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Places to stay near Smathers Beach

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Top-rated vacation rentals near Smathers Beach

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

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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

4.81 out of 5 average rating, 326 reviews

Key West Houseboat Paradise

5 Years SuperHost Rated with over 300 reviews!! ~ Single Stateroom with Queen Bed, ideal for a couple. Sleeps 1-4. Spacious living room, big sofas. Full kitchen, Full Bath, large Rooftop Sun Deck, 15 min to Duval St. The land-side isn't fancy. Light industrial, Old-school Key West feel. Blue collar, friendly working class, wooden dock with a working auto garage & warehouse but the water view of dozens of green mangrove island with 2 Sea Kayaks waiting for you to take exploring is a Hidden Gem.

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, 510 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

4.87 out of 5 average rating, 326 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 living area is depicted, featuring a light blue couch, a decorative armchair, and a coffee table made of reclaimed wood. Large glass doors open to a balcony with waterfront views, allowing natural light to brighten the room. A ceiling fan is visible above, enhancing comfort.

Condo in Key West

4.84 out of 5 average rating, 239 reviews

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

Time to relax! Bring your family & friends to this 1200 sqft Waterfront home - Stay spacious in Key West. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.

Houseboat in Key West

4.95 out of 5 average rating, 126 reviews

Full houseboat with large observation deck

We invite you to stay at our unique houseboat “Wild One”. Wild One is anchored minutes (by boat) from Garrison Bight Marina which is at the heart of Key West. Rides will be given to and from Wild One at the beginning and end of your stay. We will provide one in and out ride per day during your stay. Ride times must also work around our charter schedule which you will be advised of. Rides can be requested after nightfall but are accepted on a case to case basis. Last ride is at 10pm

A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.

Condo in Key West

4.89 out of 5 average rating, 244 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

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, 103 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.

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, 206 reviews

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.*

Top guest favorite

A cozy living area features a sectional sofa in a muted tone, paired with a wicker chair. A round coffee table sits in the center, with light blue area rug beneath. Large windows provide views of an outdoor space while allowing natural light to fill the room.

Apartment in Key West

4.96 out of 5 average rating, 284 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

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, 299 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, 421 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

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, 77 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

4.87 out of 5 average rating, 149 reviews

Rooftop Penthouse

The living room features a spacious green sofa complemented by wicker armchairs. A glass dining table sits at the center, with light streaming through open shutters. The backdrop showcases ocean views, enhancing the connection to the balcony and natural surroundings.

Condo in Key West

4.85 out of 5 average rating, 55 reviews

Ocean front 1BR/1BA Suite w/ kitchen & living rm

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

A charming two-story building with light pastel-colored siding and white railings is shown. The entrance features a circular window and a welcoming porch with comfortable seating. Lush greenery and a white picket fence frame the entrance, enhancing the inviting exterior.

Condo in Key West

4.89 out of 5 average rating, 172 reviews

A Perfect Getaway

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.

Condo in Key West

4.95 out of 5 average rating, 156 reviews

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

A spacious bedroom features a dark wooden bed framed by warm lamps on either side. A gray blanket covers the bed, complemented by decorative pillows. Natural light fills the room through a large window with sheer drapes, enhancing the soft, neutral tones of the walls and flooring.

Condo in Key West

4.9 out of 5 average rating, 98 reviews

The Island Suite @ KW vacation

Family-friendly house rentals

A two-story home features light green siding and a covered balcony, providing outdoor seating. The area beneath the house is open and includes parked vehicles and a picnic table, surrounded by tropical plants. The clear blue sky enhances the welcoming appearance of the property.

Home in Cudjoe Key

4.45 out of 5 average rating, 40 reviews

Fabulous Florida Keys!

A charming cottage entrance is framed by lush tropical vegetation, including palm leaves and colorful plants. A small heated jacuzzi is visible beside the brick pathway leading to a light blue door with white trim. Two rocking chairs sit on the welcoming porch.

Home in Key West

4.77 out of 5 average rating, 60 reviews

Historic Key West - Cigar House - Sleeps 4

A serene waterway is shown, flanked by palm trees and waterfront homes. A boat is seen navigating the calm waters, with clear skies enhancing the tranquil scene. The reflection of the surroundings is visible on the surface, creating a peaceful atmosphere.

Home in Cudjoe Key

4.63 out of 5 average rating, 171 reviews

Ocean Front Home in Great Location

A well-maintained community pool is surrounded by lush tropical landscaping. Palm trees add to the serene atmosphere, while poolside loungers and a shaded area provide relaxation options. The water glistens under the clear blue sky, enhancing the inviting outdoor space.

Home in Key West

4.85 out of 5 average rating, 159 reviews

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

A private outdoor deck features a two-person Solana spa surrounded by lush greenery. A striped umbrella provides shade over a chair, while a towel hangs against a white fence. Natural light filters through the tropical plants, enhancing the tranquil atmosphere.

Home in Key West

4.97 out of 5 average rating, 262 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

A charming conch cottage is showcased, featuring a light pink exterior and a welcoming front porch with white railings. Lush greenery and palm trees surround the home, offering a tropical atmosphere. Bright sunlight enhances the inviting entrance and adds warmth to the scene.

Home in Key West

4.9 out of 5 average rating, 117 reviews

Fleming Street 2/1 private home Key West getaway

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

Home in Cudjoe Key

4.81 out of 5 average rating, 94 reviews

Palm Breezes! Room for Everyone on the Ocean.

A two-story oceanfront home is shown, featuring a pastel blue exterior with white railings. Palm trees and lush greenery surround the property, while a gravel path leads to the entrance. Views of the water are visible in the background, enhancing the setting.

Home in Summerland Key

5 out of 5 average rating, 3 reviews

Family Retreat

Apartment rentals with air conditioning

A private balcony is adorned with festive garland, offering a view of a serene pool area surrounded by lush greenery. Two wicker chairs provide a comfortable spot to relax and enjoy the outdoors, with sun loungers visible beside the pool.

Apartment in Key West

5 out of 5 average rating, 11 reviews

Casa Caribe 2bed2bath sleeps 6 beautiful decorated

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, 150 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

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, 369 reviews

Key West - Sunrise ❀ The Green House

The spacious studio features two large beds with light bedding. A contemporary sofa and chairs are arranged around a coffee table in the living area. The room includes a flat-screen TV mounted on the white wall, with ceiling fans and wooden flooring enhancing the bright atmosphere.

Apartment in Key West

4.89 out of 5 average rating, 280 reviews

#203 Key West Suites

A warm-toned room features wood-paneled walls accented by natural light from two windows. A spacious bed with an orange bedspread is positioned alongside a cozy seating area comprising two cream-colored couches facing a small round table.

Apartment in Key West

4.84 out of 5 average rating, 810 reviews

Duval Balcony - Street Suite

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, 240 reviews

Studio Near Downtown - The Bartlum

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

The modern building is designed with balconies overlooking a serene pool area. A turquoise pool is bordered by lounge chairs and palm trees, creating a refreshing outdoor space. The backdrop features a clear sky and a sandy waterfront, enhancing the tranquil ambiance.

Apartment in Key West

4.91 out of 5 average rating, 33 reviews

Oceanfront Condo in Key West, FL

Other great vacation rentals near Smathers Beach

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

4.86 out of 5 average rating, 106 reviews

Ocean Front Suite with Direct Beach Access

A charming two-story home is framed by lush greenery and palm trees. A spacious driveway leads to a parked golf cart. The front porch features white railings and inviting seating, while the exterior showcases a light yellow facade under clear blue skies.

Home in Key West

4.92 out of 5 average rating, 13 reviews

Oceanfront, Resort-like luxury home with private p

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

Home in Upper Sugarloaf Key

4.94 out of 5 average rating, 95 reviews

Lighthouse - Beach Houses Key West

Top guest favorite

The vibrant outdoor area features a large swimming pool surrounded by lush tropical landscaping. Comfortable seating is available under a red umbrella, alongside a dining table. The two-story townhouse showcases balconies that overlook the pool, creating a spacious and inviting atmosphere.

Home in Key West

5 out of 5 average rating, 17 reviews

Kittyhouse on Catherine, Tropical Pool, Parking

A spacious living area features comfortable seating arrangements, including a large sofa and armchair. Large glass sliding doors provide access to the private balcony, showcasing ocean views. A television and coffee table occupy the center space, while a ceiling fan overhead adds a breezy touch.

Home in Key West

4.6 out of 5 average rating, 55 reviews

Brisa Del Mar by AvantStay | Ocean Front Community

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, 273 reviews

Stunning Townhouse * Full kitchen! * Sleeps 6

A motor yacht glides over the turquoise waters, leaving a wake in its path. The skyline of a city is visible in the distance, complemented by a clear blue sky and scattered clouds. The scene captures a moment of elegance and adventure on the open water.

Boat in Key West

5 out of 5 average rating, 7 reviews

FREE TIME 50’ 2 Cabin Yacht-Key West

The yacht 'Just Chillin' is illuminated at night, showcasing its sleek design and multiple levels. Soft light emanates from the upper deck, highlighting the covered patio. Reflections of the boat shimmer on the water, creating a serene nighttime setting.

Boat in Key West

4.94 out of 5 average rating, 18 reviews

Yacht Just Chillin': Anchored Out on the Ocean!

Destinations to explore

Beachfront rentals Smathers Beach