
Places to stay near Smathers Beach
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Top-rated holiday rentals near Smathers Beach
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Waterfront Condo Dock Pool Downtown Near Duval
Time to relax and vacation in this spacious 1,350 sq ft waterfront corner condo in downtown Key West. Bring your family and friends and enjoy a private balcony with marina views, full kitchen, and open living space. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator access, and secure entry. Located about 1 mile from Duval Street and 10 minutes from EYW airport.
4.91 out of 5 average rating, 280 reviews
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 & drip coffee New stainless appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, Beach, beach towels One parking space, no charge
4.95 out of 5 average rating, 212 reviews
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.
4.99 out of 5 average rating, 141 reviews
Penthouse in Paradise
Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.
4.85 out of 5 average rating, 149 reviews
The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.
4.93 out of 5 average rating, 134 reviews
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
4.93 out of 5 average rating, 241 reviews
Studio Blu | Stylish Key West Studio + Bikes
Stay like a local at Studio Blu, a stylish private studio in Key West’s historic Cuban district. Walk or bike to Old Town, Duval Street, beaches, restaurants, and cafés, then return to a quiet residential retreat with a full kitchen, vintage claw-foot tub, private entrance, free Wi-Fi, and complimentary bikes. Perfect for couples or solo travelers looking for a comfortable home base close to everything without being in the middle of the crowds.
4.95 out of 5 average rating, 484 reviews
Castaway Cove: Pet-friendly 2/2 condo near beach!
Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.
4.89 out of 5 average rating, 122 reviews
KW Luxury 2/2 Beachfront resort Tropical Oasis
1357 s f Lux beachfront resort condo w/ all the amenities - beachfront huge heated pool, 3 lighted tennis courts, 20 man hot tub, tropical gardens, beach, saunas, Gym, BBQ Grills everything to make your vacation spectacular! You must be at least 25 years old to rent this property. This is a no animal rental due to extreme allergies of the owner. 16% mgmt fee is Abnb fee.
4.92 out of 5 average rating, 201 reviews
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.
4.91 out of 5 average rating, 562 reviews
Paradise found
Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.
4.94 out of 5 average rating, 159 reviews
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!
4.78 out of 5 average rating, 315 reviewsPopular amenities for holiday rentals near Smathers Beach
Condo rentals with Wi-Fi

Rooftop Penthouse
4.89 out of 5 average rating, 193 reviews
Tropical Escape at Sunrise
4.91 out of 5 average rating, 182 reviews
Tropical Heron Hideaway w/ Hot Tub + Pool
4.94 out of 5 average rating, 129 reviews
Oceanfront 3 bed condo Ocean Edge w/ optional slip
4.97 out of 5 average rating, 101 reviews
Tropical Old Town Bungalow
4.9 out of 5 average rating, 304 reviews
Sky Loft - Steps from Duval Street & Shared Pool
4.74 out of 5 average rating, 188 reviews
Orchid Suite @ the Old Town Villas, steps from
4.76 out of 5 average rating, 110 reviews
Key West Condo with Balcony Ocean View
5.0 out of 5 average rating, 46 reviewsFamily-friendly house rentals

Cudjoe Key Home with a View
4.96 out of 5 average rating, 213 reviews
Key West Paradise
4.89 out of 5 average rating, 100 reviews
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
4.97 out of 5 average rating, 328 reviews
Duval Vibes • Pool • 10 Guests
4.92 out of 5 average rating, 136 reviews
Palm Breezes! Room for Everyone on the Ocean.
4.83 out of 5 average rating, 112 reviews
Waterfront Anchor House with Boat Basin & Ramp!
4.95 out of 5 average rating, 116 reviews
Pool Access + Local Art • Walk to Southernmost
4.81 out of 5 average rating, 103 reviews
Gorgeous Romantic Private Villa, Steps from Duval!
4.96 out of 5 average rating, 111 reviewsApartment rentals with air conditioning

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
4.98 out of 5 average rating, 565 reviews
Island Color Suite
4.89 out of 5 average rating, 225 reviews
Key West Condo 2B/2B with Pool & Boat FREE Slip
4.89 out of 5 average rating, 105 reviews
#201 Key West Suites
4.86 out of 5 average rating, 323 reviews
Duval Balcony - Street Suite
4.84 out of 5 average rating, 899 reviews
King Bed | Key West *Best Downtown Locations *Cool
4.84 out of 5 average rating, 152 reviews
The Bartlum - Steps to Duval Street
4.85 out of 5 average rating, 266 reviews
Duval Street Suites full kitchen and heated pool
4.92 out of 5 average rating, 123 reviewsOther great holiday rentals near Smathers Beach

Stay on Roxie - free transport & snacks, BYOB.
4.89 out of 5 average rating, 247 reviews
Beautiful Houseboat in Key West
4.93 out of 5 average rating, 230 reviews
KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK
4.81 out of 5 average rating, 16 reviews
Key West Outpost: eco-vacation
4.95 out of 5 average rating, 84 reviews
*Off Grid Boat Key West
4.96 out of 5 average rating, 95 reviews
Wake Up On The Water | Luxury Marina | Key West
5.0 out of 5 average rating, 18 reviews
Walking on Sunshine at The Beach
4.8 out of 5 average rating, 30 reviews
Best Resort in Key West, 2BD/2BA
5.0 out of 5 average rating, 4 reviewsDestinations to explore
- Sombrero Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Southernmost Point
- Florida Keys Aquarium Encounters
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium





