Vacation Rentals in Cudjoe Key, FL

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Cudjoe Key, FL vacation rentals
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438 Vacation rentals and Airbnb in Cudjoe Key, FL

Best family friendly Cudjoe Key, FL vacation rentals

Among the 438 accommodations in Cudjoe Key, FL, here are the 4 best family friendly rentals

Reel Island Retreat #273 At Venture Out In The Florida Keys - Cudjoe Key, FL
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.
Water At Your Back Door - Cudjoe Key, FL
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.
Tree Top Paradise - Cudjoe Key, FL
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.
Cozy 2 Br/2 Bath Home In Cudjoe - Cudjoe Key, FL
9.8 85 reviews
Cudjoe Key, FL
14/10 – 20/10
₹28602/nighttotal: ₹171612 (6 )

Cozy 2 Br/2 Bath Home In Cudjoe

1 2
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

139 M² House ∙ 3 Bedrooms ∙ 6 Guests - Cudjoe Key, FL
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.
Ocean Breeze @ Vo - Kayaks, Bikes, 30 Min From Kw - Cudjoe Key, FL
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.
Enjoy Caribbean Weather In The Usa. Openings April 2026 - Cudjoe Key, FL
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.
Tree Top Paradise - Cudjoe Key, FL
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

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Best Cudjoe Key, FL holiday rentals with a balcony

Island Oasis ~ Your Paradise Awaits In Venture Out Resort! - Cudjoe Key, FL
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.
2br,2ba W King Master,35' Seawall-ss And Quartz Kitchen,bikes, Kayaks And Views - Cudjoe Key, FL
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.
Save Big $$$ May!!  Waterfront 4 Bikes & 2-2 Person Kayaks. King & Queen Beds - Cudjoe Key, FL
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.
Bright 2br 2ba In Cudjoe Key| Sleeps 6 | Wifi | Washer Dryer | Near Water & Key West - Cudjoe Key, FL
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

Imagine In The Keys - Venture Out Unit 073 - Cudjoe Key, FL
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.
Little Piece Of Paradise #233 - 35' Seawall - Cudjoe Key - Cudjoe Key, FL
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.
Latitude Adjustment #598, Canal Front-ocean Views - Cudjoe Key, FL
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.
Pet-friendly Keys Cottage At Plankton's Palace - Pool, Patio & Gated Access - Cudjoe Key, FL
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.
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