Pet Friendly Vacation Rentals in Key West

(16 rentals)
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4 BR | 3 BA | Sleeps 10 | Quick View

1

$636

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny and bright, ...

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Property Type

Key West House

"Perfection in every way"

This home is beautifully appointed, spacious, quiet, comfortable and perfectly located. The pool is a haven on hot afternoons, the upper deck is amazing on warm nights for stargazing and the kitchen has ...

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Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.5 miles to South Beach

$250

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning included * 2 wall AC units * flat screen TV * Shared gas grill * porch with ...

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Property Type

Key West Condo

"Perfect Place to Stay"

This was our 3rd time staying in Pam's wonderful little cottage. My husband and I really love this place. Pam is awesome to work with, she always answers all my questions quickly. It was great being close ...

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3 BR | 3 BA | Sleeps 6 | Quick View

1

$470

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside ...

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Property Type

Key West House

"Perfect pet-friendly vacation cottage"

The house is tucked away on a lane in Old Town within walking distance to everywhere. It is very private with lush plantings and a variety of outdoor spaces to sit. The house is well equipped and the owners ...

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3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Higg's Beach

$378

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district ...

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Property Type

Key West House

"Great home to enjoy Key West!"

Four of us , and our dog, stayed at Lynda’s beautiful home in Casa Marina area. We had a wonderful month there. The location was great and quiet. We spent most of our time enjoying the covered deck ...

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Fort Zachary Taylor State Park

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Dog-friendly home in great location with fenced yard, & lanai.Welcome to your own private, dog-friendly oasis in the heart of Key West, just one and a half blocks off Duval St. and within walking distance of a public swimming pool, park, the beach, the Southernmost Point, shops, restaurants, ...

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Property Type

Key West House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

**Available for rent by the month. Although you rent it for a month, you may of course come late and/or leave early. The monthly price will generally be the same as for a comparable unit rented by the day for 10-14 days. It does however give you a lot more options and freedom.Located on a side ...

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Property Type

Key West Townhome

"Beautiful Stay!"

This unit is in a tucked away little oasis one street over from all the action on Duval street. If is a very peaceful and unique spot. The unit itself is exceptionally clean and well appointed. It has ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discriminating travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos ...

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Property Type

Key West House

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2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 1 miles to Fort Zachery Taylor State Park

$347

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for the guest who wants to feel like a local and enjoy ...

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Property Type

Key West House

"I wish I didn't write this review."

Mainly because it will lessen our chances to get back here. My wife and I used to live in Key West for close to 10 years. We had our house and a couple of rental properties and vacation properties. Then ...

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2 BR | 2 BA | Sleeps 6 | Quick View

7

Distance to beach: 1 miles to Smathers Beach

$378

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool

About this property

Enjoy the comforts of home in the midst of paradise.Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, tennis court and Internet service. The unit is on the 3rd floor, accessible by ...

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Property Type

Key West Condo

"Great place!"

Nicely decorated and comfortable. Convenient location with a nearby convenience store within walking distance. Great pool area.

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3 BR | 3 BA | Sleeps 6 | Quick View

1

$170

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor ...

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Property Type

Key West House

"Soon to be there"

I have not stayed there yet, but will gladly take $5 for this review. I hope is as nice as it its described

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2 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park

$390

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My over sized two bedroom, one bathroom condominium end unit (cross ventilation) ...

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Property Type

Key West Condo

"A touch is all you need…"

A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area ...

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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

$411

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for ...

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Property Type

Key West Cottage

"Island Magic"

Great location! Great people! Very nice place that gave us memories of a lifetime! I’ll be returning soon!

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Studio | 1 BA | Sleeps 2 | Quick View

5

Distance to beach: 0.5 miles to South Beach

$250

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $90 * WiFi included * King size bed * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress for free travel around Old Town This ...

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Property Type

Key West Condo

"Fantasic studio unit and a great location."

Very clean and well-equipped unit. It comes with cable tv and great internet. It is a great location, one block from Duval st.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Pet friendly
  • Private pool

About this property

When they say it's all about the location, this home says it all!By city ordinance, you must rent this property for 29 days or longer!!Welcome to this beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street.A stairway decorated with wainscoting will lead you to the ...

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Property Type

Key West House

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3 BR | 2.5 BA | Sleeps 6 | Quick View

$458

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Welcome to this charming, three-bedroom, 2 1/2-bathroom home located in the coveted Meadows neighborhood.By city ordinance, you must rent this property for 29 days or longer!!This home is beautifully furnished with wood floors, high ceiling beams, and Bahama shutters throughout.The Master ...

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Property Type

Key West House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Looking for a SUMMER GETAWAY for remote work or fun?! LAST MINUTE DEALS ON AUGUST, SEPTEMBER & OCTOBER thru 10/15. Reply or call for discount pricing.**#SUGARFOOT_SUNSETS** ENJOY PRIVATE BEACH, BRING YOUR BOAT A TRUE SUNSET FACING OASIS with incomparable view, Perfect remote workspace with ...

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Property Type

Key West House

"Perfect Vacation Home for our big dogs and us!"

A perfect vacation home for us and our 2 big boxer dogs. The yard was completely fenced in where our large dogs could have a lot of space to run yet not be where our cars would park. They could be with ...

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Key West Vacation Rentals