Boutique hotel vacation rentals in Key West

Speakeasy Inn - Room 1B (1 Queen Bed)

This room sleeps 2 and has a queen size bed. It is located upstairs behind Room 1A with a sitting area on the wrap around balcony. This room has a private bath with shower, hair dryer and a clawfoot bathtub. The kitchenette is equipped with a refrigerator, microwave, toaster, coffee maker and dishware. A flat screen TV with cable channels, WiFi, individual A/C and iron and ironing board are among the many amenities in this room. Parking available on a first come first serve basis.

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.

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.

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!

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.

Marathon Oceanfront Room | King Bed + 5 Pools

Indulge in oceanfront luxury with the Oceanfront Balcony | King room. Featuring a plush king bed, a spa-like bath with a deep soaking tub and walk-in rainfall shower, and a private oceanview terrace, this serene retreat is perfect for relaxation. Enjoy modern comforts, complimentary WiFi, five pools, beachfront dining, and endless coastal adventures in the heart of the Florida Keys.

Waterfront Two Bedroom Suite

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 w/ Private Balcony & Breakfast

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.

Historic Cigar Barons Mansion

Upscale historic cigar barons mansion in walking distance to everything you desire in Key West. 3 spacious 1Br’s with outdoor living at its finest. Each guest suite has its own separate entrance to the gardens. pool, sitting areas, BBQ, 2 off street parking spaces, free laundry and Wi-Fi.

Room in the Heart of Key West: Enjoy Poolside Fun

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!