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Dog Friendly Vacation Rentals in Key West - FlipKey

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26 pet friendly house rentals in Key West

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$81

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$549

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$326

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$327

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$514

New Listing Family Friendly

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 33 minutes

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Price per night from

$367

Old Town Eyebrow:Luxurious/Private Home

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$562

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 2 hours 32 minutes

Match: Pets allowed

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Price per night from

$264

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$100

OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$162

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Price per night from

$124

Private, heated pool. Private yard.

Key West condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$126

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Price per night from

$262

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

2 bedrooms / 1 bathroom / sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

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Price per night from

$101

key west tree house

Key West apartment

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$194

Ocean View Estate with Private Pool 15 minutes from Key West

Key West house

4 bedrooms / 2 bathrooms / sleeps 10

“Absolutely Perfect for Our Family of 11” We couldn't have asked for a better place for our family. Everyone had a comfortable bed, we had everything we needed for cooking, and there was plenty for everyone to do. If we needed something, we could find it easily, or we called Cynthia---her help and knowledge is priceless! Kris stopped in twice to check on us, and we found him delightful. He knows so much history about the area! There is a large pool and a large play area with anything and everything you can imagine to play with, Since we had very young children with us, we were very happy with the lack of ocean access, as well as the locking gates to the pool area and the outside stairs. When we come back to the Keys, we will definitely stay at the White Ibis Inn!

Responds fast! avg. 3 hours 52 minutes

Match: Pets allowed

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Price per night from

$544

Island Hideaway

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$303

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Price per night from

$174

Eleanor's Place in Key West Old Town - Dogs Ok

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$148

Key Lime Pie by AT HOME IN KEY WEST

Key West cottage

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$152

Great rentals within 20 miles that match your search

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 32 minutes

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Price per night from

$172

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$169

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$370

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

Sugarloaf house

5 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$286

Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

5 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$383

Coconut Mallory #411, Key West Convenience + Resort Amenities, Pools, Hot Tub an

Stock Island condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$174

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