Beachfront vacation rentals in Key West

4.97 out of 5 average rating, 29 reviews

An aerial view showcases the beachfront location of the condominiums, with a gleaming pool surrounded by well-kept lawns. White sandy beaches meet the clear turquoise waters, while tropical palm trees sway gently in the breeze. Nearby canals and homes create a serene coastal community.

Condo in Marathon

*NEW* Private Beach, pool & fully loaded kitchen

Escape to paradise in our brand new, beautifully furnished Sun Life Vacation Homes beachfront oasis in the heart of Key Colony Beach, Florida, (some still call it Marathon). This luxurious two-bedroom, two-bathroom condominium invites you to experience the ultimate coastal retreat with private beach & pool access, tiki huts and BBQ grills. Come and experience the ultimate beachfront getaway at our Sun Life Vacation Homes, Key Colony Beach Club vacation rental. We recommend all guests purchas

4.88 out of 5 average rating, 113 reviews

A row of townhomes is positioned along the water's edge, surrounded by well-maintained landscaping. Lush green trees provide shade, and the calm water reflects the serene environment. The horizon reveals a glimpse of distant trees and open water.

Condo in Duck Key

Villa 5027 on Duck Key BOAT SLIP available

Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

4.91 out of 5 average rating, 95 reviews

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

Ocean Front Studio private Sandy Beach in Key West

Studio unit with fridge, microwave, settings for 2 and a king sized bed. Doors that open to a balcony overlooking the Atlantic Ocean. There is pool, hot tub, and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street. The resort is located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. There is free garage parking with the room. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy air conditioning.

4.98 out of 5 average rating, 56 reviews

Grouper Getaway @ Ocean Isles Fishing Village

Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautiful brand new fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic Ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.

4.75 out of 5 average rating, 4 reviews

A bright and inviting living area showcases a comfortable seating arrangement of a sofa and chairs, with tropical-patterned accents. A glass dining table is set to accommodate four, while a large sliding door opens to the screened balcony, revealing views of lush greenery.

Condo in Marathon

Garden Oasis Ocean Views Pool Beach U27

Uncover a hidden gem in our charming condo overlooking a tranquil garden with two unexpected side views of the ocean. It’s perfect for couples seeking a value-packed Keys getaway. A peaceful retreat, it is steps from the beach and pool, featuring a king bed, updated decor, and a screened balcony. With a full kitchen, it's your cozy base for exploring Marathon's beauty. Dive into relaxation or adventure, all while enjoying the comforts of our island home. Discover your Marathon haven today!

5 out of 5 average rating, 10 reviews

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

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!

Home in Upper Sugarloaf Key

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.

4.94 out of 5 average rating, 109 reviews

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.

4.93 out of 5 average rating, 263 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

A spacious balcony provides views of the ocean and pool area, with comfortable seating arrangements including two chairs and a table. The gentle wave pattern of the sea is visible in the background, along with a poolside and a nearby pier.

4.94 out of 5 average rating, 36 reviews

Ocean Oasis!OceanView-Private Beach/Pool/TikiHuts

Welcome to Ocean Oasis, your tropical haven in Marathon, Florida! Our stunning 2-bedroom, 2-bathroom condo is located at 501 E Ocean Dr, Marathon, FL 33050. Ocean Oasis offers the ultimate beachfront retreat, with a King-sized bed in the master bedroom and two full-sized beds in the second bedroom, comfortably sleeping six. The spacious balcony boasts breathtaking views of the ocean and pool, perfect for sipping morning coffee or enjoying a sunset cocktail. No Pets Allowed.

4.97 out of 5 average rating, 111 reviews

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

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 tiki hut with a thatched roof provides shaded seating, surrounded by tall palm trees. Clear blue waters extend to the horizon, while the sandy beach features white lounge chairs arranged nearby, creating a serene coastal setting.

4.85 out of 5 average rating, 115 reviews

Beachside Unit 37 - Come Relax on the Atlantic!

Unit 37 Details: Second Floor, Walk-in shower, Two Queen Beds, Twin Sofa Sleeper, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.” Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean.

4.88 out of 5 average rating, 127 reviews

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Popular amenities for Key West beachfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

New place to stay

Beach Home and Boater’s Paradise Sombrero

The image captures a sparkling private pool overlooking the water, with a sandy beach and a wooden dock in the distance. A yellow kayak is positioned nearby, and several lounge chairs are arranged by the pool, inviting relaxation under the tropical sky.

4.9 out of 5 average rating, 42 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

An aerial view of a canal-front home showcases a spacious backyard with a private swimming pool. A long dock extends into the water, bordered by lush greenery. The surrounding neighborhood features a mix of single and multi-story homes, with palm trees dotted throughout the landscape.

Sale! Lux Home, Walk to Beach, 90' Dock, Pool

5 out of 5 average rating, 4 reviews

A sunlit deck features white lounge chairs positioned towards a private beach and ocean view. A thatched-roof tiki hut provides shade, while a hammock is nestled nearby among greenery. The calm waters reflect the blue sky, enhancing the serene coastal setting.

Home in Islamorada

Charming Beach House directly ON the beach

Tiny homes in Big Pine Key

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.

4.81 out of 5 average rating, 21 reviews

RV In The Keys | Tropical Retreat

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

4.83 out of 5 average rating, 271 reviews

Key West Luxury Houseboat at Yacht Club Resort

A private backyard showcases a tranquil pool surrounded by a stone deck. Comfortable lounge chairs are positioned for relaxation, with a vibrant float placed in the water. The blue exterior of the house enhances the outdoor space under a partly cloudy sky.

4.93 out of 5 average rating, 85 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

A shaded outdoor porch features four blue adirondack chairs arranged around a round table, overlooking tranquil water views. The surrounding area is adorned with lush greenery and distant views of a bridge, creating a serene space for relaxation.

Townhouse in Duck Key

4.8 out of 5 average rating, 205 reviews

Vibrant Beachfront Villa

Beachfront home rentals with a pool

4.85 out of 5 average rating, 281 reviews

A spacious room features a large wooden bed with crisp white bedding. Light from a sliding glass door illuminates the space, revealing a view of palm trees and the outdoors. A ceiling fan and two bedside lamps provide ambient lighting, with a small desk and seating area visible.

Hotel room in Marathon

Wreckers House King Room - Adults Only

4.86 out of 5 average rating, 42 reviews

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

Powell Family Resort

An outdoor balcony space features a round table surrounded by two armchairs and a spacious sofa, all in light wicker with patterned cushions. Palm trees frame the serene ocean view, creating a relaxing retreat.

Hotel room in Marathon

5 out of 5 average rating, 5 reviews

Oceanfront Balcony King, Isla Bella, Beach Resort

Apartment in Marathon

Ocean front with private beach and pool!

A private pool area features two connected sections, including a spacious swimming area and a jacuzzi. Surrounding palm trees and well-maintained landscaping create a serene atmosphere. Bright blue skies and fluffy clouds reflect on the water's surface, inviting relaxation.

Vacation home in Islamorada

Port Antigua NEW lux apart

A sandy beach scene is depicted with palm trees swaying gently in the breeze. A rainbow arches over the turquoise sea, while a wooden dock stretches into the water. Two lounge chairs are positioned near the shoreline, creating a relaxing outdoor space.

Hotel room in Layton

4.59 out of 5 average rating, 17 reviews

Amazing Beachfront Studio w/ Stunning Gulf Views!

Townhouse in Layton

4.87 out of 5 average rating, 15 reviews

Florida Keys Getaway w/ Stunning Ocean Views

A serene beach scene features gentle waves lapping against a sandy shore. Lush palm trees provide shade in the foreground, while a bright blue sky with scattered clouds stretches overhead. Stones border the beach, enhancing the tranquil coastal atmosphere.

Sandy Beach Just Steps Away

Private beachfront home rentals

A spacious bed is adorned with crisp white linens and a vibrant throw pillow featuring a fish design. Large windows frame the room, allowing natural light to illuminate the interior while offering views of the ocean and nearby palm trees.

4.96 out of 5 average rating, 227 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

4.85 out of 5 average rating, 107 reviews

Beachside Unit 14 - Brand New Kitchen and Bathroom

A spacious sleeping area includes a king-sized bed with crisp white bedding and decorative pillows. Metal fish sculptures adorn the wall, complemented by two bedside lamps. A dark sectional sofa is positioned nearby, creating a comfortable seating area for relaxation.

4.92 out of 5 average rating, 313 reviews

Key Colony Beach Luxury Condo, New Modern Interior

A modern living area is displayed with light-colored walls and a wood-style floor. A comfortable sectional sofa and vibrant blue seating surround a circular table. A flat-screen television mounts on the wall, and natural light enters through two windows, enhancing the bright atmosphere.

4.96 out of 5 average rating, 263 reviews

Keys Breeze Ocean View Condo & Pool - Key Colony

4.92 out of 5 average rating, 253 reviews

Modern Beachfront Steps to Beach/Pool, Key Colony

A well-furnished bedroom features a spacious bed adorned with blue accent pillows and crisp white bedding. Two bedside lamps with decorative fish motifs sit on woven side tables. Colorful art pieces and wooden oars are displayed on the walls, complementing the relaxing atmosphere.

4.95 out of 5 average rating, 200 reviews

Keys Time Condo Oceanfront Complex Heated Pool

A bright and airy bedroom features a spacious bed with crisp white bedding and decorative pillows. Nightstands with turquoise lamps flank the bed, and starfish art adorns the walls. Natural light filters through the shutters, creating a fresh and inviting atmosphere.

4.91 out of 5 average rating, 245 reviews

Poolside 2 Bdrm in Oceanfront Complex, Key Colony