
Places to stay near Smathers Beach
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Top-rated holiday rentals near Smathers Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Gorgeous Ocean View in Paradise, Close to Key West
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

Amazing houseboat with 2nd floor observation deck
Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in 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.

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage
Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

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.

Atlantis House's Banyan Suite-voted top 25 in USA
This suite The Banyan Suite (previously called Garden Suite) is nestled in the corner of the lush backyard with a private French door entrance off the deck. This charming hideaway offers a large flat screen TV visible from the sofa and spacious king bed. RA corner bar table provides the perfect spot to enjoy a quick bite from the quaint kitchenette equipped with a mini-fridge, microwave oven, toaster, and coffeemaker, featuring famous Cuban coffee!

Poolside Cottage #411
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat 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, kayaks, paddle boards and golf carts can be rented locally

Duval St Apartment w/ Balcony w/parking Adult Only
This large apartment overlooks Duval Street from a private balcony. Perfect location in the heart of Old Town within easy walking distance of restaurants, live music, and historic sites. Guests enjoy daily complimentary continental breakfast in the garden and dips in our heated pool. *Please note you must be 21 or older to make a reservation on this property and all guests must be at least 18 years old.*

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 We have a Website specific to our Condo where we offer special pricing, discounts and additional pictures Search-keywestbeachsidecondo

#201 Key West Suites
Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is on Duval Street! Although this a vacation rental and not a hotel per se with a lobby etc, we kept hotel in the name in keeping with historic nostalgia, "Key West Suites Hotel"

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!

Studio Blu -Hip Studio/Old Town
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this Studio apartment is minutes from everything on the island. No cars are necessary, bikes & beach chairs are provided free of charge.
Popular amenities for holiday rentals near Smathers Beach
Condo rentals with Wi-Fi

Condo de Paradise/Salt Water Pool/Boat Dock

Rooftop Penthouse

Palm Garden retreat with Hot Tub & Prime Key West

Tropical Escape at Sunrise

EYW Getaway

A Perfect Getaway

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

The Island Suite @ KW vacation
Family-friendly house rentals

The Barnacle at Venture Out - Waterfront with Dock

Cudjoe Key Home with a View

106- Newly Renovated House with Oceanview and Pool

Waterfront Haven House with Boat Basin & Ramp!

Fleming Street 2/1 private home Key West getaway

Oct. & Nov. 50% off! Oceanfront, 4 Bikes 2 Kayaks

Roost Haven w/ free private parking spot

Waterfront Sanctuary in the Keys!
Apartment rentals with air conditioning

Castaway Cove: Pet-friendly 2/2 condo near beach!

Duval Balcony - Street Suite

Duval Street Suites with full kitchen heated pool,

Sunrise - Best Downtown Locations

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

Key West Condo 2B/2B with Pool & Boat FREE Slip

Studio Near Downtown - The Bartlum

Henry's Penthouse On The Ocean
Other great holiday rentals near Smathers Beach

Off Grid Boat "Shanty Pineapple" Key West

Airstream Key/RV rental&delivery, campsite require

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Southard Comfort ~ Feel Key West Vibe In Old Town

Oceanfront Cottage with 60’ Dock

Hyatt Beach House-Quiet Key West Spot!

NEW! - The Jolly Rooster Cottage - Walk to Duval

Key West Cottage Du Soleil w/ Pool!