Top 50 Sugarloaf Key Vacation Rentals

Houses (811)
Condos (497)
Cottages (113)
Golf rental (953)
Beachfront (405)
Ocean view (271)

Discover popular destinations in and around Sugarloaf Key

Saddlebunch Keys

1,704 vacation rentals

Upper Sugarloaf Sound

1,712 vacation rentals

Lower Sugarloaf Sound

1,707 vacation rentals

Bay Point

9 vacation rentals

Lower Sugarloaf Key

1,696 vacation rentals

Explore a selection of Sugarloaf Key vacation rentals

Oceana Vista - Oceanfront Home w/ Private Beach, Pool...
Guests10
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$247 avg/night
2 beds
2 Bathrooms
Guests 10
Beautiful 3 Bedroom Home on Canal in Cudjoe Gardens
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$142 avg/night
3 beds
2 Bathrooms
Guests 6
5 reviews
Paradise Awaiting!!!
Guests6
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$133 avg/night
3 beds
2 Bathrooms
Guests 6
Fabulous Key West Water Front 3 Bed 3 Bath Home
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$350 avg/night
3 beds
2 Bathrooms
Guests 8
7 reviews
Ground level home in Cudjoe Gardens with heated pool, boat doc...
Guests10
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$190 avg/night
3 beds
2 Bathrooms
Guests 10
Beautiful Bay Views in Lower Sugarloaf Key
Guests6
Bedrooms2
Bathrooms3
Wonderful 5 / 5
$183 avg/night
2 beds
3 Bathrooms
Guests 6
1 reviews
Family Friendly House In Paradise
Guests8
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$183 avg/night
5 beds
3 Bathrooms
Guests 8
2 reviews
BAY HARBOR VIEW - Waterfront Monthly Rental w/ Spectacular Views
Guests18
Bedrooms5
Bathrooms3
Wonderful 3.8 / 5
$212 avg/night
5 beds
3 Bathrooms
Guests 18
8 reviews
Bayside Beauty on Open Water
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$259 avg/night
3 beds
2 Bathrooms
Guests 8
37 reviews
The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$150 avg/night
2 beds
2 Bathrooms
Guests 6
2 reviews
Beautifully landscaped & appointed canal-front home w/beach access...
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$229 avg/night
3 beds
3 Bathrooms
Guests 8
2 reviews
Lush and Tropical Waterfront Home with Private Pool
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$250 avg/night
3 beds
3 Bathrooms
Guests 6
1 reviews
Tropical Custom Home with Gorgeous Sunset Views - available...
Guests6
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$150 avg/night
3 beds
2 Bathrooms
Guests 6
Wonderful, pet friendly home for rent
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$126 avg/night
3 beds
2 Bathrooms
Guests 8
2 reviews
Gorgeous Brand New Canal Front 4/3 Heated Pool/Spa & Large Boat...
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$207 avg/night
4 beds
3 Bathrooms
Guests 10
4 reviews
Tropical Island House
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$175 avg/night
3 beds
2 Bathrooms
Guests 8
1 reviews
Large, dog-friendly home on three secluded acres w/ balconies...
Guests10
Bedrooms5
Bathrooms3
Wonderful 4.3 / 5
$394 avg/night
5 beds
3 Bathrooms
Guests 10
47 reviews
Beautiful quiet waterfront private swim canal & boat dock "PET...
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$207 avg/night
4 beds
4 Bathrooms
Guests 8
Tortuga Hammock-Gated Community near Key West
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$268 avg/night
2 beds
2 Bathrooms
Guests 4
4 reviews
Stunning Sunsets over Crystal Clear Water in a family friendly...
Guests8
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$200 avg/night
2 beds
2 Bathrooms
Guests 8
15 reviews
Open Water Luxury 3/2 Pool
Guests10
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$286 avg/night
3 beds
3 Bathrooms
Guests 10
38 reviews
Water front home with spectacular open water view, dock, and...
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$205 avg/night
3 beds
2 Bathrooms
Guests 8
1 reviews
Unique opportunity! Sept and Oct 2017; offering 50% reduction in...
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.5 / 5
$232 avg/night
4 beds
2 Bathrooms
Guests 8
12 reviews
OCEAN SUNRISE Located on Saddlebunch Key
Guests6
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$286 avg/night
3 beds
2 Bathrooms
Guests 6
VINTAGE SUGARLOAF SHORES HOME ON OPEN WATER CORNER LOT
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$200 avg/night
3 beds
2 Bathrooms
Guests 8
4 reviews
BAYVIEW RETREAT Located on Saddlebunch Key
Guests6
Bedrooms3
Bathrooms2
Wonderful 0 / 5
$187 avg/night
3 beds
2 Bathrooms
Guests 6
Stylish & Beautiful Home on Pristine Canal, 4 Minutes to Open Water
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$133 avg/night
2 beds
2 Bathrooms
Guests 6
1 reviews
Open Water View in Sugarloaf Key within minutes of Downtown Key...
Guests10
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$643 avg/night
5 beds
3 Bathrooms
Guests 10
2 reviews
Paradise on the Golf
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$84 avg/night
2 beds
2 Bathrooms
Guests 6
5 reviews
Charming Condo in Old Town Key West's Truman Annex
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$171 avg/night
1 bed
1 Bathroom
Guests 2
94 reviews
Lazy River Pool and Enchanting Gardens in Old Town Key West
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$103 avg/night
2 beds
2 Bathrooms
Guests 4
16 reviews
Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key...
Guests10
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$285 avg/night
3 beds
2 Bathrooms
Guests 10
115 reviews
The Conch Farmhouse
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$289 avg/night
2 beds
1 Bathroom
Guests 4
34 reviews
Beautiful Duval St. Condo, Location, Location!!!!
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$220 avg/night
2 beds
1 Bathroom
Guests 4
87 reviews
Captain D's Hideout - Beautiful waterfront home in the heart of a...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$100 avg/night
2 beds
2 Bathrooms
Guests 6
57 reviews
Royal Keys House-Ocean View 20m from Keywest
Guests10
Bedrooms5
Bathrooms3
Wonderful 4.7 / 5
$600 avg/night
5 beds
3 Bathrooms
Guests 10
50 reviews
Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$154 avg/night
2 beds
2 Bathrooms
Guests 6
94 reviews
Coral Hammock Tropical Getaway 3/3, sleeps 6 to 8, very charming
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$350 avg/night
3 beds
3 Bathrooms
Guests 8
53 reviews
Quiet, Quaint and 2.5 blocks off of Duval St!
Guests2
Studio
Bathroom1
Wonderful 4.6 / 5
$144 avg/night
Studio
1 Bathroom
Guests 2
43 reviews
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.6 / 5
$150 avg/night
2 beds
2 Bathrooms
Guests 6
44 reviews
Quiet, Quaint And Conveniently Located!
Guests2
Studio
Bathroom1
Wonderful 4.3 / 5
$156 avg/night
Studio
1 Bathroom
Guests 2
89 reviews
Key West Condo in Truman Annex with 2 Bikes and Pool!
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$171 avg/night
2 beds
1 Bathroom
Guests 4
73 reviews
Beach House with Ocean View
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$213 avg/night
1 bed
1 Bathroom
Guests 4
16 reviews
Beach Chic with a Water View
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$365 avg/night
2 beds
1 Bathroom
Guests 4
43 reviews
Dock 80'Heated Pool Deep Channel Tennis 15 Min Key West
Guests4
Bedrooms2
Bathroom1
Wonderful 4.4 / 5
$125 avg/night
2 beds
1 Bathroom
Guests 4
24 reviews
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$200 avg/night
2 beds
1 Bathroom
Guests 4
98 reviews
Simonton Studio, an Old Town get-away for 2
Guests2
Studio
Bathroom1
Wonderful 4.8 / 5
$145 avg/night
Studio
1 Bathroom
Guests 2
91 reviews
Simonton Studio, an Old Town get-away for 2
Guests2
Studio
Bathroom1
Wonderful 4.8 / 5
$145 avg/night
Studio
1 Bathroom
Guests 2
91 reviews
Conch Retreat in Beautiful Truman Annex with 2 Bikes
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$171 avg/night
2 beds
1 Bathroom
Guests 4
81 reviews
Beautiful Tropical House 3 bedrooms - 2 King Beds! Sleeps 8
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$343 avg/night
3 beds
3 Bathrooms
Guests 8
138 reviews

Sugarloaf Key, FL, USA Vacation Rentals

Discover popular destinations in and around Sugarloaf Key

Oceana Vista - Oceanfront Home w/ Private Beach, Pool...

Beautiful 3 Bedroom Home on Canal in Cudjoe Gardens

Paradise Awaiting!!!

Fabulous Key West Water Front 3 Bed 3 Bath Home

Ground level home in Cudjoe Gardens with heated pool, boat doc...

Beautiful Bay Views in Lower Sugarloaf Key

Family Friendly House In Paradise

BAY HARBOR VIEW - Waterfront Monthly Rental w/ Spectacular Views

Bayside Beauty on Open Water

The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17

Beautifully landscaped & appointed canal-front home w/beach access...

Lush and Tropical Waterfront Home with Private Pool

Tropical Custom Home with Gorgeous Sunset Views - available...

Wonderful, pet friendly home for rent

Gorgeous Brand New Canal Front 4/3 Heated Pool/Spa & Large Boat...

Tropical Island House

Large, dog-friendly home on three secluded acres w/ balconies...

Beautiful quiet waterfront private swim canal & boat dock "PET...

Tortuga Hammock-Gated Community near Key West

Stunning Sunsets over Crystal Clear Water in a family friendly...

Open Water Luxury 3/2 Pool

Water front home with spectacular open water view, dock, and...

Unique opportunity! Sept and Oct 2017; offering 50% reduction in...

OCEAN SUNRISE Located on Saddlebunch Key

VINTAGE SUGARLOAF SHORES HOME ON OPEN WATER CORNER LOT

BAYVIEW RETREAT Located on Saddlebunch Key

Stylish & Beautiful Home on Pristine Canal, 4 Minutes to Open Water

Open Water View in Sugarloaf Key within minutes of Downtown Key...

Paradise on the Golf

Charming Condo in Old Town Key West's Truman Annex

Lazy River Pool and Enchanting Gardens in Old Town Key West

Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key...

The Conch Farmhouse

Beautiful Duval St. Condo, Location, Location!!!!

Captain D's Hideout - Beautiful waterfront home in the heart of a...

Royal Keys House-Ocean View 20m from Keywest

Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key...

Coral Hammock Tropical Getaway 3/3, sleeps 6 to 8, very charming

Quiet, Quaint and 2.5 blocks off of Duval St!

Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

Quiet, Quaint And Conveniently Located!

Key West Condo in Truman Annex with 2 Bikes and Pool!

Beach House with Ocean View

Beach Chic with a Water View

Dock 80'Heated Pool Deep Channel Tennis 15 Min Key West

Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and...

Simonton Studio, an Old Town get-away for 2

Simonton Studio, an Old Town get-away for 2

Conch Retreat in Beautiful Truman Annex with 2 Bikes

Beautiful Tropical House 3 bedrooms - 2 King Beds! Sleeps 8