Lodging Options
Southwinds Motel
- Great for a room block
- Convenient downtown location: access to all of Key West’s attractions and water sports within walking distance including a convenience store, shops and restaurants.
- Beach access with complimentary chairs and towels* at South Beach (next to Southernmost Beach Resort)
- Includes parking and continental breakfast in the $15 resort fee
- 3 swimming pools
Santa Maria Suites
- Perfect location for it is only one block away from Duval St where all the restaurants and nightlife is located for your stay;
- All suites are 2 bedroom and 2 bath suites that can sleep up to 5 people in each suite and they allow Children;
- These suites have full kitchens;
- Suites are either a flat style or a bi level style;
- Features include two courtyard pools, poolside bar, and 24-hour Concierge;
- Beach Access with Chairs, Umbrellas and Towels & Attendance Service.
Southernmost Beach Resort
- Is hands down THE best on island!!!
- Features include 3 pools, gardens, royal palm walk way, hammocks, Adirondack chairs to gaze out on the ocean, entertainment and games scheduled during the day, and a full beach that you can walk right into;
- There pricing will reflect the level of their location – but if you are looking for a special location for you and your guests this is it – it is as family friendly as it is romantic – we can do a room block – does require a guarantee – call Family Affair for more details
Sunset Key Cottages
- Just off our little Key West Island is Sunset Key Island, you take short boat ferry to this very exclusive island;
- One, two, three or four bedrooms, with garden, partial ocean or full ocean views;
- Fully equipped kitchen;
- Private verandas with Adirondack chairs and tables;
- 24-hour boat transportation to and from Margaritaville Key West Resort & Marina;
- Spacious white sand beach;
- Tropical swimming pool and two whirlpools;
- Beach and poolside concierge services;
- Two tennis courts;
- Private docks for boats up to 200 feet at Margaritaville Key West Resort & Marina.
Margaritaville Key West Resort & Marina
- Ideally located at sunset end of the island, right on the waterfront of Old Town within a working cruise ship port and just steps from the famous Mallory Square and one block from Duval St., you can walk to everything ;
- Features include pool, whirlpool and restaurants.
- Boat to Sunset Key’s Beach
Havana Cabana
- (Requires shuttle to Duval) The new Havana Cabana hotel overlooking the Atlantic Ocean is set along Highway 1.
- Amenities include the largest outdoor pool in the island, a poolside Tiki hut bar and a hot tub, as well as a food truck serving Cuban fare. Live entertainment is also offered.
- Free parking
Sheraton Suites
- (Requires shuttle to Duval) an all-suite hotel in Key West
- Ideally situated across from Smather`s Beach and just minutes from Key West International Airport our beachfront resort offers travelers a low-key retreat brimming with sophistication and style
- Complimentary on-site parking
- Outdoor Heated Pool and a Whirlpool
- Hot breakfast, fee from: 15 USD
Marriot Beach Side
- (Requires shuttle to Duval) This location is just at the start of the island.
- Key West hotel suites featuring gourmet kitchens, dining rooms, living rooms and master bedrooms;
- These rooms are stunning and this property is great fun;
- You also get the hotel’s complementary downtown shuttle to experience everything Key West has to offer and no resort fee;
- Continental breakfast, fee from: 15.95 USD
- Tanning Beach, Outdoor Waterfront pool and a Whirlpool.
Southernmost Inn
- The Southernmost Inn is located one block from Duval Street, but is towards the quieter end;
- Great location where you can find an array of nightlife, dining, and entertainment;
- Continental Breakfast, 24-hour Starbucks Coffee/Tea, Two Pools and one hot tub and a Gym are included in the daily amenity fee of $24.99 + tax.
Avalon B&B
- This Bed and Breakfast is located on the quieter end of Duval St., just one block away from the Southernmost point and only steps away from the beach;
- Refined rooms with private bathrooms, canopy beds, minifridges and cable TV. There’s also a cottage with a porch;
- Continental breakfast is served on the front porch overlooking Duval Street;
- Plunge pool and a side deck.
Cayo Hueso Resorts
- These are more like vacations properties style with outstanding Key West architecture and amenities, located just steps off Duval St., South Beach & Southernmost Point (yet totally discreet and private);
- They have private homes, cottages and bungalows fully-equipped, that can fit up to 8 guests;
- Full Kitchens plus Blender, Microwave & Dishwasher;
- Private Sundecks with Gas BBQ Grill, Table & Umbrella;
- Heated Pool with Waterfall, surrounded by Lush Tropical Landscaping;
- Complimentary Laundry Facilities;
- Complimentary Wireless Internet Access and complimentary Free Local Calls;
- Complimentary Welcome Basket.
Center Court Cottages
- This location is central just off Truman Avenue you can walk to Southernmost Beach or Mallory Square with ease;
- They have plenty of outside space to relax, a pool for guests only, with lounge chairs and tables with chairs; and a rooftop sun deck;
- Second pool across the street available for adults only;
- Each of their suites has many great amenities including WiFi, air conditioning, toaster oven, refrigerator, coffee maker (complete with coffee, cream and sugar), and a blender;
- Many of our suites have a private spa within your own gated courtyard.
Wicker guest house
- Just across the street from the Center Court Cottages is the Wicker Guests House back door (front door on Duval) – so it is a great location to have overflow of your guests who can not fit in the Cottages;
- Heated swimming pool, patio with lounge chair and hammocks and a Sundeck;
- Free, limited parking. First come, first served;
- Complimentary poolside continental breakfast.
Kimpton Winslow’s Bungalows
- In the heart of Old Town;
- Outdoor pool with bar service, afternoon poolside refresher and pool towels;
- Beach kit: borrow a beach bag filled with mask, snorkel and a walking map to nearby beach attractions;
- Explore Key West on custom-designed loaner bikes — available for all our guests to enjoy;
- Yoga mats and turkish robes in every guestroom;
- Boozy welcome arrival w/ signature Passionfruit Shandy Beer;
- Complimentary Continental Breakfast served from 8 a.m. to 10 a.m. daily;
- Onsite concierge to help you make the most of your Key West stay;
- Complimentary Wifi;
- $30+ Tax Daily Guest Amenities Fee;
- Pet Friendly
Kimpton Fitch Lodge
- Minutes from the Key West Historic Seaport;
- Casual retreat refreshingly removed from the bustle of Duval Street;
- Outdoor pool with afternoon poolside refresher and pool towels;
- Beach kit: borrow a beach bag filled with mask, snorkel and a walking map to nearby beach attractions;
- Explore Key West on custom-designed loaner bikes — available for all our guests to enjoy;
- Yoga mats and turkish robes in every guestroom;
- Boozy welcome arrival w/ signature Passionfruit Shandy Beer;
- Complimentary Continental Breakfast served from 8 a.m. to 10 a.m. daily;
- Onsite concierge to help you make the most of your Key West stay;
- Complimentary Wifi;
- $30+ Tax Daily Guest Amenities Fee;
- Pet Friendly
Kimpton Ridley House
- Of their five Kimpton Key West hotels, Ridley House is the most elegant—ideal for honeymooners and VIP stays.
- Outdoor pool with afternoon poolside refresher and pool towels;
- Beach kit: borrow a beach bag filled with mask, snorkel and a walking map to nearby beach attractions;
- Explore Key West on custom-designed loaner bikes — available for all our guests to enjoy;
- Yoga mats and turkish robes in every guestroom;
- Boozy welcome arrival w/ signature Passionfruit Shandy Beer;
- Complimentary Continental Breakfast served from 8 a.m. to 10 a.m. daily;
- Onsite concierge to help you make the most of your Key West stay;
- Complimentary Wifi;
- $30+ Tax Daily Guest Amenities Fee;
- Pet Friendly
Kimpton Lighthouse Hotel
- Located mango-throwing distance to iconic Key West Lighthouse and Hemingway’s home
- Outdoor pool with afternoon poolside refresher and pool towels;
- Beach kit: borrow a beach bag filled with mask, snorkel and a walking map to nearby beach attractions;
- Explore Key West on custom-designed loaner bikes — available for all our guests to enjoy;
- Yoga mats and turkish robes in every guestroom;
- Boozy welcome arrival w/ signature Passionfruit Shandy Beer;
- Complimentary Continental Breakfast served from 8 a.m. to 10 a.m. daily;
- Onsite concierge to help you make the most of your Key West stay;
- Complimentary Wifi;
- $30+ Tax Daily Guest Amenities Fee;
- Pet Friendly