Boutique hotel vacation rentals in Key West

A bright cabana room features a spacious bed adorned with colorful pillows. Large glass doors open to a view of the pool area, allowing natural light to brighten the space. Vibrant floral wallpaper complements the light tones of the decor, contributing to a tropical ambiance.

4.96 out of 5 average rating, 56 reviews

Marrero's Guest Mansion Adult Only (21+) Room 12

Adult Only Boutique Hotel (21+). Experience the grandeur of their stately Victorian home, thoughtfully updated and lovingly converted into a boutique hotel. We are located in the heart of Old Town, just half a block from Duval Street. This beautiful room is right next to our revitalizing saltwater-treated pool. Separate from the main house, this cabana room offers guests a more private tropical escape. This room features a pillow top king bed with a private bath and sitting area.

A waterfront rental property is shown, featuring a two-story building painted in a soft peach hue. Several palm trees frame the scene, while wooden docks extend into the calm waters. A spacious balcony overlooks the dock area, providing access to the scenic Florida Bay.

5 out of 5 average rating, 33 reviews

Conch Key Villas #1. Fun, fishing & great sunsets

Studio One's waterfront rental is located on the ground level. Our units differ vastly from other Florida Keys lodgings because our property is right on Florida Bay. If you trailer your boat, the dockage is a few feet from the back door. Our docks can handle boats up to 25’ and you can park your trailer in our front lot. There is a boat ramp just two blocks away. Studio 1 can sleep 2 adults and one child (up to 12 years). We have a king size bed and a futon.

4.89 out of 5 average rating, 457 reviews

Mallory House Room #3

There is no better place for your Key West stay than Mallory House. This historic circa 1890’s home is located on Duval Street in the Gato Cigar Factory Village. Mallory House is steps away from famous attractions, restaurants, cafés, bars and shops. Stay within close proximity to the Southernmost point and beach, the Hemingway house and lighthouse. Enjoy a complimentary cup of coffee on our spacious balcony overlooking world famous Duval Street.

Superhost

A spacious room features a large wooden bed with crisp white bedding. Light from a sliding glass door illuminates the space, revealing a view of palm trees and the outdoors. A ceiling fan and two bedside lamps provide ambient lighting, with a small desk and seating area visible.

4.84 out of 5 average rating, 264 reviews

Wreckers House King Room - Adults Only

Adults-only building for guests ages 21+ only. Thoughtfully furnished with mixed metals and woods, the Wreckers House tells the story of ships and their crews of "wreckers" who once salvaged goods from the sunken ships in the Florida Keys. Enjoy a sunrise view and an ocean breeze from your private balcony that overlooks the pool and the Atlantic. This room has a mini fridge and an espresso machine.

A serene pool area is surrounded by lush palm trees and provides multiple lounge chairs with blue and white striped canopy umbrellas. The water in the pool glistens under a clear blue sky, enhancing the inviting relaxation experience.

Marathon Oceanfront Room | 2Queens + Spa-Like Bath

Wake up to breathtaking ocean views in the Oceanfront Balcony | Double Queen room. Featuring two plush queen beds, a spa-like bath with a deep soaking tub and walk-in rainfall shower, and a private oceanview balcony, this retreat offers the perfect blend of comfort and luxury. Experience premium amenities, five breathtaking resort pools, beachfront dining, and an array of endless adventures.

A serene sunset illuminates the sky over a marina, with various boats docked along the waterfront. Palm trees dot the landscape, and a building is visible in the background, complementing the relaxed coastal atmosphere of Duck Key.

Tropical Escape | King Room w/ Resort Perks

Experience casual elegance in the Resort King—a perfect island-inspired retreat for two. Relax on the private balcony with lush resort views, or unwind indoors with a plush king bed and thoughtful amenities like a coffee maker and workspace. Whether you're exploring Duck Key or savoring the resort's laidback pace, this room offers a cozy, well-appointed base to recharge between adventures.

A sparkling outdoor swimming pool is framed by swaying palm trees and lush tropical plants. Sun loungers are arranged around the pool area, providing ample space for relaxation. The backdrop features a charming white building with balconies and blue accents, creating a serene atmosphere.

4.9 out of 5 average rating, 10 reviews

2BR Unit, Enjoy Paradise with On-site Pools!

Step into a world of white sands and glimmering pools, where boat drinks and watersports are just steps from your front door. Explore vibrant Duval Street's shops and nightlife. Lounge at Smathers Beach via our complimentary shuttle. Immerse in historic Old Town Key West's charm. Adventure with kayaking and water sports, then unwind at our four pools. Your ideal Key West getaway awaits!

The exterior of The Cabana Inn features a charming two-story wooden structure bordered by a light green picket fence. Lush tropical plants and palm trees surround the entrance, creating a welcoming atmosphere. The inn's sign is prominently displayed near the well-maintained walkway leading to the front door.

4.8 out of 5 average rating, 20 reviews

Cabana Inn Private Loft In Old Town with Breakfast

When tropical oasis meets Duval Street, you know you have arrived at the Cabana Inn. Located just a block from Duval Street, our adult-only Key West inn is hidden amongst the shady trees to create a tranquil paradise. The historic conch estate, with cottages that were meticulously converted into a comfortable Key West hotel, features modern designs throughout the interior and exterior.

A bright room features two plush queen-size beds dressed in crisp white linens. Large windows offer views of lush greenery and the Gulf beyond. A stylish bedside lamp and a decorative rug add functional elegance to the space. Soft, natural light filters through sheer curtains.

4.67 out of 5 average rating, 12 reviews

Partial Water View Villa 3 Queens, 1 King Bed

The island life awaits you at the Parrot Key Hotel and Villa in Key West. The Island getaway has an authentic ambiance with locally-inspired rooms and views of the Gulf of Mexico. Your room charge will be paid prior to your arrival. The remaining balance of taxes (12.5%) and facility fee ($51 resort fee + 12.5% tax + $30 valet fee) will be charged upon arrival.

A charming white building is framed by palm trees and a picket fence, showcasing a welcoming front porch. Light and airy windows complement the grey roof, while the property is nestled among vibrant tropical foliage.

4.55 out of 5 average rating, 99 reviews

NYAH 6 Person Room with Breakfast Included

True Floridian vibe accentuated by a unique, adult-only concept, only steps from world-famous Duval Street, the head-turning Gulf, and countless eateries and shops. Our guests will quickly discover three crystal-clear pools, a Jacuzzi, a small fleet of bicycle rentals, high-speed Wi-Fi, a continental breakfast bar, and free 24-hour Starbucks coffee.

A bright room features two spacious beds, each dressed in white linens. A small nightstand with a lamp sits between the beds, offering a viewing window that opens to a lush exterior landscape. Light-colored walls and natural light create an inviting atmosphere.

4.76 out of 5 average rating, 112 reviews

Deluxe Two Double

This room has a queen bed, a double bed, refrigerator and microwave. It is located on the second floor of the guest building and is adjacent to a large deck that faces toward the aviaries and the landscape. Enjoy the free use of Kayaks.

A bright and airy hotel room features two queen beds and a wooden desk. A balcony with chairs invites guests to enjoy the palm tree views outside. Large windows allow natural light to fill the space, complemented by neutral-toned decor and hardwood flooring.

Hotel room in Islamorada

A Place You'll Surely Enjoy! Outdoor Swimming Pool

Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive into water sports. Enjoy nearby attractions like Anne's Beach, Theater of the Sea, and the History of Diving Museum.

Popular amenities for Key West boutique hotels

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly boutique hotels

A well-lit room features two sets of bunk beds with white linens, offering a clean and modern design. A red phone is mounted on the wall, while a wooden chair with a woven seat is positioned on the carpeted floor, providing additional seating.

4.4 out of 5 average rating, 5 reviews

NYAH 2 Bedroom Suite w Breakfast

4.17 out of 5 average rating, 6 reviews

Boutique Hotel w/ Pool Access, Free Breakfast!

A bright bedroom features a spacious bed with white linens and a light wood headboard. Sheer curtains frame a large window that offers views of the outdoor scenery. A cozy area rug adds warmth to the floor, complementing the neutral color palette.

3.67 out of 5 average rating, 3 reviews

Waterfront Villa 2 Kings, 1 Queen Bed

A modern kitchen is featured, equipped with stainless steel appliances, including an oven, microwave, and a sleek sink. Bright white cabinetry contrasts with the aqua wall, while ample countertops allow for food preparation. Natural light enters through the window, enhancing the functional space.

Hotel room in Islamorada

4.66 out of 5 average rating, 32 reviews

Resort View Family Suite

An aerial view of the resort highlights a tranquil lagoon surrounded by sandy shores and shaded cabanas. The swimming pools are visible amid lush greenery, with the blue waters of the waterway showcasing recreational activities. The property blends harmoniously with the natural coastal landscape.

4.6 out of 5 average rating, 63 reviews

Duck Key | Water View King Balcony | No Hidden Fee

A light-filled living area is showcased, featuring a teal couch with decorative pillows. A soft blue coffee table is positioned in front. Beyond, a doorway leads to a bedroom, while large windows allow natural light to illuminate the space.

Hotel room in Islamorada

Oceanfront King Family Suite

A well-lit room features a spacious bed with a light-colored duvet. Natural light filters through sheer curtains, illuminating the space. A small seating area includes a bright blue chair near a balcony door, offering a glimpse of tropical greenery outside.

Partial Water View Two Bedroom Suite w/Living Room

A private oceanview terrace is presented, furnished with two comfortable chairs and a round table. Lush palm trees are visible in the background, framing the serene view of the ocean. Natural light enhances the welcoming atmosphere of this outdoor space.

Marathon Oceanfront | ADA Queen + 5 Pools

Boutique hotels with a patio

A vibrant room features a spacious bed adorned with decorative pillows, set against a botanical wallpaper. Bright yellow curtains frame a window, while a round mirror and artwork add an artistic touch. Two closets are visible on the opposite wall, enhancing the functional space.

4.92 out of 5 average rating, 53 reviews

Marrero's Guest Mansion Adult Only (21+) Room 11

A serene waterfront view showcases calm waters reflecting the sky, with docks extending into the bay. Palm trees are positioned on the shore, and an American flag gently waves in the breeze. Outdoor seating is visible along the patio area.

4.85 out of 5 average rating, 33 reviews

Conch Key Villas #2 Peaceful waterfront lodging

A well-appointed guest room features a spacious bed adorned with decorative pillows against a vibrant yellow floral wallpaper. Natural light floods the space through large windows draped with sheer curtains. A decorative fan enhances the room, while a wall-mounted TV offers entertainment options.

4.89 out of 5 average rating, 47 reviews

Marrero's Guest Mansion Adult Only (21+) Room 10

Superhost

The room features two wooden beds with crisp white linens and a contemporary design. Natural light enters through glass doors leading to a balcony. A comfortable chair is positioned beside a flat-screen TV and a wooden dresser, adding to the room's serene ambiance.

4.91 out of 5 average rating, 98 reviews

Wreckers House Double Queen Room - Adults Only

Superhost

A spacious room features a four-poster bed with a dark wooden frame. Two vibrant orange chairs and a small round table are placed nearby. A large window offers views of the outdoors, while light-colored curtains frame the scene. A dark leather sofa adds comfort to the space.

Galleon King Suite - Adults Only

Other boutique hotel vacation rentals

A serene beach area is framed by palm trees, featuring sun loungers under blue umbrellas. Soft sand leads to clear water that gently meets the shore, creating a tranquil atmosphere. The landscape is complemented by lush greenery, enhancing the coastal setting.

Marathon Oceanfront Suite | King Bed + Kitchenette

A spacious room features a king bed with a decorative tropical pillow and stylish wall-mounted lighting. Light-colored walls and polished floors contribute to a bright atmosphere. A doorway leads to a private patio surrounded by tropical greenery, enhancing the serene environment.

Perfect for a Relaxing Getaway w/ Free Breakfast

A serene pool area is surrounded by lounge chairs with striped canopies, offering a relaxing atmosphere. Palm trees sway gently in the breeze, while the backdrop features the resort buildings set against a clear sky. Lush green grasses border the scene, enhancing the natural beauty.

Marathon Oceanfront | 2 King Beds + Balcony

An inviting outdoor pool is surrounded by lounge chairs and umbrellas, framed by palm trees and lush tropical foliage. The backdrop features a two-story building with balconies, enhancing the serene atmosphere of the pool area.

2 Units- Beach Getaway, Poolside Bar, Onsite Pools

The exterior of a charming boutique hotel is highlighted, featuring a light green façade and a spacious, covered porch supported by white columns. The second floor is accessed by a bright blue overhang. Vibrant landscaping with tropical plants and flowers frames the inviting entrance.

4 out of 5 average rating, 27 reviews

Southernmost Inn Private Deluxe King Room with Breakfast

An outdoor terrace overlooks the ocean, featuring a glass-topped table and comfortable seating. Lush palm trees sway gently in the breeze, and the tranquil waters glisten under bright sunlight, creating a serene backdrop to the private retreat.

Marathon Oceanfront Suite | Balcony + 2 Luxe Baths

A calm bedroom is furnished with two queen beds, each adorned with white linens and decorative pillows. A light-colored dresser is positioned against the wall, complemented by a mirror and a lamp. A piece of art depicting a figure on a horse enhances the serene ambiance.

4.42 out of 5 average rating, 279 reviews

Two Bedroom Suite

A spacious suite features vaulted ceilings with wooden beams, enhancing the open feel. A full kitchen is visible, along with a dining area that includes a round table and four chairs. Natural light floods the room through large windows, and a king bed is prominently placed.