Boutique hotel holiday rentals in Key West

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.

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.

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.

Double Queen Room | Resort Perks | No Hidden Fee

Relax in the Resort Double Queen, a sunlit space ideal for families or friends seeking a peaceful retreat. Featuring a private balcony with serene resort views, two comfy queen beds, and thoughtful amenities, this room is perfect for recharging after a day of exploring. Located at Hawks Cay Resort, it offers effortless access to unforgettable island adventures, refreshing dips, and laid-back luxury.

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.

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!

Parrot Key, Garden 2 Bedroom Suite w/ Living Room

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.

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.

Romantic Room near The Lighthouse: Key West Bliss

Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southernmost Point. Enjoy vibrant local culture and easy access to top attractions. Perfect for couples and friends seeking a memorable getaway!