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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 ﺩ.ﺇ 257 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 & 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

  • Wi-Fi availability

    280 of Cudjoe Key vacation 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 vacation rentals in Cudjoe Key

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

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Top guest favorite
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
4.94 out of 5 average rating, 175 reviews

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.

Guest favorite
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, 124 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.

Guest favorite
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, 175 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 favorite
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

Lobstering paradise 2 houses from open water, deep 60' canal, gorgeous water views, direct access to the Atlantic/Gulf, 35' dock/seawall. 3 zone mini split A/C and heat, overhead ceiling fans, fully stocked kitchen, microwave, washer/dryer, 42" Smart TV in living room and master bedroom, WIFI. King size bed in the master, queen bed in 2nd bedroom, and a queen sofa in the living room. Beach towels, linens. Marina store with bait & fuel onsite, 2 wide boat ramps, pool, hot tub & Rec center.

Top guest favorite
Home in Summerland Key
4.97 out of 5 average rating, 30 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 favorite
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
4.88 out of 5 average rating, 155 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, 124 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 favorite
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, 201 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.

Top guest favorite
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.

Guest favorite
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.

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
4.87 out of 5 average rating, 132 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.

Guest favorite
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.
Home in Cudjoe Key
4.91 out of 5 average rating, 115 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.

Popular amenities for Cudjoe Key vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Cudjoe Key house rentals

Top guest favorite
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!

Top guest favorite
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
4.96 out of 5 average rating, 27 reviews

Aug. Discount, Waterfront Retreat/Pool/golf cart

Superhost
Home in Cudjoe Key
4.92 out of 5 average rating, 92 reviews

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

Guest favorite
A serene outdoor space features palm trees swaying gently by the water's edge, with a small floating dock visible. Loungers are arranged by the pool, surrounded by pebbled landscaping and lush greenery, all under a clear blue sky.
Home in Cudjoe Key
4.9 out of 5 average rating, 39 reviews

White House - Receive $400 towards a Boat Rental!

Guest favorite
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, 114 reviews

Waterfront Anchor House with Boat Basin & Ramp!

Guest favorite
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, 56 reviews

Relaxing and Inviting home with 35' Private Dock

Top guest favorite
A serene patio area showcases a private pool with illuminated edges, creating a calming ambiance. Outdoor furniture is arranged on a synthetic grass surface, framed by lush greenery and a tranquil water view, as the sky transitions to sunset hues in the background.
Home in Marathon
4.97 out of 5 average rating, 35 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Top guest favorite
Home in Cudjoe Key
5 out of 5 average rating, 40 reviews

Oceanfront Cottage with Open Water Views

Other great vacation rentals in Cudjoe Key

Superhost
A charming exterior of a coastal home is presented, framed by tall palm trees. The front features a covered porch with steps leading to the entrance. Large windows allow natural light to enter. A spacious driveway is visible, complimented by a gravel landscape.
Home in Cudjoe Key
4.54 out of 5 average rating, 68 reviews

Relaxing Cottage in Cudjoe

Guest favorite
Cottage in Cudjoe Key
5 out of 5 average rating, 5 reviews

FL Keys Retreat - Community pool and hot tub

Guest favorite
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
4.97 out of 5 average rating, 33 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Top guest favorite
A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.
Houseboat in Marathon
4.92 out of 5 average rating, 86 reviews

b watervibe

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

Ocean Breeze Retreat w/ Dock| Keys Escape

Guest favorite
The exterior of a yellow house is shown with multiple windows providing natural light. A bike stands parked on the gravel beside a garden featuring tropical plants. Stairs lead to the entrance, and the surrounding area is landscaped with pebbles.
Home in Cudjoe Key
4.85 out of 5 average rating, 34 reviews

Fisherman's Paradise Cudjoe Key

Guest favorite
A waterfront view of a series of light-colored homes with multiple balconies, situated along the edge of a calm bay. Colorful Adirondack chairs are arranged on the porch, and a wooden walkway leads towards the structures, enhancing the coastal ambiance.
Home in Cudjoe Key
4.94 out of 5 average rating, 34 reviews

Oceanside home 107,dock,kayaks,bikes,pool,fishing,

Superhost
Tiny home in Summerland Key
4.92 out of 5 average rating, 65 reviews

Cottage

When is the best time to visit Cudjoe Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,102ﺩ.ﺇ 1,135ﺩ.ﺇ 1,212ﺩ.ﺇ 955ﺩ.ﺇ 918ﺩ.ﺇ 918ﺩ.ﺇ 988ﺩ.ﺇ 918ﺩ.ﺇ 819ﺩ.ﺇ 867ﺩ.ﺇ 918ﺩ.ﺇ 1,050
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.

All about Cudjoe Key

Flutter your eyelids as you travel down the Overseas Highway and you might just miss Cudjoe, an under-the-radar island perched between the more recognizable Sugarloaf and Big Pine Keys. At less than 6 square miles and with fewer than 2,000 residents, this island is shaped like an elephant’s head and serves mostly as a tranquil beach escape, with easy access to neighboring attractions. There’s Blue Hole, the region’s largest freshwater lake, which provides opportunities for spotting turtles, alligators, and exotic birds. There’s also diving and snorkeling at the nearby Looe Key National Marine Preserve, but the real fun here happens during the yearly Florida Keys Underwater Music Festival. Key West and its plentiful attractions are just a coconut’s toss — okay, 20 miles — to the southwest.

What are the top things to do in Cudjoe Key?

Key West

The eccentric crown jewel of Florida’s archipelago is worth a visit for its classic Caribbean-inspired homes and lively nightlife scene. Visit old stamping grounds popularized by famous writers and cruise over to Fort Zachary Taylor Historic State Park, where you can swim with some big fish.

Looe Key National Marine Preserve

More than 150 fish species, along with plenty of sharks and rays, are known to shimmy through these waters and along the abundant coral reef, making this preserve a solid snorkeling and diving spot. There’s also an artificial reef about three miles west, where a 210-foot sunken ship offers superb wreck diving.

Blue Hole

This former limestone quarry is now a freshwater lake replenished by rainfall and visited by a large variety of wild animals, including Key deer, alligators, turtles, and numerous species of birds. The lake is part of the National Key Deer Refuge, and worth a visit for a chance to spot the majestic and miniature endangered creatures.

Destinations to explore

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