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Best Vacation rentals and Airbnb offers in Cudjoe Key, FL
9.4 13 reviews
Cudjoe Key, FL
10/14 – 10/20
$321/nighttotal: $1926 (6 )
Island Time #110 Ocean Views - Cudjoe Key
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apartment , Cudjoe Key
This Cudjoe Key waterfront vacation home boasts stunning views and direct water access, located within 9 miles of Upper Sugarloaf Key, Florida Keys Beaches, Lower Sugarloaf Sound, the Big Pine Key Flea Market, and the National Key Deer Refuge Visitor Center. This 820-square-foot property features three bedrooms, two bathrooms, accommodates six guests, and includes a private pool, jacuzzi, spa, tennis court, and fully equipped kitchen with all modern appliances; plus free WiFi, a Smart TV, and a washer and dryer.
9.4 56 reviews
Cudjoe Key, FL
06/18 – 06/29
$364/nighttotal: $4004 (11 )
3 Nite Minimum Stay! Spectacular Ocean Views!
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apartment , Cudjoe Key
This two-bedroom, two-bathroom vacation home is located in the Venture Out Resort on Cudjoe Key, just a short drive from the famous Seven Mile Bridge. The resort is a gated community with a mix of RV sites and manufactured homes, offering a relaxed and peaceful atmosphere. This property has earned excellent ratings for its cleanliness, location, and overall experience. The home features a spacious deck with ocean views and a comfortable interior with modern amenities. It can accommodate up to six guests and offers a range of features, including a private kitchen, air conditioning, a swimming pool, a Jacuzzi, and free Wi-Fi. Guests can also enjoy access to the resort's amenities, such as tennis courts, a marina, and boat/trailer parking.
9.6 5 reviews
Cudjoe Key, FL
10/14 – 10/20
$298/nighttotal: $1788 (6 )
Blue Mind #225 Canal-front W/dock & Pool
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apartment , Cudjoe Key
Blue Mind #225, a waterfront cottage in the gated Venture Out community on Cudjoe Key at Mile Marker 23, offers direct access to the water via a 35-foot concrete seawall, accommodating boats up to 32 feet and is a short drive from Key West and local restaurants like the Square Grouper and Morning Joint. This one-bedroom, one-bathroom vacation rental sleeps four, features a fully equipped kitchen, a private pool and jacuzzi, tandem kayaks, two bikes, and access to community amenities including tennis courts and a marina store; a nearby second property, Big Blue #230, is available for larger groups.
9.9 197 reviews
Cudjoe Key, FL
10/14 – 10/20
$254/nighttotal: $1524 (6 )
Cudjoe Key Home With A View
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apartment , Cudjoe Key
This Cudjoe Key vacation rental is located within the Venture Out community, a short walk from the pool, hot tub, and lagoon. The property has earned excellent ratings for location, cleanliness, and overall user experience. This two-bedroom, two-bathroom home comfortably accommodates six guests. Amenities include a fully equipped kitchen, air conditioning, a private swimming pool, a Jacuzzi, and a garden. Guests can also enjoy access to community amenities like tennis courts, a playground, and a boat marina.
8.7 45 reviews
Cudjoe Key, FL
06/18 – 06/29
$236/nighttotal: $2596 (11 )
Seas The Day In Cudjoe Key
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apartment , Cudjoe Key
Seas The Day is a mobile home located on Cudjoe Key, a short drive from popular Key West attractions like Ernest Hemingway Home and Museum and Duval Street. This property has received excellent ratings for location, cleanliness, and user experience. The mobile home features 2 bedrooms and 1 bathroom, providing comfortable accommodations for up to 4 guests. Enjoy amenities like a swimming pool, fitness center, and a fully equipped kitchen, perfect for relaxing and enjoying the beautiful surroundings.
Cudjoe Key, FL
06/18 – 06/29
$262/nighttotal: $2882 (11 )
Coconut Cottage - Oceanfront Community
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apartment , Cudjoe Key
This 1-bedroom apartment is located in Cudjoe Key's secure Venture Out gated community, a 10-minute drive from popular restaurants and 20 minutes from Key West. This pet-friendly condo offers accommodation for up to 4 guests with a queen bed and two full-sized pullout couches, featuring a full kitchen, free Wi-Fi, air conditioning, and access to the Venture Out community's oceanfront heated pool, jacuzzi, tennis courts, and marina.
9.6 107 reviews
Cudjoe Key, FL
10/14 – 10/20
$314/nighttotal: $1884 (6 )
Cudjoe Key Oceanfront 2b/2b In Gated Community!!
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bungalow , Cudjoe Key
This Cudjoe Key waterfront cottage offers direct ocean and Gulf access via a 35-foot concrete seawall, providing excellent boating opportunities. The recently remodeled two-bedroom, two-bathroom vacation home sleeps six, features a private pool and jacuzzi, and includes a kitchen with a fridge and microwave, plus resort amenities (fees apply).
9.6 24 reviews
Cudjoe Key, FL
10/14 – 10/20
$301/nighttotal: $1806 (6 )
2bd/1ba Waterfront Retreat W/35’ Dock
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apartment , Cudjoe Key
This Cudjoe Key waterfront cottage, situated in the Venture Out community, provides easy access to local restaurants like the Square Grouper and the Niles Road Nature Trail. The two-bedroom, one-bathroom house sleeps five, boasting a pool, jacuzzi, full kitchen, and internet access, plus nearby tennis, basketball, and pickleball courts.
9.8 85 reviews
Cudjoe Key, FL
10/14 – 10/20
$300/nighttotal: $1800 (6 )
Cozy 2 Br/2 Bath Home In Cudjoe
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apartment , Cudjoe Key
This Cudjoe Key apartment is located in the Venture Out community, just a short distance from the beach and a few miles from the historic downtown area. It has received excellent ratings for user experience, location, and cleanliness. This 2-bedroom, 2-bathroom vacation rental can comfortably accommodate up to 6 guests. Enjoy access to a shared pool, tennis courts, a playground, a private patio, a fully-equipped kitchen, and a comfortable living space perfect for relaxing and enjoying the Florida lifestyle.
Cudjoe Key, FL
06/18 – 06/29
$197/nighttotal: $2167 (11 )
House ∙ 2 Bedrooms ∙ 4 Guests
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house , Cudjoe Key
This canalfront house in Cudjoe Key's Venture Out community offers 44 ft of concrete dockage, a fish cleaning table, and a gas grill, providing direct access to the water. This fully furnished 2-bedroom, 2-bathroom vacation rental accommodates up to 4 guests and features a spacious open-concept living area, minisplit air conditioning in each room, and access to Venture Out's community pool, hot tub, and organized activities.
Cudjoe Key, FL
06/18 – 06/29
$225/nighttotal: $2475 (11 )
Island Home In Paradise #624 - Oceanfront Community!
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apartment , Cudjoe Key
This Cudjoe Key vacation home, located in the Venture Out gated community, is a 20-minute drive from Key West and 10 minutes from restaurants like the Square Grouper and Morning Joint. The 700-square-foot property boasts two bedrooms, one bathroom, and sleeps four, featuring a fully equipped kitchen, private patios with a grill, and access to community amenities including an 80-foot heated pool, Jacuzzi, and tennis courts.
8.8 34 reviews
Cudjoe Key, FL
06/18 – 06/29
$362/nighttotal: $3982 (11 )
Water At Your Back Door
3 2
cottage , Cudjoe Key
This waterfront vacation rental is conveniently located near Venture Key, Venture Out Keys, and Out Key, and is within 6 miles of Upper Sugarloaf Key and Florida Keys Beaches. It has received very good ratings from previous guests. The two-bedroom cottage can comfortably accommodate up to six guests. The home features a private pool, a hot tub, a tennis court, and a barbecue grill for your enjoyment.
Best Cudjoe Key, FL vacation rentals with a balcony
10 2 reviews
Cudjoe Key, FL
06/18 – 06/29
$333/nighttotal: $3663 (11 )
Casa Kiwi #472 - Ocean Views On Cudjoe Key
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apartment , Cudjoe Key
Casa Kiwi, located in the Venture Out community on Cudjoe Key, offers ocean views and is a short 20-minute drive from Key West, near restaurants like the Square Grouper and Morning Joint. This 860-square-foot vacation home features two bedrooms (King and Queen), two bathrooms, a modern kitchen, private pool, Jacuzzi, tennis court, and four bikes, accommodating up to six guests.
9.8 77 reviews
Cudjoe Key, FL
10/14 – 10/20
$456/nighttotal: $2736 (6 )
Vo 173 2 Bed 2 Bath Silt Canal-front, Ocean View
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apartment , Cudjoe Key
This canal-front vacation home, located in Summerland Key near Cudjoe Key, offers direct Gulf and Ocean access via a 35-foot seawall and proximity to Florida Keys attractions. This 900-square-foot rental boasts two bedrooms, two bathrooms, sleeps six, and includes a private dock with ocean views, a swimming pool, tennis court, and features such as a full kitchen, washer/dryer, and free Wi-Fi.
This three-bedroom, two-bathroom Cudjoe Key vacation rental, located in the gated Venture Out community, offers easy access to Key West (20-minute drive) and other Florida Keys attractions. The 840-square-foot stilt home features ocean views from dual porches, a private patio, a fully equipped kitchen, and community amenities including a pool, Jacuzzi, tennis courts, and a marina store; it comfortably sleeps six guests.
10 44 reviews
Cudjoe Key, FL
10/14 – 10/20
$294/nighttotal: $1764 (6 )
Wonderful Chalet, With Terrace & Private Patio 20 Miles From Key West.
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cottage , Cudjoe Key
This smoke-free cottage is located in Summerland Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, and less than four miles from Florida Keys Beaches. This "Little Gem In Paradise" is rated excellent by guests and offers a peaceful garden setting perfect for relaxing. This one-bedroom, one-bathroom cottage can accommodate up to four guests and features a private garden, terrace, and patio. Enjoy amenities like a fully equipped kitchen, washer/dryer, free WiFi, a swimming pool, a tennis court, and barbecue grills.
Guest-Favorite Family Vacation Rentals in Cudjoe Key, FL
Find the perfect family vacation rental or Airbnb in Cudjoe Key, FL with plenty of room to spread out near local beaches.
9.6 53 reviews
Cudjoe Key, FL
10/14 – 10/20
$590/nighttotal: $3540 (6 )
Oceanfront 2br Retreat | 35' Dock, Open Views, Boater's Paradise
2 2
apartment , Cudjoe Key
Coconut Telegraph #221 is a 2-bedroom, 2-bathroom condo located in the Venture Out resort community on Cudjoe Key, offering direct open ocean waterfront with a 35-foot concrete dock and a 20-minute drive to Key West. This 860 sq ft residence accommodates up to 4 guests and features central air, Wi-Fi, a full kitchen, an outdoor propane grill, and access to resort amenities including a heated saltwater pool, hot tub, and sports courts, with proximity to Looe Key for snorkeling and diving.
9.8 207 reviews
Cudjoe Key, FL
10/14 – 10/20
$306/nighttotal: $1836 (6 )
Relax By Florida Keys Beaches, Just A 7-min Drive Away
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apartment , Cudjoe Key
This waterfront vacation home is located in Cudjoe Key, Florida, within a 15-minute walk of Venture Key and Venture Out Keys, and within 6 miles of Upper Sugarloaf Key and Florida Keys Beaches. This 2-bedroom house comfortably accommodates 5 guests and features a private pool, a spa tub, and a fully equipped kitchen with a refrigerator, oven, stovetop, and microwave.
9.0 2 reviews
Cudjoe Key, FL
10/14 – 10/20
$396/nighttotal: $2376 (6 )
Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape
2 2
apartment , Cudjoe Key
This waterfront condo is located in Venture Out on Cudjoe Key, a private gated community, approximately 20 miles from Key West and 10 miles from popular Florida Keys restaurants. This 860 sq ft condo offers 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests with direct waterfront access, a 35' seawall for boats up to 32', a private fish-cleaning station, and full access to Venture Out's resort amenities.
8.6 29 reviews
Cudjoe Key, FL
10/14 – 10/20
$400/nighttotal: $2400 (6 )
3 Night Minimum! Spectacular Ocean Views!
2 2
apartment , Cudjoe Key
This Cudjoe Key vacation home is located in Summerland Key, a short walk from Venture Key and within 10 kilometers of Upper Sugarloaf Key and other Florida Keys beaches. Travelers will enjoy the peaceful and laid-back ambiance of the surrounding area. The house has received very good user ratings. The house has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy modern amenities such as free Wi-Fi, a fully equipped kitchen, a private pool, a tennis court, and a barbecue grill, perfect for al fresco dining.
Frequently Asked Questions about vacation rentals in Cudjoe Key, FL
Which walking or cycling routes are the best in Cudjoe Key, FL?
Cudjoe Key is pretty flat, so it's great for walking and cycling. You can walk or bike the length of the island, which is about 6 miles. There are also some nice trails in the Cudjoe Key State Forest, where you can find some great views of the water.
What are the best Airbnb and vacation rentals in Cudjoe Key, FL?
What sports or outdoor activites can visitors enjoy in and around Cudjoe Key, FL?
Cudjoe Key is a paradise for water sports! You can go fishing, snorkeling, diving, kayaking, paddleboarding, and even jet skiing. The Florida Keys National Marine Sanctuary is just offshore, so you'll have plenty of opportunities to see amazing marine life.
What are the most popular Airbnbs in Cudjoe Key, FL?
What other towns or cities can be easily accessed from Cudjoe Key, FL?
You're right in the heart of the Keys! Key West is just a short drive away, and you can easily get to Marathon, Islamorada, and Big Pine Key. The Overseas Highway is a scenic drive, and it's easy to get around the Keys by car.
What are the best vacation rentals with a pool in Cudjoe Key, FL?
What amenities are commonly available in vacation rentals in Cudjoe Key, FL?
Vacation rentals in Cudjoe Key usually have all the basics, like a kitchen, bathroom, and bedrooms. Many also have private pools, hot tubs, and outdoor grilling areas. You can find rentals with everything from basic accommodations to luxurious beachfront villas.
What are the best rentals for families and kids in Cudjoe Key, FL?
What time of year is best to rent a vacation rental Cudjoe Key, FL?
The best time to visit Cudjoe Key is during the winter months, from November to April. The weather is perfect for swimming, sunbathing, and enjoying all the water sports the Keys have to offer. It can get pretty hot and humid during the summer, so if you're not a fan of the heat, you might want to visit during the cooler months.
What are the best rentals or Airbnbs with a jacuzzi in Cudjoe Key, FL?
This waterfront vacation home is located on Cudjoe Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, with Florida Keys Beaches a quick drive away. Guests have consistently rated this property as very good for cleanliness and location, and excellent overall. This 1-bedroom, 1-bathroom property offers 730 square feet of space, comfortably accommodating up to 4 guests. Enjoy amenities like a swimming pool, jacuzzi, and a fully equipped kitchen, perfect for relaxing and enjoying the beautiful Cudjoe Key surroundings.
9.8 24 reviews
Cudjoe Key, FL
10/14 – 10/20
$304/nighttotal: $1824 (6 )
The Lookout #659 Venture Out - Gated Community
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apartment , Cudjoe Key
This Cudjoe Key vacation rental, located in the gated Venture Out community, is a short 20-minute drive from Key West and offers oceanfront access to resort amenities including a heated pool and hot tub. The two-bedroom, two-bathroom condo features a fully equipped kitchen with a dishwasher, a BBQ grill, and sleeps four guests comfortably, providing access to tennis, pickleball, and other recreational facilities within the community.
9.4 3 reviews
Cudjoe Key, FL
06/18 – 06/29
$437/nighttotal: $4807 (11 )
Mermaid House - Venture Out Lot 089
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apartment , Cudjoe Key
Mermaid House, a waterfront home in Summerland Key, offers easy access to Bahia Honda State Park and other Florida Keys attractions. This 860-square-foot house features two bedrooms, two bathrooms, and accommodates up to six guests, boasting a private dock, swimming pool, Jacuzzi, and proximity to kayaking and snorkeling.
9.0 314 reviews
Cudjoe Key, FL
10/14 – 10/20
$270/nighttotal: $1620 (6 )
Cottage With Swimming Pool And Dockage, Just Minutes To Key West!
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cottage , Cudjoe Key
This Cudjoe Key oceanfront cottage, located within three miles of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offers stunning ocean views and easy beach access. This 390-square-foot, one-bedroom, one-bathroom vacation home sleeps two guests and features a fully equipped kitchen, laundry facilities, a patio, a swimming pool, and on-site barbecue grills.
Check Out Vacation Rentals with a Pool in Cudjoe Key, FL
A vacation rental with a pool in Cudjoe Key, FL is the ideal way to complement your daily coastal adventures.
9.0 14 reviews
Cudjoe Key, FL
10/14 – 10/20
$254/nighttotal: $1524 (6 )
Judy's Place ~ 2 Bedroom, 1 Bathroom Home In Venture Out Community!
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apartment , Cudjoe Key
This two-bedroom, one-bathroom apartment rental in Summerland Key, near Cudjoe Key, offers convenient access to Blue Hole and Wilhelmina Harvey Park. The 670-square-foot unit at Venture Out Resort features a kitchen with a fridge and microwave, a terrace, a swimming pool, pet-friendly accommodations for two small dogs under 40 pounds, and sleeps up to six guests with two queen beds and a sleeper sofa; on-site amenities include tennis and pickleball courts, a heated pool, a spa, and BBQ grills.
9.9 23 reviews
Cudjoe Key, FL
10/14 – 10/20
$281/nighttotal: $1686 (6 )
Paradise Palms In Cudjoe Key #635
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apartment , Cudjoe Key
This Keezy home is located in the Venture Out gated community on Cudjoe Key, 19 miles from Key West, offering easy access to local restaurants and attractions. The two-bedroom, two-bathroom vacation rental sleeps five, features a fully equipped kitchen with stainless steel appliances, a private porch, and access to community amenities including a heated saltwater pool, hot tub, and marina.
8.0 18 reviews
Cudjoe Key, FL
06/18 – 06/29
$363/nighttotal: $3993 (11 )
Sirena Key Cottage In Venture Out
2 2
apartment , Cudjoe Key
This Cudjoe Key condo rental boasts a waterfront location, a 15-minute walk from Venture Out Keys, Venture Key, and Out Key, and 2.4 miles from Florida Keys Beaches. The 860-square-foot apartment features three bedrooms, two bathrooms, sleeps six, and includes a furnished balcony, swimming pool, jacuzzi, and free WiFi in common areas.
9.5 64 reviews
Cudjoe Key, FL
10/14 – 10/20
$299/nighttotal: $1794 (6 )
Waterfront Fl Keys Cottage @ Venture Out
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apartment , Cudjoe Key
The Keys Cottage 116 is located on Cudjoe Key, just 20 minutes from Key West, offering a peaceful retreat in the heart of the Florida Keys. This charming cottage is part of the Venture Out community, providing access to a range of amenities and activities. The cottage features two bedrooms, one bathroom, and can accommodate up to six guests. Enjoy the spacious backyard with its coconut palms, large BBQ, and outdoor seating, perfect for relaxing and soaking up the tropical atmosphere.
Top-Rated Oceanfront Vacation Rentals in Cudjoe Key, FL
These seaside vacation rentals in Cudjoe Key, FL provide an excellent base for exploring the coast. Browse top local properties and plan your beach-town trip.
9.3 126 reviews
Cudjoe Key, FL
10/14 – 10/20
$221/nighttotal: $1326 (6 )
Vo Community 501 Midrise 2bd/1.5ba Large Open Deck
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apartment , Cudjoe Key
9.7 123 reviews
Cudjoe Key, FL
10/14 – 10/20
$313/nighttotal: $1878 (6 )
Island Oasis ~ Your Paradise Awaits!
2 2
apartment , Cudjoe Key
8.8 96 reviews
Cudjoe Key, FL
06/18 – 06/29
$254/nighttotal: $2794 (11 )
Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West
2 2
cottage , Cudjoe Key
9.4 142 reviews
Cudjoe Key, FL
06/18 – 06/29
$255/nighttotal: $2805 (11 )
Enjoy Caribbean Weather In The Usa. Openings April 2026
2 2
apartment , Cudjoe Key
Discover 5-Star Vacation Rentals in Cudjoe Key, FL
Refined interiors and prime locations make these luxury waterfront vacation rentals in Cudjoe Key, FL the ideal choice for your stay.
9.1 323 reviews
Cudjoe Key, FL
10/14 – 10/20
$321/nighttotal: $1926 (6 )
Quaint Cottage, Pool, Dockage Just Minutes To Key West!
2 2
cottage , Cudjoe Key
Best Vacation Rentals with a Steam Room in Cudjoe Key, FL
Maximize your recovery with an on-site sauna, a standard feature at these premier Cudjoe Key, FL vacation rentals.