Holiday Rentals in Cudjoe Key, FL

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.

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.

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.

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.

This Keezy home is situated in the Venture Out gated community on Cudjoe Key, Florida, approximately 30.6 kilometres from Key West.
The two-bedroom, two-bathroom property sleeps five guests and boasts a private porch, fully equipped kitchen with stainless-steel appliances and a gas stove, access to an oceanfront heated saltwater pool, hot tub, and marina, plus community amenities including tennis and pickleball courts.

This canalfront flat in Cudjoe Key's Venture Out community offers direct open-water views and quick access to fishing grounds, located just 3.2 kilometres from restaurants such as Square Grouper and Morning Joint, and 32 kilometres from Key West.
This accommodation for six features two bedrooms, two bathrooms, a 35-foot seawall for boats up to 32 feet, a private dock with a swim ladder and fish-cleaning station, and access to Venture Out's heated pool, jacuzzi, and tennis courts, with two bicycles provided for exploring the island.

Bimini Breeze, a two-bedroom holiday home in Cudjoe Key, offers convenient access to amenities such as a swimming pool, marina, shop, and tennis courts, all within walking distance.
This fully furnished property sleeps six, boasts a newly remodelled kitchen and dining area, a private garden, jacuzzi, and in-unit laundry facilities; overflow parking is available on a first-come, first-served basis.

This charming cottage is situated in the Venture Out community on Cudjoe Key, just 32 kilometres from Key West, offering a peaceful escape from the hustle and bustle of the city.
The property features two bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a private swimming pool, jacuzzi, and a spacious garden with direct access to the water, perfect for enjoying the beauty of the Florida Keys.

This charming cottage is situated in Summerland Key, just a short distance from Upper Sugarloaf Key, Upper Sugarloaf Sound, Venture Key, Venture Out Keys, and Out Key, offering easy access to a variety of water activities. The cottage has received very good ratings from previous guests.
The property features two bedrooms and one bathroom, providing comfortable accommodation for a small family or group of friends. Guests can enjoy the peaceful surroundings and take advantage of the cottage's proximity to restaurants, shops, and other amenities in the area.

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.

This Cudjoe Key oceanfront property offers stunning views and direct beach access, situated 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 80-square-metre house sleeps four guests in two bedrooms and two bathrooms, boasting a private patio, swimming pool, jacuzzi, barbecue grills, free Wi-Fi, and a fully equipped kitchen including a dishwasher.

This smoke-free cottage is located in Summerland Key, a short walk from Venture Key, Venture Out Keys, and Out Key, and a short drive from Florida Keys Beaches. It has received excellent user ratings.
The "Little Gem In Paradise, With Terrace & Private Patio In Resort With Amenities" cottage offers a private patio and a terrace, and can sleep up to four guests. Amenities include a fully equipped kitchen, a washing machine and dryer, free Wi-Fi, barbecue grills, a swimming pool, tennis courts, and a garden.

This Cudjoe Key waterfront property, a 76 square metre (820 square feet) house, boasts stunning views and direct water access, lying within 14.5 kilometres of Upper Sugarloaf Key, Florida Keys beaches, and Lower Sugarloaf Sound, as well as the Big Pine Key Flea Market and National Key Deer Refuge Visitor Centre.
Sleeping up to six guests in three bedrooms and two bathrooms, this self-catering holiday home offers a fully equipped kitchen, swimming pool, Jacuzzi, spa, tennis court, free Wi-Fi, and parking; enjoy on-site barbecues and a hot tub.

This charming cottage is located on Summerland Key, just a short drive from Cudjoe Key, and is close to both the Coupon Bight Aquatic Preserve and Bahia Honda State Park, offering easy access to beautiful natural surroundings. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
The cottage spans 74 square metres and comfortably accommodates up to four guests in its two bedrooms and one bathroom. It features a well-equipped kitchen, a large patio with outdoor seating, a swimming pool, a jacuzzi, a garden, and free Wi-Fi, providing everything you need for a relaxing and enjoyable holiday.

This waterfront holiday home is situated in Cudjoe Key, just 2.4 kilometres from Florida Keys Beaches and within a 10-minute walk of Venture Key, Venture Out Keys, and Out Key, offering a peaceful escape in a beautiful location. The property has received very good user ratings, an excellent location rating, and a very good cleanliness rating.
This single-bedroom property offers 68 square metres of space and can accommodate up to four guests. Enjoy stunning water views, a swimming pool, a jacuzzi, and a fully equipped kitchen, ideal for relaxing and enjoying the tranquil surroundings.

This waterfront property is situated in Cudjoe Key, just 3.8 kilometres from Florida Keys Beaches and a short walk from Venture Key, Venture Out Keys, and Out Key, offering a tranquil setting for a relaxing getaway. The property has received excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom house, spanning 69 square metres, comfortably accommodates up to four guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a fitness centre, a tennis court, and parking, providing a range of activities and comforts for a memorable vacation.