Holiday rentals with a patio in Big Pine Key

4.94 out of 5 average rating, 141 reviews

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

Cottage in Cudjoe Key

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

4.97 out of 5 average rating, 115 reviews

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

Home in Key Colony Beach

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Palm trees are seen swaying gently in the breeze, framing the entrance to the cottage, which features a welcoming front porch with two wooden chairs. The interior showcases a modern dining area, complete with a chandelier and decorative plants. A plunge pool is visible in the outdoor space, surrounded by tropical greenery.

4.93 out of 5 average rating, 102 reviews

Conch Cottage at Hawks Cay - Chic Tropical Retreat

Welcome to our tropical Conch Cottage, a lovely place to create memories on your idyllic Florida Keys vacation in paradise. Our stylish waterfront villa sits alongside a clear turquoise canal on picturesque Duck Key, inside the Hawk's Cay resort, and just 10 minutes from busy Marathon. Get involved in on-site activities like snorkeling, scuba diving, fishing, boating and dolphin encounters—or simply lay out on the coral stone patio, soak up the sun, and slide into your private plunge pool.

4.95 out of 5 average rating, 155 reviews

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

Villa in Duck Key

Beach House - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

4.87 out of 5 average rating, 116 reviews

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Home in Upper Sugarloaf Key

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

4.94 out of 5 average rating, 105 reviews

Lighthouse - Beach Houses 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. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

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.

4.87 out of 5 average rating, 106 reviews

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***

4.9 out of 5 average rating, 393 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!

4.97 out of 5 average rating, 122 reviews

A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.

Cottage in Islamorada

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

4.91 out of 5 average rating, 101 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!

4.94 out of 5 average rating, 102 reviews

The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.

Apartment in Marathon

Canal View Condo w/ Pool, Balcony & Bar

Celebrate the season in paradise at THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, accommodating up to 4 guests. Featuring a complete kitchen, balcony, and access to resort amenities including a pool, Tiki Bar, restaurant, Marina, and more! Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.

4.98 out of 5 average rating, 53 reviews

The Barnacle at Venture Out - Waterfront with Dock

Welcome to “The Barnacle” your waterfront home in the Florida Keys! Dock your boat behind this charming two bedroom home with 35’ sea wall! We have direct access to some of the best fishing, snorkeling and diving in the Keys! Beautiful neighborhood loaded with amenities. Bring a pole and fish from the dock! Relax, enjoy and have a wonderful vacation experience. Visit YouTube “The Barnacle at Venture Out”. Swim, Fish, Dive …Repeat!

Popular amenities for rentals with patio in Big Pine Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Flat rentals with a patio

A private balcony is adorned with festive garland, offering a view of a serene pool area surrounded by lush greenery. Two wicker chairs provide a comfortable spot to relax and enjoy the outdoors, with sun loungers visible beside the pool.

5 out of 5 average rating, 15 reviews

Casa Caribe 2bed2bath sleeps 6 beautiful decorated

4.94 out of 5 average rating, 18 reviews

A clear view of a private white sandy beach stretches along the coastline, framed by a thatched roof. Gentle waves lap at the shore, and a wooden pier is visible in the distance, under a bright blue sky scattered with clouds.

Flat in Marathon

*NEW* Sea La Vie-Pool & Beach

A light and airy living area features a modern blue sofa adorned with patterned throw pillows. A wooden coffee table sits in front, complemented by a tall indoor plant. A full-length mirror reflects the space, while natural light brightens the room through the patio door.

4.85 out of 5 average rating, 20 reviews

Duval Corner - Pet friendly with Balcony

A spacious outdoor patio is displayed, featuring a dining table surrounded by six chairs. The railing offers a view of Garrison Bight Marina, where boats are docked and palm trees sway. Sunlight casts patterned shadows across the patio floor.

4.89 out of 5 average rating, 56 reviews

Key West Condo 2B/2B with Pool & Boat FREE Slip

5 out of 5 average rating, 21 reviews

A scenic outdoor area features a thatched-roof gazebo overlooking the ocean. Palm trees sway gently in the breeze, and a paved pathway leads to the waterfront. The blue waters reflect the sky, creating a tranquil coastal atmosphere.

Flat in Marathon

#1 Island Hideaway 89 - OCEAN FRONT

A spacious bedroom features a checkered bedspread atop a cozy bed. Soft blue walls surround the area, and three framed artworks hang on the wall above the bed. Light hardwood flooring adds warmth to the room, complemented by a nearby open doorway leading to another living space.

5 out of 5 average rating, 3 reviews

Downtown Apartment in Key West

A well-lit bedroom features wooden paneling and a spacious bed with a patterned blanket. Shelves filled with books are situated beside the bed. A sliding glass door leads to an outdoor area, while warm lighting enhances the cozy atmosphere.

4.89 out of 5 average rating, 35 reviews

Apartment at Safe Harbor Marina

4.97 out of 5 average rating, 66 reviews

A welcoming living area features a dark gray sofa and armchair, complemented by patterned cushions. A light wooden coffee table sits atop beige tile flooring. A large flat-screen TV is mounted on the wall, and natural light filters through window coverings, creating a bright atmosphere.

Flat in Marathon

Dock POOL Kayaks Bikes Beach2mi WalkToStores

House rentals with a patio

An aerial view captures the duplex home situated near a canal with multiple boats docked along the water. The vibrant homes are seen in a tangle of greens and blues, with sandy pathways and lush landscaping complementing the serene coastal environment.

5 out of 5 average rating, 26 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

5 out of 5 average rating, 7 reviews

KCB Tropical Escape

4.9 out of 5 average rating, 113 reviews

A serene pool area is surrounded by lush tropical palm trees and vibrant landscaping. Sunlight reflects off the clear water, creating a calming ambiance. Nearby, a white lounge chair is positioned for relaxation, with a life preserver visible on the side.

Home in Key West

Gone Coastal

A serene outdoor space features a private pool surrounded by stone decking. Two lounge chairs with blue cushions are positioned nearby, while a tiki hut adds a tropical touch. Lush palm trees and a canal lined with vegetation provide a tranquil backdrop.

4.98 out of 5 average rating, 65 reviews

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

5 out of 5 average rating, 3 reviews

An aerial view showcases a waterfront half duplex with a private dock along an extra wide canal. Tropical landscaping, palm trees, and nearby golf course greenery are visible, while the surrounding area features residential homes and clear blue skies.

Home in Key Colony Beach

New Listing Discount! Dockside Paradise

Two pelicans are perched on a wooden dock, surrounded by rippling water. The dock is supported by green posts, providing a serene setting in a tropical landscape. Subtle foliage in the foreground enhances the natural ambiance of the scene.

5 out of 5 average rating, 18 reviews

Oceanside home 111, dock,kayaks,bikes,pool,fishing

A tranquil pool is surrounded by lush palm trees, offering a serene atmosphere. The water reflects sunlight, while seating options are provided by the poolside. The design features a curved edge and a spa section, creating an inviting outdoor retreat.

5 out of 5 average rating, 8 reviews

The Roseate House at Grassy Key

5 out of 5 average rating, 31 reviews

The waterfront patio features a wooden dock leading into the calm water, surrounded by neatly arranged lounge chairs and palm trees. The single-story home is seen in the background with large glass doors and windows, allowing for ample natural light.

Home in Key Colony Beach

Boat Dock+King Beds & Cabana Club

Apartment rentals with a patio

A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.

4.96 out of 5 average rating, 80 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

4.86 out of 5 average rating, 99 reviews

A modern kitchen features stainless steel appliances and white cabinetry, complemented by a light countertop. A dining area and living space are visible in the background, along with a staircase leading to the upper level. Large sliding doors provide access to an outdoor view.

Apartment in Duck Key

Villa 5087 on Duck Key BOAT SLIP available

4.8 out of 5 average rating, 20 reviews

A modern game area features a slate bumper pool table surrounded by turquoise chairs. A wall-mounted dartboard adds to the entertainment options. The adjacent kitchen, equipped with stylish cabinetry and contemporary appliances, is partially visible, providing a seamless flow between activities.

Apartment in Marathon

Reel Hip– Heated Pool, Boat Slip, Heat, King Bed

5 out of 5 average rating, 18 reviews

An elevated swimming pool is featured with clear blue water, surrounded by a spacious deck. Palm trees are visible in the background, providing a tropical ambiance. Ocean views extend beyond the pool area, enhancing the serene atmosphere.

Apartment in Marathon

Oceanside Spacious Studio Escape

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, 105 reviews

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

A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

5 out of 5 average rating, 41 reviews

EYW Getaway

Apartment in Key Colony Beach

An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.

5 out of 5 average rating, 20 reviews

Private Beach in Marathons Key Colony Beach

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.