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Places to stay near Smathers Beach

Book unique vacation rentals, homes, and more on Airbnb

Top-rated vacation rentals near Smathers Beach

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

Home in Key West

4.95 out of 5 average rating, 355 reviews

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.

Top guest favorite

A bright and welcoming living space features a galley kitchen with a counter and two stools. The refrigerator is visible along with colorful walls in shades of yellow and coral. A TV unit stands nearby, and a red sofa adds a pop of color to the cozy area.

Apartment in Key West

4.98 out of 5 average rating, 517 reviews

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

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

A three-story historic building is framed by palm trees and tropical foliage. White decorative railings and an ornate archway lead to the entrance, while soft sunlight brightens the exterior's yellow siding. The inviting architecture complements the serene surroundings.

Vacation home in Key West

4.86 out of 5 average rating, 335 reviews

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

A spacious bedroom features a large bed with a plaid blanket, accented by a collection of framed artwork on a bright blue wall. Wood flooring complements the overall decor, while a nearby closet provides convenient storage.

Apartment in Key West

4.78 out of 5 average rating, 372 reviews

Key West - Sunrise ❀ The Green House

AUGUST, SEPTEMBER, OCTOBER – We have significantly lowered our prices for the off-season. Please use part of the discount to purchase travel insurance at the time of booking. AirBnB Cancellations and Major Disruptive Events Policy excludes weather or natural conditions that are common enough to be foreseeable in a given location. Hurricanes are considered common and foreseeable in Florida between June and November, with peak activity typically occurring in August, September, and October.

A large heated Olympic-sized pool is set within a tropical landscape, surrounded by palm trees and lounging chairs. The inviting blue water reflects the sky and is complemented by the nearby resort building, which features multiple levels and balconies.

Apartment in Key West

4.92 out of 5 average rating, 192 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

1357 s f Luxury beachfront resort condo w/ all the amenities - beachfront heated Olympic 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. Thank you for understanding. Spalling work hs begun on the balconies of the other building this may impact your enjoyment of the pool

Top guest favorite

A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.

Condo in Key West

4.9 out of 5 average rating, 219 reviews

"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).

Top guest favorite

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

Condo in Key West

4.97 out of 5 average rating, 106 reviews

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.

Top guest favorite

A 2007 420 Lagoon Catamaran is anchored in clear turquoise waters, displaying its sleek white hull and tall masts against a backdrop of vibrant clouds and blue sky.

Boat in Key West

4.87 out of 5 average rating, 156 reviews

All Inclusive! Snorkel • Sail • Sun & Fun

Stay aboard our 42’ Lagoon 420 catamaran anchored off downtown Key West. Hosted by Captain Dan, a 10-year Superhost, your all-inclusive stay includes snorkeling, sailing, spear fishing, and fishing gear. Relax in the private queen cabin with ensuite bath, enjoy the fully equipped galley, and unwind in the air-conditioned salon. Quick dinghy rides bring you to Key West’s vibrant dining and nightlife. Your perfect floating island escape!

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

Condo in Key West

4.89 out of 5 average rating, 147 reviews

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.

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

Apartment in Key West

4.9 out of 5 average rating, 151 reviews

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

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

Condo in Key West

4.78 out of 5 average rating, 300 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!

Top guest favorite

A spacious bed is framed by elegant side tables, each topped with a softly glowing lamp. Above the headboard, three framed artworks create a balanced focal point. Decorative pillows add a touch of color, while a leafy plant provides a natural element to the serene space.

Apartment in Key West

4.95 out of 5 average rating, 430 reviews

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 vacation rentals near Smathers Beach

Free parking on premises

Air conditioning

Condo rentals with wifi

Condo in Key West

4.82 out of 5 average rating, 286 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

A balcony view reveals the expansive Atlantic Ocean, featuring a peir extending into the water. Palm trees are visible, adding a tropical ambiance. The serene blue waters and clear sky harmonize in the background, enhancing the coastal experience.

Condo in Key West

4.9 out of 5 average rating, 89 reviews

Ocean Front Studio private Sandy Beach in Key West

A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.

Condo in Key West

4.96 out of 5 average rating, 78 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

A serene waterfront view reveals gentle waves lapping against a sandy shoreline. Beach chairs are arranged near the water, providing a relaxing spot to enjoy the scenery. Lush palm trees frame the tranquil setting, enhancing the sense of peacefulness.

Condo in Key West

4.95 out of 5 average rating, 42 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

An open-concept living area features large floor-to-ceiling windows allowing natural light to fill the space. A glass dining table with modern chairs is positioned adjacent to a comfortable seating arrangement. The area extends to a private terrace, enhancing the seamless indoor-outdoor living experience.

Condo in Key West

4.88 out of 5 average rating, 154 reviews

Rooftop Penthouse

A private hot tub is framed by lush tropical greenery and palm trees. Surrounding plants in individual pots contribute to a serene atmosphere. Nearby, a shaded dining area is visible, furnished with a table and chairs, offering an inviting space for outdoor meals.

Condo in Key West

5 out of 5 average rating, 8 reviews

Palm Garden retreat with Hot Tub & Prime Key West

Condo in Key West

4.88 out of 5 average rating, 34 reviews

New Listing! Key Lime Paradise/Condo

Condo in Key West

4.72 out of 5 average rating, 67 reviews

Frost Free in Key West

Family-friendly house rentals

A serene outdoor area features a tranquil saltwater pool surrounded by vibrant tropical landscaping. The brick pathway leads to a spacious porch, creating an inviting atmosphere. Lush green shrubs and colorful plants enhance the ambience, while the home’s elegant architecture is visible in the background.

Home in Key West

4.91 out of 5 average rating, 23 reviews

Easy Livin' by AvantStay | Mins to the Ocean!

An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

Home in Cudjoe Key

4.97 out of 5 average rating, 167 reviews

Cudjoe Key Home with a View

Aerial view of a waterfront property featuring a semi-circle dock leading to a small island. Brightly colored chairs in green and turquoise sit on sandy areas, surrounded by clear blue water and lush tropical vegetation. Nearby, additional properties can be seen amidst palm trees.

Home in Summerland Key

4.91 out of 5 average rating, 101 reviews

Waterfront Haven House with Boat Basin & Ramp!

An inviting outdoor space features two lounge chairs facing a private heated saltwater pool surrounded by tropical plants. The deck area showcases wooden flooring and complementary side tables, while light filters through the palm leaves under a partly cloudy sky.

Home in Key West

4.9 out of 5 average rating, 113 reviews

Mango Cottage, a charming Key West home ready for

The outdoor swimming pool features a circular design surrounded by tropical palm trees and lounge chairs. Bright blue umbrellas provide shade for guests, while the clear blue sky enhances the vibrant atmosphere of the gated community.

Home in Key West

4.94 out of 5 average rating, 112 reviews

Paradise found

A spacious outdoor area is centered around a clear blue pool, surrounded by lush palm trees. A dining table is set nearby, with comfortable seating in the background. Glass doors provide a view into the elegant interior, while a barbecue grill is stationed beside the pool.

Home in Key West

5 out of 5 average rating, 13 reviews

Cheerful 3 Bedroom with Pool, Off Street Parking

Top guest favorite

A spacious living area is seen with a comfortable brown sofa and a dining table for four. Decorative elements include marine-themed art on the walls and a ceiling fan. Light is provided by floor lamps and windows, creating a bright and inviting environment.

Home in Key West

4.94 out of 5 average rating, 18 reviews

Seagull Suite | Inviting Studio, Just Steps From D

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

Home in Cudjoe Key

4.86 out of 5 average rating, 108 reviews

Waterfront Sanctuary in the Keys!

Apartment rentals with air conditioning

A well-lit bedroom features a spacious bed adorned with striped bedding and decorative pillows. A red dresser contrasts with the soft blue accent wall. Natural light floods in through windows, highlighting the warm wooden floor.

Apartment in Key West

4.87 out of 5 average rating, 69 reviews

Lovely Apartment *Key West Best Locations *Sunset

A bright living area features light-colored furniture, including a comfortable sofa and armchair. A wooden coffee table is centrally placed. Art displays adorn the walls, enhancing the inviting ambiance. Nearby seating accommodates dining for four, with large windows allowing natural light to flow in.

Apartment in Key West

4.91 out of 5 average rating, 76 reviews

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

A modern living area is presented with a comfortable grey sofa and two patterned chairs facing a large sliding door. Natural light fills the space, illuminating a textured wood coffee table and a side table with a lamp. A mounted television displays vibrant sunset imagery.

Apartment in Key West

4.98 out of 5 average rating, 52 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

Top guest favorite

A charming entrance is framed by lush tropical plants and palm trees. The light green door complements the inviting beige exterior of the home. A cozy seating area is situated on the porch, and brick pathways lead through a landscaped yard filled with vibrant foliage.

Apartment in Key West

5 out of 5 average rating, 27 reviews

Heron Hideaway

An open concept studio apartment features a modern kitchen with stainless-steel appliances, including a coffee maker and oven. A dining table with black chairs is positioned near the kitchen. In the background, a spacious bed is visible, illuminated by natural light from large windows.

Apartment in Key West

4.85 out of 5 average rating, 244 reviews

Studio Near Downtown - The Bartlum

Top guest favorite

An aged metal watering can is suspended, filled with a mix of colorful flowers. The subtle rust and faded blue paint of the can contrast with the fresh blooms, creating a charming focal point amidst a lush green backdrop.

Apartment in Key West

5 out of 5 average rating, 9 reviews

The Garden Cottage

The exterior of the resort is displayed along a waterfront, featuring a charming building with multiple balconies. Lush palm trees sway beside the property, and clear blue waters are visible in the marina, enhancing the relaxing coastal ambiance.

Apartment in Key West

5 out of 5 average rating, 10 reviews

Downtown KeyWest 2Bed Oceanfront

A well-lit bedroom features a queen-sized bed with white linens and a wooden frame. A lay flat couch is situated against the wall. Two bedside lamps and a wooden dresser with rattan detail enhance the space. An air conditioning unit is visible on the window.

Apartment in Key West

4.9 out of 5 average rating, 209 reviews

Duval St Apartment w/ Balcony w/parking Adult Only

Other great vacation rentals near Smathers Beach

Top guest favorite

A serene sunset casts warm orange and golden hues over the water, creating a calming reflection. The houseboat is visible with a cozy chair positioned towards the horizon. The surrounding calm waters and boats in the distance emphasize the peaceful setting.

Boat in Key West

4.97 out of 5 average rating, 29 reviews

Off Grid Boat "Shanty Pineapple" Key West

An open living area is showcased with a light brown leather sofa and a modern dining set positioned by large windows, allowing natural light and views of the marina. A sleek kitchen with a white countertop and stainless steel appliances is visible, creating a welcoming gathering space.

Boat in Key West

4.92 out of 5 average rating, 51 reviews

Waterfront & Heated Pool - Awai's Floating Villa

A sandy beach transitions to calm waters, framed by palm trees and greenery. Sun loungers are arranged neatly along the shore. A private spiral staircase leads to the beach, while a wooden dock extends into the water, inviting leisurely excursions.

Condo in Key West

4.83 out of 5 average rating, 120 reviews

Ocean Front Suite with Direct Beach Access

The interior of the boat features wood-paneled walls and cozy seating areas. A plush gray sofa and an accent chair surround a star-patterned rug. A flat-screen TV is mounted on the wall, while the galley area is visible in the background, highlighting the boat's spacious layout.

Boat in Key West

4.79 out of 5 average rating, 42 reviews

Boat life with all the amenities

An outdoor lanai features a round glass table surrounded by four green cushioned chairs. A ceiling fan is mounted above, and a tree partially shades the area, providing a serene setting for relaxation.

Home in Key West

5 out of 5 average rating, 7 reviews

Roost Haven

A spacious living room features two sofas, one of which is a fold-out bed, and a coffee table centered on a patterned area rug. Large windows with wooden blinds allow light to fill the room, highlighting the full kitchen area and breakfast bar in the background.

Houseboat in Key West

4.8 out of 5 average rating, 332 reviews

Key West Houseboat Paradise

An open-concept living area features wraparound seating in dark leather surrounding a polished wooden dining table. Abundant natural light filters through panoramic windows, reflecting off the rich wooden flooring. Tropical-themed wall decor and greenery enhance the inviting aesthetic. A well-equipped kitchen is visible in the background.

Boat in Key West

5 out of 5 average rating, 5 reviews

Sailboat Stay + Resort Amenities

Top guest favorite

The image captures a serene pool area surrounded by lush palm trees and well-lit walkways. The clear water reflects the sky, while sun loungers are positioned nearby for relaxation. Two-story buildings are visible in the background, adorned with balconies overlooking the pool.

Townhouse in Key West

4.97 out of 5 average rating, 280 reviews

Stunning Townhouse * Full kitchen! * Sleeps 6

Destinations to explore

Beachfront rentals Smathers Beach