Mallory Square Holiday Rentals

      Highly Rated

Condo

Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount

• Key West
• ·
• Truman Annex
• 0.21 mi to center

10.0

Exceptional

(219 Reviews)

2 Bedrooms 1 Bath 4 Guests 700 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

R7,072/Night 7 Nights - R49,502

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House

Mar Y Sol Ocean Front

• Florida
• ·
• Key West
• 1.56 mi to center

10.0

Exceptional

(4 Reviews)

3 Bedrooms 2 Baths 8 Guests 2002.09 ft²

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  View

R15,667/Night 7 Nights - R109,670

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House

Parrot Perch by Avantstay Old Town Key West w/Shared Pool Month-long Stays Only

• Key West
• ·
• Truman Annex
• 0.02 mi to center

10.0

Exceptional

(5 Reviews)

1 Bedroom 1 Bath

• 
  Parking
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

R6,919/Night 7 Nights - R48,433

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      Highly Rated

Condo

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West

• Key West
• ·
• Truman Annex
• 0.20 mi to center

10.0

Exceptional

(194 Reviews)

2 Bedrooms 1 Bath 5 Guests 700 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

R5,011/Night 7 Nights - R35,072

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House

Yellowfin Ledge

• Key West
• ·
• Uptown - Upper Duval
• 0.06 mi to center

10.0

Exceptional

(4 Reviews)

1 Bedroom 1 Bath 3 Guests 398.26 ft²

• 
  View
• 
  Pet Friendly
• 
  Child Friendly
• 
  Security/Safety

R5,982/Night 7 Nights - R41,876

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Apartment

Sunnyside Up by Brightwild Pool Parking

• Key West
• ·
• Old Town
• 0.38 mi to center

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath

• 
  Parking
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

R12,510/Night 7 Nights - R87,565

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      Highly Rated

House

Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday

• Key West
• ·
• Truman Annex
• 0.17 mi to center

10.0

Exceptional

(193 Reviews)

2 Bedrooms 2 Baths 4 Guests 1080 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

R10,859/Night 7 Nights - R76,011

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House

Harbor House Suite A

• Key West
• ·
• Historic Seaport
• 0.28 mi to center

10.0

Exceptional

(3 Reviews)

4 Bedrooms 4 Baths 12 Guests 2346.53 ft²

• 
  Internet
• 
  Child Friendly
• 
  Laundry
• 
  Security/Safety

R44,266/Night 7 Nights - R309,863

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Apartment

Duval Dream Loft by Brightwild Right on Duval

• Key West
• ·
• Downtown
• 0.19 mi to center

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath

• 
  Internet
• 
  Child Friendly
• 
  Guest Services

R12,693/Night 7 Nights - R88,847

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      Highly Rated

House

Everything Key West has to offer @ Mango Cottage

• Key West
• ·
• Old Town
• 0.43 mi to center

10.0

Exceptional

(188 Reviews)

2 Bedrooms 2 Baths 6 Guests 765 ft²

• 
  Private Pool
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

R10,697/Night 7 Nights - R74,877

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Apartment

Poolside Suite

• Key West
• ·
• Downtown
• 0.12 mi to center

10.0

Exceptional

(3 Reviews)

2 Bedrooms 1 Bath 6 Guests 645.83 ft²

• 
  Parking
• 
  Pool
• 
  View
• 
  Air Conditioner

R22,006/Night 7 Nights - R154,044

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      Highly Rated

Condo

Central Condo w/Deck & Pool Access in Key West!

• Key West
• ·
• Truman Annex
• 0.21 mi to center

10.0

Exceptional

(178 Reviews)

1 Bedroom 1 Bath 2 Guests 1000 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

R3,240/Night 7 Nights - R22,680

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House

ARIA at Azul Mansion Key West

• Key West
• ·
• Old Town
• 0.25 mi to center

10.0

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 2 Guests

• 
  Breakfast
• 
  Parking
• 
  Pool
• 
  View

R4,150/Night 7 Nights - R29,040

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      Price Dropped

Condo

Key West Beachfront Luxury 2/2 Condo A212

• Florida
• ·
• Key West
• 1.63 mi to center

10.0

Exceptional

(173 Reviews)

2 Bedrooms 2 Baths 6 Guests 1357 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

R9,649/Night 7 Nights - R67,547

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      Highly Rated

Cottage

Heart of Downtown Key West Cottage With Off-Street Parking

• Key West
• ·
• Bahama Village
• 0.13 mi to center

10.0

Exceptional

(169 Reviews)

2 Bedrooms 1 Bath 3 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R7,083/Night 7 Nights - R49,584

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      Highly Rated

Condo

Your Condo by the Beach with Ocean View

• Florida
• ·
• Key West
• 1.70 mi to center

10.0

Exceptional

(169 Reviews)

1 Bedroom 1 Bath 2 Guests 750 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

R5,163/Night 7 Nights - R36,140

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      Highly Rated

Condo

*FOLLOW THE SUN* Ocean Condo/Pool & Tennis + Last Key White Glove Service.

• Florida
• ·
• Key West
• 1.56 mi to center

10.0

Exceptional

(164 Reviews)

2 Bedrooms 2 Baths 6 Guests 1357 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

R7,563/Night 7 Nights - R52,937

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      Highly Rated

Condo

La Brisa - Ocean Views Across from Smathers Beach

• Florida
• ·
• Key West
• 1.69 mi to center

10.0

Exceptional

(152 Reviews)

2 Bedrooms 2 Baths 6 Guests 1463 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

R9,646/Night 7 Nights - R67,531

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      Highly Rated

House

Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard

• Key West
• ·
• Old Town
• 0.41 mi to center

10.0

Exceptional

(140 Reviews)

2 Bedrooms 2 Baths 4 Guests

• 
  Private Pool
• 
  Oceanfront
• 
  Parking
• 
  Pool

R23,434/Night 7 Nights - R164,036

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      Highly Rated

House

FLEMING-O (Flamingo) Cottage is the perfect getaway

• Key West
• ·
• Key West Historic District
• 0.14 mi to center

10.0

Exceptional

(139 Reviews)

2 Bedrooms 1 Bath 6 Guests 792 ft²

• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

R8,139/Night 7 Nights - R56,963

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      Price Dropped

House

~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.

• Key West
• ·
• Key West Historic District
• 0.12 mi to center

10.0

Exceptional

(133 Reviews)

2 Bedrooms 2 Baths 4 Guests 840 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Ocean View

R10,102/Night 7 Nights - R70,719

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      Highly Rated

Condo

*ATLANTIC REFLECTIONS @ THE BEACH* Penthouse + Last Key White Glove Service.

• Florida
• ·
• Key West
• 1.55 mi to center

10.0

Exceptional

(129 Reviews)

2 Bedrooms 2 Baths 6 Guests 1357 ft²

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

R9,804/Night 7 Nights - R68,632

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      Price Dropped

Condo

Upscale end unit home @ Truman Annex close to Duval St

• Key West
• ·
• Truman Annex
• 0.19 mi to center

10.0

Exceptional

(125 Reviews)

1 Bedroom 1 Bath 3 Guests

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

R4,214/Night 7 Nights - R29,501

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      Highly Rated

House

HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w/Community Pool!

• Key West
• ·
• Key West Historic District
• 0.14 mi to center

10.0

Exceptional

(111 Reviews)

1 Bedroom 1 Bath 2 Guests 277 ft²

• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

R5,596/Night 7 Nights - R39,181

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