Holiday rentals with outdoor seating near Sombrero Beach

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

4.99 out of 5 average rating, 151 reviews

Sea Ray Cove w/ Pool, Beach, 80' Dock & Tiki hut

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

4.95 out of 5 average rating, 146 reviews

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

Villa in Marathon

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

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.

4.93 out of 5 average rating, 117 reviews

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.

4.96 out of 5 average rating, 157 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.

Condo in Key Colony Beach

A spacious bed is adorned with crisp white linens and a vibrant throw pillow featuring a fish design. Large windows frame the room, allowing natural light to illuminate the interior while offering views of the ocean and nearby palm trees.

4.96 out of 5 average rating, 221 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

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.

4.99 out of 5 average rating, 108 reviews

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.

Condo in Key Colony Beach

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

4.87 out of 5 average rating, 139 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.

4.97 out of 5 average rating, 124 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

4.89 out of 5 average rating, 123 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 modern interior showcases a spacious living area with a sectional sofa adorned with decorative cushions. Adjacent, a bright kitchen is visible, alongside a dining table. A cozy bedroom features a bed with plush linens. Outdoor seating is arranged on a covered patio, surrounded by greenery.

4.89 out of 5 average rating, 170 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.

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

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

4.89 out of 5 average rating, 111 reviews

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.

Villa in Marathon

Villa in Paradise. Plunge pool. Middle of the Keys

Baja Breeze 🏝, a freshly updated, family-friendly, resort-style villa in the ♥ of the Keys. ♥ Please save Baja Breeze by clicking on the heart in the top right hand corner, this will help you find it again and share with others! 🛶 Waterfront canal view 🌴 Gated Resort Area 👙 Private spa pool 📍 Halfway between Key Largo and Key West ☀️ Outdoor dining/lounge area 🍳 Fully stocked Kitchen 📶 300Mbps+ Wifi

Popular amenities for outdoor seating rentals near Sombrero Beach

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A serene outdoor area features a heated pool surrounded by lush greenery and palm trees. Two chaise loungers sit on a small patch of grass, offering a perfect spot for relaxation. The ocean is visible beyond the white fence, enhancing the tranquil setting.

5 out of 5 average rating, 47 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

A spacious wooden dock extends over calm waters, featuring a thatched tiki hut and several lounge chairs in a soft blue hue. Lush greenery surrounds the area, complemented by a serene sky at sunset, providing a peaceful atmosphere for relaxation.

5 out of 5 average rating, 32 reviews

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

A heated saltwater pool is set on a spacious deck, surrounded by lounge chairs. Adjacent to the pool, a serene canal view features lush greenery and residential homes lining the waterway.

4.9 out of 5 average rating, 30 reviews

Steps to Sombrero Beach | Dock + Pool + Dogs OK

5 out of 5 average rating, 18 reviews

Waterfront 2-bedroom Home w/Pool and Spa

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.

4.95 out of 5 average rating, 128 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

An open living space is featured, highlighted by a round dining table surrounded by comfortable seating. A large television is mounted on the wall, while light-colored walls enhance the bright atmosphere. A serene coastal artwork depicting a pier adds a calming touch to the decor.

5 out of 5 average rating, 27 reviews

Bohemian Beach Bungalow

A private deck overlooks lush greenery leading to the ocean. A circular table with six chairs sits under a large umbrella, providing a shaded spot. The scene features bright blue skies and a calm sea, creating a serene atmosphere.

5 out of 5 average rating, 56 reviews

Oceanview Escape

An airy dining area features a white stone-topped table positioned beneath a stylish light fixture. Large glass doors allow natural light to flood the space, connecting indoor and outdoor seating areas. The wooden floor adds warmth to the contemporary design.

4.83 out of 5 average rating, 6 reviews

SeaEsta! Bring your boat & 1 block to the beach!

Apartment rentals with outdoor seating

An aerial view of the beachfront condo building is captured, revealing its three stories and proximity to the ocean. Surrounding palm trees enhance the tropical ambiance, while the serene blue water reflects sunlight. A small parking area is visible in front of the property.

4.83 out of 5 average rating, 18 reviews

Seaside Villa~ Charming Beachfront Condo w/ Pool!

A modern kitchen features stainless steel appliances and granite countertops, complemented by a circular dining table. A comfortable chair is positioned next to a small side table. The living area includes a large wall-mounted TV displaying a serene ocean scene.

5 out of 5 average rating, 20 reviews

Ocean Breeze Gated Community

The resort-style pool is framed by comfortable lounge chairs in vibrant blue and white. A shaded clubhouse with a metal roof overlooks the sparkling water, offering a relaxing spot for guests. Lush palm trees provide a tropical backdrop against a clear blue sky.

4.8 out of 5 average rating, 5 reviews

#1 Island Hideaway Marathon

A tranquil pool area features lounge chairs arranged around a crystal-clear pool. Palms sway gently nearby, and a tiki bar with a roof can be seen in the background, overlooking calm waters. The sky transitions to a soft blue as evening approaches.

5 out of 5 average rating, 3 reviews

Marathon Studio on Lovely Gulf Front Resort

An open-concept living space showcases floor-to-ceiling windows framing expansive ocean views. A sectional sofa invites relaxation, placed on a neutral-toned floor with a glass coffee table. A dining area is visible in the background, accentuated by colorful art pieces and natural light.

Apartment in Islamorada

Ocean View Duplex Penthouse | Pool | Vista One

The open living space features a cozy couch and vibrant armchair, with a seating area seamlessly connected to the kitchen and dining space. Large glass doors offer a view of the balcony and serene harbor, allowing natural light to brighten the room.

5 out of 5 average rating, 6 reviews

Boot Key Harbor Penthouse

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.

4.97 out of 5 average rating, 67 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

Apartment in Key Colony Beach

The room features two spacious beds with light-colored bedding, complemented by decorative pillows. A ceiling fan is present above, while large windows with shutters allow natural light. Colorful artwork depicting flamingos adorns the walls beside bedside tables and lamps.

5 out of 5 average rating, 14 reviews

2 Bdrm Oceanfront Complex Private Beach & Pool

Condo rentals with outdoor seating

5 out of 5 average rating, 16 reviews

"O" Fish Ally Paradise @Ocean Isle Fishing Village

4.88 out of 5 average rating, 109 reviews

A row of townhomes is positioned along the water's edge, surrounded by well-maintained landscaping. Lush green trees provide shade, and the calm water reflects the serene environment. The horizon reveals a glimpse of distant trees and open water.

Condo in Duck Key

Villa 5027 on Duck Key BOAT SLIP available

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.

4.81 out of 5 average rating, 21 reviews

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

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

An ocean view from a balcony showcases the vast Atlantic, framed by palm trees. Below, the community's pathways are visible, leading towards the water. Nearby structures feature a tropical design with thatched umbrellas. A stylish chair adds a pop of color, inviting relaxation.

5 out of 5 average rating, 3 reviews

Seashell Sanctuary 1B/2Ba Pool Clubhouse Elevator

Condo 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 balcony view overlooking the Gulf of Mexico features a railing framing the scenic water below, where sunlight glimmers on the surface. Lush greenery is visible nearby, enhancing the serene coastal atmosphere.

4.94 out of 5 average rating, 47 reviews

2-story condo w/ panoramic bay views and balconies

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.

4.96 out of 5 average rating, 110 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

Other holiday rentals with outdoor seating

An outdoor seating area features a sectional sofa and high-top bar stools with a view of the water. A peaceful ambiance is created by the surrounding palm trees and the gentle waves of Vaca Cut. Laundry facilities are visible on the left side of the image.

4.95 out of 5 average rating, 44 reviews

Florida Keys Oceanside Utopia

5 out of 5 average rating, 65 reviews

An outdoor dining area is presented with a rectangular table and six chairs, surrounded by lush greenery and serene water. A partially opened umbrella offers shade, while a compact air conditioning unit is positioned nearby on the rooftop surface.

Boat in Marathon

Dan’s 2024 catamaran cruiser vessel can’t be moved

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, 55 reviews

Marathon Keys Escape • Pool • Hot Tub • Near Beach

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

A private pool is framed by a smooth deck with lounge chairs for sunbathing. Surrounding palm trees provide a tropical backdrop, while clear skies and gentle clouds reflect a serene atmosphere. The pool’s water is inviting and crystal clear, perfect for relaxation.

4.96 out of 5 average rating, 27 reviews

Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool

A spacious outdoor area features a tiki hut with a thatched roof, a swimming pool surrounded by lounge chairs, and a boat docked beside a canal. Lush palm trees provide shade, enhancing the tropical ambiance of the property. The home is visible in the background.

4.97 out of 5 average rating, 77 reviews

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

A private pool is framed by a well-maintained lawn and patio area. Umbrellas provide shade for seating, while a tranquil canal with boats is visible in the background, enhancing the serene outdoor environment.

5 out of 5 average rating, 86 reviews

“La casa azul” step 3’ to a private pool

An outdoor theater area is outlined by a modular seating arrangement with blue cushions and dark wicker. A large projection screen is mounted on a wooden wall, creating an inviting space for movie nights. Soft lighting from overhead strands completes the ambiance.