Holiday rentals with outdoor seating in Islamorada

4.92 out of 5 average rating, 394 reviews

The eco-friendly two-story River Queen vessel is anchored in a calm harbor, showcasing a modern design. The structure features large windows and a rooftop terrace, with a wind turbine on the left. The surrounding landscape includes lush greenery, complementing the serene water view.

Boat in Tavernier

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.

4.98 out of 5 average rating, 237 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

4.97 out of 5 average rating, 136 reviews

A serene pool area is framed by lush palm leaves, highlighting a sparkling pool with a bubbling spa. Sun loungers are arranged around the pool, complemented by a large blue umbrella providing shade.

Cottage in Islamorada

Charming 2BR cottage in prime keys location w/pool

Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

Houseboat in Islamorada Tavernier

4.9 out of 5 average rating, 264 reviews

Florida Keys Houseboat, unique waterfront stay-

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

4.92 out of 5 average rating, 132 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.

4.97 out of 5 average rating, 196 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.

4.9 out of 5 average rating, 111 reviews

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks

NO RESORT, GUEST OR MANAGEMENT FEES WHEN BOOKING MY HOMES! Welcome to your Key Largo vacation rental. This oceanside villa is family friendly and filled with amenities, including a private golf cart, one adult kayak and three kids kayaks, pickleball and tennis courts, multiple pools, and a unique swimming lagoon. Spend your days kayaking, fishing, boating, snorkeling, or the beach John Pennekamp. Our villa has earned hundreds of 5-star reviews on all major platforms. No hidden fees!

4.93 out of 5 average rating, 377 reviews

A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.

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.

5 out of 5 average rating, 101 reviews

A private backyard features a heated pool surrounded by tropical landscaping. Lounge chairs are positioned on the wooden deck beside the pool. The two-story home includes large glass doors that open onto the deck, providing easy access to outdoor spaces.

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

4.9 out of 5 average rating, 397 reviews

A window reveals a lush garden filled with tropical plants and flowers. The words 'Keys Life' are displayed on a wooden sign above the window, enhancing the connection to the surrounding nature.

Cottage in Key Largo

Cottage By The Sea

Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Be sure to meet Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals

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, 113 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 wooden dock extends over the turquoise waters, supported by sturdy wooden posts capped with white tops. The clear sky above complements the tranquil scene, with hints of distant land visible along the horizon.

4.91 out of 5 average rating, 445 reviews

Your Keys Getaway!

Beautiful two bedrooms, 1 bath Keys Home fully renovated interior in a quiet residential neighborhood. Large breeze veranda for open air meals and relaxation. Large fence yard for sunbathing or playing around. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada. Once you've been here you will want to come back.

Popular amenities for outdoor seating rentals in Islamorada

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

5 out of 5 average rating, 7 reviews

Lux Waterfront: Dock, Volleyball, Putt Putt, More

A two-story duplex is set amidst palm trees, featuring a blue exterior and multiple balconies. A vehicle is parked in the driveway, with a pathway leading towards the entrance, surrounded by landscaped areas that include gravel and greenery.

4.92 out of 5 average rating, 187 reviews

Blue House Marine in Key Largo

The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.

4.92 out of 5 average rating, 190 reviews

Beachfront Villa - Florida Keys

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, 124 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

An aerial view showcases a waterfront property featuring two light-colored homes. A manicured green lawn, lined with palm trees, leads to a private boat slip. A spacious covered area offers an outdoor seating arrangement, enhancing the outdoor living space near the water.

4.73 out of 5 average rating, 37 reviews

Waterfront Paradise Key Largo. Casa Luna

A heated pool is situated in the backyard, surrounded by lounge chairs. Lush palm trees and a view of the waterfront create a serene outdoor space, with gentle clouds drifting across a bright blue sky.

5 out of 5 average rating, 39 reviews

Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront

A charming oceanfront house is set against the backdrop of the tranquil Atlantic Ocean. Lush greenery surrounds the property, while a vibrant blue pool is visible beneath the spacious overhang. The home features a light-colored exterior and a green metal roof, harmonizing with the coastal environment.

5 out of 5 average rating, 8 reviews

Amazing Oceanfront Home

5 out of 5 average rating, 4 reviews

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

Apartment rentals with outdoor seating

A bright living area features a light-colored sofa adorned with decorative pillows, complemented by a glass coffee table. Large windows invite natural light, revealing views of the lush landscape outside. A mounted television and coastal artwork complete the serene environment.

5 out of 5 average rating, 30 reviews

Oceanfront Bliss • Wall-to-Wall Water Views + Pool

A bright living area features large windows, allowing natural light to fill the space. Soft blue walls complement the light-colored furnishings, including a spacious curved sofa and a distinctive wooden coffee table. A ceiling fan circulates air, while a decorative plant adds a touch of greenery.

5 out of 5 average rating, 13 reviews

New Coastal Escape 2BR/2BA Oceanfront Condo

4.86 out of 5 average rating, 136 reviews

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.

Flat in Key Colony Beach

Beachside Unit 22 - Private Beach on Atlantic

5 out of 5 average rating, 11 reviews

Flat in Marathon

New! Waterfront Views | Pool & Tiki Bar

A serene beachfront area is depicted, featuring rows of blue sun loungers arranged on soft white sand. Lush greenery and palm trees border the beach, while the tranquil turquoise waters stretch towards the horizon. A wooden pier extends into the water, enhancing the coastal view.

5 out of 5 average rating, 58 reviews

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

4.9 out of 5 average rating, 109 reviews

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.

Flat in Key Largo

Little Peace of Haven

Aerial view of the resort showcases a heated pool surrounded by palm trees and lounge chairs, alongside multiple tennis courts. The backdrop features lush greenery and tranquil ocean waters, highlighting the beauty of the surrounding natural environment.

4.91 out of 5 average rating, 33 reviews

Welcome to the Pelican Lodge !

4.9 out of 5 average rating, 316 reviews

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.

Flat in Key Largo

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

Apartment rentals with outdoor seating

4.87 out of 5 average rating, 108 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

A private beach area is revealed, featuring rows of blue lounge chairs set on soft, sandy ground. Lush greenery borders the beach, while a wooden pier extends into the calm, turquoise water. A thatched gazebo provides shade, and scattered palm trees complete the coastal scene.

4.95 out of 5 average rating, 134 reviews

Your Happy Place - Oceanfront

4.94 out of 5 average rating, 140 reviews

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

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.

4.95 out of 5 average rating, 166 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

A wooden pier extends over calm waters, leading toward a thatched-roof gazebo. The scene is illuminated by a vibrant sunset, casting warm hues across the sky and reflecting on the water's surface. Lush greenery frames the sides, enhancing the serene atmosphere.

4.97 out of 5 average rating, 103 reviews

Ocean views at “Sangria Sunrise” 10% off Charters

A well-lit living area showcases a comfortable sectional sofa and a wooden dining table with light-colored chairs. A decorative bowl of lemons sits at the center of the table, while large windows offer views of the surrounding landscape and allow natural light to fill the space.

4.93 out of 5 average rating, 161 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

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.

4.84 out of 5 average rating, 116 reviews

🏝 Oceanfront Paradise Awaits You

A light-filled living space features a turquoise sofa with yellow accent pillows, paired with a round glass dining table. Rattan chairs complement the decor, which includes a vibrant tropical wall mural and a circular mirror. Modern appliances are visible in the kitchen area.