Pet Friendly Holiday Rentals in Key West
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331 rentals in Key West.
Key West Room Retreat | Two Family Ready Suites Perfect For Long Stays
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Poinciana Place Garden: First Floor, Hot Tub, Walk to Beach & Downtown!
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**SOUTHERN STAR * THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps, Pet friendly
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Conch Cottage Retreat in the heart of Old Town Key West
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, Pet friendly
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**Welcome To Poseidon's Paradise** Midtown Home & Incredible Pool *28 Nights Min
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The Standard Double Queen Hearing Accessible at The Gates Hotel Key West
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
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Comfortable Family Resort Room w/ Ocean Views, Kayak Rentals & Six Pools
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Unwind in Paradise: Playful Historic Bungalows with Resort-Like Amenities
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Colorful waterfront condo with pool & hot tub, AC, W/D, & WiFi - dogs OK
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Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Fantastic Land and Sea Vacation! Amazing Ocean View Room w/ King Bed, Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Serene Retreat w/ Waterfront Balcony & Easy Access to Paddleboarding
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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**SWEET AMERICANA * OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
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Escape to the Keys! Modern Pet-friendly Unit! EV Charger and Parking! Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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Dog-friendly home with pool & walk to parks & beach - snowbirds welcome
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Room in Coastal Resort w/ Oceanview - Six Pools & Pvt Oceanview Balcony
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, Pet friendly
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Amazing Land and Sea Getaway! Four Convenient Rooms, Close to Nearest Beach
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps, Pet friendly
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Carey’s Corner | Updated Studio with Heated Pool
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St
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Ocean View Balcony 2 Queen at Oceans Edge Key West, Saltwater Pools - 2 Units
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Spacious 2/2 Waterfront Condo w/Pool&Dock
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A Touch Of Cuba In Key West
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Best Place to Stay in Key West! 4 Stylish Units, Pool! Parking & EV Charger
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps, Pet friendly
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TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!
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Casa De Cubana | New! Cuban-Style Home Steps from Duval Street
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
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Key West Getaway! Pool, Restaurant, Bar, Gym, Parking!
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SWEET LIKE SUMMERTIME ~ 3 BR/2Ba Home w/ Pool and Yard!
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Old Town Key West Retreat | Seaport Paradise Room with Pool Access | 3 Rooms
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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Stunning Key West Stay Perfect for a Romantic Escape! Outdoor Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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Garden of Roses | Private Hot Tub, Prime Key West Location! - Monthly Rental
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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Amazing Stay in the Keywest! Two Deluxe Pool View Two Queen Beds
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Unique Island-Style Rooms with Custom Furniture & Art in Key West
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Heron House | Canal Front 3-Bedroom Home w/ Private Boat Docking in Key Haven
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Pet friendly
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Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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Relax in Romantic Lodge w/ Pool Minutes from Vibrant Duval Street
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Ritaville | New! Waterfront Paradise with Private Pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps, Pet friendly
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Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval! Shared Pool
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Dog-friendly condo with pool & hot tub - walk or bike to beach
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3 Oceanfront Two Queen, Pier House Resort, Beachfront Leisure, Key West Sunset
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
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Harbor Oasis Room: Tranquil Seaport & Water Fun
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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4 Key West Stays with Spa, Private Beach & Culinary Delights - On Duval St.
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps, Pet friendly
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Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Living the Dream Key West Style
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Relaxing Key West Haven with Full-Service Spa and Legendary Dining
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Pet friendly
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