
Pet-friendly holiday rentals in Key West
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Key West
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

Duval Vibes • Pool • 10 Guests
Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, family reunions, or any celebration that bring you to town. This 3 bedroom/ 2.5 bathroom home has a full kitchen, spacious outdoor living space, outdoor shower, private second story sundeck, and a pool. Your group of up to 10 will love being steps away from all KW has to offer- be Hemingway's neighbor! Add this listing to your wishlist by clicking the ♥ in the upper right hand corner.

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
Bring friends and family to this 1,350 sq ft waterfront corner condo in historic Downtown Key West. Just 1 mile to Duval Street, the Historic Seaport, and the Hemingway House. Enjoy a heated pool, tiki bar, BBQ grills, parking, building elevator, secure keyless entry, and an adjacent park with tennis courts. Please note: The condominium dock will be under construction beginning April 27, 2026 for approximately 30 days; dock access will be unavailable and daytime construction noise is expected.

The Writer's Block- Key West
Discover tranquility aboard this unique floating haven. It's a sleek modern retreat for those who crave space to read, write or find inspiration far from the stresses of the modern world --yet it's steps away from upscale restaurants, two fabulous pools, a gym and so much more. From a king bed to a full-sized shower and kitchenette, you'll enjoy the comforts of home while living directly on the water. Features a large private deck with panoramic views of the marina and its glorious sunsets.

Waterfront Cozy Cottage with Boat Ramp & Dock!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Duval Corner - Pet friendly with Balcony
Welcome to Duval Corner! A beautifully updated one-bedroom condo in the heart of Downtown Key West. This second-floor retreat is perfect for travelers wanting to be steps from it all. Within walking distance to iconic attractions like the Southernmost Point, The Ernest Hemingway Home, and Mallory Square, plus dining hotspots such as Blue Heaven, 7 Fish, and Louie's Backyard; Duval Corner is the ideal base for your Key West adventure.

Poinciana Treetop ~ Casual Second Floor Duplex
Vacation near historic Duval Street with parking and a treetop view. Or vacation with friends by renting both floors of this duplex. This conveniently located home allows you to have plenty of fun and enjoy a respite in your own private space. THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key West charm and contemporary touches.

Sale! Cabana Club, Kayaks, Dock, Pet Friendly
Coral Cabana Welcome to Coral Cabana, your own private tropical oasis in Key Colony Beach! This stunning 2-bedroom, 2-bathroom half duplex is the perfect escape for those seeking a captivating and enchanting vacation experience. As you step inside, you'll be greeted by a beautifully updated interior that breathes coastal charm.

Houseboat in Key West
Enjoy this 45-ft '71 houseboat, single stateroom with queen bed, perfect for a couple or solo adventure. No resort frills, just old-school Key West vibes, mile-wide water views, and mangroves. Full bath, full kitchen, and a spacious sun deck to enjoy stunning sunsets and stargazing at its finest. 15 mins to Duval.
Popular amenities for Key West pet-friendly home rentals
Pet-friendly house rentals

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

Key West Paradise

Waterfront Oasis w/Private Pool-Dockage-Beach

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Dolphin Daydreams at Venture Out

Kingfish Keep | Lively Escape on Duval! Balcony!

Waterfront House with 37 ft Dock & Cabana Club

Gorgeous Ocean View Home!
Pet-friendly home rentals with a pool

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

Ocean~View*Pool*Dock*Kayaks*King Bed

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Paradise Ocean Front 4/3Home Heated Pool

COZY Family Home- 5 minutes from sombrero beach

Waterfront w/pool and hot tub

Luxurious 40' Sailing Yacht!
Private, pet-friendly home rentals

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

Private Parking , Heated Pool - Key Lime Cottage

Seashells Getaway - Boat Slip, Ramp, Pool

Cozy Houseboat Experience & Scenic Views @ Perry

2BR Suite | Pool | Hot Tub | Tennis | Dog Friendly

New Waterview 2/1 Cabins w Boat Ramp (No Loft)

Key West Houseboat Paradise

KW Beach house with heated pool, dock, accessible
When is the best time to visit Key West?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $670 NZD | $699 NZD | $665 NZD | $584 NZD | $549 NZD | $462 NZD | $471 NZD | $439 NZD | $408 NZD | $494 NZD | $582 NZD | $596 NZD |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
Quick stats about holiday rentals that are pet-friendly in Key West

Total holiday rentals
Explore 680 holiday rentals in Key West

Nightly prices starting at
Key West holiday rentals start at $166 NZD per night before taxes and fees

Verified guest reviews
Over 21,070 verified reviews to help you choose

Family-friendly holiday rentals
430 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
520 properties feature pools

Rentals with dedicated workspaces
440 properties have a dedicated workspace

Wi-Fi availability
670 of Key West holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Key West rentals

4.8 Average rating
Key West stays are highly rated by guests—averaging 4.8 out of 5!
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- Pet-friendly rentals Monroe County
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