Beachfront vacation rentals in Key West

4.96 out of 5 average rating, 25 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, 109 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.

An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.

5 out of 5 average rating, 20 reviews

Private Beach in Marathons Key Colony Beach

Atlantic Ocean location with a beautiful ocean view. The beach is private for sunbathing, fishing, diving, and snorkeling. The sea life off the beach is abundant. Watching the boats come in and out of Vaca Cut is very cool. In addition to the onsite pool there is a Tiki Hut, beachside barbecue area, and a beautiful grass lawn. Being on the third floor offers beautiful ocean views. Please see my host guidebook for detailed info on a few of the local attractions including fav restaurants.

4.98 out of 5 average rating, 50 reviews

Home in Marathon

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.

A spacious studio features a comfortable bed dressed in soft blue and white linens, complemented by decorative pillows. A cozy seating area with a light blue sofa and armchair stands nearby. Windows provide unobstructed ocean views, framed by tropical artwork and natural light.

4.92 out of 5 average rating, 253 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.

4.97 out of 5 average rating, 29 reviews

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.

Condo in Marathon

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.

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, 105 reviews

Lighthouse - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

4.97 out of 5 average rating, 108 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 beachside tiki hut provides shaded seating, surrounded by palm trees and white sandy shores. The clear blue ocean extends toward the horizon, reflecting sunlight. Lounge chairs are positioned nearby, inviting guests to relax in a tropical outdoor setting.

4.89 out of 5 average rating, 158 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Unit 39 Details: Second Floor Unit, Tub with Shower, Two Queen Beds, 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. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

4.89 out of 5 average rating, 123 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.

5 out of 5 average rating, 36 reviews

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.

4.97 out of 5 average rating, 108 reviews

A light-filled living room features a blue sofa, a comfortable chair, and a glass coffee table. Large sliding doors open to a balcony with ocean views. A soft area rug lies on the tiled floor, adding warmth to the space, while sunlight illuminates the room.

Apartment in Marathon

Beachfront Condo w/ Ocean Views in Marathon

Beautifully decorated 2nd floor end unit with stunning panoramic ocean views from the balcony, living room and master bedroom. Two bedrooms / two full bathrooms and washer and drier in unit. Full kitchen. Directly on the beach! Beach chairs, umbrellas and towels provided for you. Guests have access to the heated swimming pool, tennis court and beach. Master bedroom king-size memory foam mattress

Popular amenities for Key West beachfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

4.88 out of 5 average rating, 40 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

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

5 out of 5 average rating, 7 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)

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.

Home in Marathon

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

Camper/RV 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.

4.79 out of 5 average rating, 19 reviews

RV In The Keys | Tropical Retreat

A stilted house stands proudly under a bright sky, surrounded by palm trees. A gravel driveway is visible, accommodating vehicles. The exterior reflects tropical charm, showcasing a mix of light-colored siding and wooden accents while a nearby patio area offers additional outdoor space.

Home in Marathon

4.8 out of 5 average rating, 65 reviews

7 Mile Ocean Bliss

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

4.84 out of 5 average rating, 260 reviews

Key West Luxury Houseboat at Yacht Club Resort

4.87 out of 5 average rating, 55 reviews

A waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.

Apartment in Marathon

Little Venice in Marathon (in the Beautiful Keys)

Beachfront home rentals with a pool

4.85 out of 5 average rating, 265 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

4.83 out of 5 average rating, 18 reviews

An aerial view of the beachfront condo building is captured, revealing its three stories and proximity to the ocean. Surrounding palm trees enhance the tropical ambiance, while the serene blue water reflects sunlight. A small parking area is visible in front of the property.

Apartment in Marathon

Seaside Villa~ Charming Beachfront Condo w/ Pool!

An outdoor swimming pool is surrounded by palm trees, with lounge chairs and umbrellas arranged neatly around its perimeter. The pool reflects the sky's colors while the sandy beach and ocean are visible in the distance, creating a serene beachside environment.

Hotel room in Islamorada

5 out of 5 average rating, 3 reviews

Ideal Mix of Comfort & Value! Free Parking/ Pool

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, 3 reviews

Oceanfront Balcony King, Isla Bella, Beach Resort

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

4.77 out of 5 average rating, 13 reviews

Amazing Beachfront Studio w/ Stunning Gulf Views!

An aerial view of a condo complex along a serene beachfront. The clear blue Atlantic Ocean stretches into the distance, while a heated pool is visible in the center of the complex. Lush palm trees and well-maintained landscaping surround the buildings.

Condo in Marathon

4.83 out of 5 average rating, 6 reviews

Beachfront Condo on Coco Plum Beach w/heated pool

A bright and airy studio room features two queen-sized beds with crisp white bedding and anchor-themed decorative pillows. Light blue accents are present throughout, complemented by coastal artwork on the walls. Large windows allow natural light to fill the space, enhancing its serene atmosphere.

4.91 out of 5 average rating, 323 reviews

Coastal Key Colony Beach Condo, Oceanfront Complex

A serene pool area is surrounded by lush palm trees and provides multiple lounge chairs with blue and white striped canopy umbrellas. The water in the pool glistens under a clear blue sky, enhancing the inviting relaxation experience.

Hotel room in Marathon

Marathon Oceanfront Room | 2Queens + Spa-Like Bath

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 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, 220 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

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, 299 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.

4.97 out of 5 average rating, 252 reviews

Keys Breeze Ocean View Condo & 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, 195 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, 237 reviews

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

A bright studio condo is shown with two queen beds, separated by privacy screens. Tropical decor includes a seahorse sculpture and dolphin wall accents. A cozy blue couch is present, accompanied by a light-colored accent chair. A dining table with floral artwork completes the inviting space.

4.91 out of 5 average rating, 153 reviews

Seaside Whimsy - Beach and Pool, Key Colony Beach