Places to stay near Smathers Beach

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK

Your own private Key West hideaway awaits. Surrounded by lush tropical landscaping, this peaceful home offers a large pool, outdoor shower, grill, and fire pit — perfect for relaxing days and starlit evenings. Enjoy complete privacy indoors and out, with three comfortable bedrooms, a fully equipped kitchen, washer/dryer, and 66' of canal frontage- bring your own boat or ask one of our favorite captains to pick you up! Whether out on the town or relaxing in your own home, you will love it here!

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Studio Blu -Hip Studio/Old Town

*Recent Update (2025): We’ve made a wonderful upgrade to the studio bathroom — it’s now fully enclosed with walls extending to the ceiling and a new exhaust fan for ventilation. Situated in the heart of the Cuban district, just steps from arguably the best café con leche in Key West, this bright and breezy studio apartment is minutes from everything on the island. No car needed — bikes and beach chairs are provided free of charge so you can explore at your own pace.

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

Beautiful Houseboat in Key West

Enjoy a unique and peaceful stay on our cozy houseboat in Key West. Perfect for couples or small families who want a relaxing water experience close to town. Comfortable sleeping area, deck space, and beautiful sunset views. Check-in is by appointment with personal captain meet-and-greet and boat transfer from the marina. A memorable island stay surrounded by nature and ocean air.

Affordable Beachfront Luxury Condo Sleeps 6

My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families