
Pet-friendly vacation rentals in Sunset Key
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Top-rated pet-friendly home rentals in Sunset Key
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.
WalkabilityOutdoor spacesParks

Cottage 30 min from Key West, free parking, pool
Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!
WalkabilityOutdoor spacesGetting around

Key West Outpost: eco-vacation
The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.
PetsOutdoor spacesView

McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
Beautifully decorated, step inside with cool pastel colors. The amenities include a blue tooth speaker, Alexa Echo, and a full kitchen with dishwasher. End your day by relaxing in front of the 65" Smart TV (bring your login information for Netflix/Amazon). The tumbled marble shower adds a luxurious touch to your stay. Located in a gated compound with 3 other units, you'll have privacy during your stay. The heated family pool is next door, while the adult heated pool is across the lane.
PetsWalkabilityLong stay

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!
WalkabilityOutdoor spacesAmenities

Waterfront Dock Pool Condo Near Duval St Pet OK
Bring friends and family to this spacious 1,350 sq ft waterfront corner condo in historic downtown Key West. Enjoy a full kitchen, open living space, and a private balcony with marina and pool views. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, and Hemingway House. Amenities include a heated pool, tiki area, BBQ grills, parking, elevator, and secure entry.
Outdoor spacesPetsLaundry

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***
PetsOutdoor spacesAmenities

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.
PetsWalkabilityQuiet

The Dancing Rooster - 1 Block to Duval!
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.
Outdoor spacesWalkabilityFamily

Private Parking , Heated Pool - Key Lime Cottage
Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the historic seaport and downtown. After a day of exploring, relax in the shared pool or enjoy a barbecue on the patio, perfect for connecting with other guests. Divided into six individual units, the guest house offers flexibility for both solo stays or group bookings, making it ideal for your next Key West vacation.
WalkabilityOutdoor spacesHospitality

Castaway Cove: Pet-friendly 2/2 condo near beach!
Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.
PetsWalkabilityAccess

The Guest House - Sugarloaf Beach Key West
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. A truly one-of-a-kind beachfront retreat offering a private sandy beach and dock with boat dockage. This tropical escape delivers a relaxed, family-friendly atmosphere that makes you feel as if you’re on your own private island in the Florida Keys. .
WalkabilityPetsBeach
Popular amenities for Sunset Key pet-friendly home rentals
Pet-friendly house rentals

Family Home 3-bedrooms/3-bathrooms
Outdoor spacesWalkabilityBeach

Key West House
Outdoor spacesKitchenAccuracy

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK
WalkabilityPetsAir conditioning

Casa Calypso 3bed3bath sleeps 8 beautiful decorate
WalkabilityPetsDecor

Tropical Dreaming by AvantStay | 4 Blocks to Beach
WalkabilityOutdoor spacesIndoor spaces

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

Key West Paradise
Outdoor spacesPetsQuiet

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks
Outdoor spacesWalkabilityBathroom
Pet-friendly home rentals with a pool

Strictly Pleasure | Unique Yacht Stay in the Keys
WalkabilitySleep qualityBathroom

Cottage
Outdoor spacesPetsSleep quality

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
PetsOutdoor spacesCondition

43' Classic Yacht Views, Pools, Duval Shuttle
Outdoor spacesWalkabilityAir conditioning

Oceanfront Bungalow Venture Out
Outdoor spacesHot tubHospitality

The Butterfly Nest | Newly Updated w/ Shared Pool
AmenitiesBathroomBeach

Dream Catamaran
Sleep qualityNearbyHospitality

A Perfect Getaway
WalkabilityOutdoor spacesSleep quality
Private, pet-friendly home rentals

Love Shack: 2BR Houseboat w/ Decks & Views
Outdoor spacesAir conditioningQuiet

Houseboat in Key West
PetsOutdoor spacesHospitality

Apartment in Key west
ValueHospitalityNearby

Entire townhouse pool front in Key West
WalkabilityPetsPool

Key West Houseboat Paradise
Outdoor spacesWalkabilityView

Deluxe Bungalow
WalkabilityOutdoor spacesCheck-in

Seaside Retreat: Waterfront Home with private heat
Outdoor spacesWalkabilityAccess

Key West Condo 2nd Floor 2BDR beach, pool, balcony
WalkabilityOutdoor spacesCondition
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- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Southernmost Point
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium





