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Waterfront vacation rentals in Sunset Key

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Sunset Key

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

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Top guest favorite

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

Home in Marathon

4.99 out of 5 average rating, 145 reviews

Cancellation Deal; Sept 27 thru Oct 04; Save now!

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

Cottage in Cudjoe Key

4.93 out of 5 average rating, 135 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

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.

An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

Home in Cudjoe Key

4.86 out of 5 average rating, 103 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

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

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

Boat in Key West

4.91 out of 5 average rating, 200 reviews

Stay on the Roxie!

Enjoy, peaceful, ocean-breezy, star-filled nights, on the water! Free parking and free round trip transport 1 to & 1 from Roxie per night’s stay! Roxie is anchored in a protected, shallow 3-4ft lagoon. We live on a boat a half-mile away should you need anything. 😊 Roxie has a Keurig, snacks like chips, breakfast muffins or donuts , Keurig pods, bread, peanut butter and jelly, and bottled waters. No cooking but you may bring to go food, drinks. 🛥️🌴

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!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). 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 point and enjoy the underwater scenery!

A serene pool area features a clear blue water swimming pool surrounded by lounge chairs and umbrellas. A lush landscape of palm trees and green foliage complements the setting, with a charming cottage visible in the background.

Townhouse in Key West

4.92 out of 5 average rating, 165 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

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 comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.

Home in Cudjoe Key

4.9 out of 5 average rating, 114 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

A scenic view of the waterfront reveals a calm harbor lined with boat slips. The vibrant blue water reflects the sky, while a tiki hut and chaise lounge chairs surround a heated pool in the foreground, enhancing the coastal ambiance.

Condo in Key West

4.87 out of 5 average rating, 218 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just 1 mile to Duval St, the Seaport, and Hemingway House. Enjoy on-site boat slips, heated pool, tiki bar, BBQ grills, parking, elevator, and secure keyless entry. Fish cleaning station and commercial ice machine available. Large park with tennis courts next door. Walk or bike everywhere—only 10 minutes from EYW airport!

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

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

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A space thats all yours, with room for everyone

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Sunset Key waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

The resort-style pool is framed by comfortable lounge chairs in vibrant blue and white. A shaded clubhouse with a metal roof overlooks the sparkling water, offering a relaxing spot for guests. Lush palm trees provide a tropical backdrop against a clear blue sky.

Apartment in Marathon

4.8 out of 5 average rating, 5 reviews

#1 Island Hideaway Marathon

A spacious outdoor patio is displayed, featuring a dining table surrounded by six chairs. The railing offers a view of Garrison Bight Marina, where boats are docked and palm trees sway. Sunlight casts patterned shadows across the patio floor.

Apartment in Key West

4.9 out of 5 average rating, 51 reviews

Key West Condo 2B/2B with Pool & Boat FREE Slip

The property is positioned near the shoreline, featuring a modern design with multiple balconies. Lush palm trees frame the exterior, while a landscaped garden adds greenery. The serene ocean can be seen in the background under a twilight sky.

Apartment in Key West

5 out of 5 average rating, 5 reviews

Hyatt Windward Pointe! Great Location!

A spacious pool area features a large swimming pool surrounded by lounge chairs and vibrant blue umbrellas. Lush palm trees provide shade, and ocean views are visible in the background, enhancing the tranquil atmosphere of the outdoor space.

Apartment in Key West

5 out of 5 average rating, 7 reviews

Henry's Penthouse On The Ocean

The open living space features a cozy couch and vibrant armchair, with a seating area seamlessly connected to the kitchen and dining space. Large glass doors offer a view of the balcony and serene harbor, allowing natural light to brighten the room.

Apartment in Marathon

5 out of 5 average rating, 6 reviews

Boot Key Harbor Penthouse

A spacious living area is furnished with a comfortable sofa and armchair, complemented by a wooden coffee table. A large entertainment center features a television, while soft lighting enhances the room's ambiance. The space is adorned with tasteful decor and tiled flooring.

Apartment in Key West

The Galleon Resort - Key West

Top guest favorite

A welcoming living area features a dark gray sofa and armchair, complemented by patterned cushions. A light wooden coffee table sits atop beige tile flooring. A large flat-screen TV is mounted on the wall, and natural light filters through window coverings, creating a bright atmosphere.

Apartment in Marathon

4.97 out of 5 average rating, 65 reviews

Dock POOL Kayaks Bikes Beach2mi WalkToStores

A refreshing pool area is surrounded by green palm trees and blue umbrellas. Lounge chairs are arranged neatly around the pool, while tables with chairs provide seating for guests. The clear blue sky enhances the inviting atmosphere of the community space.

Apartment in Key West

4.87 out of 5 average rating, 106 reviews

Penthouse in Paradise

Waterfront house rentals

A modern interior showcases a spacious living area with a sectional sofa adorned with decorative cushions. Adjacent, a bright kitchen is visible, alongside a dining table. A cozy bedroom features a bed with plush linens. Outdoor seating is arranged on a covered patio, surrounded by greenery.

Home in Marathon

4.89 out of 5 average rating, 168 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Top guest favorite

A serene outdoor space features a clear swimming pool surrounded by palm trees. A covered lounge area provides shade, while lounge chairs offer spots for relaxation. The tranquil waters are visible in the background, enhancing the overall atmosphere of the private retreat.

Home in Marathon

5 out of 5 average rating, 14 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

Home in Cudjoe Key

5 out of 5 average rating, 17 reviews

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

A spacious waterfront deck features a thatched-roof structure providing shade. Comfortable seating arrangements are positioned around the area, with panoramic views of the calm Atlantic Ocean and distant islands visible in the background.

Home in Cudjoe Key

4.97 out of 5 average rating, 30 reviews

Tiki Time in Cudjoe Key 136

An aerial view of a spacious villa surrounded by lush greenery and palm trees. A tile roof highlights the second floor balcony which features comfortable seating. The property is situated near calm waters, enhancing its coastal appeal.

Home in Marathon

4.91 out of 5 average rating, 182 reviews

Beachfront Villa - Florida Keys

A modern beach home stands parallel to a wooden dock, set against a clear blue sky. Lush greenery borders the property, while palm trees offer a tropical feel. The two-story structure features a spacious front porch, enhancing the outdoor living experience.

Home in Marathon

4.9 out of 5 average rating, 48 reviews

Tropical Dream Vacation - 3bdrm/2bath CANAL FRONT!

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

Home in Cudjoe Key

4.81 out of 5 average rating, 277 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

An aerial view displays a charming home situated on a canal, surrounded by lush greenery. A wooden dock extends along the water, complemented by native plants. The building features a sloped roof and wrap-around porch, offering a serene and inviting water access area.

Home in Marathon

4.95 out of 5 average rating, 74 reviews

Private 174ft Dock, Boat Launch, Sombrero Beach

Waterfront condo rentals

A tranquil outdoor space features a large swimming pool surrounded by lounge chairs. Lush palm trees provide shade, while the Gulf of Mexico is visible in the background. A small marina is seen with boats, enhancing the serene waterfront atmosphere.

Condo in Key West

The Galleon Resort in beautiful Key West-2 bedroom

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, 79 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

A balcony view captures a sunset over the water, with palm trees framing the scene. A small table and two wooden chairs overlook the harbor, providing a perfect setting for relaxation. The horizon is painted in warm hues, with boats visible in the distance.

Condo in Key West

4.69 out of 5 average rating, 16 reviews

Spacious 2BR Oceanfront | Balcony | Pool

A spacious balcony features a round table surrounded by four high-backed chairs. The railing offers unobstructed ocean views complemented by serene skies. Lush greenery and distant buildings can be seen beyond the balcony, creating a relaxed outdoor space.

Condo in Key West

4.72 out of 5 average rating, 99 reviews

Top floor Ocean Views, Spacious 2 Bedroom Condo, V

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

A private balcony features a round table set with soft blue plates and glasses of juice. Comfortable chairs surround the table, with a bowl of fresh fruit placed in the center. Lush greenery and partial ocean views contribute to a serene outdoor setting.

Condo in Key West

4.85 out of 5 average rating, 158 reviews

Anchor Drop modern elegance upgrades throughout vi

Condo in Marathon

4.8 out of 5 average rating, 5 reviews

M18 - Spacious 3 bedroom, 2 bath Gulf side condo!

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