Vacation rentals with beach access in Cudjoe Key

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.

4.95 out of 5 average rating, 185 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

4.95 out of 5 average rating, 378 reviews

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

4.96 out of 5 average rating, 100 reviews

The living room features a light-colored couch and love seat, complemented by decorative pillows. A coffee table sits in the center, and a Smart TV is mounted on the wall. Natural light is provided by the sliding glass doors, leading to an outdoor space.

Cottage in Cudjoe Key

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

A serene view of a canal populated by several pelicans floating on the water's surface. Palm trees line the shore, and colorful houses are visible in the background. A boat is docked nearby, enhancing the peaceful coastal scene.

4.98 out of 5 average rating, 121 reviews

Waterfront House with 37 ft Dock & Cabana Club

Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

A covered Tiki Hut is featured at the waterfront, furnished with comfortable seating arrangements. Views of the water and dock are visible beyond the structure, framed by lush greenery and palm trees. The space is designed for relaxation and enjoyment of the serene surroundings.

4.92 out of 5 average rating, 128 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

4.85 out of 5 average rating, 107 reviews

Beachside Unit 14 - Brand New Kitchen and Bathroom

Unit 14 Details: Second Floor Unit, Walk-In Shower, King Bed and Queen Sized Sofa Pull-Out Bed, 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.”

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.

4.93 out of 5 average rating, 112 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.

4.88 out of 5 average rating, 137 reviews

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

Home in Cudjoe Key

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

A spacious bedroom features a king bed with light bedding and decorative throw pillows. Large windows offer unobstructed ocean views and allow natural light to fill the room. A comfortable seating area is positioned nearby, facing the beach and tiki huts.

4.91 out of 5 average rating, 202 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated ground floor with a stunning, clean white interior and just a few steps from our private beach and heated pool. Continental Inn Unit #10 offers one King size bed that sleeps two people. A fully equipped kitchen with essentials (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Reliable WiFi and Smart TV.

The living area features contemporary furnishings and large windows, allowing for bright natural light and views of the waterways. A dining table is positioned beside the seating area. The spacious lanai showcases an outdoor dining setup with a view of the dock and water.

4.95 out of 5 average rating, 130 reviews

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

4.87 out of 5 average rating, 125 reviews

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

*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.

Townhouse in Key Colony Beach

A stilt home is shown alongside a crystal clear canal, featuring a sand-colored patio with a tiki hut. Coastal greenery is visible, along with a white railing lining the water's edge. The building showcases multiple balconies and provides a sunlit atmosphere.

4.81 out of 5 average rating, 156 reviews

KCB Waterfront Split Home Walkable to Cabana Club

3BR/ 2 BA stilt home on crystal clear canal with open water views on deep water with 30 foot boat slip on a cul de sac. Short walking distance to multiple restaurants/bars, shops, and the Cabana Club with beach, pool, and hot tub. Fenced in waterfront patio with tiki hut. Kid friendly, with toys and high chair. Covered parking. Guests required to sign Regulations for Key Colony Beach form.

Popular amenities for Cudjoe Key beach-access accommodations

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

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.

4.91 out of 5 average rating, 160 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

A warm-toned room features wood-paneled walls accented by natural light from two windows. A spacious bed with an orange bedspread is positioned alongside a cozy seating area comprising two cream-colored couches facing a small round table.

4.84 out of 5 average rating, 854 reviews

Duval Balcony - Street Suite

5 out of 5 average rating, 21 reviews

Apartment in Marathon

#1 Island Hideaway 89 - OCEAN FRONT

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.

4.89 out of 5 average rating, 9 reviews

Henry's Penthouse On The Ocean

Apartment in Marathon

New place to stay

Waterfront Suite w/ Marina, Pool, Tiki Bar

4.94 out of 5 average rating, 71 reviews

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

Dock POOL Kayaks Bikes Beach2mi WalkToStores

Apartment in Key Colony Beach

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.

5 out of 5 average rating, 22 reviews

2 Bdrm Oceanfront Complex Private Beach & Pool

5 out of 5 average rating, 6 reviews

Oceanview condo w/pool, jacuzzi

House rentals with beach access

An outdoor seating area features a sectional sofa and high-top bar stools with a view of the water. A peaceful ambiance is created by the surrounding palm trees and the gentle waves of Vaca Cut. Laundry facilities are visible on the left side of the image.

4.92 out of 5 average rating, 49 reviews

Florida Keys Oceanside Utopia

A two-story house is surrounded by lush greenery and palm trees. A spacious backyard features a heated pool and a wooden dock. Loungers are arranged near the pool, providing a relaxing outdoor space. The exterior showcases large windows and a balcony with seating.

4.97 out of 5 average rating, 75 reviews

Sombrero beach vacation paradise, great location

4.95 out of 5 average rating, 142 reviews

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

A beach home with a turquoise roof is nestled among palm trees and tropical landscaping. Two sets of chairs in yellow and blue are positioned on the sandy area in the foreground, inviting relaxation. A private pool and lush greenery are visible in the background.

4.92 out of 5 average rating, 72 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.

4.91 out of 5 average rating, 186 reviews

Beachfront Villa - Florida Keys

An inviting living area features a dark sofa adorned with decorative pillows, complemented by two orange armchairs. A wooden coffee table sits centrally. The dining area includes a round table surrounded by wicker chairs, illuminated by natural light from windows with blinds.

4.92 out of 5 average rating, 26 reviews

Casa Blanca

A private wooden dock extends over calm waters, featuring a boat with a blue canopy and a small table with colorful umbrellas nearby. Palm trees line the waterfront, and a series of pastel-colored homes are visible across the canal, creating a serene setting.

5 out of 5 average rating, 122 reviews

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

The waterfront patio features a wooden dock leading into the calm water, surrounded by neatly arranged lounge chairs and palm trees. The single-story home is seen in the background with large glass doors and windows, allowing for ample natural light.

5 out of 5 average rating, 32 reviews

Boat Dock+King Bed & Cabana Club

Condo rentals with beach access

5 out of 5 average rating, 17 reviews

The image presents a view from a balcony overlooking the tranquil ocean. Palm trees line the property, and the aquamarine water can be seen in the distance. Nearby, a well-maintained path separates the buildings from the fishing dock.

Condo in Marathon

"O" Fish Ally Paradise @Ocean Isle Fishing Village

The living area features comfortable blue sofas complemented by decorative pillows. A large flat-screen TV is positioned on a wooden console. Natural light fills the space through floor-to-ceiling glass doors, which offer views of greenery outside. A light area rug adds texture to the tiled floor.

4.83 out of 5 average rating, 46 reviews

Conch in the Treetops at The Beach

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.

4.91 out of 5 average rating, 95 reviews

Ocean Front Studio private Sandy Beach in Key West

4.87 out of 5 average rating, 106 reviews

A modern kitchen features stainless steel appliances and white cabinetry, complemented by a light countertop. A dining area and living space are visible in the background, along with a staircase leading to the upper level. Large sliding doors provide access to an outdoor view.

Condo in Duck Key

Villa 5087 on Duck Key BOAT SLIP available

5 out of 5 average rating, 13 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)

A beachfront view captures a well-maintained property featuring multiple levels of balconies. Sun loungers are arranged on the sandy shore, accompanied by vibrant beach umbrellas. The ocean's gentle waves meet the sand under a clear blue sky, enhancing the coastal atmosphere.

4.97 out of 5 average rating, 32 reviews

*NEW LUXURY*Sea Glass with Cabana Club Access

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 306 reviews

Affordable Beachfront Luxury Condo Sleeps 6

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.