New Construction At Venture Out! 3 Night Minimum Stay!
2 5
apartment , Cudjoe Key
This Cutthroat Harbour Estates property is conveniently located less than 1km from Venture Out Keys, Venture Key, and Out Key, and within 10km of Upper Sugarloaf Key and Florida Keys beaches. This two-bedroom, two-bathroom house sleeps six, includes in-house laundry facilities, and offers a smoke-free environment; nearby attractions include exploring the keys and relaxing on the beaches.
9.4 143 reviews
Cudjoe Key, FL
29/08 – 03/09
232 €/nighttotal: 1160 € (5 )
Enjoy Caribbean Weather In The Usa. Openings June 2026 Forward!
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.
10 1 review
Cudjoe Key, FL
04/08 – 07/08
148 €/nighttotal: 444 € (3 )
35'x70'wf Rv Site On Canal For Rent For Rv Owners. Pet Friendly Gated Community.
1 2
resort , Cudjoe Key
This Summerland Key holiday park, offering the '35'x70'wf RV Site On Canal For Rent For RV Owners' rental, is conveniently located within 14.5km of Upper Sugarloaf Key, Lower Sugarloaf Sound, and Big Pine Key attractions, including the National Key Deer Refuge Visitor Centre and Big Pine Key Flea Market. The single-bedroom, single-bathroom mobile home sleeps six guests and features an on-site pool, hot tub, and fitness centre, providing a comfortable base for exploring the Lower Keys.
9.4 57 reviews
Cudjoe Key, FL
29/08 – 03/09
326 €/nighttotal: 1630 € (5 )
Relax At Keys Time 2br Waterfront Rental And Boat Dock
2 4
apartment , Cudjoe Key
This canal-front house in the Venture Out community on Cudjoe Key, 35km north of Key West and 52km south of Marathon, offers convenient access to both the Atlantic and Gulf. The 80 square metre, two-bedroom, two-bathroom property sleeps six, boasting a private dock, swimming pool, Jacuzzi, tennis court, and three bicycles and kayaks for guest use.
8.7 45 reviews
Cudjoe Key, FL
29/08 – 03/09
268 €/nighttotal: 1340 € (5 )
Seas The Day In Cudjoe Key
2 4
apartment , Cudjoe Key
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.
9.7 31 reviews
Cudjoe Key, FL
29/08 – 03/09
207 €/nighttotal: 1035 € (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.
9.7 32 reviews
Cudjoe Key, FL
29/08 – 03/09
245 €/nighttotal: 1225 € (5 )
Fisherman's Paradise Cudjoe Key
1 4
apartment , Cudjoe Key
This Cudjoe Key waterfront property boasts a private 30' dock, offering direct access to the water and is a short drive (distance unspecified) from Key West. The two-bedroom, two-bathroom house sleeps four, features a fully equipped kitchen with a gas range and fridge, a swimming pool, Jacuzzi, and access to Venture Out community amenities.
9.6 35 reviews
Cudjoe Key, FL
29/08 – 03/09
237 €/nighttotal: 1185 € (5 )
Isle Be Back To The Sunny Keys
2 4
cottage , Cudjoe Key
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.
8.0 106 reviews
Cudjoe Key, FL
19/09 – 26/09
622 €/nighttotal: 4354 € (7 )
Private Secluded Ocean View & Pool Near Key West
4 8
apartment , Cudjoe Key
This eco-friendly holiday home is located in Summerland Key, just 15 minutes' drive from Key West Golf Club, the beach, restaurants, and shops. The property is rated very good by previous guests and offers a tranquil tropical setting. This four-bedroom, two-bathroom house provides 297 square metres of space and sleeps up to 10 guests. Amenities include a swimming pool, Jacuzzi, terrace, garden, spa, parking, and a kitchen equipped with a fridge, microwave oven, and dishwasher.
9.6 14 reviews
Cudjoe Key, FL
04/08 – 07/08
458 €/nighttotal: 1374 € (3 )
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.
9.6 90 reviews
Cudjoe Key, FL
04/08 – 07/08
291 €/nighttotal: 873 € (3 )
Waterfront Venture Out Home
1 2
apartment , Cudjoe Key
This Venture Out Cottage apartment in Cudjoe Key offers a one-bedroom, one-bathroom self-catering unit with convenient access to local beaches and attractions, though precise distances aren't specified. The property boasts a full kitchen, dining area, sleeper sofa and trundle bed accommodating up to five guests, plus community amenities including a heated swimming pool, hot tub, tennis and basketball courts, marina, boat ramp, on-site laundry, and a convenience store.
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 holiday 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
289 €/nighttotal: 1445 € (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.
8.9 23 reviews
Cudjoe Key, FL
29/08 – 03/09
311 €/nighttotal: 1555 € (5 )
Pelican's Roost, Waterfront Comfort At Venture Out
2 4
house , Cudjoe Key
This beachfront property is situated on Cudjoe Key, a mere 37 kilometres from both the Ernest Hemingway Home and Museum and Duval Street in Key West. The two-bedroom house, spanning 80 square metres, offers a private pool, hot tub, tennis court and a fully equipped kitchen, accommodating up to nine guests.
9.8 138 reviews
Cudjoe Key, FL
29/08 – 03/09
442 €/nighttotal: 2210 € (5 )
Open Water View From Porch , Golf Cart, Dock, Bikes, Kayaks, Trailer Parking
2 4
apartment , Cudjoe Key
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 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.
Best Cudjoe Key, FL holiday rentals with a pool
Among the 438 accommodations in Cudjoe Key, FL, here are the 4 best rentals with a pool
9.6 28 reviews
Cudjoe Key, FL
29/08 – 03/09
214 €/nighttotal: 1070 € (5 )
2bd/1ba Waterfront Retreat W/35’ Dock
1 4
apartment , Cudjoe Key
This Cudjoe Key waterfront holiday home is situated within the Venture Out community, offering easy access to restaurants such as the Square Grouper and the Niles Road Nature Trail. Sleeping up to five guests, this two-bedroom, one-bathroom property boasts a private pool and jacuzzi, direct ocean access, and is close to Murray's Market for grocery shopping.
9.4 3 reviews
Cudjoe Key, FL
25/07 – 01/08
448 €/nighttotal: 3136 € (7 )
Bimini Breeze - Vo 313
2 5
apartment , Cudjoe Key
This Cudjoe Key seaside property is situated within 14.5 kilometres of Upper Sugarloaf Key, Florida Keys Beaches, Lower Sugarloaf Sound, the Big Pine Key Flea Market, and the National Key Deer Refuge Visitor Centre. This three-bedroom, one-bathroom house offers 70 square metres of space, sleeping up to six guests and boasting a swimming pool, jacuzzi, terrace, garden, parking, and free Wi-Fi; barbecue facilities are also available for al fresco dining.
9.8 21 reviews
Cudjoe Key, FL
04/08 – 07/08
303 €/nighttotal: 909 € (3 )
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
2 2
apartment , Cudjoe Key
This Cudjoe Key holiday home is located in the Venture Out gated community, offering easy access to the ocean and local amenities. The two-bedroom, one-bathroom dwelling sleeps six guests and boasts a fully equipped kitchen, private garden, swimming pool, jacuzzi, and access to community tennis and bocce courts; bikes and a tricycle are also provided.
10 2 reviews
Cudjoe Key, FL
19/09 – 26/09
739 €/nighttotal: 5173 € (7 )
232 M² House ∙ 5 Bedrooms ∙ 10 Guests
5 8
house , Cudjoe Key
This five-bedroom, three-bathroom detached residence, offering accommodation for ten guests, is situated within a secluded, gated 8-hectare estate in the Florida Keys wildlife preserve, just 24 kilometres from Key West's shops and nightlife, and conveniently close to notable Florida Keys restaurants. This property boasts a private 107-metre dock for boat access, a heated swimming pool and spa, complimentary bicycles and kayaks, and high-speed 1 gig ATT fibre internet, with cleaning included in the rates.
Frequently asked questions about holiday rentals in Cudjoe Key, FL
What sports or outdoor activites can visitors enjoy in and around Cudjoe Key, FL?
Cudjoe Key is a great place for water sports. You can go swimming, snorkeling, diving, fishing, or kayaking. You can also go boating or sailing. There are also plenty of opportunities for hiking and biking, as well as birdwatching and nature walks.
What are the best Airbnb and holiday rentals in Cudjoe Key, FL?
What other towns or cities can be easily accessed from Cudjoe Key, FL?
You can easily access Key West, Marathon, and Islamorada from Cudjoe Key. These towns offer a range of attractions, from museums and art galleries to restaurants and shops.
What are the most popular Airbnbs in Cudjoe Key, FL?
What amenities are commonly available in vacation rentals in Cudjoe Key, FL?
Vacation rentals in Cudjoe Key usually include amenities like a kitchen, a living room, a bedroom, and a bathroom. Many rentals also have a private pool, a hot tub, and a patio or balcony. Some even come with a boat dock.
What are the best holiday rentals with a pool 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 warm and sunny, and there are fewer crowds. But if you're looking for a more affordable trip, you can visit during the shoulder seasons, from May to June or September to October.
What are the best rentals for families and kids in Cudjoe Key, FL?
Best Cudjoe Key, FL holiday rentals with a balcony
9.0 2 reviews
Cudjoe Key, FL
29/08 – 03/09
357 €/nighttotal: 1785 € (5 )
Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape
2 4
apartment , Cudjoe Key
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.
10 16 reviews
Cudjoe Key, FL
29/08 – 03/09
326 €/nighttotal: 1630 € (5 )
July Discount. Waterfront, Dock ,Kayak, Paddleboard,golf Cart, Bikes,
2 4
resort , Cudjoe Key
This Summerland Key holiday home, part of the Park Place Waterfront Resort Villa, is situated approximately 19km from Florida Keys Beaches and 13km from Upper Sugarloaf Key, offering easy access to Bahia Honda State Park and other attractions; take advantage of the New Listing Discount. Sleeping up to six guests in two bedrooms and one bathroom, the property boasts a fully equipped kitchen, in-unit laundry, a private garden with swimming pool and hot tub, plus free Wi-Fi – perfect for a relaxing Florida Keys getaway.
9.6 53 reviews
Cudjoe Key, FL
04/08 – 07/08
530 €/nighttotal: 1590 € (3 )
Oceanfront 2br Retreat | 35' Dock, Open Views, Boater's Paradise
2 2
apartment , Cudjoe Key
Coconut Telegraph #221 is a two-bedroom flat located in the private, gated Venture Out community on Cudjoe Key, offering direct oceanfront access and a 35-foot dock, situated a 10-minute drive from local restaurants and 32 kilometres from Key West. This 80-square-metre holiday let accommodates four guests and boasts amenities including a swimming pool, jacuzzi, spa, tennis court, and a full kitchen, with easy access to Looe Key for snorkelling and diving, and proximity to both Atlantic and Gulf fishing spots.
This waterfront property is located on Cudjoe Key, just two miles from Upper Sugarloaf Key and Upper Sugarloaf Sound, offering stunning views and easy access to the surrounding area's natural beauty. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay. The two-bedroom, three-bathroom house spans 111 square metres and comfortably accommodates up to six guests. This family-friendly property offers a range of amenities for a relaxing and enjoyable stay, including a private swimming pool, a fitness centre, a garden, a terrace, and a fully equipped kitchen.
Best Cudjoe Key, FL holiday rentals with parking
10 1 review
Cudjoe Key, FL
19/09 – 26/09
567 €/nighttotal: 3969 € (7 )
218 M² House ∙ 6 Bedrooms ∙ 14 Guests
6 8
house , Cudjoe Key
This oceanfront property on Cudjoe Bay, offering panoramic Atlantic views, is located 32 kilometres from Key West and within 1.6 to 12.8 kilometres of local eateries. This spacious 218 square metre holiday home accommodates up to 14 guests with 6 bedrooms and 4 bathrooms, featuring direct ocean access, a private dock, a heated beachfront pool, provided kayaks, and new memory foam mattresses in its king and queen rooms.
8.6 129 reviews
Cudjoe Key, FL
29/08 – 03/09
270 €/nighttotal: 1350 € (5 )
Charming Cottages, Dockage, Pool, Just Minutes To Key West
2 4
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.
9.4 92 reviews
Cudjoe Key, FL
19/09 – 26/09
869 €/nighttotal: 6083 € (7 )
Family Retreat Ocean Front Pool
5 8
apartment , Cudjoe Key
This Cudjoe Key beachfront property boasts panoramic Atlantic views, a private 18-foot floating dock, and is situated approximately 32 kilometres from Key West and 24 kilometres from Bahia Honda State Park. The four-bathroom residence sleeps up to 14 guests, features a heated 3 x 6 metre pool, six bedrooms with new memory foam mattresses in several rooms, kayaks for exploring Cudjoe Bay, and a large screened-in porch with dining for twelve.
This charming cottage is located on Cudjoe Key, just a 15-minute walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to the island's natural beauty. The property has received excellent ratings for its location, cleanliness, and overall experience. The two-bedroom cottage spans 79 square metres and comfortably accommodates up to six guests. Enjoy a range of amenities including a private swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, perfect for relaxing and enjoying your stay.