Dog Friendly Vacation Rentals in Florida Keys - FlipKey

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480 pet friendly house rentals in Florida Keys

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

SPECIAL FALL RATES, INCL. LABOR DAY - BOOK NOW!

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 53 minutes

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Price per night from

$287

3BR Oasis in the Keys w/ Kayaks & Paddle Boards - Sweeping Ocean Views!

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$303

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 13 minutes

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Price per night from

$258

Canal-Front 3BR w/ Private Pool, Boat Slip, Tiki Hut & Kayaks - Near Beach

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

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$179

Waterfront Keys Home - Spectacular View, 37' Dock

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful location” My husband, son, and I had a fantastic vacation here. The private boat dock and Bay Area was perfect for our needs. We were out in the gulf in a few minutes and could reach the Atlantic via Vaca Pass or 7 Mile bridge in just a short boat ride. The house itself was the perfect size for the 3 of us(& 2 shelties), giving each of us our own space. The view from the house is great. We watched tarpon, turtles, and dolphin!! The airport right behind us was not an issue!! In fact, we thought it was kind of cool to watch some of planes/helicopters!! The storage area with the bait fridge/freezer was a great plus!! There were 2 things that I noticed could improve (but by no means a reason to not stay here!!). First there was not any pantry storage. We just used the island top. No big deal. And the lint screen for the dryer was falling apart. Again no big deal. I would not hesitate to stay here again!!

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Price per night from

$200

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 12 minutes

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Price per night from

$287

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

Cudjoe Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$184

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 12

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Price per night from

$288

75130 Overseas Highway

Matecumbe Key house

2 bedrooms / 2 bathrooms / sleeps 4

“The view and location was excellent.” The house had most of the amenities I would expect at a beach location. You can't beat the sunsets over the bay! We snorkeled at Key Largo and took a day trip into key West, so the location was perfect. The area had the best restaurants. We tried them all. Only complaints were: no outdoor grill, no wine glasses, sheets kept pulling off the bed and rusted beach chairs.

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Price per night from

$190

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$654

Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise

Conch Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 23 minutes

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$189

Key Largo Kampground Vacation

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

“Great location and pleasantly surprised!” Romberto's Camprground vacation was definitely more than i expected. There was ample room for my husband and I, the folks were nice and the area was quiet and clean. The marina was convenient (small boats only). There was a small leak in the bathroom in the overhead skylight but it was almost negligible unless it was pouring. we will definitely be back.

Responds fast! avg. 2 hours 56 minutes

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Price per night from

$144

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

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$148

Blue Bungalow

Key Largo bungalow

1 bedroom / 1 bathroom / sleeps 2

“The Cozy Blue Bungalow” We stayed for a week on January 2019. It was perfect. Laura and Janet are thoughtful hosts and seem to have considered every need of their guests. They graciously allowed us to bring our 35 and 55 lb rescue dogs with us. The small deck in the fenced in back of the house has a nice shade, a really nice grill and is a lovely place to just sit and relax. Inside, a king size day bed and a small table and chairs. While no stove/ oven, you do not need one as their is a microwave and the grill has a gas burner for cooking. The bathroom has a beautiful, large shower that I cover. Convenient location and they provide many suggestions for restaurants, fishing, etc. There is a fenced in private park on the water at the end of the street where our dogs could run freely. Can’t recommend this highly enough! We really enjoyed our stay.

Responds fast! avg. 1 hour 2 minutes

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Price per night from

$87

Brand New 3 Story Key Largo Home

Key Largo house

5 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 1 hour 24 minutes

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Price per night from

$408

Family Retreat ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 18

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Price per night from

$573

164 Plantation Shores Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$201

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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$236

Million $$ Pool Home

Key Colony Beach house

3 bedrooms / 3 bathrooms / sleeps 8

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$441

2 Great Waterfront FL Keys Homes - 1 Low Price

Marathon house

4 bedrooms / 4 bathrooms / sleeps 12

“Excellent Stay!” We rented out both sides for the week and we couldn't have asked for a better location! Great fishing, lobstering, and diving. We took the boat out almost everyday right from the house. Just enough room for our 9 people plus 1 baby. I loved how the kitchen was fully stocked with any possible cooking thing we needed. Everything worked perfect and was up to date.

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Price per night from

$372

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$482

Catch of the Day!

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$111

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

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$206

Sunset Bay (weekly rental)

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$301

Dog-friendly, tropical escape with central location, hot tub, and shared pool

Stock Island house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 40 minutes

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Price per night from

$218

Seas the Day in this Waterfront Home on Oceanside MM90

Tavernier house

5 bedrooms / 3 bathrooms / sleeps 14

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Price per night from

$201

KEY LARGO YACHT CLUB 8

Key Largo apartment

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$140

Islamorada Tropical Canalfront Paradise

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 40 minutes

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Price per night from

$316

Hidden Treasure

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$127

Waterfront in Key Largo, Terrific 1/1 Apt, 2nd Floor, Pet Friendly, Sleeps 4

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 52 minutes

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$75

Waterfront house w/ covered patio, private pool, & 75 ft. dock - dogs welcome!

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 40 minutes

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$134

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 40 minutes

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Price per night from

$1,395

Large, dog-friendly home on three secluded acres w/ balconies, deck, views

Sugarloaf Key house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 40 minutes

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$359

LITTLE BAY - Upper Duplex

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

“Classic Islamorada - Amazing Property” Little Bay was a perfect property for us! The setting is idyllic and classic keys - Huge backyard on the Bay with excellent dock area, hammocks and view of the bay. Covered porch was the full width of the house and was a great place to hang out morning and evening. The property had everything that we needed, was centrally located and have plans to visit again! Service provided by rental agency was top notch and very attentive - they showed us around, accepted packages on our behalf and were friendly and helpful throughout our entire rental experience - from planning to checkout. This is definitely on our To Re-Do List.

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Price per night from

$393

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$374

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

$286

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 28 minutes

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Price per night from

$608

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