195
AU$7,195
AU$1,028 per night
includes taxes & fees
Image gallery for Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Summerland Key, FL
8% off
Price is AU$3,694
AU$3,694
AU$528 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
(17 reviews)
Waterfront home with numerous amenities on popular Cudjoe Key!
Summerland Key, FL
15% off
Price is AU$2,831
AU$2,831
AU$404 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
(191 reviews)
Relax by Florida Keys Beaches, just a 7-min drive away
Summerland Key, FL
8% off
Price is AU$3,429
AU$3,429
AU$490 per night
includes taxes & fees
Image gallery for Comfortable Waterfront Vacation Rental
9.49.4 out of 10 rating
Exceptional
(155 reviews)
Comfortable Waterfront Vacation Rental
Summerland Key, FL
5% off
Price is AU$2,514
AU$2,514
AU$359 per night
includes taxes & fees
Image gallery for NAUTILUS...ocean front cottage retreat ~
8.48.4 out of 10 rating
Very good
(5 reviews)
NAUTILUS...ocean front cottage retreat ~
Summerland Key, FL
8% off
Price is AU$7,570
AU$7,570
AU$1,081 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 AU$3,106
AU$3,106
AU$444 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
6% off
Price is AU$11,720
AU$11,720
AU$1,674 per night
includes taxes & fees
Image gallery for Enjoy Caribbean weather in the USA. Openings in May 2025!! Book now!
9.49.4 out of 10 rating
Exceptional
(137 reviews)
Enjoy Caribbean weather in the USA. Openings in May 2025!! Book now!
Summerland Key, FL
8% off
Price is AU$2,682
AU$2,682
AU$383 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 AU$3,048
AU$3,048
AU$435 per night
includes taxes & fees
Image gallery for Bay View 2 Bed / 2.5 Bath Vacation Townhome Rental in Key West Area
9.89.8 out of 10 rating
Exceptional
(82 reviews)
Bay View 2 Bed / 2.5 Bath Vacation Townhome Rental in Key West Area
Summerland Key, FL
8% off
Price is AU$4,859
AU$4,859
AU$694 per night
includes taxes & fees
Image gallery for 2 Bedroom 2.5 Bath Luxury Townhome 26 Miles from Downtown Key West
9.69.6 out of 10 rating
Exceptional
(27 reviews)
2 Bedroom 2.5 Bath Luxury Townhome 26 Miles from Downtown Key West
Summerland Key, FL
8% off
Price is AU$4,662
AU$4,662
AU$666 per night
includes taxes & fees
Image gallery for Island Therapy
9.89.8 out of 10 rating
Exceptional
(55 reviews)
Island Therapy
Summerland Key, FL
8% off
Price is AU$3,368
AU$3,368
AU$481 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Upper Sugarloaf Key
Waterfront Home
Sleeps 4 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
163 reviews(163 reviews)
Sunny Gens - Venture Out #606
Sleeps 6 · 2 bedrooms · 2 bathrooms
6.06.0 out of 10
1 review(1 review)
Moana Hale Paradise #164 at Venture Out in Cudjoe Key
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 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)
The most setup home in BPK TIKI HUT,POOL ,GRILL ,CANAL FRONT, FREE UNLIMITED ICE
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
5 reviews(5 reviews)
Paradise in the Lower Keys!
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
19 reviews(19 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