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Holiday rentals in Cudjoe Key

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Quick stats about holiday rentals in Cudjoe Key

  • Total holiday rentals

    Explore 310 holiday rentals in Cudjoe Key

  • Nightly prices starting at

    Cudjoe Key holiday rentals start at €70 per night before taxes and fees

  • Verified guest reviews

    Over 6,610 verified reviews to help you choose

  • Family-friendly holiday rentals

    230 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 160 rentals that welcome pets

  • Holiday rentals with a pool

    250 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    270 of Cudjoe Key holiday 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 holiday rentals in Cudjoe Key

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

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Top guest favourite
Home in Cudjoe Key
5 out of 5 average rating, 37 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

Superhost
Home in Cudjoe Key
4.86 out of 5 average rating, 7 reviews

Tropical Paradise

Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.

Guest favourite
Home in Cudjoe Key
4.92 out of 5 average rating, 90 reviews

Ocean~View w/ Dock, Pool, Kayaks, King Bed

Experience waterfront luxury in Venture Out on peaceful Cudjoe Key! Enjoy stunning Atlantic Ocean views, amazing sunsets, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Keep your boat at the house and reach the Atlantic or Gulf in minutes. Near Key West, this updated Keys getaway includes resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, especially lobster season in August, so book now!

Guest favourite
Home in Cudjoe Key
4.94 out of 5 average rating, 16 reviews

Serenity Now Seaside Escape - Brand New Build!

Relax and rejuvenate at Serenity Now – Seaside Escape, a brand-new canal-front home just steps from the Atlantic. Nestled in the peaceful Venture Out resort on Cudjoe Key, this retreat offers resort-style amenities including a pool, hot tub, gym, and tennis courts. Bring your boat! The area is perfect for boating, fishing, or sunset cruises. With a private waterside deck, outdoor entertainment space, and fresh, contemporary interiors, it’s the ideal spot to unwind in the Florida Keys.

Guest favourite
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
4.97 out of 5 average rating, 32 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

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, 123 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
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
4.87 out of 5 average rating, 38 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.

Top guest favourite
Home in Cudjoe Key
4.96 out of 5 average rating, 53 reviews

Tiki Time in Cudjoe Key 136

Open water, upscale Oceanfront Retreat! This waterfront gem offers amazing views of the Atlantic Ocean and is the perfect getaway for your next vacation in Paradise. This 2 bedroom, 2 bathroom vacation home is equipped with everything you need to unwind and relax. Offering a high end kitchen, stainless appliances, three smart tv's and a 54-foot seawall to dock your boat. VO COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY.

Top guest favourite
Home in Key West
4.97 out of 5 average rating, 36 reviews

3 Bedroom Home - Perfect Location & Private Pool

The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street and all major attractions. This rental listing includes the second and third floors of the home, which features three bedrooms, a private swimming pool, spacious living areas inside and outside, off-street parking, and a newly renovated chef's kitchen to prepare meals. The first story of the home will be left vacant when this listing is rented.

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, 110 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.

Superhost
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
4.88 out of 5 average rating, 131 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.

Superhost
Home in Cudjoe Key
5 out of 5 average rating, 4 reviews

Oceanfront 2BR w/ 35’ Dock & Stunning Views

Oceanfront 2BR/2BA escape with stunning Atlantic views and a 35’ dock for up to a 32’ boat. Open-concept living, smart TVs, Wi-Fi, and a fully equipped kitchen with both drip and Keurig coffee makers. Enjoy easy access to Looe Key, nearby sandbars, and both ocean and backcountry fishing. Relax after a day on the water with a NexGrill propane grill and outdoor picnic table—perfect for true Keys living.

Popular amenities for Cudjoe Key holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Cudjoe Key

Cottage in Cudjoe Key
5 out of 5 average rating, 3 reviews

FL Keys Retreat - Community pool and hot tub

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
4.97 out of 5 average rating, 199 reviews

Cudjoe Key Home with a View

Guest favourite
Home in Cudjoe Key
4.92 out of 5 average rating, 197 reviews

106- Newly Renovated House with Oceanview and Pool

Guest favourite
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.
Home in Cudjoe Key
4.88 out of 5 average rating, 89 reviews

Cozy 2 br/2 bath home in Cudjoe

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, 30 reviews

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

Top guest favourite
Home in Summerland Key
4.96 out of 5 average rating, 28 reviews

Starlight Serenity - Hideaway with Stunning Views

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
4.88 out of 5 average rating, 17 reviews

Blue Heaven Waterfront Home

Superhost
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
4.84 out of 5 average rating, 55 reviews

Relaxing and Inviting home with 35' Private Dock

When is the best time to visit Cudjoe Key?

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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

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  5. Cudjoe Key