Pet-friendly holiday rentals in Key West

5 out of 5 average rating, 3 reviews

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

Your own private Key West hideaway awaits. Surrounded by lush tropical landscaping, this peaceful home offers a large pool, outdoor shower, grill, and fire pit — perfect for relaxing days and starlit evenings. Enjoy complete privacy indoors and out, with three comfortable bedrooms, a fully equipped kitchen, washer/dryer, and 66' of canal frontage- bring your own boat or ask one of our favorite captains to pick you up! Whether out on the town or relaxing in your own home, you will love it here!

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5 out of 5 average rating, 66 reviews

Marathon Keys Escape • Pool • Hot Tub • Near Beach

Welcome to Paradise Palms: ⭑ 1750 sqft liveable space on 10,500 sqft estate ⭑ Private home, deck, patio & backyard, overlooking a beautiful scenic landscape ⭑ Crystal pool, hot tub, movie theater, remote workspace, game room with arcade & more ⭑ Secure parking for up to six vehicles, boat trailer parking, RV and EV charging ⭑ 10 min to sombrero beach & just minutes to all island attractions ⭑ Fully stocked kitchen ⭑ Extremely safe neighborhood License #VACA-24-20 License #VACA-24-32

A spacious balcony overlooks the harbor, featuring a dining table and wooden chairs. Lush palm trees are visible nearby, with the serene water reflecting the blue sky. The scene is perfect for outdoor relaxation and enjoying the coastal ambiance.

4.88 out of 5 average rating, 121 reviews

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Time to relax and unwind in this spacious 1,350 sq ft waterfront corner condo in historic Downtown Key West. Walk or bike everywhere—less than 1 mile to Duval Street, the Historic Seaport, and the Hemingway House. Enjoy a heated pool, tiki bar, BBQ grills, building elevator, and secure keyless entry. 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.

Cottage in Little Torch Key

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

4.89 out of 5 average rating, 177 reviews

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!

4.94 out of 5 average rating, 135 reviews

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

Home in Key Colony Beach

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.

A spacious outdoor area is surrounded by tropical landscaping, featuring a BBQ grill and a hot tub. Comfortable lounge chairs are available under umbrellas, with a gravel walkway leading to various seating arrangements. Sunlight filters through the palm fronds, creating a relaxing atmosphere.

4.96 out of 5 average rating, 45 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

License#VACA-23-370. Hot Tub, BBQ. Bring Your Boat, RV Parking. Conch Home located in the Heart of Marathon. Home sits on 8,000+sf lot w/2 bed (king in main BD & 2 twins in 2nd BD) 1 bath home w/ fully equipped kitchen & full bath w/shower & tub + lots of natural light & garden view all around. W/D, new mini split ACs in living room, & both bedrooms, back deck has a BBQ, Hot Tub & huge yard w/plenty of parking for a boat and trailer. YOUTUBE VIDEO TOUR: SEARCH sandys conch cottage

4.89 out of 5 average rating, 515 reviews

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

Villa in Marathon

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!

A private outdoor area features a hot tub surrounded by tropical foliage. A dining table with chairs is situated nearby on a wooden deck, offering shade from the overhead structure and a relaxing atmosphere for outdoor meals.

4.87 out of 5 average rating, 106 reviews

Near Duval: Hot Tub, Sleeps 6, Top Location

Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.

4.95 out of 5 average rating, 112 reviews

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

A round dining table is set for four, featuring orange napkins and glassware. Natural light fills the space through large windows adorned with wooden shutters, creating a warm atmosphere. A pineapple centerpiece adds a tropical touch, and kitchen cabinetry is visible in the background.

4.93 out of 5 average rating, 40 reviews

Casita Angelita at Old Town

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** This Old Town condo is perfect for anyone who can't get enough of Key West's famous nightlife scene. CASITA ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district.

4.92 out of 5 average rating, 255 reviews

Apartment in Key West

Sunset Suite-Historic 2 BR, K/Q, Sleeps 4, Spa!

Historic 1880's Cigar Maker's cottage completely renovated. 1 K and 1 Q BR’s, half bath upstairs between BR’s, 32” Smart TV's, Full kitchen with granite counter tops, new stainless steel appliances. A newly remodeled bath with tumbled marbled tile, hairdryer. Also a totally private outdoor shower located in your private patio. All bath amenities provided, plus pool towels and daily housekeeping!

5 out of 5 average rating, 4 reviews

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor

Captain's Cove, your 4BR waterfront escape in Marathon, set on a quiet canal with direct ocean access. Designed for unforgettable Keys living for families and boaters alike. 🏊‍♂️ Private backyard pool ⛵ 30’ boat dock + 4 kayaks 🍳 Covered outdoor kitchen & BBQ 🚿 Spa-style rain & jet showers w/ luxury toiletries 🛏️ Ground-level comfort for 8 🐾 Pet & kid friendly

Popular amenities for Key West pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A well-maintained community pool is surrounded by lush tropical landscaping, featuring lounge chairs with blue umbrellas. The clear water reflects the bright blue sky and palm trees, creating a relaxing atmosphere for guests to enjoy.

4.87 out of 5 average rating, 82 reviews

Key West Paradise

A private backyard features a hot tub and a shallow pool, surrounded by tropical greenery. Lounge chairs in teal are positioned nearby, and a grill is placed on the concrete patio. The canal is visible in the background, lined with palm trees.

4.94 out of 5 average rating, 48 reviews

Waterfront w/pool and hot tub

A private wooden dock extends over calm waters, featuring a boat with a blue canopy and a small table with colorful umbrellas nearby. Palm trees line the waterfront, and a series of pastel-colored homes are visible across the canal, creating a serene setting.

5 out of 5 average rating, 122 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

A shared pool is surrounded by lush tropical foliage and palm trees, providing a serene atmosphere. Two lounge chairs are visible beside the pool, inviting relaxation while the nearby fence adds a touch of privacy.

4.76 out of 5 average rating, 37 reviews

Paradise Place by AvantStay | Condo w/ Shared Pool

4.94 out of 5 average rating, 16 reviews

Home in Cudjoe Key

Blue Palms Retreat

An inviting outdoor area features a swimming pool surrounded by a manicured lawn. Comfortable lounge chairs provide ample seating, and a large umbrella offers shade. A canal with docked boats is visible in the background, complemented by palm trees swaying in the breeze.

4.98 out of 5 average rating, 63 reviews

Waterfront Heated Pool 120 ft Boat Dock

The living area features a comfortable sofa arranged around a coffee table, with large windows offering views of the balcony. A modern kitchen with granite countertops and stainless steel appliances is visible, providing ample space for meal preparation.

4.92 out of 5 average rating, 12 reviews

Sombrero Getaway Poolside Retreat with Canal Views

An outdoor view reveals a spacious coastal retreat featuring a private pool and hot tub. Surrounding areas include outdoor seating and a dining table under a shade structure. Lush landscaping and palm trees frame the setting, while the home’s second floor is elevated, providing an inviting ambiance.

4.67 out of 5 average rating, 6 reviews

Rest A Shore Waterfront Home, New Private Pool

Pet-friendly home rentals with a pool

4.77 out of 5 average rating, 13 reviews

Boat in Key West

43' Classic Yacht Views, Pools, Duval Shuttle

4.87 out of 5 average rating, 93 reviews

A bright living area features light-colored furniture, including a comfortable sofa and armchair. A wooden coffee table is centrally placed. Art displays adorn the walls, enhancing the inviting ambiance. Nearby seating accommodates dining for four, with large windows allowing natural light to flow in.

Apartment in Key West

Castaway Cove: Pet-friendly 2/2 condo near beach!

4.91 out of 5 average rating, 11 reviews

The outdoor deck provides a spacious area for dining and relaxation, framed by lush greenery. Two flags flutter gently in the breeze, while a mix of natural wood and beige gravel enhance the serene atmosphere of this tropical retreat.

Cottage in Key West

The Southern Cross

4.96 out of 5 average rating, 25 reviews

An aerial view showcases a private dock with a boat alongside a heated pool. Lounge chairs are positioned near the pool, complemented by vibrant palm trees and neatly arranged outdoor furniture. The tranquil waters reflect the bright surroundings, enhancing the overall relaxing atmosphere.

Home in Key Colony Beach

Paradise Cove! 50ft Dock Pool BBQ

Home in Upper Sugarloaf Key

A sandy beach area is framed by swaying palm trees, leading to a two-story bungalow elevated on stilts. Lounge chairs are arranged on the shore, providing a relaxing spot, while kayaks are visible in the background, enhancing the inviting beach setting.

4.75 out of 5 average rating, 103 reviews

Palm - Beach Houses Key West

4.94 out of 5 average rating, 67 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

A private pool is surrounded by a paved patio, featuring lounge chairs and a small table. Lush tropical plants provide a natural backdrop. In the distance, a boat dock is visible along with outdoor dining furniture and an umbrella. Soft lighting enhances the inviting outdoor space.

5 out of 5 average rating, 19 reviews

Waterfront home w/pool, dock & close to beach

5 out of 5 average rating, 3 reviews

Home in Cudjoe Key

Wake Up to Sunrises & Oceanfront Views

Private, pet-friendly home rentals

4.79 out of 5 average rating, 78 reviews

An aerial view of the cottage surrounded by lush greenery and the calm waters of a mangrove area. The property features a spacious driveway leading to the home, with natural landscapes extending towards the Gulf of Mexico in the background.

Home in Summerland Key

Kelly’s Kabin - Private FL Keys Cottage

4.75 out of 5 average rating, 182 reviews

The view from the patio showcases a vibrant sunset reflecting on the tranquil water. Lush palm trees frame the scene, with the illuminated pool area visible below. A distant pier extends into the water, enhancing the serene ambiance of the location.

Villa in Marathon

Sunset Villa in Duck Key

A shared pool area is showcased, featuring a sparkling blue pool with a gentle fountain. Light-colored lounge chairs surround the pool, and greenery adds a natural touch to the space. A white wooden fence provides privacy while a clear sky is visible overhead.

4.73 out of 5 average rating, 166 reviews

Walkable 1BR | Deck | Pool | Dog Friendly

5 out of 5 average rating, 7 reviews

The Grand Cayman | Beautifully Remodeled Key West!

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.

Houseboat in Key West

4.82 out of 5 average rating, 279 reviews

Key West Luxury Houseboat at Yacht Club Resort

A bright and inviting exterior view captures the charming two-story townhome nestled among tropical foliage. A white picket fence surrounds the property, and the entrance features double doors flanked by decorative plants. Sunlight bathes the scene, enhancing the serene outdoor environment.

Townhouse in Key West

4.84 out of 5 average rating, 104 reviews

Location Location Beach Paradise in the Keys Duval

4.73 out of 5 average rating, 41 reviews

A floating home is anchored in clear waters, surrounded by lush greenery. The structure is highlighted by solar panels on the roof and a spacious white deck, featuring railings that outline the edges. Bright blue skies and distant mangroves create a serene backdrop.

Houseboat in Islamorada

Perfect escape to the ocean