Big Pine Resort Cottages - Vacation Rentals in Key West Shipwreck Museum

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From US $1,243

         

10.0 (80 Reviews)

Cottage

"Tranquility " At Ann Street Gardens Steps From Duval

• Air Conditioner
• Pool
• TV

• Key West
• Historic Seaport

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From US $273

         

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10.0 (1 Review)

Apartment

Pilar Cottage - Harbor Walk Hideaways

• Pet Friendly
• Pool
• Security/Safety

• Key West
• Historic Seaport

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From US $462

         

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10.0 (5 Reviews)

Cottage

Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!

• Air Conditioner
• Parking
• Pool

• Key West
• New Town

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From US $184

         

9.6 (14 Reviews)

Cottage

PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/Shared Heated Pool!

• Air Conditioner
• Pool
• TV

• Key West
• Old Town

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From US $437

         

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9.4 (132 Reviews)

Bed & Breakfast

Andrews Inn & Garden Cottages

• Air Conditioner
• Parking
• Pool

• Key West
• Downtown

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From US $404

         

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9.0 (4 Reviews)

Cottage

Tranquility by Avantstay Close to Duval St w/BBQ & Shared Pool

• Air Conditioner
• Pool
• TV

• Key West
• Key West Historic District

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From US $325

         

10.0 (20 Reviews)

Cottage

~ COPA CABANA ~ Classic Key West cottage just a stone’s throw from the water.

• Air Conditioner
• Pool
• TV

• Key West
• Old Town

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From US $350

         

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9.3 (27 Reviews)

Apartment

Prime Downtown Key West Spot - The Cozy Little Cottage

• Parking
• Pet Friendly
• Balcony/Terrace

• Key West
• Old Town

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From US $467

         

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8.0 (2 Reviews)

Cottage

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

• Air Conditioner
• Parking
• Pool

• Key West
• Old Town

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From US $1,595

         

10.0 (229 Reviews)

Cottage

PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest

• Air Conditioner
• Parking
• Pool

• Key West
• Downtown

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From US $1,907

         

10.0 (224 Reviews)

Cottage

~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Uptown - Upper Duval

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From US $532

         

10.0 (209 Reviews)

Cottage

Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex

• Air Conditioner
• Parking
• Pool

• Key West
• Truman Annex

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From US $1,367

         

10.0 (145 Reviews)

Cottage

*DARLING OF DUVAL @ OLD TOWN* Estate Cottage + Spa + LAST KEY SERVICES…

• Air Conditioner
• Parking
• TV

• Key West
• Historic Seaport

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From US $495

         

10.0 (142 Reviews)

Cottage

Heart of Downtown Key West Cottage With Off-Street Parking

• Air Conditioner
• Parking
• TV

• Key West
• Historic Seaport

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From US $828

         

10.0 (133 Reviews)

Cottage

The Dancing Rooster: 2 Blocks from Duval in Old Town.

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Old Town

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From US $422

         

10.0 (25 Reviews)

Cottage

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

• Air Conditioner
• Pet Friendly
• TV

• Key West
• Uptown - Upper Duval

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From US $423

         

10.0 (24 Reviews)

Cottage

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Uptown - Upper Duval

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From US $917

         

10.0 (11 Reviews)

Cottage

~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool

• Air Conditioner
• Pool
• TV

• Key West
• Historic Seaport

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From US $314

         

10.0 (8 Reviews)

Cottage

CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest

• Air Conditioner
• Parking
• Pool

• Key West
• Key West Historic District

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From US $257

         

10.0 (5 Reviews)

Cottage

Old Town Elegance Island Breezes and Poolside Bliss- December 2025 Opening

• Air Conditioner
• Pool
• TV

• Key West
• Old Town

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From US $582

         

10.0 (4 Reviews)

Cottage

~ROBINSON CRUSOE COTTAGE~ Delight in island vibes in this home with a pool.

• Air Conditioner
• Pet Friendly
• Pool

• Key West
• Key West Historic District

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From US $1,093

         

10.0 (1 Review)

Cottage

~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!

• Air Conditioner
• Pet Friendly
• Pool

• Key West
• Key West Historic District

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From US $544

         

10.0 (1 Review)

Cottage

Old Town Key West Cottage 3bed/2bath

• Air Conditioner
• Pet Friendly
• Pool

• Key West
• Downtown

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From US $301

         

10.0 (1 Review)

Cottage

Old Town home a short walk to Duval/Couples Oasis

• Air Conditioner
• Parking
• TV

• Key West
• Old Town

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