Sugarloaf Key Vacation Rentals

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Vacation Rentals in Sugarloaf Key

Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking

Key West FL

With a stay at Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking in Key West (Old Town Key West), you'll be a 4-minute walk from Florida Keys Beaches and 11 minutes by foot from Duval Street.

Pool

Pet friendly

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Big Pine Key FL

$545 nightly

$604 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at this vacation home in Big Pine Key (Sands), you'll be within a 15-minute drive of Florida Keys Beaches and Bahia Honda State Park.

Kitchen

Washer

New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis

Key West FL

With a stay at this vacation home in Key West (Beachside), you'll be within a 5-minute drive of Duval Street and Florida Keys Beaches.

Pool

Hot Tub

NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

Key West FL

$828 nightly

$892 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 9 minutes by foot from Florida Keys Beaches.

Pool

Kitchen

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Key West FL

A stay at this vacation home places you in the heart of Key West, within a 15-minute walk of Duval Street and Florida Keys Beaches.

Pool

Kitchen

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Key West FL

$1,985 nightly

$2,203 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 3 minutes by foot from Ernest Hemingway Home and Museum.

Pool

Kitchen

TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!

Key West FL

With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 5 minutes by foot from Florida Keys Beaches.

Pool

Kitchen

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

Key West FL

When you stay at this vacation home in Key West, you'll be by the sea, within a 10-minute drive of Duval Street and Smathers Beach.

Kitchen

Washer

Private Secluded Ocean View & Pool Near Key West

Summerland Key FL

With a stay at this vacation home in Summerland Key, you'll be by the sea, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.

Pool

Hot Tub

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key FL

With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.

Pool

Kitchen

Casa De Cubana | New! Cuban-Style Home Steps from Duval Street

Key West FL

$1,201 nightly

$1,320 total

Dec 11 - Dec 12

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 5 minutes by foot from Florida Keys Beaches.

Kitchen

Washer

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

Key West FL

A stay at this vacation home places you in the heart of Key West, within a 10-minute walk of Duval Street and Florida Keys Beaches.

Pool

Kitchen

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.