Holiday rentals with outdoor seating in Islamorada

Houseboat in Islamorada Tavernier

4.89 out of 5 average rating, 247 reviews

Florida Keys Dockside Paradise, Luxury Houseboat

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers a unique blend of comfort, adventure, and waterfront living. Wake up to breathtaking sunrises, sip your morning coffee with all the marine life, and fall asleep to the gentle movement of the boat. Whether your celebrating something special or simply want a one of a kind getaway-it's the perfect home base for Keys adventures or peaceful retreats. An amazing experience Free park

4.96 out of 5 average rating, 163 reviews

A serene waterfront view is framed by palm trees, with two green chaise lounges positioned for relaxation. The setting sun casts warm hues across the sky, reflecting on the water's surface. A Tiki structure adds charm, creating an inviting outdoor space.

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Superhost

A charming cabin is nestled among lush greenery, featuring a cozy porch with comfortable seating. The pathway is lined with vibrant tropical plants and palms, creating a serene and inviting entrance. Sunlight filters through the canopy, illuminating the peaceful surroundings.

Guesthouse in Key Largo

4.86 out of 5 average rating, 469 reviews

Romantic cozy peaceful Guesthouse beach Sunsets.

Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

4.96 out of 5 average rating, 156 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.

Holiday home in Key Largo

A private porch overlooks the tranquil harbor, featuring blue chairs beside a white railing. A boat is secured at the dock, with sailboats moored in the distance. Bright sunlight reflects off the water's surface, creating a serene atmosphere.

4.99 out of 5 average rating, 223 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

4.97 out of 5 average rating, 164 reviews

A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.

Tiny home in Key Largo

Oasis2 in Key Largo With a million dollar view

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

4.93 out of 5 average rating, 164 reviews

Vibrant bougainvillea flowers in shades of pink and deep red create a lush display against the greenery. The dense foliage adds a natural texture, while drops of water may suggest recent rainfall, enhancing the overall freshness of the scene.

Guesthouse in Key Largo

Seaside Bungalow

Very private entire Cottage brand new walking distance to world famous Tiki Bar jet ski rentals kayaks Extremely private surrounded by exotic flowers and orchids.Less than 2 miles from Baker's Cay and close to the Key Largo and Islamorada wedding venues. We have a fully stocked home size kitchen. All the condiments coffee creamers sugar ketchup mustard etc. Giant stone shower with shampoos and conditioner and plenty of plush towels. Beach towels and chairs as well as 2 bicycles.

4.95 out of 5 average rating, 126 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.

4.93 out of 5 average rating, 356 reviews

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

4.99 out of 5 average rating, 108 reviews

A backyard area features white sand, surrounding palm trees, and a tall American flag. The A-frame house is visible in the background, complemented by a wooden dock leading to the water. Lounge chairs are arranged neatly, enhancing the outdoor space's appeal.

Home in Key Colony Beach

ABeachBungalow-60’dock w/ access to pool and beach

"A Beach Bungalow" A-frame has everything you need for a relaxing vacation. 2 bedroom, 2 bath Key Colony Beach rental home with easy ocean access. Fully equipped kitchen with all new appliances. Living room with dining area, flat screen tv, wifi, cable, bbq and beautiful views of the water. Master bedroom with king bed and bathroom with large shower. 2nd bedroom (loft) with 2 twin beds and closet. Tackle room to store gear with extra refrigerator. Boat trailer parking on site.

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!

4.94 out of 5 average rating, 110 reviews

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

Popular amenities for Islamorada outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

5 out of 5 average rating, 20 reviews

A resort-style swimming pool is surrounded by lush palm trees, offering a relaxing atmosphere. Comfortable lounge chairs are positioned around the pool, with tranquil ocean views in the background. Clear blue skies complement the serene setting, suggesting an inviting space for leisure.

Home in Islamorada

Pristine pool front home w/ocean views Anglers 148

4.9 out of 5 average rating, 109 reviews

Home in Key Largo

NEW! CASA PALMA - Golf Cart, 2 Kings, Pool, Kayaks

The entrance to the home is framed by lush greenery and colorful plants. A welcoming pathway leads to the front door, which features intricate wooden detailing. Bright flowers and palm trees enhance the tropical ambiance of the exterior.

4.94 out of 5 average rating, 194 reviews

Spacious, 70ft Dock, Near Beach VACA23-16

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

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, 9 reviews

The Roseate House at Grassy Key

4.95 out of 5 average rating, 104 reviews

Aerial view of a waterfront community featuring multiple homes surrounded by lush greenery. Two circular pools are visible in the foreground, with docks extending into the water. A sailboat is seen on the horizon, showcasing the serene setting.

Home in Key Largo

Large Waterfront Home, w/Efficiency, Pool, Kayaks

5 out of 5 average rating, 13 reviews

An aerial view captures a winding pool surrounded by lush palm trees and beach loungers. The pool's turquoise waters reflect the surrounding greenery and the bright sun. White buildings with large windows are visible in the background, enhancing the inviting atmosphere.

Home in Key Largo

New! 4-Story Villa w/ Rooftop & 3 Private Suites

A tray displays two coconut cups filled with a refreshing beverage, each adorned with a pink paper umbrella. Slices of watermelon are arranged on a plate beside the drinks. The vibrant blue water of the heated pool glistens in the sunlight, surrounded by tropical greenery.

5 out of 5 average rating, 60 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

Apartment rentals with outdoor seating

Apartment in Key Colony Beach

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

4.85 out of 5 average rating, 126 reviews

Beachside Unit 22 - Private Beach on Atlantic

A corner two-story townhouse is shown, situated beside a tranquil saltwater lagoon. Lush greenery surrounds the property, and a staircase leads to a diving platform over the water. The reflection of the structure and trees can be seen on the still lagoon surface.

4.99 out of 5 average rating, 163 reviews

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

A cozy living area features a light-colored sofa with decorative pillows, complemented by a coffee table and a patterned area rug. Expansive glass sliding doors provide natural light and views of palm trees outside, while a small dining table adds functionality to the space.

4.89 out of 5 average rating, 301 reviews

Seaside Vista - Ocean Front 2/1 with dockage

4.94 out of 5 average rating, 34 reviews

A relaxing outdoor area features a sparkling pool surrounded by lounge chairs and vibrant blankets draped over the edge. Lush greenery and palm trees provide natural shade, creating an inviting space for leisure and family gatherings.

Apartment in Islamorada

La Casa HMH

A sandy pathway leads to the water's edge, bordered by lush green mangroves. Wooden benches are positioned along the path, providing seating to enjoy the scenic view of the calm water and distant greenery. The clear blue sky creates a bright and open ambiance.

4.84 out of 5 average rating, 288 reviews

Key's Cottage Escape

A dining area is presented with a round white table surrounded by four black and white patterned chairs. A light-colored runner with subtle stripes lays across the table, complemented by a decorative pineapple centerpiece. Natural light filters through the nearby window, enhancing the space.

4.9 out of 5 average rating, 100 reviews

Little Peace of Haven

A modern studio is showcased, featuring a comfortable queen-sized bed and lounge area equipped with a Smart TV. Natural light floods the space from large windows. The kitchen is outfitted with stainless steel appliances, while the outdoor area includes tiki huts with thatched roofs, ideal for relaxation.

4.92 out of 5 average rating, 300 reviews

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

4.95 out of 5 average rating, 213 reviews

A light-filled living area features a blue sofa with decorative pillows and a wooden coffee table atop a woven area rug. Two accent chairs frame the seating arrangement, while natural decor elements, including tall grasses and wall art, enhance the welcoming ambiance.

Apartment in Tavernier

Boho FL Keys Condo

Condo rentals with outdoor seating

5 out of 5 average rating, 29 reviews

The view from the screened-in lanai displays a serene boat basin framed by palm trees. A ceiling fan adds a functional touch above a round dining table, while boats are moored in the distance under clear blue skies.

Condo in Islamorada

Luxury condo with boat slip overlooking the bay

A sandy beach area is captured, featuring several lounge chairs arranged under swaying palm trees. The turquoise waters of the Atlantic Ocean can be seen in the background, with a shaded gazebo and a wooden dock visible on the horizon.

4.89 out of 5 average rating, 169 reviews

2BR - Key Largo Sunshine Getaway

An open-concept living area features a comfortable sofa and loveseat, designed for relaxation. A stylish dining table accommodates four. A wall-mounted TV and electric fireplace add modern touches, while large sliding glass doors offer natural light and views of the surrounding landscape.

4.94 out of 5 average rating, 157 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

4.88 out of 5 average rating, 140 reviews

Condo in Key Largo

Waterfront Apt Key Largo #4, 10% Off 7+, 5% Off 4+

4.99 out of 5 average rating, 115 reviews

A private dock extends over calm waters, lined with white posts and illuminated by a golden sunset. A thatched-roof structure is visible at the end of the dock, surrounded by gentle waves reflecting the muted sky.

Condo in Key Largo

Enjoy sunsets & sunrise in your home away home.

Superhost

A wooden boardwalk leads to a thatched-roof gazebo, illuminated by soft lighting. The sky displays shades of orange and purple at sunset, reflecting on the calm ocean waters. Navigational markers can be seen along the path, adding to the scenic view.

4.77 out of 5 average rating, 384 reviews

Florida Keys Getaway - Slps 4 - Ocean View

4.96 out of 5 average rating, 110 reviews

A light-filled living area is visible, featuring a comfortable seating arrangement and a mounted television. A dining table occupies the foreground, adorned with a bowl of oranges. The walls are painted in soft blue, providing a relaxed atmosphere, with a ceiling fan overhead.

Condo in Marathon

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

A panoramic view captures the pristine turquoise waters extending to the horizon, adjacent to lush greenery and the resort's amenities. The interior showcases a bright, airy living space, featuring a well-equipped kitchen with modern appliances and a comfortable seating area with ocean views.