Holiday Rentals in Cudjoe Key, FL

This waterfront holiday flat in the Venture Out community on Cudjoe Key offers direct open water views and convenient access to restaurants such as Square Grouper and Kiki's Sandbar, located within a 10-minute drive, with Key West being a 20-minute drive away.
This 80-square-metre holiday flat accommodates up to six guests across two bedrooms and features a fully equipped kitchen with stainless steel appliances, air conditioning, Wi-Fi, a swimming pool, jacuzzi, and a 35-foot seawall suitable for boats up to 32 feet, complete with a private fish-cleaning station.

This five-bedroom oceanfront house on Cudjoe Key's Highway 1, a 32km drive from Key West, offers private dock access to Cudjoe Bay and is near the Square Grouper restaurant.
The 279 square metre property boasts a heated pool, Jacuzzi, and private dock (shallow water), sleeps 12 guests, and includes kayaks for exploring Cudjoe Bay, a gas grill, and full WiFi.

This Summerland Key holiday home, situated approximately 9.6km from Upper Sugarloaf Key and Upper Sugarloaf Sound, offers easy access to Venture Out Keys, Venture Key, and Out Key.
The two-bedroom property sleeps four, boasting a private patio, swimming pool, tennis court, and fully equipped kitchen including a fridge and dishwasher; BBQ facilities are available for al fresco dining.

This waterfront holiday home is located on Cudjoe Key, just 6 kilometres from Upper Sugarloaf Key and Florida Keys Beaches, providing easy access to the area's attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The 81 square metre property offers two bedrooms and can accommodate up to four guests. It boasts a range of amenities, including a swimming pool, jacuzzi, spa, tennis court, and a barbecue grill, making it perfect for relaxation and entertainment.

This two-bedroom flat in Cudjoe Key is located within the private, gated community of Venture Out at MM23, offering direct canal access with a 35-foot seawall and dock suitable for boats up to 10.36 metres, just a 20-minute drive from Key West and 10 minutes from restaurants such as Square Grouper and Mangrove Mamas.
This 80-square-metre holiday home sleeps up to six guests and features air conditioning, Wi-Fi, a kitchen with a fridge, microwave, and dishwasher, a swimming pool, jacuzzi, spa, tennis courts, and a dedicated fish cleaning station, with an under-home storeroom for gear and four adult bikes provided.

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 two-bedroom apartment, part of the Venture Out Resort in Summerland Key, is conveniently located near Cudjoe Key, offering easy access to beaches and attractions such as the Blue Hole.
The 62 square metre self-catering property sleeps six, features a kitchen with fridge and microwave, a patio with BBQ, resort amenities including a pool and tennis courts, and allows two small dogs under 18kg.

This charming cottage is located in the Venture Out Community on Cudjoe Key, just a short drive from the famous Seven Mile Bridge. The property boasts excellent user, location and cleanliness ratings, making it a popular choice for visitors.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to six guests. It features a fully equipped kitchen, a private garden, a swimming pool, a jacuzzi, and a spacious open porch with a gas grill, perfect for enjoying the tropical climate.

This canal-front holiday home, located in Summerland Key, offers easy access to the ocean and Gulf, and is close to Bahia Honda State Park.
The 79 square metre property boasts two bedrooms, two bathrooms, a pull-out sofa, a private 35-foot dock, kayaks, bicycles, and a full kitchen, comfortably sleeping six guests.

This three-bedroom, two-bathroom holiday home is located in the Venture Out gated community on Cudjoe Key, a short drive from Key West and other Florida Keys attractions.
The 78-square-metre property boasts a fully equipped kitchen, private patio, access to a community pool, Jacuzzi, tennis courts, and marina store, comfortably sleeping six guests and offering ocean views from both porches.

This Cudjoe Key holiday home is conveniently located within a 6km radius of Upper Sugarloaf Key and Florida Keys beaches, and a 1.6km walk from Venture Out Keys, Venture Key, and Out Key.
This 80 square metre property boasts two bedrooms, two bathrooms, sleeps six, and includes a swimming pool, Jacuzzi, tennis court, and free Wi-Fi.

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 oceanfront cottage offers stunning views and direct beach access, situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key.
The 36-square-metre self-catering property sleeps two guests in one bedroom and one bathroom, boasting a fully equipped kitchen, private terrace, swimming pool, and free Wi-Fi.

Mahi House #440, situated in the Venture Out gated community on Cudjoe Key, offers direct waterfront access via a boating canal, a 16km drive from Key West and close to local restaurants.
This two-bedroom, two-bathroom property boasts 68 square metres of living space, sleeping up to six guests and includes a private pool, Jacuzzi, and access to resort amenities such as tennis courts; two bicycles are provided for exploring the island.

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.

This waterfront apartment in the Venture Out community on Cudjoe Key, Florida, offers easy access to Key West (32km) and local restaurants such as the Square Grouper and Morning Joint, all within a short drive.
The 67-square-metre property features two bedrooms, one bathroom, sleeps six guests, and boasts resort-style amenities including a swimming pool, Jacuzzi, tennis court, and private dock with kayak and Hobie Cat access.