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Luxury Vacation Rentals in Cudjoe Key

(6 rentals)
Big Torch Key House
Sleeps 14, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome to Barefoot Retreat, where you will feel as though you are on your own private island! As you drive through the remote, lush tropical island road to access the estate, drive slow as you might be greeted by the quite friendly protected Key Deer, roaming free about the property.As you approach...

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$833
avg per night
Key West House
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants...

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Featured review

"Perfect in every way."

This is the perfect place for a Florida vacation. It has everything we were looking for and more. Private beach, quiet location, mature trees with coconuts and bananas. Tiki hut with a wet bar and comfy...

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$896
avg per night
New
Summerland Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Summerland Escape lives up to the name in every possible way! This oceanfront property offers 2 bedrooms, 2 bathrooms, beautiful living room and dining areas with spectacular ocean views. The well-appointed open concept kitchen with all stainless appliances offers plenty of space for relaxing or entertaining....

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$750
avg per night
Key West Yacht
Sleeps 6, 3 bedrooms, 3.5 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Lady Grace will not be in Florida for the 2025-2026 season. Come visit her in the BAHAMAS!Bahama Cruise with exploration in the Exuma IslandsFor guests who want to enjoy a vacation on the move, our cruise aboard Lady Grace is for you. Nassau, Bahamas is the center of our winter cruise program,...

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Featured review

"Girls trip"

The Lady Grace was awesome and Kelly and Capt Jamie were phenomenal. Everyone loved the yacht and everything she had. Plenty of beds bathrooms and gathering places. The sunset cruise was excellent and so...

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$5,000
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Oceanfront
  • Pool
  • WiFi

About this property

Construction Notice – La Brisa Condominium March 2, 2026 through, June 19, 2026.Construction is underway in the East Building to repair walkway spalling. Some construction noise may occur during your stay. Elevators are currently unavailable due to repairs and modernization. Access to the unit...

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Featured review

"Vacation"

Very thing was good the condo was perfect and the pool was great the parking was close to the elevator

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$1,828
avg per night

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Key West Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. This construction WILL impact your stay if you are staying during the week days. Please contact All Florida Keys Property Management for more detailed information....

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$1,068
avg per night
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