
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.

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

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.

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!

Hidden Beach Duplex, Best Place in Key West
Go to sleep and wake up smiling listening to the waves. 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. This is an extraordinary condo on an extraordinary property. This is nicest unit of 3 for rent at Hidden Beach. If you are discerning, this really is best place place to stay in Key West.

Tropical Escape at Sunrise
We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

Hemingway - Beach Houses Key West
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Off the beaten path you will find a unique location and a beach front bungalow with endless unobstructed views of the ocean from every bedroom. Featuring an open family area, full kitchen, deck and its own tiki, excellent for grilling, having a cold drink or just gazing at the ocean.

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.

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.

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.

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

Moonlight Paradise Upgraded Family oasis Tropical
Moonlight is a totally renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own private balcony. Beautiful tropical decor. No attention to detail has been spared. Stainless Appliances & luxurious finishes.
Popular amenities for holiday rentals near Smathers Beach
Apartment rentals with wifi

Seas the Breeze – Poolside Condo Near the Beach

Condo de Paradise/Salt Water Pool/Boat Dock

Rooftop Penthouse

Waterfront Condo Dock Pool Near Duval St

Tropical Heron Hideaway w/ Hot Tub + Pool

EYW Getaway

Henry's Piece of Paradise On The Ocean In Key West

Cuban Paradise @ Cuban Club
Family-friendly house rentals

Pool Access + Local Art • Walk to Southernmost

Duval Vibes • Pool • 10 Guests

Cudjoe Key Home with a View

MERMAID COVE- Funky Getaway on Duval

Gorgeous Romantic Private Villa, Steps from Duval!

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

Sea Glass Cottage in Historic Key West

Palm Breezes! Room for Everyone on the Ocean.
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,

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

The Bartlum - Steps to Duval Street

Sky Suite with Balcony Overlooking Duval Street

Waterfront Condo FREE Slip & Pool 2B2B in Key West

King Bed | Key West *Best Downtown Locations *Cool
Other great holiday rentals near Smathers Beach

*August/September specials* off Grid Boat Key West

Cozy Tiny Houseboat: Find Your Peace and Balance

Duval Corner - Pet friendly with Balcony

3BR In Resort Village, Pools, Free Kayak & Shuttle

Newly Renovated 2/2 Bath Condo, with shared pool

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

NEW! - The Jolly Rooster Cottage - Walk to Duval

Key West Outpost: eco-vacation
Destinations to explore
- Sombrero Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Florida Keys Aquarium Encounters
- Southernmost Point
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium





