Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West
2 2
cottage , Cudjoe Key
This charming waterfront cottage is located just 3km from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offering easy access to the surrounding area's attractions. The property has received very good ratings from previous guests. The cottage provides 2 bedrooms and 1 bathroom in a 70 square meter space, comfortably accommodating 4 guests. It boasts a fully equipped kitchen, air conditioning, a private swimming pool, a terrace, a garden, and parking, as well as access to the water for fishing, kayaking, or simply relaxing by the shore.
8.4 8 reviews
Cudjoe Key, FL
25/07 – 01/08
₹48602/nighttotal: ₹340214 (7 )
Fl Keys Cottage With Ocean Views - Venture Out Unit 395
2 5
cottage , Cudjoe Key
This charming cottage is located on Cudjoe Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, and a short drive from Florida Keys Beaches. It has received very good user ratings, making it a popular choice for travellers. The cottage has two bedrooms and one bathroom, providing comfortable accommodation for up to six guests. Enjoy the peace and quiet of the seafront location, relax in the spa tub, and make use of the fully equipped kitchen, barbecue grills, and swimming pool.
This two-bedroom house is situated on Summerland Key, just under 5 kilometres from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key. The 111 square metre property boasts a fully-equipped kitchen, a swimming pool, a terrace, and a garden, comfortably accommodating up to six guests.
9.2 12 reviews
Cudjoe Key, FL
14/10 – 20/10
₹10872/nighttotal: ₹65232 (6 )
Luxury Pull Thru Rv Lot With Access To All The Resorts Amenities!
1 2
resort , Cudjoe Key
Luxury RV Lot With Access To All The Resorts Amenities! is situated in the Venture Out community on Cudjoe Key, Florida, at mile marker 23, offering Atlantic Ocean views and easy access to Summerland Key attractions. This spacious 21 x 11 metre pitch provides water, sewer, and 50/30 amp electrical hook-ups, accommodating up to six guests and including access to an 80-foot communal pool, hot tub, tennis and pickleball courts, plus a recreation centre, convenience store, boat ramp, and laundry facilities.
8.6 165 reviews
Cudjoe Key, FL
14/10 – 20/10
₹25758/nighttotal: ₹154548 (6 )
Cottage With Pool And Boat Dockage Just Minutes To Key West!
1 2
cottage , Cudjoe Key
This Cudjoe Key waterfront cottage, situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offers stunning views and direct water access. The 36 square metre property sleeps two in one bedroom, one bathroom, and boasts a fully equipped kitchen, private terrace, swimming pool, garden, and barbecue facilities.
9.6 5 reviews
Cudjoe Key, FL
14/10 – 20/10
₹28400/nighttotal: ₹170400 (6 )
Blue Mind #225 Canal-front W/dock & Pool
1 2
apartment , Cudjoe Key
Blue Mind #225 is a waterfront cottage situated in the Venture Out gated community on Cudjoe Key, Florida Keys, approximately 32km from Key West and a short drive from restaurants like the Square Grouper and Morning Joint. This pet-friendly one-bedroom, one-bathroom property sleeps four, boasting a fully equipped kitchen, in-unit laundry, a private seawall accommodating boats up to 10m, kayaks, bicycles, and access to community amenities including a swimming pool, tennis courts, and a marina store.
9.1 7 reviews
Cudjoe Key, FL
25/07 – 01/08
₹43788/nighttotal: ₹306516 (7 )
Comfortable Home W/ Amenities In Gated Community
1 5
apartment , Cudjoe Key
This two-bedroom house is located within the Venture Out gated community on Cudjoe Key, offering convenient access to local marinas and proximity to other Lower Keys attractions. The self-catering property sleeps five, boasting a fully equipped kitchen, private parking, access to a swimming pool, jacuzzi, and resort amenities including tennis and pickleball courts, and is within easy reach of the local boat ramps.
9.8 207 reviews
Cudjoe Key, FL
14/10 – 20/10
₹29230/nighttotal: ₹175380 (6 )
Relax By Florida Keys Beaches, Just A 7-min Drive Away
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apartment , Cudjoe Key
This waterfront house in Cudjoe Key is situated just 9.6 kilometres from Upper Sugarloaf Key and Florida Keys Beaches, offering easy access to the region's natural beauty. The two-bedroom property sleeps up to five guests and boasts a private pool, spa tub, and barbecue grills, perfect for relaxing after a day of exploring the local area.
8.6 129 reviews
Cudjoe Key, FL
14/10 – 20/10
₹30682/nighttotal: ₹184092 (6 )
Charming Cottages, Dockage, Pool, Just Minutes To Key West
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cottage , Cudjoe Key
This Summerland Key holiday home is situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, Venture Key, Venture Out Keys, and Out Key, offering easy access to these nearby islands. The 73 square metre property sleeps four guests in two bedrooms and one bathroom, and includes a fully equipped kitchen, washing machine, barbecue, swimming pool, and parking, plus Wi-Fi access.
10 17 reviews
Cudjoe Key, FL
25/07 – 01/08
₹47525/nighttotal: ₹332675 (7 )
New Construction. $299 Per Night.
1 5
apartment , Cudjoe Key
This brand new Cudjoe Key holiday home, part of the Venture Out Resort, is conveniently located near Marathon and Key West, offering easy access to backcountry Gulf-side fishing and the Turtle Hospital. The two-bedroom, two-bathroom property sleeps six guests and boasts a fully equipped kitchen, private decks with water views, and access to resort amenities including an Olympic-sized heated pool, hot tub, and tennis courts.
9.6 55 reviews
Cudjoe Key, FL
29/08 – 03/09
₹37632/nighttotal: ₹188160 (5 )
Mile Marker Mahi - Venture Out #465
2 4
cottage , Cudjoe Key
This charming cottage is situated on Cudjoe Key, just 1.5km from Venture Key and 4km from Florida Keys Beaches, offering a peaceful escape from the hustle and bustle. The cottage has received excellent guest reviews, highlighting its tranquil setting and comfortable amenities. The property features two bedrooms and two bathrooms, spanning 79 square metres and accommodating up to four guests. Guests can enjoy a fully equipped kitchen, a private patio, a luxurious spa tub, and barbecue grills, making it perfect for a relaxing and enjoyable stay.
This charming cottage is situated on Cudjoe Key, a short 15-minute walk from Venture Key and Venture Out Keys, offering a peaceful retreat close to local attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The cottage spans 79 square metres and comfortably accommodates up to six guests in its two bedrooms and two bathrooms. Guests can enjoy a range of amenities including a private swimming pool, jacuzzi, and a fully equipped kitchen, making it ideal for both relaxation and entertaining.
Best family friendly Cudjoe Key, FL vacation rentals
Among the 438 accommodations in Cudjoe Key, FL, here are the 4 best family friendly rentals
8.6 9 reviews
Cudjoe Key, FL
29/08 – 03/09
₹31933/nighttotal: ₹159665 (5 )
Reel Island Retreat #273 At Venture Out In The Florida Keys
2 4
apartment , Cudjoe Key
This Cudjoe Key waterfront holiday home, situated in the Venture Out community of Summerland Key, is a 20-minute drive from Key West. The 76-square-metre (820 sq ft) property boasts three bedrooms, two bathrooms, sleeps six, and includes a private dock, Tiki bar, swimming pool, Jacuzzi, tennis court, and is close to restaurants such as the Square Grouper and Morning Joint.
8.8 34 reviews
Cudjoe Key, FL
29/08 – 03/09
₹40068/nighttotal: ₹200340 (5 )
Water At Your Back Door
3 4
cottage , Cudjoe Key
This waterfront cottage is situated on Cudjoe Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to local attractions and a peaceful island setting. The cottage has received very good ratings from previous guests. The property has two bedrooms and can accommodate up to six guests. Guests can enjoy a private pool, spa tub, barbecue grills, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
8.7 50 reviews
Cudjoe Key, FL
29/08 – 03/09
₹26749/nighttotal: ₹133745 (5 )
Tree Top Paradise
2 4
house , Cudjoe Key
Tree Top Paradise, a holiday home in Cudjoe Key, Florida, is situated approximately 37 kilometres from the Ernest Hemingway Home and Museum and Duval Street, and 39 kilometres from the Southernmost Point. This 78-square-metre property boasts two bedrooms, two bathrooms, sleeps up to 11 guests, and includes a private pool, Jacuzzi, tennis court, and free Wi-Fi; nearby activities include snorkelling, cycling, and fishing.
9.8 85 reviews
Cudjoe Key, FL
14/10 – 20/10
₹28602/nighttotal: ₹171612 (6 )
Cozy 2 Br/2 Bath Home In Cudjoe
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apartment , Cudjoe Key
This two-bedroom apartment is situated in the Venture Out community on Cudjoe Key, just a short drive from the famous Seven Mile Bridge and a few minutes from the beach. The property has received excellent ratings for location, cleanliness, and user experience. The apartment features two bedrooms, two bathrooms, and can accommodate up to six guests. It boasts a well-equipped kitchen, a private patio with a lounge area and grill, and access to community amenities such as a swimming pool, tennis courts, and a children's playground.
Best Cudjoe Key, FL vacation rentals with a pool
Among the 438 accommodations in Cudjoe Key, FL, here are the 4 best rentals with a pool
9.8 8 reviews
Cudjoe Key, FL
25/07 – 01/08
₹44388/nighttotal: ₹310716 (7 )
139 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 5
house , Cudjoe Key
This oceanfront property is located within the Florida Keys National Wildlife Refuge on Cudjoe Key, offering direct Atlantic access and situated approximately 14 kilometres from the attractions of Key West. This spacious 139 square metre house, ideal for up to six guests, features three bedrooms, two bathrooms, air conditioning, a swimming pool, jacuzzi, and a private terrace, with exceptional fishing and diving opportunities available directly from the estate.
9.7 31 reviews
Cudjoe Key, FL
29/08 – 03/09
₹22821/nighttotal: ₹114105 (5 )
Ocean Breeze @ Vo - Kayaks, Bikes, 30 Min From Kw
1 4
apartment , Cudjoe Key
This Cudjoe Key cottage boasts spectacular sunrise and ocean views, situated directly across from the open water and a 48km drive from Duval Street in Key West. The self-catering property sleeps three guests in one bedroom with a queen-size bed, and features a private swimming pool, jacuzzi, and access to resort amenities including tennis and pickleball courts; two kayaks and two bicycles are also available for guest use.
9.4 142 reviews
Cudjoe Key, FL
29/08 – 03/09
₹25638/nighttotal: ₹128190 (5 )
Enjoy Caribbean Weather In The Usa. Openings April 2026
2 4
apartment , Cudjoe Key
This Cudjoe Key holiday home is situated near Venture Out Keys, Venture Key, and Out Key (within a 9.6km walk), and is also within 9.6km of Upper Sugarloaf Key and Florida Keys Beaches. This 80 square metre property sleeps six guests in three bedrooms and one bathroom, boasting a private pool, spa, barbecue grills, free Wi-Fi, and a fully equipped kitchen; nearby activities include tennis.
9.5 104 reviews
Cudjoe Key, FL
29/08 – 03/09
₹33224/nighttotal: ₹166120 (5 )
Tree Top Paradise
3 4
apartment , Cudjoe Key
This family-friendly property is located in Summerland Key, a short 4km drive from Florida Keys Beaches and within a 5-minute walk of Venture Key, Venture Out Keys, and Out Key. It has received excellent user ratings for location, cleanliness, and overall experience. The 80 square metre house has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Guests can enjoy a range of amenities including a swimming pool, a jacuzzi, a tennis court, a garden, and a terrace, making it ideal for a relaxing and enjoyable stay.
Frequently asked questions about holiday rentals in Cudjoe Key, FL
Which walking or cycling routes are the best in Cudjoe Key, FL?
The Cudjoe Key is a small island, so there aren't many dedicated walking or cycling routes, but you can enjoy a leisurely stroll or bike ride along Overseas Highway (US-1). It's a scenic route with views of the ocean and the mangroves. You can also walk or cycle along the Cudjoe Key Beach, which is a beautiful stretch of white sand.
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?
You can go fishing, kayaking, paddleboarding, and diving in the crystal clear waters around Cudjoe Key. If you're feeling adventurous, you can even try your hand at snorkelling or scuba diving at Sombrero Reef, which is just a short boat ride away. There's also windsurfing and kiteboarding in the area.
What are the most popular Airbnbs in Cudjoe Key, FL?
What other towns or cities can be easily accessed from Cudjoe Key, FL?
You can easily get to Marathon and Key West from Cudjoe Key. Marathon is just a short drive away, and Key West is about an hour and a half drive. You can also take a ferry to Key West from Marathon.
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?
Most vacation rentals in Cudjoe Key come with amenities like a kitchen, a living room, a dining area, and a bathroom. Many also have a private balcony or patio, and some have a swimming pool or hot tub. Some rentals also offer access to a shared dock, boat ramp, or kayak launch.
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, when the weather is warm and sunny. The summer months can be hot and humid, and there is a chance of hurricanes.
What are the best rentals or Airbnbs with a jacuzzi in Cudjoe Key, FL?
Best Cudjoe Key, FL holiday rentals with a balcony
9.6 14 reviews
Cudjoe Key, FL
14/10 – 20/10
₹27916/nighttotal: ₹167496 (6 )
Island Oasis ~ Your Paradise Awaits In Venture Out Resort!
2 2
cottage , Cudjoe Key
Island Oasis ~ Your Paradise Awaits In Venture Out Resort! is a waterfront cottage in Cudjoe Key, Florida, conveniently located within a 2.4-kilometre radius of Florida Keys Beaches and a 15-minute walk from Venture Out Keys, Venture Key, and Out Key. This two-bedroom, two-bathroom holiday home sleeps six guests and boasts a fully equipped kitchen, private balcony, swimming pool, tennis court, and access to barbecue grills; enjoying stunning views and easy water access.
9.9 203 reviews
Cudjoe Key, FL
14/10 – 20/10
₹65437/nighttotal: ₹392622 (6 )
2br,2ba W King Master,35' Seawall-ss And Quartz Kitchen,bikes, Kayaks And Views
3 2
cottage , Cudjoe Key
This family-friendly cottage is located in Summerland Key, just a short walk from Venture Key and a short drive from Florida Keys Beaches. It has received excellent ratings for its location, cleanliness, and overall experience. The cottage has two bedrooms and two bathrooms, spanning 81 square metres and accommodating up to six guests. It offers a range of amenities including a private pool, spa tub, barbecue grills, an arcade/game room, and a fully equipped kitchen.
9.5 438 reviews
Cudjoe Key, FL
14/10 – 20/10
₹48183/nighttotal: ₹289098 (6 )
Save Big $$$ May!! Waterfront 4 Bikes & 2-2 Person Kayaks. King & Queen Beds
2 2
apartment , Cudjoe Key
This holiday home is located in Summerland Key, just a short walk from Venture Key and Venture Out Keys, and less than 800 metres from Out Key. It has consistently received excellent ratings for location, cleanliness, and overall user experience. The property offers 80 square metres of living space, comfortably accommodating up to six guests in two bedrooms and two bathrooms. Guests can enjoy a range of amenities, including a swimming pool, Jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for a relaxing and enjoyable stay.
Cudjoe Key, FL
29/08 – 03/09
₹34622/nighttotal: ₹173110 (5 )
Bright 2br 2ba In Cudjoe Key| Sleeps 6 | Wifi | Washer Dryer | Near Water & Key West
3 4
apartment , Cudjoe Key
This three-bedroom, two-bathroom flat is located within the private, gated community of Venture Out on Cudjoe Key, offering convenient access to local dining within a 10-kilometre drive and Key West just 32 kilometres away. This 77-square-metre holiday home accommodates up to six guests and features air conditioning, a fully equipped kitchen, Wi-Fi, a swimming pool, jacuzzi, spa, and tennis courts, with a marina store and oceanfront beach area available within the community.
Best Cudjoe Key, FL holiday rentals with parking
9.6 4 reviews
Cudjoe Key, FL
14/10 – 20/10
₹29699/nighttotal: ₹178194 (6 )
Imagine In The Keys - Venture Out Unit 073
2 2
cottage , Cudjoe Key
This Cudjoe Key waterfront holiday home, situated 3.9km from Florida Keys Beaches and 9.7km from Upper Sugarloaf Key and Upper Sugarloaf Sound, offers stunning water views and direct water access. The 74 square metre property boasts two bedrooms, two bathrooms, a private patio, swimming pool, jacuzzi, and barbecue facilities, sleeping up to six guests.
8.0 1 review
Cudjoe Key, FL
14/10 – 20/10
₹27419/nighttotal: ₹164514 (6 )
Little Piece Of Paradise #233 - 35' Seawall - Cudjoe Key
2 2
apartment , Cudjoe Key
This canal-front apartment is situated within the Venture Out gated community on Cudjoe Key, Florida, a short drive from Key West and other Florida Keys attractions. The 68 square metre (732 square feet) self-catering property sleeps four guests, boasting three bedrooms, one bathroom, a fully equipped kitchen with a bait freezer, in-unit laundry, private grill, direct canal access with a 35' seawall and dock, and access to Venture Out's amenities including an 80' heated pool, jacuzzi, and tennis courts.
9.7 6 reviews
Cudjoe Key, FL
14/10 – 20/10
₹26450/nighttotal: ₹158700 (6 )
Latitude Adjustment #598, Canal Front-ocean Views
1 2
apartment , Cudjoe Key
This canal-front holiday home is situated in the private, gated Venture Out community on Cudjoe Key, approximately 32 kilometres from Key West and a short drive to local dining and attractions. This two-bedroom, two-bathroom holiday let accommodates up to six guests and features direct canal access with a 35-foot seawall, a 32-foot boat dock, a covered patio with canal and ocean views, a fully equipped kitchen, and access to community amenities including a heated swimming pool and tennis courts.
10 1 review
Cudjoe Key, FL
14/10 – 20/10
₹24760/nighttotal: ₹148560 (6 )
Pet-friendly Keys Cottage At Plankton's Palace - Pool, Patio & Gated Access
2 2
apartment , Cudjoe Key
This Summerland Key waterfront property, a short drive from Bahia Honda State Park, offers stunning views and is conveniently located near other Lower Keys attractions. The 68-square-metre (732 sq ft) self-catering holiday home sleeps four guests across two bedrooms, one bathroom, and boasts a private terrace, garden, hot tub, and fitness centre access.