Dog Friendly Vacation Rentals in Key West - FlipKey

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202 pet friendly house rentals in Key West

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 56 minutes

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$105

Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

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$257

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$480

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

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$147

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

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

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$285

A Touch Of Havana In Key West

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 8 minutes

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Price per night from

$351

William's Loft

Key West cottage

2 bedrooms / 1 bathroom / sleeps 3

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$87

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$107

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 49 minutes

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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

Responds fast! avg. 3 hours 52 minutes

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Price per night from

$360

New Listing Family Friendly

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 38 minutes

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Price per night from

$367

Coconut Cottage

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$77

Poinciana House

Key West house

1 bedroom / 2 bathrooms / sleeps 4

“Awesome” The house was just as Historic Hideaways pictured and described...beautiful. The house was very clean, a pool service came twice a week to clean the pool and Tim, (agent) was very informative and helpful. Everything was supplied from towels to suntan lotion. There was nothing we needed to bring except our clothes & food. I would definitely stay here again.

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$385

Ibis

Key West house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$75

Old Town Eyebrow:Luxurious/Private Home

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$492

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

“Wonderful Experience” Beautiful decor! Perfect location - just off the beaten path but out of the hustle and bustle. Convenient to everything we wanted to do! I whole heartedly recommend this condo for a couple. Also would work nicely for three people. Might be a bit tight for four adults, but it was perfect for my husband and me.

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$250

Conch Republic Retreat

Key West cottage

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$107

Duval On The Square

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“A really good place to stay” Duval Square is a very good location. Crowd noise is not a problem. However the parrots from the New York restaurant below can get annoying. The inside of the apartment is nicely done. The balcony's overlooking the square are nice but are in need of painting. Service from the rental company was excellent. They respond quickly to requests. Bringing the baggage up to the apartment is easier when you use a shopping cart and the elevator. If a cart is not in the garage take the elevator up to the 2nd floor. They are usually left by the elevator. The worst problem is the parking at the check in site. It is extremely tight and it is a damaged fender waiting to happen. The service once inside is very good.

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$100

Key Lime Pie

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Loved Off Season Key West” Spent a month in this very secluded house within walking distance of everything, including the marina, Duval Street and my favorite Watering Hole, Finnegan's Irish Wake pub. Renting in October, the off season, meant I got to experience an uncrowded Key West. And best of all, at the end of the month, to experience Fantasy Fest in its entirety. What a rush. House was wonderful. Had it all including a hot tub. Private parking, a real plus in Key West. Plan to do it again.

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$87

Perfect Pineapple

Key West house

2 bedrooms / 1 bathroom / sleeps 4

“Kudos to Owner” The owners updated many things such as new bathroom tile, area rugs, washer and dryer area as well as painting. Still needed are more dinner and salad plates as it is necessary to run the dishwasher almost every day. The timer system for the garden lights needs to be repaired. Guests came to visit and it was very crowded with 4 people even with two bedrooms. This is a perfect place for a couple. The big negative is the Iguana's who wander from the cemetery area . A 3 1/2 foot Iguana can scare the heck out of you.

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$100

tropical Casita

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$107

The Prive

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“What a wonderful place to forget the long cold winter and renew” The house was beautiful . The neighborhood was quiet and peaceful. It was everything we had hoped it would be. Everything you could possibly need in a house was there. The house was spotless, bright and airy. The back yard was beautiful! If you need a place to relax and rejuvenate this is it! I can't wait to rent it again!

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$325

Amelia Home

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect” We loved this house! It was the perfect little getaway. It was in a great location, very convenient to everything. The house was beautiful with very nice decorating inside to the beautiful lush garden outside. If we visit Key West again, I’d stay here without hesitation. I highly recommend!.

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Price per night from

$330

Poolside Paradise

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$100

Rosalie's House

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$167

A Touch of Bermuda in Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Lovely Home and Great Location for our Key West Vacation” We had a great time at The Touch of Bermuda Cottage on Truman annex. We knew this was a good location from previous trips, and we also knew we wanted to find an individual home with all the amenities we needed for our stay in Key West. The Cottage certainly fitted the bill. It was very spacious, well equipped, with lots of homely touches, and had a nice private back yard where we could breakfast in the morning or come back after a long day to relax in the evening. On two floors so plenty of privacy for our party, and 2 bathrooms which isn't the case with every 2 bed property in the annex. The owner, Jack, was very responsive and helpful before we arrived and real pleasure to deal with. The Cottage is close to the Truman entrance, so easy to walk to all the main attractions, but far enough away to be nice and quiet after dark. The communal pool is a very short walk away down the back path. Overall it's a good rental property in a well kept development. We would go back there.

Responds fast! avg. 2 hours 8 minutes

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Price per night from

$400

Tropical Dreaming

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Oasis in busy Key West” We have stayed at Tropical Dreaming several years in a row. It is a lovely setting a couple of blocks off Duval so it is its own oasis.

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$360

Paradise Place

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

“The Condo was all we had hoped it would be and more.” The condo was clean, good size, and fully stocked (i.e. linens, towels, kitchen equipment & necessary supplies. Oh yes, and two large Tv's (we like to watch the news). Wish it was located a little closer to Duval..Otherwise you will need to rent a bike or a scooter. We enjoyed sitting on the front porch and watching the people passing by. We needed an alarm clock & after we requested a clock, a clock was delivered almost immediately. They have their service down to a science. Great Experience!

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Price per night from

$160

Key West Ginger Whole House

Key West cottage

2 bedrooms / 2 bathrooms / sleeps 6

“Ginger House = Perfect Getaway” Rented this property for Labor Day Weekend for a Bachelor Party and the location was ideal. House was clean and in good condition and it was perfect. It's not large, so keep your party relatively small but I was impressed by the rental company and the property itself. Would use again 100%!

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Price per night from

$230

Here Tomorrow

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

“Exceeded our expectations” We loved this house! Super location - just one block off Duval - and also near to the beach; we went to the Southernmost beach a lot. We thought that the house is bigger then it looks in the photographs. We were expecting a small little conch cottage whereas we got a nice size 3 storey house. The bedrooms in particular were very roomy and of course the main bathroom with the jacuzzi bath, the doublesize waterfall shower (with sit down area) and double vanity area was fabulous. It had all the expected amenities and we made particular good use of the ice machine for cocktails by the pool :-) Decor is modern. Very nice bed linen and lots of towels were provided. The pool area was a little small (but no smaller then we expected from the photographs). Was not great for sunbathing as the sun only hits in one spot but as I mentioned earlier we went to the beach a lot. All in all a great house. Also must mention the good service from At Home in Key West when booking. I found the Live Chat service really useful. We had no need to contact them during our stay (no issues with house etc) so cannot comment on service during our stay. Eating: We ate at out the majority of the time and aside from the fish we caught (we went fishing with Captain John's Greyhound V) we never cooked at home. Our favourite place is A&B lobster house/Alonzos, Santiagos Bodega and Firefly. Shopping: Coach and Banana Republic on Duval are probably the only two good stores - only you are looking for tee-shirts!!!! Red Gallery near Flagler Station museum is good for quirky gifts. Recommendations things to do: Custom House Museum Lighthouse tour Little White House Hemingway House Fishing with Captain John's Greyhound V is always good

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$117

Duval Street Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Bachelorette Paradise” I spent the weekend in Key West with a group of girlfriends for my bachelorette party. We could not be more pleased with the Duval Street Suite. The apartment had a beautiful wrap around porch, great for people watching. The kitchen was equipped with all the necessary utensils and appliances. The late check in and check out processes were very quick and easy. The apartment was clean and decorated nicely. The suite was in walking distance to all of the popular bars, restaurants, and attractions. I can’t speak highly enough about the Duval Street Suite. I will definitely reserve this spot for my next Key West trip. Thank you Historic Hideaways!!

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$200

The Blue Pelican - Comes With 6 Passenger Gas Golf Cart

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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$573

key west tree house

Key West apartment

1 bedroom / 1 bathroom / sleeps 3

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$191

Private, heated pool. Private yard.

Key West condo

1 bedroom / 1 bathroom / sleeps 4

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$138

Seaside Condo 2 pools JANUARY SPECIAL

Key West condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 55 minutes

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Price per night from

$100

Atlantis Dream Escape

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

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$324

Sunrise off Southard- A Tropical Sanctuary Newly Remodeled in May

Key West condo

1 bedroom / 1 bathroom / sleeps 3

“Sunrise on Sourhard” A beautifully decorated condo fitting all our needs. We especially appreciate the the 2 brand new bikes to get us around the the island, as it saved us from renting any other transportation!! The back deck is spacious and comfortable as well!

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Price per night from

$327

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Price per night from

$229

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