Calendar View
  • Dates
    Any
  • Occupancy
    Any
    - +
    - +
    - +
  • Rooms
    Any
  • Price Range
    Any
  • Amenities
    Any
  • List
  • Map
  • Calendar

Sugarloaf Key Vacation Rentals

1 - 42 of 66 rentals
  PrevNext  
Wed 22 Feb Thu 23 Feb Fri 24 Feb Sat 25 Feb Sun 26 Feb Mon 27 Feb Tue 28 Feb Wed 1 Mar Thu 2 Mar Fri 3 Mar Sat 4 Mar Sun 5 Mar Mon 6 Mar Tue 7 Mar Wed 8 Mar Thu 9 Mar Fri 10 Mar
Lower Keys Backcountry Escape - Sugarloaf Key, FL Vacation Rental
99 99 99 99 115 99 - - - - - - - - - - -
Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - - - - 230 - - - - - - 245 - - - -
White Sands in Paradise - Islamorada, FL Vacation Rental

White Sands in Paradise

Islamorada, FL
2 Bed 2 Bath Sleeps 6
295 295 295 295 315 315 315 270 270 270 270 255 - - - - -
Dolphin Retreat - Marathon, FL Vacation Rental

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Oasis in the Keys - Marathon, FL Vacation Rental

Oasis in the Keys

Marathon, FL
3 Bed 2.5 Bath Sleeps 8
- - - 270 330 330 330 320 - - - - - - - 320 285
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- 240 - - - - - 265 265 - - - - - - - -
Perfect Boater's Retreat - Key Largo, FL Vacation Rental

Perfect Boater's Retreat

Key Largo, FL
3 Bed 2 Bath Sleeps 6
90 90 90 90 99 99 99 99 99 99 99 99 99 99 99 99 90
Ninth Street Suite - Key Colony Beach, FL Vacation Rental
- - - - - - - - - 140 150 140 - - - - -
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
- - - - - - - 280 280 - - 265 - - - - 320
No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - 165 175 175 150
Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - 250 260 260 260 260 260 260 260 260 260 260
Fisherman's Canal Getaway - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
195 220 220 220 220 - - - - - - - - - - - -
Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - - - - - - - - - - - - - -
Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - - - 185 - - - - - - - - -
The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Fishing and Kayaking Dream Cove - Marathon, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
White Dunes Retreat  - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - 190 195 195 195 195
Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
- - - - - - - - - - - - - - - - -
Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Boater's Dream Come True - Marathon, FL Vacation Rental

Boater's Dream Come True

Marathon, FL
4 Bed 2.5 Bath Sleeps 12
- - - - - - - - - - - - - - - - -
Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Fantastic Fifth Street - Key Colony Beach, FL Vacation Rental

Fantastic Fifth Street

Key Colony Beach, FL
4 Bed 2.5 Bath Sleeps 10
- - - 140 160 160 155 - - - - - - - - - -
Eleventh Street Legacy - Key Colony Beach, FL Vacation Rental
- - - - - - 155 - - - - - - - - - -
Fisher's Paradise - Key Colony Beach, FL Vacation Rental

Fisher's Paradise

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Comfort in the Keys - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Ninth Street Splendor - Key Colony Beach, FL Vacation Rental
- - - - - - 180 190 190 160 - - - - - - -
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- - - - - - - - - 125 - - - - - - -
Downhome Cabin by the Canal - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - 165 175 175 175 175 175 165 - -
Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Fisherman's Dream Pad - Key Largo, FL Vacation Rental

Fisherman's Dream Pad

Key Largo, FL
3 Bed 2 Bath Sleeps 6
- - - - - - - 136 136 136 136 136 136 136 136 136 136
Bright as Beach Sand - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Tavernier Waterfront Retreat - Islamorada, FL Vacation Rental
140 - - - - - - - - - - - - - - 145 -
Breezy Palms - Key Colony Beach, FL Vacation Rental

Breezy Palms

Key Colony Beach, FL
4 Bed 4 Bath Sleeps 9
- - - - - - - - - - - - - - - - -
Page 1 of 2

About Sugarloaf Key

Sugarloaf Key rated 4.3 out of 5 based on 28 reviews Sugarloaf key, FL

Let the tropical island trio of warm breezes, white sand beaches, and fun in the sun guide you to deep relaxation in one of our Sugarloaf Key vacation rentals. 

Deriving its name from a type of pineapple once grown in the area, Sugarloaf Key is comprised of an upper and lower island and belongs to Florida’s lower keys. The area’s abundant wildlife and great fishing make it a sportsman’s paradise, while the white sand beaches and laid-back island atmosphere appeals to casual vacationers including families, couples, and retirees.

Things to Do in Sugarloaf Key, FL

Located between Saddlebunch Keys to the west and Cudjoe Key to the east, both upper and lower islands of Sugarloaf Key sit on open, shallow waters that play host to world-class sport-fishing. Home to tarpon, bonefish, grouper and many more large fish species, this area is particularly well-suited for those looking to land a trophy fish. Hire a guide for the day at any of the island’s fishing charters, and head out by boat to the area's prime fishing grounds, known as flats, where you’ll hook a 150-pound tarpon and have the fight of a lifetime trying to reel it in. 

Non-fisherfolk will also find plenty to do! Rent kayaks and paddle into the Upper Sugarloaf Sound, where you can the explore mangrove swamp coastline alongside dolphins playing in the surf. If you prefer to have your adventures on land, grab your family and head down to see the Sugarloaf Key Bat Tower a tower built in 1929 to entice bats and provide a solution to the area’s mosquito problem. Kids will love watching the bats fly frenetically around the structure, catching insects in mid-flight. 

Day Trips from Sugarloaf Key

Our Florida Keys vacation rentals in Sugarloaf Key are only 15 miles from the region's biggest draw: Key West. Head into the larger city for an afternoon touring the Hemingway Home & Museum, then take in the sunset and spectacle at Mallory Square Dock. Grab a margarita and some fresh fish tacos at one of the local restaurants...unless your fridge back in Sugarloaf Key is full of your own daily catch! 

Want to avoid the Key West crowds? Head 15 miles back toward the mainland to the kayaking, scuba, and snorkeling paradise surrounding Big Pine. Divers can explore the undersea wreckage of the Adolphus Bush, and snorkelers will be well-rewarded with a trip out to the coral reefs at Looe Key.

For a fantastic home base with direct access to the best of Florida’s world-class fishing and island adventure, a stay in one of our Sugarloaf Key vacation rentals can’t be beat! 

Photo credit: flickr user donielle

  • Searching ...
  • 42 of 66
No results in this area. Move map or change filters for more rentals.
  • More Map
  • Less Map
Search Here