Montgomery Cottages - Vacation Rentals in Ripley's Believe It or Not

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From US $1,032

         

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 $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 $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 $1,422

         

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 $2,215

         

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 $597

         

10.0 (206 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 $1,421

         

10.0 (144 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 $486

         

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 $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 $1,010

         

10.0 (8 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 $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 $559

         

10.0 (3 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 $1,406

         

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 $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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★ Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Ripley's Believe It or Not.