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Downtown KeyWest 2Bed Oceanfront

This is a great unit with large balcony. Sunset Harbor is perfectly located in downtown Key West. Walk along the boardwalk/head to Duval Street only a couple blocks away. The resort has pool, hot tub, grills for use during your stay. There are laundry facilities free of charge. There are NO daily resort fees, parking is extra. Each unit has a King sized bed , Queen sized bed, and sofa bed. Specific units are assigned by front desk. No guarantee about floor but all 2 bedrooms have ocean views.

Sea Glass Cottage in Historic Key West

Spend time in beautiful Key West and live like a local in a Conch Home! The Sea Glass Cottage is perfect for groups with 4-6 guests & a furry friend! A fully-renovated 2 bedroom, 2 bath home on the second floor with a queen pull-out sofa. Located in an historic neighborhood in downtown KW near beaches, and parks. Enjoy beautiful foliage on your private porch with seating/ grill. Reserve its sister cottage, the Coral Cottage, to accommodate parties of 8-10 in separate units within the same home.

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

King Bed | Key West *Best Downtown Locations *Cool

AUGUST, SEPTEMBER, OCTOBER – We have significantly lowered our prices for the off-season. Please use part of the discount to purchase travel insurance at the time of booking. AirBnB Cancellations and Major Disruptive Events Policy excludes weather or natural conditions that are common enough to be foreseeable in a given location. Hurricanes are considered common and foreseeable in Florida between June and November, with peak activity typically occurring in August, September, and October.

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

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.

Orchid Bay Condo + Pool • Old Town • Walk to Duval

Stay in a beautifully restored historic building, originally built circa 1889, in the heart of Key West’s Historic Seaport. Just 3 blocks from Duval Street, you’ll be within walking distance of the waterfront, shops, restaurants, and nightlife. Relax by the shared pool after a day of exploring Old Town, then return to your comfortable private suite. Experience authentic island charm, modern comfort, and one of Key West’s best locations.

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 75” Smart TV. Bose blue tooth speakers and Alexa's. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 6 person Jacuzzi. 2 heated pools!

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!

Beautiful Old Town Key West! Near Duval!

Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located near the Gulf of Mexico. Outside the property enjoy the charms of Duval Street and a nightly sunset celebration at Mallory Square. There are also many activities like diving, scuba or snorkeling, parasailing, fishing charters, boat tours, and more.

Tiki Suites ~ Original Tiki ~ Floating Bungalows

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

2 BR Condo Banyan Tree, Key West,FL

With pools, a hot tub, Tiki Bar, BBQ grills, and a kitchen in each unit you can enjoy the lush private surroundings and still be close to the heart of Key West, Hemingway Museum, Sloppy Joe's, 1 block off Duval. ONLY dates on calendar are available.