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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 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

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!

4.89 out of 5 average rating, 178 reviews
Guest favourite
A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.
Home in Cudjoe Key

SEPT/OCT. Save$Oceanfront 4 BIKE/2 Kayak KING Bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. At MM# 23 only 25min to Key West. In a gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C *Fully equipped kitchen *Includes grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library. Too much to list! WE WILL NEED YOUR EMAIL WHEN YOU CONFIRM THE BOOKING IN ORDER TO SEND YOU THE REGISTRATION FORMS AND THE RULE PACKET.

4.81 out of 5 average rating, 324 reviews
Top Guest favourite
A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.
Cottage in Cudjoe Key

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

4.95 out of 5 average rating, 182 reviews
Top Guest favourite
Home in Cudjoe Key

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

5.0 out of 5 average rating, 51 reviews
Superhost
Home in Cudjoe Key

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!

4.92 out of 5 average rating, 98 reviews
Superhost
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.
Home in Upper Sugarloaf Key

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.

4.93 out of 5 average rating, 134 reviews
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

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!

4.88 out of 5 average rating, 162 reviews
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

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.

4.96 out of 5 average rating, 213 reviews
Top Guest favourite
Home in Cudjoe Key

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.

4.97 out of 5 average rating, 60 reviews
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

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.

4.83 out of 5 average rating, 112 reviews
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

Ocean front classic keys cottage

This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breathtaking sunrises and romantic moonrises, seabirds,dolphins, and a nearly south-easterly breeze. This lovely hideaway is next to last home on dead end street, this 3 BRs, 2 baths ground level home has a large kitchen and Master suite. this location is only 30 minutes from the historic key west, close to restaurants and a nearby marina.

4.95 out of 5 average rating, 20 reviews
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

*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.

4.88 out of 5 average rating, 136 reviews

Popular amenities for Cudjoe Key holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Cudjoe Key

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

2Bd/1Ba Waterfront Retreat w/35’ Dock

4.81 out of 5 average rating, 37 reviews
Guest favourite
Home in Cudjoe Key

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

4.94 out of 5 average rating, 18 reviews
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

Oceanfront Bungalow Venture Out

4.8 out of 5 average rating, 30 reviews
Top Guest favourite
A serene view overlooks the water at sunrise, with soft pastels reflecting on the surface. A white patio table and chairs are positioned under the covered porch, inviting relaxation. The horizon features gentle clouds and distant islands, creating a peaceful atmosphere.
Home in Cudjoe Key

Rise And Shine On The Water

4.91 out of 5 average rating, 75 reviews
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

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

4.99 out of 5 average rating, 75 reviews
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

Relaxing and Inviting home with 35' Private Dock

4.85 out of 5 average rating, 61 reviews
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

Cozy 2 br/2 bath home in Cudjoe

4.88 out of 5 average rating, 91 reviews
Guest favourite
Home in Summerland Key

Starlight Serenity - Hideaway with Stunning Views

4.95 out of 5 average rating, 39 reviews

When is the best time to visit Cudjoe Key?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$421 AUD$434 AUD$463 AUD$399 AUD$376 AUD$362 AUD$378 AUD$351 AUD$313 AUD$331 AUD$351 AUD$402 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