Beachfront rentals near Smathers Beach

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Top-rated beachfront rentals near Smathers Beach

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

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Guest favourite

An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

Cottage in Cudjoe Key

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

ViewBeachValue

4.89 out of 5 average rating, 178 reviews

Guest favourite

A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.

Cottage in Cudjoe Key

Calypso Cottage

This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat (larger boat? just ask!) right outside your door, enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, board games, wifi & roku) and of the community (Pools, spa, boat launch, pickle ball, bocce, tennis) even a library and general store!). This is a magical location to launch all your Florida keys adventures! Canal patio for drinks? Lush screen porch for coffee? It's on!

BeachWalkabilityQuiet

4.75 out of 5 average rating, 194 reviews

Top guest favourite

Two pelicans are perched on a wooden dock, surrounded by rippling water. The dock is supported by green posts, providing a serene setting in a tropical landscape. Subtle foliage in the foreground enhances the natural ambiance of the scene.

Home in Cudjoe Key

Oceanside home 111, dock,kayaks,bikes,pool,fishing

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #111 and I also rent adjacent homes 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

ViewBeachDecor

4.97 out of 5 average rating, 33 reviews

Home in Cudjoe Key

Latitudes-Ocean Front Pool

This tropical 6 bedroom 4 bath oceanfront home has a private heated salt water pool and huge outdoor living space. There is beach access, shared dock space and outdoor gazebo to watch sunsets. There is a 3rd story balcony that offers spectacular views of the sunrise and sunset. Bring up to a 24' boat or paddle out on one of the shared kayaks onsite. Fully equipped kitchen, linens, beach towels, a propane BBQ grill and 2 washer/dryers. This home is priced based on the number of guests.

ViewBeachQuiet

4.75 out of 5 average rating, 20 reviews

Hotel room in Key West

Traditional King, The Pier House, Pet-Friendly

The Pier House Resort & Spa at 1 Duval Street is Key West's premier island-chic destination — featuring a private white sand beach, full-service spa, award-winning dining at One Duval, the Three Palms Beach Bar, and easy access to Mallory Square and the island's legendary nightlife. The Traditional King is a comfortable and well-designed room with custom furnishings and locally inspired artwork. A solid Key West base with all resort amenities at hand. HAVANA HEIGHTS TWO BEDROOM SUITE

BeachGetting aroundNearby

5.0 out of 5 average rating, 6 reviews

Superhost

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

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.

WalkabilityViewBiking

4.9 out of 5 average rating, 136 reviews

Superhost

The exterior of the Sugarloaf Key Hotel is framed by palm trees and lush tropical vegetation. The two-story building features multiple balconies with clear railings, set against a blue sky. Colorful plants enhance the vibrant ambiance surrounding the hotel.

Condo in Summerland Key

Standard Suite at Sugarloaf Key Hotel

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 4-person vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

ViewBeachParking

5.0 out of 5 average rating, 7 reviews

Guest favourite

An Olympic-sized swimming pool is surrounded by a sun deck, featuring lounge chairs and palm trees. The pool’s clear water reflects the sky, creating a serene atmosphere. The ocean and well-maintained tropical garden can be seen in the background.

Condo in Key West

Oceanfront Key West Condo

Discover the charm and grace of Old Key West in a new and distinctive setting. Luxury, two-bedroom, two-bath, waterfront condominium set in a tropical garden paradise with sweeping balconies overlooking the Atlantic Ocean. Your vacation hideaway is decorated in authentic island tradition with fully-equipped modern kitchen, living room with wet bar, and dining room. Washer/dryer, phone, TVs, stereo, and over-sized jacuzzi tub in the master suite.

BeachViewHospitality

4.83 out of 5 average rating, 30 reviews

Guest favourite

A hand holds a tall, fluted glass filled with a yellow beverage against a backdrop of palm trees and the Atlantic Ocean. The clear blue sky complements the tranquil scene, with greenery visible in the foreground and a beach path in the distance.

Condo in Key West

Key West Condo with Balcony Ocean View

Enjoy beautiful views of the Atlantic Ocean while enjoying a private balcony. Newly re-modeled kitchen. Air conditioning and ceiling fans located in every room. Amenities include pool, hot tub, and tennis courts. Just a few steps across the street in Smathers Beach which offers beach chairs, umbrellas, paddle boards, kayaks and sailboats available for rent. Two vehicles max. NO TRAILERS of any kind allowed to park on property.

ViewBeachAmenities

5.0 out of 5 average rating, 46 reviews

Apartment in Key West

2BR Private Beachfront Coconut Oasis

Thank you for Visiting Chimera Vacations LLC! We look forward to welcoming you to a private beachfront oasis of your own. Private pool deck and hot tub open onto a small intimate sandy beach, where you can stroll right on over to "Louie's Backyard" the waterfront bar and eatery just next door. 7-Nights Stay Required (SATURDAY-SATURDAY for our weekly rate offers) -otherwise additional fee may apply

Sleep qualityCleanlinessAccuracy

A multi-level condominium is situated near the Atlantic Ocean, featuring a distinctive architectural design with a peaked roof and multiple balconies. Lush palm trees and a well-maintained garden contribute to the coastal ambiance, with the ocean visible in the background under a clear blue sky.

Resort in Key West

Hyatt Windward Pointe - Key West - Amazing Resort!

Atlantic ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium offering a master suite with king bed and adjoining bath with walk-in shower and jetted tub, and guest bedroom with queen bed and full bath. Deluxe amenities include full kitchen, dining area, living room with TV and stereo CD player, furnished balcony and wireless Internet

HospitalitySleep qualityIndoor spaces

5.0 out of 5 average rating, 4 reviews

Guest favourite

A clear, inviting outdoor pool is surrounded by lush tropical landscaping. Palm trees are scattered around, softening the edges of the pool area. A multi-story building with a light-colored exterior provides a backdrop, featuring several balconies with white railings.

Condo in Key West

Hyatt Beach House-Quiet Key West Spot!

Located 2.7 miles from Smathers Beach and 3.8 miles from the Ernest Hemingway Home & Museum, this quiet piece of Key West is the best location for relaxation. The property is on a corner of the island featuring its own private beach and water access. Other activities in the area include scuba diving, snorkeling, parasailing, fishing, dolphin watching, and boating.

ViewWalkabilityHot tub

5.0 out of 5 average rating, 22 reviews