Beachfront holiday rentals in Key West

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.

4.96 out of 5 average rating, 25 reviews

*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

Superhost

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.

Apartment in Duck Key

4.88 out of 5 average rating, 109 reviews

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.

4.98 out of 5 average rating, 49 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.

Apartment in Key Colony Beach

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

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

4.93 out of 5 average rating, 356 reviews

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

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.

4.96 out of 5 average rating, 27 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.

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.

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.

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.

Apartment in Key Colony Beach

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

4.87 out of 5 average rating, 135 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in 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.

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.

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.

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.

Flat 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 beachfront rentals in Key West

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

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

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.

Apartment in Summerland Key

5 out of 5 average rating, 6 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

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

4.85 out of 5 average rating, 259 reviews

Key West Luxury Houseboat at Yacht Club Resort

4.87 out of 5 average rating, 54 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.

Flat in Marathon

Little Venice in Marathon (in the Beautiful Keys)

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

4.82 out of 5 average rating, 190 reviews

Vibrant Beachfront Villa

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

Beachfront home rentals with a pool

Superhost

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.

Flat in Marathon

4.83 out of 5 average rating, 18 reviews

Seaside Villa~ Charming Beachfront Condo w/ Pool!

A screened balcony offers views of the ocean and pool, framed by palm trees. A round table and chairs provide a space for relaxation. Blue-green decorations hang from the ceiling, complementing the coastal atmosphere.

4.8 out of 5 average rating, 5 reviews

Beachfront paradise, heated pool and ocean view #9

A clear view of a swimming pool is framed by palm trees and greenery. Lounge chairs are positioned alongside the pool, and the ocean can be seen in the distance. The scene conveys a relaxed outdoor atmosphere, inviting guests to enjoy the coastal surroundings.

5 out of 5 average rating, 4 reviews

Key West 2 BR Deluxe, Beach Front, sleeps: 6

A spacious living area features large glass doors that allow natural light to fill the room, offering views of the surrounding landscape. Comfortable blue sofas are arranged around a central coffee table on tiled flooring, complemented by a stylish armchair. Decor elements include framed pictures and modern lamps.

4.6 out of 5 average rating, 149 reviews

Colorful 2BR Oceanfront 4th-Floor | Balcony

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

Superhost

A spacious outdoor area features a heated pool surrounded by lounge chairs and shaded palapas. The beach is visible in front of the property, with palm trees providing natural accents. The layout includes several benches, creating inviting spaces for relaxation and enjoyment of the ocean breeze.

Apartment in Islamorada

4.85 out of 5 average rating, 20 reviews

Den Suite Two Balconies- Islamorada

4.94 out of 5 average rating, 48 reviews

A spacious living area features a gray sectional sofa adorned with blue accent pillows. Light wood tables complement the hardwood floor. A large painting of a coastal scene is displayed on the wall, and natural light filters in through shuttered windows.

Holiday home in Marathon

Cabana Club Condo: Key Colony Beach, FL

5 out of 5 average rating, 9 reviews

The room features two spacious beds with light-colored bedding, complemented by decorative pillows. A ceiling fan is present above, while large windows with shutters allow natural light. Colorful artwork depicting flamingos adorns the walls beside bedside tables and lamps.

Flat in Key Colony Beach

2 Bdrm Oceanfront Complex Private Beach & Pool

Private beachfront home rentals

4.98 out of 5 average rating, 82 reviews

A serene outdoor seating area features two woven chairs facing a sunset over the bay. A small metallic table sits between the chairs, and palm trees are visible in the distance, framing the tranquil water view.

Townhouse in Islamorada

Bayside Townhome in Islamorada with Boat Slip

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.

4.83 out of 5 average rating, 6 reviews

Beachfront Condo on Coco Plum Beach w/heated pool

A wooden dock extends into clear waters, surrounded by soft sandy shores. The sky is bright with fluffy white clouds, reflecting a peaceful coastal atmosphere. The gentle waves lap against the dock, inviting relaxation and exploration.

Townhouse in Layton

4.83 out of 5 average rating, 12 reviews

Florida Keys Getaway w/ Stunning Ocean Views

4.96 out of 5 average rating, 53 reviews

The exterior of Sunset Villas is presented, showcasing a two-story building surrounded by lush palm trees and tropical flora. A dock extends into the water, providing access for boats. The clear waters reflect the building's vibrant color, enhancing the inviting waterfront atmosphere.

Hotel room in Conch Key

1-bedroom suite - Full Kitchen, Dockage, Boat Ramp