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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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Superhost
The RV interior features warm wood cabinetry and dark furnishings, creating a homey environment. A fully equipped kitchen is seen beside a cozy living area with a sofa and two armchairs. Natural light filters through the window, illuminating the space with a soft glow.
Camper/RV in Big Pine Key
4.7 out of 5 average rating, 60 reviews

LARGE LOT & RV | Fishermen Camp

A classic Keys RV. RV is a 2010 5th wheel in original condition w/bedroom, 2 flat screen tv’s & full kitchen (mini fridge & cooler) - a true keys camping experience in a park w/pool and coin laundry. Clean, private & fenced in yard. Parking for 1 vehicle & Boat trailer. We have park bathrooms available for hot showers: sitting area (enclosed w/screen). Perfect location to explore the lower keys-just 30 minutes to Key West 10 minutes to Bahai Honda State Park. Free local boat ramp 3 miles away

Guest favorite
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
4.9 out of 5 average rating, 159 reviews

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!

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
4.72 out of 5 average rating, 159 reviews

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!

Top guest favorite
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
5 out of 5 average rating, 18 reviews

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.

Guest favorite
A three-story oceanfront home is showcased, featuring a spacious outdoor deck and private pool area. Lush palm trees surround the property, and a sandy pathway leads to the entrance. The home is painted in a light color, blending with the bright blue sky.
Home in Cudjoe Key
4.91 out of 5 average rating, 11 reviews

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.

Guest favorite
An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.
Condo in Summerland Key
5 out of 5 average rating, 6 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

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 6-person pet-friendly 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!

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, 107 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.

Guest favorite
A private beach scene features four adirondack chairs in white and turquoise, positioned in soft, sandy areas under palm trees. The calm ocean extends to the horizon, with a distant dock visible on the water. Bright clouds hover in a blue sky.
Home in Sugarloaf Key
4.82 out of 5 average rating, 120 reviews

The Guest House - Sugarloaf Beach Key West

One of a kind beach house with a private sandy beach, dock and boat dockage . Featuring a tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Ocean views. natural Florida Keys private beach, great for swimming, snorkeling, kayaking, paddle boarding or just reading a book by a palm tree * "Dock is currently undergoing maintenance, dockage will not be available until further notice"

Guest favorite
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
5 out of 5 average rating, 36 reviews

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.

A private screened-in balcony features a glass table set with breakfast items and a beverage. Two wicker chairs surround the table, while a guest enjoys the ocean view in the background, framed by palm trees and an evening sky.
Resort in Key West
4.89 out of 5 average rating, 9 reviews

Hyatt Windward Pointe Resort: Beachfront Condo

Experience this tropical paradise as you relax in a family friendly timeshare within the Hyatt Residence Club. Have breakfast on the oceanfront balcony followed by a dip in the pool/hot tub or visit the nearby spa. There are 2 bedrooms and 1 sofa bed which can fit 6 people. 2 bathrooms with a spa tub in master bedroom. Fully functioning kitchen and dining area in addition to an in-home washer/dryer unit.

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.
Houseboat in Key West
4.85 out of 5 average rating, 259 reviews

Key West Luxury Houseboat at Yacht Club Resort

PANORAMIC Ocean Views - POOL 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, 500 square foot Rooftop Sky-Deck - 2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV, 42 inch TV, 32 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

Guest favorite
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
5 out of 5 average rating, 9 reviews

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.

Popular amenities for beachfront rentals near Smathers Beach

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Pet-friendly beachfront home rentals

A spacious hotel room features a king-sized bed with crisp white linens, complemented by a dark wooden headboard. A ceiling fan is visible above, while a television and dresser provide practical amenities. Artwork adorns the walls, and natural light is introduced through a partially opened door leading to a hallway.
Hotel room in Key West

Elegant Stay! Pet-friendly, Pool, Near Cliff Walk!

A serene pool area is surrounded by tropical palm trees and lush greenery. The clear water reflects the bright sky, while lounge chairs with umbrellas are arranged neatly around the pool's perimeter, offering a relaxing space for guests.
Hotel room in Key West

Traditional 2 Queen, The Pier House, Beach Access

A stylish bar area features a long dark wooden counter with high-backed stools. Soft lighting creates a welcoming ambiance, while shelves stocked with various spirits are visible in the backdrop. The adjacent dining space is furnished with modern tables and chairs.
Hotel room in Key West

3 Waterfront Rooms Perfect for Family Vacation!

A spacious Junior Suite features a comfortable sitting area with a sofa adorned with decorative cushions, accompanied by a wooden coffee table and a modern reading chair. Two bedside lamps provide soft lighting, and natural light enters through double doors leading to a private balcony.
Hotel room in Key West

Pure Wellness Spa Jr Suite, The Pier House Resort

The room features two queen beds with white linens, complemented by bedside lamps. A large television is mounted on the wall opposite the beds, with a sleek dresser beneath it. French doors provide access to a patio with garden views, enhancing the space's natural light.
Hotel room in Key West

Serene Resort w/ Private Beach & Spa in Key West

An outdoor dining area features elegantly set tables with clean white linens, surrounded by beige wicker chairs. Large umbrellas provide shade against the blue sky and distant ocean views. Potted greenery adds a touch of nature, creating a relaxed atmosphere for guests.
Hotel room in Key West

2 Traditional Two Queen, Pier House, Near Duval St

Superhost
A large swimming pool is surrounded by a protective fence, showcasing a connected spa. Sun loungers are placed around the pool, while tropical plants and stones enhance the outdoor setting. The serene ocean view is visible in the background.
Home in Cudjoe Key
4.2 out of 5 average rating, 5 reviews

Oasis

A view from a balcony overlooks a private white sand beach and the turquoise waters of the ocean. Lush palm trees surround the area, while the hotel building is seen with large windows accommodating guests. Sun loungers and umbrellas are arranged along the beach.
Hotel room in Key West

Seaside Getaway! Gym, Spa, Pool Harbor Access

Beachfront home rentals with a pool

This hotel room showcases two Queen beds with crisp white linens and decorative pillows. A stylish wooden dresser and a flat-screen TV are positioned for convenience. Natural light floods the room from a balcony offering ocean views, complemented by a comfortable seating area.
Hotel room in Key West

Key West Perfect Family Vacation! Pets Allowed

A comfortable living area is visible, featuring a light brown sofa with tropical-themed cushions. A glass table sits in front of the sofa. Floor-to-ceiling doors open onto a balcony with a view of the ocean, where a pair of black outdoor chairs is positioned.
Hotel room in Key West

Relaxing Ocean View Stay! Pool & Onsite Dining!

Hotel room in Key West

Pet-friendly Accommodation, Balcony, Outdoor Pool!

A hotel room features two spacious queen beds with white linens, complemented by a wooden headboard. A large flat-screen TV is mounted on a dresser, and natural light filters in through multiple windows adorned with wooden shutters, creating a bright and inviting ambiance.
Hotel room in Key West

Lanai Two Queen, The Pier House, Beach Access

A spacious hotel room features a king bed and a sitting area. A large television is mounted on the wall, and a coffee table sits between two comfortable chairs. Bright light enters through opened French doors that lead to a private outdoor area.
Hotel room in Key West

Tropical Paradise Resort Near Southernmost Point

A bright and airy hotel room is presented, featuring a spacious king size bed with crisp white linens. A comfortable chair stands to the side, complemented by a television and a wooden dresser. Large windows showcase lush greenery outside, adding a touch of nature.
Hotel room in Key West

Key West Find: Oceanfront Suite, Pvt Beach Access

A spacious outdoor dining area features multiple round tables set for a meal, each adorned with elegant place settings and floral centerpieces. The ocean and sunset provide a stunning backdrop, with soft clouds reflecting warm hues across the sky.
Hotel room in Key West

2 Relaxing Seafront Stays Near Historic Landmarks

A spacious bed showcases a fresh, crisp white coverlet, complemented by decorative pillows featuring a floral design. A sleek bedside table with a blue lamp is positioned alongside, adding a subtle pop of color to the neutral-toned room.
Hotel room in Key West

Spa, Pool, Gym | Near Downtown Newport

Private beachfront home rentals

A screened-in balcony features a wooden dining table surrounded by sturdy chairs with bright yellow cushions. A comfortable seating area includes a dark wicker chair and a gray sofa, while palm trees sway gently in the background, enhancing the tropical atmosphere.
Apartment in Key West

Beach House Resort + Premium Amenities, 2BR Condo

A serene sunset view is captured from a wooden dock extending over calm waters. Silhouetted figures can be seen seated at the end of the dock, with vibrant orange and purple hues reflecting off the surface. Framed by natural foliage, the scene offers a peaceful atmosphere.
Home in Summerland Key
4.87 out of 5 average rating, 39 reviews

Powell Family Resort

A vibrant sunset casts warm hues over the water, creating a mirror-like reflection. A wooden dock extends into the foreground, leading to the horizon, surrounded by silhouettes of trees along the shoreline. Outdoor seating is visible near the water's edge.
Home in Summerland Key
4.59 out of 5 average rating, 93 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Superhost
A spacious bedroom is furnished with a large bed layered in neutral linens. Shuttered windows provide natural light and a view of lush greenery. A patterned armchair adds comfort to the room, creating a relaxing retreat.
Condo in Key West
4.5 out of 5 average rating, 8 reviews

Galleon Resort - Walk to Duval & Mallory Square!

Superhost
A well-maintained 28-ft Grey Wolf RV is parked on a gravel lot, surrounded by tropical greenery. Two lounge chairs are positioned on a green patch of grass, creating a relaxing outdoor seating area. Sunshine filters through the clouds, adding a bright ambiance to the scene.
Camper/RV in Big Pine Key
4.79 out of 5 average rating, 19 reviews

RV In The Keys | Tropical Retreat

Superhost
A sandy beach area is framed by swaying palm trees, leading to a two-story bungalow elevated on stilts. Lounge chairs are arranged on the shore, providing a relaxing spot, while kayaks are visible in the background, enhancing the inviting beach setting.
Home in Upper Sugarloaf Key
4.74 out of 5 average rating, 96 reviews

Palm - Beach Houses Key West

Guest favorite
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
4.79 out of 5 average rating, 24 reviews

Oceanfront Key West Condo

Guest favorite
A waterfront view of a series of light-colored homes with multiple balconies, situated along the edge of a calm bay. Colorful Adirondack chairs are arranged on the porch, and a wooden walkway leads towards the structures, enhancing the coastal ambiance.
Home in Cudjoe Key
4.96 out of 5 average rating, 23 reviews

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

Luxury beachfront home rentals

A private balcony features patio seating with two wicker chairs and a round table. Lush palm trees and the ocean are visible in the background, offering scenic views of the calming water and distant boats. Bright sunlight illuminates the area, enhancing the tranquil setting.
Hotel room in Key West

Oceanfront 2Q, The Pier House, Private Beach, Pets

A well-appointed hotel room features two queen beds with crisp white linens. A light wood dresser stands against one wall, complemented by a flat-screen TV. Natural light filters through sliding doors leading to a private outdoor space, which is framed by lush greenery.
Hotel room in Key West

1BR Suite 2 Queen, The Pier House, Resort-style

A private balcony offers panoramic ocean views, featuring two lounge chairs with folded towels. A cozy sectional sofa with decorative pillows is positioned beside swaying palm trees, while the tranquil sea horizon stretches into the distance. Soft natural light illuminates the relaxation area.
Hotel room in Key West

Oceanfront Suite, The Pier House, Beach Resort

Hotel room in Key West

Havana Heights 2BR Suite at The Pier House Resort

A waterfront view showcases the serene Gulf of Mexico, flanked by swaying palm trees. The marina is visible with several boats docked, while the vibrant blue water contrasts with the lush greenery in the foreground. A clear sky enhances the tranquil atmosphere.
Apartment in Key West

Waterfront Galleon Marina+Beach, Near OldTown, 1BR

A waterfront balcony is showcased with dark wicker chairs and a matching table. Palm trees and the blue gulf are visible, creating a serene coastal environment. The tiled flooring complements the relaxing outdoor space, inviting moments of leisure and tranquility.
Hotel room in Key West

Oceanfront King, The Pier House, Pvt Beach Access

A coastal-themed hotel room is depicted with a king-size bed and a large window offering waterfront views. A small balcony is visible, furnished with a chair. A flat-screen TV and a light blue lamp are positioned on a white countertop, complementing the room's neutral tones.
Hotel room in Key West

Oceanfront Stay Near Hemingway Home - 5 Min Walk

A private patio or balcony area features decorative shutters that open to lush greenery. A round, dark wicker table stands at the center, enhancing the serene outdoor setting surrounded by tropical plants.
Hotel room in Key West

Stunning Views | Pool + Near Historic Sites

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