Entire home

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Photo gallery for Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Exterior
Outdoor dining
Living area
Living area
Living area

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 6840 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View in a map
Cudjoe Key, FL
  • Place, Florida Keys Beaches
    ‪8 min drive‬
  • Place, Upper Sugarloaf Key
    ‪8 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪9 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪38 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Guest Bedroom

1 Queen Bed

Primary Bedroom

1 King Bed

2 bathrooms

Guest Bathroom

Bathtub or shower · Toilet

Primary Ensuite

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Dining area

About this property

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Stunning Waterfront Getaway | 56’ Dock + Ocean Views
Welcome to Keys to Paradise #95, your perfect Florida Keys escape. This beautiful 2-bedroom, 2-bath waterfront home is tucked away on a quiet cul-de-sac in the gated community of Venture Out on Cudjoe Key, offering breathtaking ocean views, direct boating access, and lots of amenities. Whether you’re here for world-class fishing, a family getaway, or simply to relax by the water, this home has everything you need for an unforgettable vacation.
Highlights - Prime Waterfront Location – Overlooks dazzling ocean views with private patio seating for sunrise coffee or evening cocktails.
56’ Dock with Deep Water Access – Perfect for large boats or two smaller vessels, with cleats, water, and power. Quick access to the Atlantic and Gulf for fishing or sandbar hopping.
Outdoor Living – Covered balcony with dining set, spacious downstairs patio with loungers, Adirondack chairs, BBQ grill, picnic table, and space to play cornhole or relax in the breeze.
Amenities at Venture Out – Heated Olympic-size pool, hot tub, saltwater lagoon, tennis, pickleball, marina with fuel, store, and more—all within steps of your front door.
Inside the Home - Open Living Room – Bright and airy with a wall of windows and sliding glass doors framing the ocean. Includes a 55” TV, leather sofa, and chairs with ottomans.
Fully Equipped Kitchen & Dining – Granite island with barstools, seating for six, and everything you need for meals at home.
Spacious Bedrooms – Primary Suite: King bed, ensuite bath with walk-in shower, TV, and closet space.
Guest Room: Queen bed, private balcony, TV, and easy access to a full bath with tub/shower combo.
Additional Sleeping: Futon in the living room + queen air mattress.
Conveniences – Washer/dryer, high-speed WiFi, and a cargo lift to make moving luggage and groceries easy.
Extra Perks - Kayaks & Bikes – 4 kayaks and 4 bikes included for exploring the Keys by land or water.
Fish Cleaning Station & Swim Ladder – Anglers can prep the day’s catch with ease, and adventurous guests can take a refreshing dip right from the dock.
Renter’s Closet – Extra refrigerator/freezer for bait or fish storage.

Whether you’re boating, fishing, kayaking, or simply lounging by the ocean, this Florida Keys waterfront retreat offers the perfect balance of comfort, convenience, and adventure. Just 20 minutes from Key West and close to some of the best restaurants in the Lower Keys, Keys to Paradise #95 is your gateway to an unforgettable island vacation.

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, pickleball 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.

Important Notes - Sleeps up to 6 guests. Sorry, no pets allowed. 3 exterior security cameras: two in front (entry & storage) and one rear (dock area).

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 for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay. Boat trailer parking is also available on a first come, first serve basis for an additional nightly fee. If the overflow parking is full when you arrive, no worries, we work with several other nearby storage lots.
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.

Social Media -
@bluescaperealestate
YouTube Videos @bluescapevacations

Book your stay today and experience the beauty of waterfront living!

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Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Summerland Key

Located in Summerland Key, this holiday home is on the waterfront. Florida Keys Beaches and Bahia Honda State Park reflect the area's natural beauty and area attractions include Blue Hole and Wilhelmina Harvey Park. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Cudjoe Key, FL

What's nearby

  • Florida Keys Beaches - 8 min drive - 7.4 km
  • Upper Sugarloaf Key - 8 min drive - 7.6 km
  • Upper Sugarloaf Sound - 9 min drive - 8.9 km
  • Lower Sugarloaf Sound - 12 min drive - 12.5 km
  • National Key Deer Refuge Visitor Center - 17 min drive - 18.2 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 33 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬10 min drive
  • ‪Morning Joint - ‬4 min drive
  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪Mangrove Mama's - ‬8 min drive
  • ‪Square Grouper Bar and Grill - ‬4 min drive

Frequently asked questions

Does Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool?

As of 13 Apr, 2026, prices found for a 1-night stay for 2 adults at Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool on 7 Jun, 2026 start from S$736, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool pet-friendly?

No, pets are not allowed at this property.

How much is parking at Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool?

On-site parking is available at the property.

What time is check-in at Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool?

Check-in begins at 4:00 PM.

What time is check-out at Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool?

Checkout is at 10:00 AM.

Where is Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool located?

Situated on the waterfront, this holiday home is within 9 miles (15 km) of Upper Sugarloaf Key, Florida Keys Beaches and Lower Sugarloaf Sound. Big Pine Key Flea Market and National Key Deer Refuge Visitor Center are also within 9 miles (15 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 128 out of 146 reviews
Rating 8 - Good. 16 out of 146 reviews
Rating 6 - Okay. 2 out of 146 reviews
Rating 4 - Poor. 0 out of 146 reviews
Rating 2 - Terrible. 0 out of 146 reviews

10/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Andy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice property in a beautiful location. Great place to sit and enjoy the scenery and activities.
Sunrise from the patio
Stayed 4 nights in Feb 2026
Response from VrboOwner on 4 Mar, 2026
Thank you, Andy! It was a pleasure hosting you and we look forward to welcoming you back anytime!
Verified

10/10 Excellent

Lisa D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful location and house. The house is well stocked and very clean. Definitely a 5 star experience!
Stayed 3 nights in Feb 2026
Response from VrboOwner on 3 Mar, 2026
Guest was communicative, followed guidelines, and left the accommodation in good order. Welcome back anytime.
Verified

10/10 Excellent

Allicia W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacation

Super relaxing! Great location! Wonderful views!
Stayed 4 nights in Jul 2025
Response from VrboOwner on 15 Jul, 2025
Alicia, Thank you for taking time to review your stay with us. Any feedback is greatly appreciated. We are so glad you enjoyed your visit to the Florida Keys. We would love to host you again!
Verified

10/10 Excellent

Cindy Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was so kind to have a card on the counter to greet us with a message for our friends celebrating their 40th wedding anniversary-there was a bottle of champagne and a key lime pie too! Another great memory each morning was enjoying our coffee on the balcony while witnessing outstanding sunrises! The unit was exactly as envisioned, we used the four kayaks and the bikes. We were all very impressed with Venture Out and the community there on Cudjoe Key. It was a very comfortable unit for the four of us.
Swimming right from our area!
Fun with the Kayaks!
Beautiful sunrises.
Relaxing!
Stayed 4 nights in Sep 2025
Response from VrboOwner on 7 Oct, 2025
Thank you so much for your kind words! We’re thrilled to hear you enjoyed your stay and that the special touches helped make your friends’ 40th anniversary even more memorable. It sounds like you truly made the most of the home and the beautiful Venture Out community — those sunrise coffees on the balcony are hard to beat! We’d love to welcome you back for another relaxing stay in the Keys. Warm regards, The Bluescape Vacation Rentals Team
Verified

10/10 Excellent

Elizabeth M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place on the water

Very clean cottage right on the corner of the harbor and the canal. Wonderful views!
Stayed 4 nights in Feb 2025
Response from VrboOwner on 12 Mar, 2025
Elizabeth, So happy you enjoyed your stay. We cant wait to host you again soon. WFR
Verified

10/10 Excellent

LINDSEY F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Vacation Spot

Had a great time and will be renting again!
Stayed 8 nights in May 2019
Response from VrboOwner on 26 Mar, 2020
We would like to thank you all for taking the time to submit a nice review we certainly appreciate we’re glad you had a great time and you’re coming back take Care and will see you all on your next Florida Keys adventure Sincerely Jim and Linda :-) :-)
Verified

8/10 Good

Nancy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Sunrises!

We enjoyed the view of this VRBO!! We escaped some cold weather and it was a wonderful place to stay in the Keys!
Stayed 8 nights in Jan 2024
Response from VrboOwner on 25 Jan, 2024
nancy, thanks for the great review...so happy you enjoyed your stay and we hope to see you again soon. waterfront keys realty
Verified

10/10 Excellent

steve a.

Beautiful

Beautiful place and location, enjoyed greatly and will come back.
Stayed 4 nights in Jan 2018
Response from VrboOwner on 26 Mar, 2020
Thanks for taking the time to write a nice review :) we certainly appreciate it. :) Thanks again for coming and we are glad you all had a great time !! look forward to seeing you on your next Florida Keys adventure thank you so much sincerely Jim and Linda :) :)
Verified

10/10 Excellent

Matthew V.

Liked: Cleanliness, communication, location, listing accuracy

Beautiful property

Beautiful property would recommend. Plenty of towels and other amenities.
Stayed 5 nights in Nov 2020
Verified

10/10 Excellent

Darren W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best vacation experience ever

We are experienced Florida renters and we were blown away by this unit. The view alone is worth the stay but we found Venture Out to be absolutely charming. Clean, comfortable, safe, kitchen is well stocked. We will be back for sure!
Stayed 4 nights in Nov 2024
Response from VrboOwner on 6 Dec, 2024
Darren, So happy to hear you enjoyed your stay. Look forward to seeing you again soon. Waterfront Keys Realty
Verified

10/10 Excellent

Tammra E.

Gorgeous views! Extremely peaceful!

Stunning views! Very clean and comfortable. Wonderful location - very serene and peaceful but still close enough to get to Key West easily. A very relaxing stay.
Stayed 4 nights in Mar 2019
Response from VrboOwner on 26 Mar, 2020
We would like to thank you for submitting a nice review it helps people like you all find a fantastic place like our home !! to have a great vacation thanks again for coming sincerely Jim & Linda owners of the home in Cudjoe Key #95
Archival

10/10 Excellent

Karen V.

Great vacation!

This rental is exactly as it looks in the pictures...gorgeous views, immaculately clean, and quiet. Owners were very generous and helpful. Definitely would stay again and recommend it to others!
Response from VrboOwner on 26 Mar, 2020
Hi Karen and family It's Jim and Linda the owners of the home you were renting we would like to thank you and your family for taking time to write such a beautiful review we appreciate when someone takes notice of all of our hard work in keeping the home in good working order we are fortunate to live close by and we're always checking in on the house to make sure that cleaning and maintenance and attention to detail is being done properly have a safe trip to your next destination and we hope to see you soon on your next Florida Keys adventure sincerely Jim and Linda
Verified

8/10 Good

Phyllis W.

Gorgeous view, clean well appointed.

Loved watching sunrise and the boats coming by.
Stayed 9 nights in May 2018
Response from VrboOwner on 26 Mar, 2020
Thanks for Taking the time to write a review we are glad you had a great time AT are home thanks again for coming sincerely Jim and Linda VO 95 STRONG :-)
Verified

10/10 Excellent

Susan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Will definitely stay here again.

Love the location and property. Going to make it my go to location in the lower keys. Property fully equipped. Beds super comfortable. Just the right size for 4 adults. In a very nice community. Gate staff very friendly and helpful. Thank you.
Stayed 4 nights in Jan 2025
Response from VrboOwner on 26 Jan, 2025
Susan, So happy to hear you enjoyed your stay. See you again soon. WFR
Verified

10/10 Excellent

Lori D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect little place for our get a way

Owner of property is very in touch throughout our stay. Will definitely book this place again. Very nice quiet neighborhood with beautiful views.
Stayed 5 nights in Aug 2019
Response from VrboOwner on 26 Mar, 2020
Thank you all for thanking the time to submit a nice review !! it was a pleasure having you all as our guest at our home in the beautiful fl keys take care from Jim & Linda :-) :-)
Verified

10/10 Excellent

Wendy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location!

What an amazing trip!! The view from this house is top notch!!
Stayed 7 nights in Sep 2019
Response from VrboOwner on 26 Mar, 2020
Thank you all for for taking the time to submit a great review you said it perfectly in a few words top notch glad you had a amazing time we appreciate your stay at our home thanks again from the owners Jim & Linda :-) :-)
Verified

8/10 Good

Stewart S.

Very relaxing,beautiful view of the bay,all new furnishings due to hurricane Irma.

Excellent I wish I was still there.
Stayed 28 nights in Jul 2018
Response from VrboOwner on 26 Mar, 2020
Hi there we want to thank you all for taking the time to write a Review we are glad you had fantastic time :-) We’ve been trying very hard since the hurricane to get everything back in order but we do see the light at the end of the tunnel thanks again and we look forward to your next years vacation Sincerely Jim and Linda Vo Strong 95 :-) I know the view is fantastic but is the view of the ocean not the bay LOL
Verified

10/10 Excellent

Marc M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Sunrise Reviews over the Ocean

We had a great stay here and everything was as advertised. The check in process was super simple and Jim&Linda kept in good contact to ensure everything went smoothly.
Stayed 5 nights in Dec 2019
Response from VrboOwner on 26 Mar, 2020
Thank you all for taking the time to submit a nice review we certainly appreciate take care from your fl keys friends Jim & Linda :-):-)
From a partner site

10/10 Excellent

Derek P.

Beautiful views of the water

Convenient for boat docking, cozy and clean, thanks!
Stayed 2 nights in Apr 2018
Response from VrboOwner on 26 Mar, 2020
Thank you for taking the time in writing a nice review we certainly appreciate it !!! we have been working very hard after Hurricane Irma to make our home better than ever for our guests it’s been very trying for us !! thanks again for coming sincerely Jim and Linda VO 95 STRONG and we hope to see you on your next Florida Keys adventure :-). :-)
Archival

10/10 Excellent

Gerri H.

Can't beat the view!

Love the Keys! Love this view!
Stayed 7 nights in May 2017
Response from VrboOwner on 26 Mar, 2020
We certainly appreciate you taking the time to write a little note about our fantastic view at are home and that you love spending time in the Florida Keys we look forward to your next visit to our home thanks again sincerely Jim and Linda :)
Verified

10/10 Excellent

Wendy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lower keys getaway

Space and location we're perfect for exploring the lower keys, in and out of the boat.
Stayed 5 nights in Sep 2021
Response from VrboOwner on 30 Sept, 2021
Thank you all for taking the time to submit a nice review we are glad you had a nice time in the beautiful Florida keys 😊🎣🌺
Verified

10/10 Excellent

Kelley W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Can’t wait to return

This home is the perfect location, the view is a dream, fully stocked kitchen, could go on and on, owners were above and beyond helpful
Stayed 5 nights in May 2021
Response from VrboOwner on 3 Jun, 2021
Thank you all so much for taking the time to submit a a wonderful review :-) :-) and taking care of our home as if it wAs yours it was a pleasure having you all as our guests:-) :-) And we look forward to seeing you on your next Florida Keys adventure😊
Verified

10/10 Excellent

Heather B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

It is an amazing property. Perfect for bringing your boat!
Stayed 7 nights in Jun 2021
Response from VrboOwner on 28 Sept, 2021
Thank you all so much for for taking the time to submit a great review we appreciate 😊🌴
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

fantastic!

Great property Great Owners. Very Clean, Fantastic Views.
Stayed 8 nights in Jan 2021
Response from VrboOwner on 14 Mar, 2021
Thanks so much for take the time to submit a nice review we appreciate from the owners Jim & Linda
Verified

10/10 Excellent

Meta J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet and relaxing

Great views, quiet neighborhood, very clean house, the owners were very helpful and attentive. We had a great time
Stayed 6 nights in Sep 2020
Response from VrboOwner on 5 Oct, 2020
Thank you all for taking the time to review your stay at our home :-) :-) we enjoyed meeting you all and thank you for taking care of our home as if it where yours hopefully will meet again on your next fl keys adventure thanks again from your fl keys friends Jim & Linda :-) :-)

About the host

Hosted by Bluescape Vacation Rentals

Host profile image
The Bluescape Vacation Rentals Team
Cudjoe Key, Florida

Languages:

English, French

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