Vacation rentals with outdoor seating in Key West

4.95 out of 5 average rating, 343 reviews

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

A bright living area features yellow walls and a wooden entertainment unit, housing a television. A blue accent chair and a lamp are positioned nearby. Framed artwork adorns the walls, and light flows in from a doorway that opens to a covered deck with outdoor seating.

4.93 out of 5 average rating, 111 reviews

WALK TO BEACH, MALLORY SQUARE, DUVAL STREET

Key West a little piece of the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street. You're just a walk away from Zachary Taylor Park (where you can do yoga on the beach, swim, snorkel, or hang hammocks between the palms). We’re near numerous shops, restaurants, and museums. Enjoy coffee in the morning, wine at night on our oversized deck. THE ADJACENT UNIT MAY BE AVAILABLE FOR ADDITIONAL SPACE.

4.99 out of 5 average rating, 186 reviews

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.

Home in Key Largo

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!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Superhost

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.

4.88 out of 5 average rating, 1,507 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. Located on a quiet street, it offers a private pool and peaceful stay for vacationers and business travelers. The unit includes a comfy Queen bed, mini fridge, microwave, iron & board, hangers, TV, and AC. Enjoy Key West's warm weather year-round. This special place is close to everything, making it easy to plan your trip. Just a heads-up: Key West’s famous roosters love to strut and crow—part of the island charm!

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

4.97 out of 5 average rating, 101 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

4.97 out of 5 average rating, 269 reviews

The image captures a serene pool area surrounded by lush palm trees and well-lit walkways. The clear water reflects the sky, while sun loungers are positioned nearby for relaxation. Two-story buildings are visible in the background, adorned with balconies overlooking the pool.

Townhouse in Key West

Stunning Townhouse * Full kitchen! * Sleeps 6

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 21/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all!

Superhost

A scenic view of the waterfront reveals a calm harbor lined with boat slips. The vibrant blue water reflects the sky, while a tiki hut and chaise lounge chairs surround a heated pool in the foreground, enhancing the coastal ambiance.

4.87 out of 5 average rating, 205 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just 1 mile to Duval St, the Seaport, and Hemingway House. Enjoy on-site boat slips, heated pool, tiki bar, BBQ grills, parking, elevator, and secure keyless entry. Fish cleaning station and commercial ice machine available. Large park with tennis courts next door. Walk or bike everywhere—only 10 minutes from EYW airport!

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.

4.85 out of 5 average rating, 239 reviews

Studio Near Downtown - The Bartlum

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!

Superhost

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.

Houseboat in Key West

4.88 out of 5 average rating, 248 reviews

Key West Luxury Houseboat at Yacht Club Resort

PANORAMIC Ocean Views - POOL 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, 500 square foot Rooftop Sky-Deck - 2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV, 42 inch TV, 32 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

A cozy living area features a sectional sofa in a muted tone, paired with a wicker chair. A round coffee table sits in the center, with light blue area rug beneath. Large windows provide views of an outdoor space while allowing natural light to fill the room.

4.96 out of 5 average rating, 281 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

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, 299 reviews

Affordable Beachfront Luxury Condo Sleeps 6

My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!

A spacious bed is framed by elegant side tables, each topped with a softly glowing lamp. Above the headboard, three framed artworks create a balanced focal point. Decorative pillows add a touch of color, while a leafy plant provides a natural element to the serene space.