Cudjoe Key Vacation Rentals

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Vacation Rentals in Cudjoe Key

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

Big Pine Key FL

$726 nightly

$807 total

Jan 13 - Jan 14, 2026

Total with taxes and fees

With a stay at this vacation home in Big Pine Key (Sands), you'll be within a 10-minute drive of Florida Keys Beaches and Coupon Bight Aquatic Preserve.

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

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

Family home in gated community w/great amenities, shared pool, fitness center

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 Smathers Beach and Florida Keys Beaches.

Kitchen

Washer

OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS

Little Torch Key FL

Located in Summerland Key, this vacation home is by the ocean, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea Market.

Kitchen

Washer

Tranquility Bayview House-Ocean Front with boat basin and boat ramp

Little Torch Key FL

With a stay at this vacation home in Summerland Key, you'll be within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea Market.

Kitchen

Washer

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

Stock Island FL

When you stay at this vacation home in Key West, you'll be on the waterfront, within a 15-minute drive of Duval Street and Smathers Beach.

Hot Tub

Kitchen

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Cudjoe 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

Kitchen

Tropical Key West out of the way

Key West FL

With a stay at this vacation home in Key West, you'll be within a 10-minute drive of Smathers Beach and Florida Keys Beaches.

Pool

Kitchen

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

Key West Florida

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