Vacation rentals with outdoor seating in Key Haven

4.94 out of 5 average rating, 165 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 MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

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.

4.95 out of 5 average rating, 191 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

4.97 out of 5 average rating, 299 reviews

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

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

4.84 out of 5 average rating, 167 reviews

A shared pool area is surrounded by lush tropical landscaping, featuring palm trees and greenery. Sun loungers and umbrellas are arranged around the pool, offering ample space for relaxation. The water reflects the clear blue sky, creating a serene and inviting scene.

Townhouse in Key West

Charming Key West Vacation Rental 3bedrm/3bath

Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler. Portable Crib, high chair & more. Items available upon request

Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.

4.98 out of 5 average rating, 124 reviews

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

4.82 out of 5 average rating, 168 reviews

A serene waterfront view captures a light-colored building with turquoise accents, surrounded by lush palm trees. The calm water reflects the structure and sky, creating a tranquil atmosphere. Soft clouds float above, enhancing the peaceful setting of the marina.

Boat in Key West

A Great Escape! Private 2 Bed Rm Beautiful Marina

Our Marina has a pool and a small private beach overlooking the beautiful Keys water! More affordable than most places in Key West while able to reconnect with nature at this private getaway on the Great Escape. As you approach the boat, you feel your dream vacation has come true . One of a lifetime. Staying on a beautiful sportfisher yacht, laying in the waters of the calm keys and in the most beautiful peaceful marina, will definitely set you free from all your worries and stress.

Cottage in Little Torch Key

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

4.89 out of 5 average rating, 178 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. 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 dock and enjoy the underwater scenery!

A refreshing pool area is surrounded by green palm trees and blue umbrellas. Lounge chairs are arranged neatly around the pool, while tables with chairs provide seating for guests. The clear blue sky enhances the inviting atmosphere of the community space.

4.86 out of 5 average rating, 133 reviews

Penthouse in Paradise

Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.

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.

4.93 out of 5 average rating, 119 reviews

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

4.86 out of 5 average rating, 234 reviews

A tranquil outdoor pool is surrounded by palm trees, with lounge chairs and tables positioned for relaxation. Umbrellas provide shade near the water, while a charming cottage can be seen in the background under a clear blue sky.

Townhouse in Key West

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

Tiny home in Big Pine Key

4.93 out of 5 average rating, 101 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!

An open concept studio apartment features a modern kitchen with stainless-steel appliances, including a coffee maker and oven. A dining table with black chairs is positioned near the kitchen. In the background, a spacious bed is visible, illuminated by natural light from large windows.

4.86 out of 5 average rating, 259 reviews

The Bartlum - Steps to Duval Street

Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, located on Caroline St, has been designed with comfort in mind, offering large windows for natural sunlight and plenty of space to spread out. Enjoy an updated kitchen, spacious bathroom, open concept layout, and all the hot spots of Key west within walking distance!

Popular amenities for Key Haven outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

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.

4.99 out of 5 average rating, 67 reviews

Waterfront, Dock, Pool, Pickleball, near Key West!

A two-story waterfront home is situated under a clear blue sky, surrounded by palm trees and lush greenery. The property features a bright white exterior with a balcony, along with a manicured yard of decorative rocks and native plants.

4.93 out of 5 average rating, 73 reviews

Keys Island Villa - Venture Out Home 354

A well-maintained community pool is surrounded by lush tropical landscaping, featuring lounge chairs with blue umbrellas. The clear water reflects the bright blue sky and palm trees, creating a relaxing atmosphere for guests to enjoy.

4.87 out of 5 average rating, 83 reviews

Key West 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.

4.96 out of 5 average rating, 27 reviews

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

A busy street scene showcases Duval Street, with clear signage pointing in both directions. Lush palm trees line the sidewalks while pedestrians, enjoying the sunny weather, walk along the path. Colorful storefronts and flags create a vibrant atmosphere typical of Key West.

4.98 out of 5 average rating, 92 reviews

Gorgeous Romantic Private Villa, Steps from Duval!

4.95 out of 5 average rating, 81 reviews

Ocean~View w/ Dock, Pool, Kayaks, King Bed

A serene outdoor space features palm trees swaying gently by the water's edge, with a small floating dock visible. Loungers are arranged by the pool, surrounded by pebbled landscaping and lush greenery, all under a clear blue sky.

4.9 out of 5 average rating, 39 reviews

White House - Receive $400 towards a Boat Rental!

A spacious living area features comfortable seating arrangements, including a large sofa and armchair. Large glass sliding doors provide access to the private balcony, showcasing ocean views. A television and coffee table occupy the center space, while a ceiling fan overhead adds a breezy touch.

4.59 out of 5 average rating, 58 reviews

Brisa Del Mar by AvantStay | Ocean Front Community

Apartment rentals with outdoor seating

A comfortable room features a spacious bed with crisp white linens, positioned against a coral-themed accent wall. Natural light streams through a window with white shutters. A small dining table and chairs complement a kitchenette area, while a large mirror enhances the sense of space.

4.86 out of 5 average rating, 1,673 reviews

At Mine | Lovely Suite steps from Duval Street

A modern kitchen and dining area feature light tile flooring and dark cabinetry. A dining table, surrounded by upholstered chairs, sits adjacent to a comfortable living space with a sofa and decorative pillows. Natural light fills the room from large windows, inviting a pleasant ambiance.

5 out of 5 average rating, 11 reviews

Key West at Hyatt Beach House

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.

4.87 out of 5 average rating, 75 reviews

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

The resort pool is surrounded by palm trees and lush greenery, creating a serene atmosphere. Several lounge chairs are arranged neatly along the pool's edge, inviting relaxation under the clear blue sky. Breezy shades from umbrellas offer spots for comfortable seating.

Hyatt Beach House, Key West - 2 bedroom suite

4.89 out of 5 average rating, 9 reviews

Duval Street Retreat | Dog-Friendly w/ Hot Tub

A modern kitchen is displayed, featuring dark blue cabinetry and stainless steel appliances. A sleek countertop hosts a sink and modern stove, while a microwave is mounted above. Natural light enters from a nearby window, enhancing the kitchen's functional layout.

5 out of 5 average rating, 3 reviews

Rare Beach Front Resort Key West- 2BD/2BA

A spacious common area features high ceilings and large windows allowing natural light to fill the room. A wooden dining table seats six, complemented by light blue chairs. A plush sofa is arranged with textured cushions. French doors open to the balcony, enhancing the indoor-outdoor connection.

4.83 out of 5 average rating, 120 reviews

Sky Suite with Balcony Overlooking Duval Street

The image captures a scenic view of a zero-entry pool surrounded by lush palm trees and manicured landscaping. Several lounge chairs are positioned nearby. In the foreground, a straw hat and two beverages are placed on the poolside, creating a relaxed atmosphere.

Hyatt Resort Club at Beach House. 2 Bedroom/2 Bath

Condo rentals with outdoor seating

A serene waterfront view reveals gentle waves lapping against a sandy shoreline. Beach chairs are arranged near the water, providing a relaxing spot to enjoy the scenery. Lush palm trees frame the tranquil setting, enhancing the sense of peacefulness.

4.95 out of 5 average rating, 44 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

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.

4.97 out of 5 average rating, 93 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 313 reviews

Affordable Beachfront Luxury Condo Sleeps 6

4.89 out of 5 average rating, 57 reviews

Key Lime Paradise 3bed 2bath Sleeps 6 Pool Hot tub

A bright and airy living space features a large sectional sofa, a dining area with a light-colored table and chairs, and large glass doors leading to a balcony with water views. Light wood paneling and artwork enhance the overall ambiance.

4.89 out of 5 average rating, 256 reviews

Waterfront 2BR Condo | Pool | Key West

A spacious balcony features two comfortable blue chairs and a small table. The view overlooks lush gardens and the Atlantic Ocean, framed by palm trees. Large sliding glass doors allow access to the interior, while the cloudy sky creates a serene ambiance.

4.89 out of 5 average rating, 105 reviews

Key Wes't Best- Upgraded condo 5 mins to Smathers

The bedroom features a spacious bed with light blue bedding against a red accent wall. A standing lamp provides soft lighting beside a dresser. A mirror reflects the bathroom area, showing a sink and light cabinetry with a contrasting black-and-white tiled floor.

4.71 out of 5 average rating, 225 reviews

Sunrise Suites Resort, Key West FL U #408 2bdr2bth

A cozy room features mid-century style furnishings, including two blue velvet chairs adjacent to a small dining table. A queen murphy bed is visible in the background, alongside a television mounted on the wall. Natural light enters through the window, highlighting the vibrant yellow walls.