Montgomery Cottages - Vacation Rentals in Duval Street

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From US $180

         

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 $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 $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 $1,422

         

10.0 (228 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 $2,588

         

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New

House

Charmayne's Cottages - Truman @ Duval

• Pet Friendly
• Security/Safety
• Child Friendly

• Key West
• Old Town

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From US $2,215

         

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 $545

         

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New

Apartment

Scott's Cottage - Truman @ Duval Unit F

• Pet Friendly
• Security/Safety
• Child Friendly

• Key West
• Old Town

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From US $631

         

10.0 (130 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 $202

         

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 $554

         

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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From US $731

         

9.8 (173 Reviews)

Cottage

CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest

• Air Conditioner
• Pet Friendly
• Pool

• Key West
• Downtown

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From US $620

         

9.8 (116 Reviews)

Cottage

Colony Sunset- Bright and airy cottage in the heart of old town Key West

• Air Conditioner
• Pet Friendly
• Pool

• Key West
• Old Town

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From US $423

         

9.8 (31 Reviews)

Cottage

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

• Air Conditioner
• Pet Friendly
• TV

• Key West
• Uptown - Upper Duval

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From US $423

         

9.8 (25 Reviews)

Cottage

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

• Air Conditioner
• Pet Friendly
• TV

• Key West
• Uptown - Upper Duval

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From US $421

         

9.8 (21 Reviews)

Cottage

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

• Air Conditioner
• Pet Friendly
• TV

• Key West
• Uptown - Upper Duval

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From US $583

         

9.6 (152 Reviews)

Cottage

Colony Poolside: A charming bungalow near Duval Street

• Air Conditioner
• Pool
• TV

• Key West
• Old Town

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From US $500

         

9.6 (94 Reviews)

Cottage

HIDDEN OASIS 3 blocks from Duval

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Old Town

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From US $613

         

9.6 (82 Reviews)

Cottage

Get your ISLAND STLYE on!

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Old Town

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From US $564

         

9.6 (54 Reviews)

Cottage

OSPREY STUDIO @ The Colony-Sleeps up to 4

• Air Conditioner
• Pet Friendly
• Pool

• Key West
• Old Town

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