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Vacation rentals in Cudjoe Key

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Quick stats about vacation rentals in Cudjoe Key

  • Total vacation rentals

    Explore 330 vacation rentals in Cudjoe Key

  • Nightly prices starting at

    Cudjoe Key vacation rentals start at $96 CAD per night before taxes and fees

  • Verified guest reviews

    Over 7,350 verified reviews to help you choose

  • Family-friendly vacation rentals

    250 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 170 rentals that welcome pets

  • Vacation rentals with a pool

    260 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    280 of Cudjoe Key vacation rentals include wifi 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 vacation rentals in Cudjoe Key

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

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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, 46 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
4.82 out of 5 average rating, 33 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.

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!

Superhost
A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.
Cottage in Cudjoe Key
4.82 out of 5 average rating, 119 reviews

OCEANIA... water front cottage retreat ~

OCEANIA... water front cottage retreat ~ Completely remodeled, direct cannal-front cottage offers everything you'll need for the perfect getaway. Boat dock (35ft), HD Smart TVs, washer & dryer, S/S appliances! 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!

Top guest favourite
Home in Summerland Key
4.97 out of 5 average rating, 35 reviews

Starlight Serenity - Hideaway with Stunning Views

Escape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance. Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility. Book your next getaway for 3 nights or more!

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, 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!

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, 127 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, 208 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 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!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our homes staying between the dates of Sept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026 Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home. Kayaks included. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

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.

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 vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Cudjoe Key

Top guest favourite
A charming waterfront villa is framed by lush palm trees, featuring a spacious sandy area with vibrant landscaping. A boat is docked nearby, with soft clouds drifting across the blue sky, contributing to a serene outdoor environment.
Home in Cudjoe Key
4.97 out of 5 average rating, 29 reviews

Jan. Disc, Waterfront Retreat/Dock/Pool/golf cart,

Top guest favourite
Home in Cudjoe Key
4.96 out of 5 average rating, 55 reviews

Tiki Time in Cudjoe Key 136

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
Home in Marathon
5.0 out of 5 average rating, 10 reviews

Beach House in Marathon with Amazing Backyard!

Guest favourite
Home in Cudjoe Key
4.94 out of 5 average rating, 18 reviews

Blue Palms Retreat

Guest favourite
Home in Cudjoe Key
4.94 out of 5 average rating, 17 reviews

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

Top guest favourite
Two pelicans are perched on a wooden dock, surrounded by rippling water. The dock is supported by green posts, providing a serene setting in a tropical landscape. Subtle foliage in the foreground enhances the natural ambiance of the scene.
Home in Cudjoe Key
4.97 out of 5 average rating, 33 reviews

Oceanside home 111, dock,kayaks,bikes,pool,fishing

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

Cottage

When is the best time to visit Cudjoe Key?

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Avg. price$413 CAD$425 CAD$454 CAD$391 CAD$369 CAD$355 CAD$370 CAD$344 CAD$307 CAD$325 CAD$344 CAD$394 CAD
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