Pet-friendly vacation rentals in Big Pine Key

A shaded tiki hut is situated on a stone patio beside a tranquil canal. The space is furnished with a table and chairs, surrounded by palm trees. Brightly colored kayaks are neatly arranged on a nearby dock, adding to the outdoor ambiance.

4.91 out of 5 average rating, 107 reviews

*New Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes

Perfectly situated in KCB w/ 37.5' of dockage on a wide and pristine canal that leads easy access to both the Ocean & the Gulf, our newly listed 1/2 duplex is newly renovated w/ brand new AC, appliances, fixtures, furniture, mattresses, & decors. Featuring 3BR 2BA accommodating up to 8 ppl in a large & open living room & backyard, provided w/ multi-game table, bikes, kayaks, 6-burners grill, 2 mins walk to Sunset park, & Cabana Club access, it is the perfect Florida Keys getaway for your family.

Tiny homes in Big Pine Key

A coastal scene showcases palm trees swaying gently by the water. Thatched roofs provide shaded seating areas along the shoreline. Sailboats are visible on the horizon, amidst clear turquoise waters under a bright blue sky, with a few fluffy clouds drifting by.

4.89 out of 5 average rating, 97 reviews

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!

Camper/RV in Big Pine Key

The exterior of the RV is set against a backdrop of lush palm trees and tropical foliage. Decorative elements, including colorful painted shells and a seahorse, adorn wooden fences. Potted plants add greenery, complementing the sandy ground.

4.68 out of 5 average rating, 34 reviews

Island Girl Big Pine Key

Come and relax at our tropical escape. Only 33 miles North of Key West and 7 miles south of Bahia Honda beach. Our new 34’ Atlas RV is just what you need for a relaxing getaway. Walking distance of restaurants, grocery stores and Pine Channel Park. Enjoy biking, as well as walking to nearby charter services, kayak and boat launches. Brand new Dutchman Atlas with King Master suite with a spacious walk through bathroom with sliding barnyard doors. Second bedroom offers a full size bunk bed.

4.84 out of 5 average rating, 117 reviews

An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

Home in Cudjoe Key

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***

4.89 out of 5 average rating, 518 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, 107 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.

5 out of 5 average rating, 6 reviews

Home in Big Pine Key

Aquahouse Paradise easy access to the ocean

Take it easy at this canal front with quick acces to the ocean unique and tranquil getaway. Big Pine Key, know it for the key deers, one of the only 2 places in the entire world where you can interact with this endangered species. you can feed it during night they love bread and eggplants, here you can enjoy the florida weather conditions all year long. lot of activities. only 30 miles away from Key West. 2 miles from supermarket,pharmacy, hardware and auto parts.

4.92 out of 5 average rating, 112 reviews

Aerial view of a waterfront property featuring a semi-circle dock leading to a small island. Brightly colored chairs in green and turquoise sit on sandy areas, surrounded by clear blue water and lush tropical vegetation. Nearby, additional properties can be seen amidst palm trees.

Home in Summerland Key

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). 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 point and enjoy the underwater scenery!

4.88 out of 5 average rating, 133 reviews

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

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.

Tiny homes in Big Pine Key

4.93 out of 5 average rating, 99 reviews

Tiny Fish Haus

Great location in the lower keys , 28 miles to Key West..8 miles to Bahia Honda State Park and right next to the National Key Deer Refuge! Relax on our covered patio next to a large Swimming Pool, Cook dinner on a Blackstone grill and enjoy WIFI, Games, a Flat Screen TV , we have Premium Organic Bedding on our Queen beds for comfort. Turkish Towels for bath and beach..Explore Big Pine Key with our 2 beach cruiser bicycles!

The exterior of a blue house is surrounded by a landscaped garden featuring palm trees and other greenery. A gravel driveway leads to the entrance, providing ample space for parking. The sky is clear and sunny, enhancing the inviting atmosphere of the property.

4.92 out of 5 average rating, 132 reviews

Beautiful Renovated Home in Marathon, FL

Cozy home centrally located in the heart of Marathon with a ton of parking space for a boat or RV... Stay at ease in this family friendly neighborhood with lots of fun nearby (within 10 minutes) such as Sombrero Beach, FL Keys Aquarium, public boat ramp, kayaking, diving, restaurants and more!!! Licensed and inspected by the City of Marathon, Lic.#VACA-21-409

Popular amenities for Big Pine Key pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

The exterior of a charming waterfront home is depicted, showcasing a canal with clear turquoise water. Lush palm trees frame the property, and well-maintained landscaping adds to the serene environment. The two-story building features a spacious porch and multiple balconies, enhancing outdoor living.

4.96 out of 5 average rating, 72 reviews

Coral Lagoon #23- Private Villa Home

4.95 out of 5 average rating, 144 reviews

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

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.

4.94 out of 5 average rating, 135 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

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

4.73 out of 5 average rating, 33 reviews

A vibrant green house is presented with large windows adorned with yellow shutters. A spacious front porch is bordered by tropical plants, while a gravel pathway leads to the entrance. Nearby, a blue trash bin is visible, along with a parked vehicle.

Home in Cudjoe Key

Tropical Island Getaway

4.97 out of 5 average rating, 296 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Two outdoor sun loungers are positioned on a concrete patio, facing a tranquil waterfront scene. A stunning sunset casts warm hues over the water, with boats visible in the distance. Wooden pilings line the dock, enhancing the idyllic setting.

4.91 out of 5 average rating, 55 reviews

Water, Water Everywhere! "The Wheel House"

A bright living area features light-colored furniture arranged for comfort. A spacious sofa is paired with woven accent chairs, offering views through large glass windows overlooking a canal. Light curtains frame the windows, allowing natural light to enhance the room's open feel.

5 out of 5 average rating, 11 reviews

Key Colony Beach Waterfront 321

Pet-friendly home rentals with a pool

4.87 out of 5 average rating, 77 reviews

An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.

Cottage in Cudjoe Key

Turtle Cove Views at Venture Out

5 out of 5 average rating, 3 reviews

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

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

Tropical Keys Retreat | Pool | Hot Tub | Cinema

4.95 out of 5 average rating, 66 reviews

A bright bedroom features a spacious bed with a white duvet cover and decorative teal throw. Art depicting fish adorns the walls. Natural light enters through the window, complemented by a stylish lamp. A wooden dresser occupies one corner, enhancing the room's coastal theme.

Bungalow in Islamorada

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

A spacious pool area is surrounded by patio tiles, featuring two green lounge chairs and multiple seating options for relaxation. Palm trees and a canal are visible in the background, enhancing the outdoor ambiance. The clear blue sky reflects a pleasant atmosphere.

4.97 out of 5 average rating, 64 reviews

Paradise Ocean Front 4/3Home Heated Pool

A wide, gravel driveway is seen leading to the duplex building. Colorful foliage borders the space, and utility poles are visible in the background. The parking area accommodates vehicles comfortably, with additional spaces towards the right for guests or boats.

4.67 out of 5 average rating, 15 reviews

Maria's 3 Bedroom. Dock. Pool Club is 1 block away

4.9 out of 5 average rating, 256 reviews

A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.

Condo in Key West

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

4.94 out of 5 average rating, 17 reviews

A 40-foot catamaran is anchored in clear turquoise waters. Two individuals are enjoying the ocean; one is swimming while another relaxes on the deck. The yacht features a modern design with a spacious deck for sunbathing and enjoying the surrounding scenery.

Boat in Key West

Luxurious 40' Sailing Yacht!

Private, pet-friendly home rentals

Aerial view of a waterfront home surrounded by the Atlantic Ocean and patch reefs. Lush palm trees dot the landscape. The canal is seen flowing between two rows of homes, with boats docked along the private docks, showcasing easy access to the water.

4.94 out of 5 average rating, 84 reviews

Oceanside, Fee-Less Pet, with kayaks - 60 FT Dock

4.92 out of 5 average rating, 38 reviews

Another Day in Paradise

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

An outdoor area features a fenced pool surrounded by colorful chairs. Palm trees provide shade, and the spacious deck above is visible. The setting reflects a relaxed atmosphere with nearby greenery enhancing the tranquil environment.

4.83 out of 5 average rating, 24 reviews

Soothing Nest

4.63 out of 5 average rating, 178 reviews

A serene waterway is shown, flanked by palm trees and waterfront homes. A boat is seen navigating the calm waters, with clear skies enhancing the tranquil scene. The reflection of the surroundings is visible on the surface, creating a peaceful atmosphere.

Home in Cudjoe Key

Ocean Front Home in Great Location

A serene waterfront scene captures colorful sunset hues reflecting off calm waters. Palm trees sway gently in the breeze, while boats are moored along the canal. The peaceful atmosphere of the neighborhood is evident in the backdrop of charming docks and nearby structures.

4.92 out of 5 average rating, 76 reviews

Blue Ocean Bungalow-May dates now available

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

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.