House in Cudjoe Key, FL
6 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this house rental
The Diving Dolphin #268 - Waterfront Getaway | 2BR/2BA | Ocean Views, 2 Kayaks, 2 Paddleboards, 35' Seawall & Pet-Friendly!
Welcome to your perfect island escape! This charming and clean two-bedroom, two-bath home sits right on a boating canal with beautiful ocean views and breathtaking sunrise scenes. Ideal for up to six guests, it's the perfect spot for relaxing, adventuring, and making memories.
Inside, you'll find two cozy bedrooms, each with a queen-sized bed, TVs and two full bathrooms for your comfort. The Primary bedroom has an ensuite full bathroom and direct access to the back patio. The guest bedroom also has a sliding door for direct access to the back patio.
There is a Queen size pull out sleeper sofa in the living room for additional sleeping accommodations.
The fully equipped kitchen makes meal prep easy, featuring a dining table for four and a kitchen island with two barstools. There is a dishwasher for convenience and a Keurig coffee machine ready to brew up your favorite cup of coffee.
A dedicated laundry area with washer and dryer adds to the ease of your stay, and beach towels are provided for your sun-soaked adventures.
Adventure awaits right outside your door! Guests have access to two paddleboards, one kayak, and one tandem kayak — perfect for exploring the surrounding islands and waterways. This location is a boater's dream with a 35' seawall, offering quick access to both the backcountry and offshore waters. There is a fish cleaning station and swim ladder on the dock for your convenience. A BBQ grill awaits to cook up your fresh catch of the day. Plenty of outdoor seating including a table and sun loungers to relax and enjoy the sea breezes!
We're pet-friendly too! Bring along up to 1 small, under 40# dog maximum (with a $250 pet fee) so the whole family can enjoy the trip.
Book your stay today and experience the beauty, adventure, and relaxation that island life has to offer! Traveling with little ones? We've made your stay a little easier with a high chair and Pack 'n Play available for guest use. These family-friendly extras mean less to pack and more time to relax and enjoy your Florida Keys getaway.
Venture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.
Adventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!
Whether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.
Located inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking Information: Parking is limited to one vehicle per unit. The vehicle must fit fully in the driveway and may not extend into the road. The driveway measurements are 19'L x 10'W. If your vehicle does not fit, you must request an overflow parking pass from the guard gate. Overflow parking is $5 per day, subject to availability (first come - first serve and is not guaranteed), limited to one overflow spot only, and has a maximum stay of 14 days.
Boat trailer overflow parking is also subject to availability: $5 per day for trailers under 20 feet and $10 per day for trailers over 25 feet.
If overflow parking is unavailable, if your trailer does not fit, or if you need more than one overflow spot, you must use an offsite parking option. For the most up-to-date availability and pricing, please reach out to the offsite companies directly. Must follow all the Rules and Regulations during your stay. Must follow all the Rules and Regulations during your stay.
Main guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee.
Book your stay today and experience the beauty of waterfront living!
Welcome to your perfect island escape! This charming and clean two-bedroom, two-bath home sits right on a boating canal with beautiful ocean views and breathtaking sunrise scenes. Ideal for up to six guests, it's the perfect spot for relaxing, adventuring, and making memories.
Inside, you'll find two cozy bedrooms, each with a queen-sized bed, TVs and two full bathrooms for your comfort. The Primary bedroom has an ensuite full bathroom and direct access to the back patio. The guest bedroom also has a sliding door for direct access to the back patio.
There is a Queen size pull out sleeper sofa in the living room for additional sleeping accommodations.
The fully equipped kitchen makes meal prep easy, featuring a dining table for four and a kitchen island with two barstools. There is a dishwasher for convenience and a Keurig coffee machine ready to brew up your favorite cup of coffee.
A dedicated laundry area with washer and dryer adds to the ease of your stay, and beach towels are provided for your sun-soaked adventures.
Adventure awaits right outside your door! Guests have access to two paddleboards, one kayak, and one tandem kayak — perfect for exploring the surrounding islands and waterways. This location is a boater's dream with a 35' seawall, offering quick access to both the backcountry and offshore waters. There is a fish cleaning station and swim ladder on the dock for your convenience. A BBQ grill awaits to cook up your fresh catch of the day. Plenty of outdoor seating including a table and sun loungers to relax and enjoy the sea breezes!
We're pet-friendly too! Bring along up to 1 small, under 40# dog maximum (with a $250 pet fee) so the whole family can enjoy the trip.
Book your stay today and experience the beauty, adventure, and relaxation that island life has to offer! Traveling with little ones? We've made your stay a little easier with a high chair and Pack 'n Play available for guest use. These family-friendly extras mean less to pack and more time to relax and enjoy your Florida Keys getaway.
Venture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.
Adventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!
Whether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.
Located inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking Information: Parking is limited to one vehicle per unit. The vehicle must fit fully in the driveway and may not extend into the road. The driveway measurements are 19'L x 10'W. If your vehicle does not fit, you must request an overflow parking pass from the guard gate. Overflow parking is $5 per day, subject to availability (first come - first serve and is not guaranteed), limited to one overflow spot only, and has a maximum stay of 14 days.
Boat trailer overflow parking is also subject to availability: $5 per day for trailers under 20 feet and $10 per day for trailers over 25 feet.
If overflow parking is unavailable, if your trailer does not fit, or if you need more than one overflow spot, you must use an offsite parking option. For the most up-to-date availability and pricing, please reach out to the offsite companies directly. Must follow all the Rules and Regulations during your stay. Must follow all the Rules and Regulations during your stay.
Main guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee.
Book your stay today and experience the beauty of waterfront living!
Amenities
Non-smoking
Pets allowed
Family friendly
Map of Cudjoe Key, FL
Ratings and reviews
10 / 10Outstanding·Nov 2025
Exactly as described and pictured. All the comforts of home included. Staff at Venture Out were friendly and welcoming. Very close to a few restaurants a very cool coffee shop/breakfast joint. A good location for exploring the lower keys.Would 100% stay here again.
8 / 10Excellent·Aug 2025
Overall it was good. There are a few things that could be better. We had to keep all curtains and blinds closed at all times. The air conditioning (mini splits)struggled to keep the unit cool. I realize it was a pet unit but it smelled like pet urine and the carpets were very dirty. Housekeeping did remove the carpets. The sugar ants were bad in the kitchen area. We just kept everything in the refrigerator. Housekeeping offered to spray but I said it was not necessary. I have stayed in Venture Out multiple times. The property itself with all of the amenities is great. The unit overall was good. Just a few minor things mentioned above.
10 / 10Outstanding·Jul 2025
This was a great little community on Cudjoe Key. The property didn't have many reviews so I was a little nervous, but it was just as described in the listing. The management company was responsive. The house was very comfortable. The two loungers pictured were brittle and cracked from being in the sun, but after I reported it they brought some better ones to replace them promptly. It's well-located for trips to nearby keys, especially Key West, while being much quieter. The kayaks and SUPs were a nice touch, though it was a bit on the windy side the whole time we were there. It's easy to get out on kayaks and explore some nearby unpopulated smaller keys. We had a lot of fun catching little snappers and grunts in the canal. Around dusk the first night, I hooked an absolute monstah on a pinfish but after fighting it for five minutes with a medium heavy rod, it broke me off at the end of the canal. I want to think it was a shark, but the neighbors tell me it was probably a giant tarpon. So, I'll be crying myself to sleep for a while for having lost it. I am not sure whether I should congratulate my discipline for not having walked onto other people's property to fight it, or condemn my weakness for bowing to such petty restrictions when glory was within my grasp.Oh, the beds were comfortable too and the kitchen was pretty well equipped. The pool was nice. The community has a ton of really nit-picky rules.
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Top rated by guests
9.8Outstanding
(6 Ratings)
"Exactly as described and pictured. All the comforts of home included. Staff at Venture Out were friendly and welcoming. Very close to a few restaurants a very cool coffee shop/breakfast joint. A good..."
Jean E.Don't miss out! Price and availability may change
