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Holiday houses in Cudjoe Key

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Quick stats about holiday rentals in Cudjoe Key

  • Total holiday rentals

    Explore 330 holiday rentals in Cudjoe Key

  • Nightly prices starting at

    Cudjoe Key holiday rentals start at $98 AUD per night before taxes and fees

  • Verified guest reviews

    Over 7,350 verified reviews to help you choose

  • Family-friendly holiday rentals

    250 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 170 rentals that welcome pets

  • Holiday rentals with a pool

    260 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    280 of Cudjoe Key holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Cudjoe Key rentals

  • 4.8 Average rating

    Cudjoe Key stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in Cudjoe Key

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
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
4.89 out of 5 average rating, 177 reviews

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!

Guest favourite
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
4.97 out of 5 average rating, 129 reviews

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.

Top Guest favourite
Home in Cudjoe Key
5.0 out of 5 average rating, 48 reviews

Oceanfront Cottage with Open Water Views

Oceanview Serenity provides stunning open water views, and a 60 foot seawall for your boat. Comes with paddle board, kayaks, and more. Newly renovated 2BR cottage sleeps MAXIMUM OF FOUR (4) GUESTS, with a King in the Master BR and one Queen size bed Guest BR (both with new JW Marriott mattresses for comfort). All new appliances! Enjoy resort amenities like a pool, hot tub, tennis, and marina store. Just 30 minutes from Key West. One-time $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON

Guest favourite
A tranquil pool is set against a backdrop of palm trees and a vibrant sunset. The water reflects the hues of the sky, creating a calming scene. Loungers are positioned along the poolside, offering a inviting space to relax.
Cottage in Cudjoe Key
4.81 out of 5 average rating, 36 reviews

2Bd/1Ba Waterfront Retreat w/35’ Dock

Discover the FL Keys in this bright & beachy 2-queen bed, 1-bath waterfront modular home in Venture Out on Cudjoe Key. Enjoy your fresh catch in the full kitchen, laundry in-house, nice wide canal with 35’ dock for your boat just steps from your door. Indulge in unparalleled amenities & scenic beauty: oceanfront pool, hot tub, marina w/marine fuel, wash station, store; tennis, bball, pickle ball, & playground. $125 add’l resort fee paid direct to Venture Out at gate. Incl Bikes & kayaks for use.

Guest favourite
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
4.81 out of 5 average rating, 114 reviews

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

Superhost
Home in Cudjoe Key
4.92 out of 5 average rating, 97 reviews

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks

Your Luxury Keys Getaway! Experience stunning Ocean views, amazing sunsets and sunrises, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Everything you need to fully enjoy the Keys experience! Keep your boat at the house and be on the Atlantic or Gulf in minutes. Located halfway between Key West and Marathon, you get access to all resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, book now!

Guest favourite
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
4.89 out of 5 average rating, 158 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!

Superhost
An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.
Home in Cudjoe Key
4.84 out of 5 average rating, 129 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Guest favourite
An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.
Home in Cudjoe Key
4.96 out of 5 average rating, 210 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Guest favourite
A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.
Home in Cudjoe Key
4.83 out of 5 average rating, 111 reviews

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

Guest favourite
A scenic waterfront area is depicted with vibrant green lounge chairs positioned on a sandy peninsula. Surrounding waters provide a tranquil blue hue. Wooden docks extend into the bay, complemented by lush palm trees and colorful buildings in the background.
Home in Summerland Key
4.95 out of 5 average rating, 116 reviews

Waterfront Anchor House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!

Top Guest favourite
A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.
Home in Cudjoe Key
4.99 out of 5 average rating, 74 reviews

Waterfront, Dock, Pool, Pickleball, near Key West!

Welcome to “The Barnacle” your waterfront home in the Florida Keys! Dock your boat behind this charming two bedroom home with 35’ sea wall! We have direct access to some of the best fishing, snorkeling and diving in the Keys! Beautiful neighborhood loaded with amenities. Bring a pole and fish from the dock! Relax, enjoy and have a wonderful vacation experience. Visit YouTube “The Barnacle at Venture Out”. Swim, Fish, Dive …Repeat!

Popular amenities for Cudjoe Key holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Cudjoe Key

Top Guest favourite
A two-story waterfront home is situated under a clear blue sky, surrounded by palm trees and lush greenery. The property features a bright white exterior with a balcony, along with a manicured yard of decorative rocks and native plants.
Home in Cudjoe Key
4.95 out of 5 average rating, 91 reviews

Keys Island Villa - Venture Out Home 354

Guest favourite
A scenic view of a calm waterway, featuring a thatched-roof hut on a dock and several palm trees. A second dock with covered areas can be seen in the distance under clear blue skies, creating a relaxing waterfront setting.
Home in Cudjoe Key
4.85 out of 5 average rating, 60 reviews

Relaxing and Inviting home with 35' Private Dock

Guest favourite
A serene canal view during sunset, showcasing vibrant orange and pink hues reflecting off the water. A concrete dock extends into the water, equipped with a fish cleaning station. A table and chairs are positioned nearby for relaxation and enjoyment of the picturesque scene.
Home in Cudjoe Key
4.89 out of 5 average rating, 18 reviews

Blue Heaven Waterfront Home

Guest favourite
A spacious outdoor dining area features a glass-top table with several red chairs, set against a vibrant backdrop of greenery and water. The view of the calm sea and fluffy clouds can be seen in the distance, enhancing the tranquil setting.
Home in Cudjoe Key
4.88 out of 5 average rating, 42 reviews

Yellow Home - Receive $400 towards a Boat Rental!

Top Guest favourite
Lounge chairs with blue umbrellas surround a sandy beach area, providing a relaxed setting by the water. Steps lead down to the shoreline, where vibrant greenery and palm trees offer a natural frame against the bright blue sky and turquoise sea.
Home in Summerland Key
4.95 out of 5 average rating, 20 reviews

Ocean front classic keys cottage

Top Guest favourite
Home in Cudjoe Key
4.97 out of 5 average rating, 58 reviews

Tiki Time in Cudjoe Key 136

Superhost
Tiny home in Summerland Key
4.94 out of 5 average rating, 80 reviews

Cottage

Superhost
A covered outdoor dining area features a round table surrounded by six cushioned chairs. Scenic views of the turquoise water and distant shoreline are visible through the railing, with soft, natural light illuminating the space.
Bungalow in Cudjoe Key
4.8 out of 5 average rating, 30 reviews

Oceanfront Bungalow Venture Out

When is the best time to visit Cudjoe Key?

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Avg. price$420 AUD$432 AUD$462 AUD$397 AUD$375 AUD$361 AUD$376 AUD$350 AUD$312 AUD$330 AUD$350 AUD$400 AUD
Avg. temp21°C22°C24°C25°C27°C29°C30°C30°C29°C27°C25°C23°C

Frequently Asked Questions

  • What are the best places to stay in Cudjoe Key?

    Vacation rentals along the waterfront, in quiet neighborhoods, or near natural preserves are often suggested for their access to kayaking and scenic views. Many stays offer outdoor spaces and a peaceful setting.

  • What are the best things to do in Cudjoe Key with kids?

    Kids can enjoy paddleboarding, snorkeling in clear waters, and spotting native birds. Exploring local marine parks or joining guided eco-tours is often recommended for family-friendly fun.

  • What are some of the best things to do in Cudjoe Key?

    Explore local mangroves by kayak or paddleboard, try sport fishing or snorkeling, and visit marine parks nearby. The area is known for its tranquil beauty and outdoor activities focused on the water.

  • How is the weather in Cudjoe Key?

    Cudjoe Key has a subtropical climate, with winter temperatures from 65–76°F (19–24°C) and warmer, humid summers around 80–91°F (27–33°C). Rainfall is higher in late summer and early fall, with breezes from the surrounding waters keeping days comfortable.

  • When is the best time to visit Cudjoe Key?

    Many visitors prefer late winter through spring, when temperatures range from about 65–80°F (19–26°C) and rainfall is lighter. Summer tends to be warmer and wetter, with vibrant marine life activities ongoing throughout the year.

  • What are the best places to visit in Cudjoe Key?

    Explore local mangroves and seagrass habitats, join kayak tours, or visit the nearby undersea exploration park. The area around Cudjoe Key is known for its natural beauty and water access.

  • What are some hiking trails in Cudjoe Key?

    Cudjoe Key has nature trails winding through mangroves and coastal habitats; nearby islands like Big Pine Key often feature more established walking and hiking paths. Bring comfortable shoes for exploring these natural areas.

  • What are some family activities we can do in Cudjoe Key?

    Families can explore kayaking through mangroves, dolphin spotting tours, and snorkeling adventures. Many visitors also enjoy fishing from local piers and discovering marine life at the nearby parks.

  • What are some of the best day trip ideas from Cudjoe Key?

    Day trips often include visiting Key West for historic sites and lively streets, exploring Bahia Honda State Park for beaches, or checking out nature reserves around Big Pine Key. Coral reef excursions and wildlife centers nearby are frequently suggested.

  • Are there any pet friendly accommodations available in Cudjoe Key?

    Cudjoe Key has pet friendly vacation rentals, making it convenient to travel with your dog or cat. Many stays are located near natural areas where pets can enjoy outdoor time, but policies may vary by property.

  • What are some local tips for visiting Cudjoe Key?

    Bring insect repellent for evenings, and check tide schedules for ideal water activities. Locals recommend exploring by kayak or paddleboard and supporting small markets for fresh produce and seafood.

  • What is Cudjoe Key known for?

    Cudjoe Key is known for its tranquil atmosphere, mangrove-lined waterways, and abundant opportunities for boating and water sports. The area is often associated with rich marine life and a relaxed, tropical vibe.

  • What are the best hidden gems to explore in Cudjoe Key?

    Look for secluded kayak spots, quiet shorelines, and lesser-known mangrove tunnels. Visiting small local markets and discovering native wildlife refuges nearby adds unique experiences.

  • What are the best foods to try in Cudjoe Key?

    Cudjoe Key has fresh seafood like grouper, snapper, and stone crab, often served with local citrus. Key lime pie, conch fritters, and locally inspired tropical drinks are frequently suggested treats.

  • What should I bring for a trip to Cudjoe Key?

    Pack lightweight clothing, sun protection like hats and sunscreen, a reusable water bottle, insect repellent, and swim gear. If you plan on exploring outdoors, water shoes and a dry bag can be helpful.

  • What is the nightlife in Cudjoe Key like?

    Cudjoe Key has a laid-back nightlife scene, centered on casual waterfront restaurants and bars. For livelier entertainment, many travelers head to nearby areas with music venues and cultural events.

  • What are the most popular events or festivals in Cudjoe Key?

    Regional events often include seafood festivals in spring and summer, as well as marine conservation celebrations. Nearby Key West hosts a variety of cultural festivals and parades throughout the year.

  • Are there family friendly vacation rentals in Cudjoe Key?

    Cudjoe Key has vacation rentals suited for families, including homes with kitchens and outdoor spaces. Some neighborhoods are near parks, making it easy to explore nature with children.

Destinations to explore