Jackson 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

R6,988/Night 7 Nights - R48,911

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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

R15,480/Night 7 Nights - R108,361

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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

R6,836/Night 7 Nights - R47,855

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      Frequently Viewed

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

R4,951/Night 7 Nights - R34,653

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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

• 
  Pet Friendly
• 
  Child Friendly
• 
  Security/Safety

R5,911/Night 7 Nights - R41,376

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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
• 
  Internet

R13,012/Night 7 Nights - R91,083

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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

R10,730/Night 7 Nights - R75,104

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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

R43,738/Night 7 Nights - R306,164

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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

R11,406/Night 7 Nights - R79,846

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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

R10,570/Night 7 Nights - R73,984

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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

R21,744/Night 7 Nights - R152,205

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New

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

R3,080/Night 7 Nights - R21,549

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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

R4,100/Night 7 Nights - R28,694

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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

R9,534/Night 7 Nights - R66,741

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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

R6,999/Night 7 Nights - R48,992

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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

R5,101/Night 7 Nights - R35,709

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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

R7,473/Night 7 Nights - R52,305

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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

R9,531/Night 7 Nights - R66,725

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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

R23,155/Night 7 Nights - R162,078

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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

R8,041/Night 7 Nights - R56,283

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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

R9,981/Night 7 Nights - R69,875

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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

R9,687/Night 7 Nights - R67,813

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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

R4,163/Night 7 Nights - R29,148

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      Highly Rated

Condo

The Palms.A beautiful space in the perfect place.

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

10.0

Exceptional

(108 Reviews)

2 Bedrooms 1 Bath 4 Guests

• 
  Oceanfront
• 
  Hot Tub
• 
  Parking
• 
  Pool

R6,155/Night 7 Nights - R43,081

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