Holiday rentals with beach access in Cudjoe Key

4.89 out of 5 average rating, 176 reviews

An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

Cottage in Cudjoe Key

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

ViewBeachComfort

4.97 out of 5 average rating, 128 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.

WalkabilityViewBreakfast

4.93 out of 5 average rating, 149 reviews

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.

Home in Key Colony Beach

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.

BeachViewTV

4.81 out of 5 average rating, 113 reviews

A clear view of the sparkling waterway is framed by lush palm trees, with a blue boat docked on the left. The scene captures a seamless blend of greenery and water, while the surrounding landscape offers unobstructed access to open waterways.

Bungalow in Cudjoe Key

Cudjoe Key OCEANFRONT 2B/2B in gated community!!

Pets are not allowed. Sparkling clean and beautifully remodeled 2Bd/2Ba vacation home that features OPEN WATER views with great boating access to the ocean or gulf! This waterfront paradise features a 35' concrete seawall. There is a resort usage fee of $125 payable upon arrival to Venture Out. Pre-registration form of guests must be completed prior to stay or when checking in at the security gate. Check out my other property right next door! airbnb.com/h/islandtherapy46444432

ViewWalkabilityOutdoor spaces

A colorful array of lounge chairs in yellow, green, and blue is positioned by a shared pool area. A thatched-roof cabana is visible, providing shaded seating near the water's edge. The lush surroundings and bright blue sky complement the inviting atmosphere.

4.94 out of 5 average rating, 33 reviews

Oceanside home 109, dock,kayaks,bikes,pool,fishing

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

ViewFamilyDecor

4.83 out of 5 average rating, 183 reviews

A serene waterfront view captures a light-colored building with turquoise accents, surrounded by lush palm trees. The calm water reflects the structure and sky, creating a tranquil atmosphere. Soft clouds float above, enhancing the peaceful setting of the marina.

Boat in Key West

A Great Escape! Private 2 Bed Rm Beautiful Marina

Our Marina has a pool and a small private beach overlooking the beautiful Keys water! More affordable than most places in Key West while able to reconnect with nature at this private getaway on the Great Escape. As you approach the boat, you feel your dream vacation has come true . One of a lifetime. Staying on a beautiful sportfisher yacht, laying in the waters of the calm keys and in the most beautiful peaceful marina, will definitely set you free from all your worries and stress.

ViewWalkabilityIndoor spaces

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.

4.89 out of 5 average rating, 157 reviews

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!

WalkabilityBeachAccuracy

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.

4.87 out of 5 average rating, 133 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.

BeachWalkabilityAccess

4.95 out of 5 average rating, 108 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)

ViewBeachPool

A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.

4.95 out of 5 average rating, 119 reviews

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

WalkabilityBeachBackyard

A bright living area features a green sofa adorned with decorative cushions, flanked by two woven ottomans. Natural light filters through the white curtains, while a large television and colorful wall art enhance the space. Rattan accents and indoor plants bring a refreshing touch.

4.91 out of 5 average rating, 117 reviews

Betty's Place

Welcome to our charming 2-bedroom, 2-bathroom getaway, nestled in the tropical surroundings of Cudjoe Key, which is located 20 miles from Key West, the most southern point in the United States. This cozy retreat offers the perfect blend of comfort and convenience, ideal for couples, families or a group of friends looking to explore the beauty of the Florida Keys.

BeachWalkabilityLaundry

4.94 out of 5 average rating, 154 reviews

The outdoor swimming pool features a circular design surrounded by tropical palm trees and lounge chairs. Bright blue umbrellas provide shade for guests, while the clear blue sky enhances the vibrant atmosphere of the gated community.

Home in Key West

Paradise found

Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.

ViewWalkabilitySleep quality

Popular amenities for Cudjoe Key Accommodation with Beach Access

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.92 out of 5 average rating, 276 reviews

Sunset Suite-Historic 2 BR, K/Q, Sleeps 4, Spa!

BeachWalkabilityOutdoor spaces

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.

4.83 out of 5 average rating, 890 reviews

Duval Balcony - Street Suite

WalkabilityBeachParks

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, 167 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

WalkabilityBeachFamily

A large heated Olympic-sized pool is set within a tropical landscape, surrounded by palm trees and lounging chairs. The inviting blue water reflects the sky and is complemented by the nearby resort building, which features multiple levels and balconies.

4.92 out of 5 average rating, 200 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

WalkabilityViewGetting around

Apartment in Key Colony Beach

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

4.86 out of 5 average rating, 152 reviews

Beachside Unit 22 - Private Beach on Atlantic

BeachWalkabilityCheck-in

5.0 out of 5 average rating, 12 reviews

Apartment in Marathon

Brand New Luxury Waterfront Condo! Pool + Tiki Bar

BeachViewBathroom

5.0 out of 5 average rating, 15 reviews

An oceanfront heated pool is presented, with clear water reflecting the sky. Surrounding palm trees harmonize with the serene coastal backdrop, and lounge chairs offer seating options. The pool area is enclosed by a fence, providing a defined relaxing space with views of the ocean.

Apartment in Marathon

OCEAN community, perfect condo

WalkabilityBeachAccess

4.92 out of 5 average rating, 13 reviews

Oceanview condo w/pool, jacuzzi and tennis court

BeachWalkabilityNearby

Holiday House Rentals with beach access

4.95 out of 5 average rating, 150 reviews

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

ViewBeachNearby

5.0 out of 5 average rating, 114 reviews

A private backyard features a heated pool surrounded by tropical landscaping. Lounge chairs are positioned on the wooden deck beside the pool. The two-story home includes large glass doors that open onto the deck, providing easy access to outdoor spaces.

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located

BeachViewAmenities

A well-lit dining area features a round wooden table surrounded by six woven chairs. A decorative centerpiece is placed on the table. Adjacent, a cozy living space is visible, showcasing a sectional sofa, a ceiling fan, and large windows allowing natural light.

4.88 out of 5 average rating, 90 reviews

Cozy 2 br/2 bath home in Cudjoe

BeachViewParking

A serene waterfront scene captures the reflection of clouds and colorful sunset hues on the calm water. Flanking the canal are inviting homes characterized by palm trees, with docks indicating easy access for boating enthusiasts. The peaceful setting suggests a tranquil atmosphere.

4.89 out of 5 average rating, 35 reviews

Pelican's Roost, Waterfront comfort at Venture Out

WalkabilityViewPool

4.94 out of 5 average rating, 18 reviews

Serenity Now Seaside Escape - Brand New Build!

ViewBeachBathroom

5.0 out of 5 average rating, 13 reviews

Waterfront home in florida keys 35’ dock for boat

Getting aroundIndoor spacesOutdoor spaces

4.93 out of 5 average rating, 81 reviews

Beach House, Private Pool, Dock, Gulf View Sunsets

BeachViewAmenities

5.0 out of 5 average rating, 3 reviews

Blue Heaven Marathon

DecorCleanlinessParking

Holiday condos with beach access

Condo in Key Colony Beach

The studio condo features two queen-sized beds with fresh linens and cotton sheets, complemented by a cozy seating area with a sectional couch. A dining table is visible nearby, and decorative blue artwork adds a coastal touch to the bright, clean interior.

4.92 out of 5 average rating, 278 reviews

Key Lime Condo, Key Colony Beach Oceanfront & Pool

WalkabilityViewAmenities

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, 208 reviews

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

WalkabilityBeachHot tub

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, 314 reviews

Affordable Beachfront Luxury Condo Sleeps 6

BeachWalkabilityGetting around

A serene pool area is visible in the foreground, bordered by lush greenery and ocean views. Tall palm trees sway gently along the shoreline, where the calm water reflects the sky. A distant pier can be seen, enhancing the coastal atmosphere.

4.94 out of 5 average rating, 181 reviews

Beach Club Ocean Front 2BR Condo

ViewWalkabilityWi-Fi

4.88 out of 5 average rating, 120 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

WalkabilityViewBackyard

4.97 out of 5 average rating, 34 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)

BeachViewPool

Condo in Key Colony Beach

5.0 out of 5 average rating, 22 reviews

*New* Turtles Pace-Private Beach

BeachWalkabilityIndoor spaces

The living room features a spacious green sofa complemented by wicker armchairs. A glass dining table sits at the center, with light streaming through open shutters. The backdrop showcases ocean views, enhancing the connection to the balcony and natural surroundings.