Entire home

Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise

Summerland Key vacation home with kitchen

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Beach
Terrace/patio
Exterior
Private kitchen
Interior

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Pool
  • Hot tub
  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Parking available

Explore the area

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

Room options

About the area

Summerland Key

Seaside stay .Within 6 miles (10 km) of this vacation home, you'll find Florida Keys Beaches and Upper Sugarloaf Key. Also within 9 miles (15 km) are Lower Sugarloaf Sound and Big Pine Key Flea Market.

What's nearby

  • Florida Keys Beaches - 7 min drive - 7.1 km
  • Upper Sugarloaf Key - 7 min drive - 7.3 km
  • Upper Sugarloaf Sound - 8 min drive - 8.6 km
  • Lower Sugarloaf Sound - 12 min drive - 12.1 km
  • National Key Deer Refuge Visitor Center - 16 min drive - 17.9 km

Getting around

  • Key West Intl. Airport (EYW) - 32 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪Morning Joint - ‬17 min walk
  • ‪Broil - ‬5 min drive
  • ‪5 Brothers Two - ‬9 min drive

About this property

Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise

Welcome to Coconut Telegraph #221 a beautiful 2 bedroom, 2 bathroom waterfront home located inside the private gated community of Venture Out on Cudjoe Key. This inviting retreat is ideal for couples, boaters, and anglers looking to enjoy the Florida Keys with direct water access, resort style amenities, and effortless island living.
The Space
This elevated coastal retreat offers an open-concept layout and is perfectly positioned along the open ocean, showcasing sweeping water views and endless horizons right from your doorstep. Enjoy front-row sunrises, refreshing sea breezes, and the peaceful rhythm of the Atlantic just beyond your deck.
The bright and airy living space is designed for comfort after a full day on the water. The dining room table has seating for 5, plus 2 extra seats at the breakfast bar. There is a Black and Decker drip coffee maker as well as a Keurig to enjoy your favorite morning brew. The living room features a 75'' Samsung smart TV and comfortable seating, creating a relaxing place to unwind.
The home is cooled by central air conditioning and offers high speed Wi-Fi throughout. A washer and dryer are also provided, making longer stays and boating trips easy and convenient.
Bedrooms & Sleeping Arrangements:
Primary Bedroom: King size bed with a 32'' Vizio smart TV
Guest Bedroom King size bed that can be converted into two twins with a 32'' Vizio smart TV
Maximum occupancy: 4 guests
Bathrooms:
The home features two full bathrooms.
Primary Bathroom: Walk-in shower
Guest Bathroom: Walk-in shower
Waterfront Living, Boating & Fishing
Coconut Telegraph #221 is a dream escape for boaters and anglers alike, set directly on the open ocean and featuring a 35-foot concrete dock that comfortably accommodates boats up to approximately 32 feet. Enjoy effortless access to open water right from your backyard, with unbeatable views to match.
Just a short boat ride away is Looe Key, one of the most famous reef systems in the Florida Keys, offering world class snorkeling, diving, and vibrant marine life in crystal clear waters. Picnic Island is a nearby local sandbar favorite, perfect for relaxing after a morning of fishing.
Enjoy quick access to both:
The Atlantic Ocean for offshore and reef fishing
The Gulf backcountry for exceptional flats and inshore fishing
After a full day in the sun, fire up the NexGrill propane grill and prepare your fresh catch or an easy island-style dinner, then relax and enjoy your meal at the outdoor picnic table while taking in the coastal breeze.
Community Amenities at Venture Out
Venture Out is one of the most amenity-rich communities in the Lower Florida Keys, offering:
Marina store with fuel, bait, and convenience items
Boat ramp and wash-down station
Beautiful stretch of island along the oceanfront with many thatched roof umbrellas and loungers to take in the clean ocean breezes and relax
Massive 80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoon
Tennis courts, basketball, bocce, and pickleball
On-site marina store/market and post office
Electric Golf cart-friendly streets throughout the community
Location
You're just minutes from popular local favorites including Square Grouper, Morning Joint, The Bent Prop, Broil, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House with mini golf, all within a 10-minute drive. Key West is only 20 minutes away, offering additional dining, nightlife, and iconic attractions.
Good to Know
Starter supplies provided: A starter supply of toilet paper and paper towels is provided and typically lasts 1 to 2 days
This home is pet friendly for 2 dogs with a $250 non refundable pet fee per dog.
Golf cart rentals available: $50 per day, subject to availability
Venture Out registration fee: $125 subject to change, paid directly to the community upon arrival. Processing fees may apply
Parking: 1 vehicle per unit. Driveway size: 9.5'W x 25'L x 9.9'H. Overflow parking may be available for an additional fee
Community rules: Guests must follow all Venture Out rules and regulations, including quiet hours from 10:00 PM to 6:00 AM
Age requirement: Primary guest must be 25 years of age or older
Payment & Booking Requirements
Signed rental agreement and government issued ID required after booking. Please reply to the email you receive after signing your rental agreement with a photo of your ID.
A 4 % credit card processing fee applies to credit card payments.

Whether you're watching the sunrise over the Atlantic, heading out for a day of fishing or diving, or simply unwinding on the deck with the ocean breeze and a cold drink in hand, Coconut Telegraph #221 captures the essence of true Florida Keys living. Book your stay today and experience oceanfront living at its finest.

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • Pets are welcome
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property is also known as

1081562

Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 44 out of 53 reviews
Rating 8 - Good. 7 out of 53 reviews
Rating 6 - Okay. 0 out of 53 reviews
Rating 4 - Poor. 2 out of 53 reviews
Rating 2 - Terrible. 0 out of 53 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Kathy A.

Liked: Cleanliness
Our stay was wonderful. Accommodations were as described and very comfortable. Location was great and the best views for the sunrise.
Stayed 4 nights in Mar 2026

4/10 Poor

Michael G.

Disliked: Cleanliness
The view was excellent. The house itself was in horrible disrepair. Lights didn’t work, appliances broke, the window treatments were broken, the toilet seat handles cracked,the stair railings were broken and dangerous,the laundry door was off the hinges and the furniture was scratched.
Stayed 8 nights in Feb 2026

10/10 Excellent

Nathan M.

Liked: Cleanliness
We enjoyed our stay here! The home is very clean and well-kept, the beds and linens were comfortable, and the kitchen had everything we needed for our short stay. We appreciated the soft shower towels and pool towels as well. We would gladly return to this property again in the future.
Stayed 2 nights in Feb 2026

10/10 Excellent

mary b.

Liked: Cleanliness
The house is really nice. I did not get to enjoy the amenities in the park since we traveled to key west. I would stay here again! It’s forcing me to do a rating on pool and facilities but I don’t know. Disregard that.
Stayed 2 nights in Feb 2026

10/10 Excellent

Piotr P.

Liked: Cleanliness
Great place!
Stayed 6 nights in Nov 2025

10/10 Excellent

Dana C.

Liked: Cleanliness
The house was amazing! Right on the water and very comfortable!
Stayed 6 nights in Nov 2025

8/10 Good

Alice c., Kansas City, Missouri

Liked: Cleanliness
It was nicely decorated. Appreciated the coffee maker, nightlights etc
Stayed 5 nights in Oct 2025

10/10 Excellent

Ben D., Birmingham Alabama

Liked: Cleanliness
This is one of the best rental units in venture out. The location on the canal looking out at the bay is very nice and gets a breeze. The furnishing and layout are great too. Would love to stay here again.
Stayed 7 nights in Oct 2025

10/10 Excellent

Brianna S.

Liked: Cleanliness
This home was a 10/10 experience. Everything was top notch from the cleanliness to the amenities available. It looks exactly like the pictures online but in person it was so much better. The view from the balcony was the best part about it as well as the boat access. We also spent lots of time at the pool on the property which was super clean and refreshing after being on the water all day. Everyone in venture out was super friendly and we rented bikes from Big Pine Bike Rental to ride around the property. Our dog enjoyed the stay too. Being able to grill and cook at home was a major plus. The home is extremely well cared for and we will be back to stay again.
The view every morning
Sunrise
Sunrise from the boat dock right outside of the home
Pool day
Stayed 9 nights in Sep 2025

10/10 Excellent

Karen K.

Liked: Cleanliness
Beautiful house, great boating and lobster area
Stayed 5 nights in Sep 2025

10/10 Excellent

Mandy P.

Liked: Cleanliness

Fantastic place to stay!

We had an awesome week at this property. I highly recommend this property ... fantastic communication, clean and exactly as described on the listing.
Stayed 7 nights in Jul 2025

10/10 Excellent

Jennifer B.

Liked: Cleanliness
Loved it! The view is unbelievable! Such a such place and tastefully decorated. Beds were comfy and it had just what we needed to cook. Nice big table to play games. We will definitely book again!
Stayed 5 nights in Jul 2025

10/10 Excellent

Jeff M.

Liked: Cleanliness

Great place

Great place to stay. Very secure and comfortable.
Stayed 6 nights in Jun 2025

10/10 Excellent

Coreen J.

Liked: Cleanliness

Vacation Getaway

Short trip to the Keys! Very pleased with the rental company and their communication! Would definitely rent again!
Stayed 5 nights in May 2025

10/10 Excellent

Rachael C.

Liked: Cleanliness

Great view

We were on the end of canal with wonderful sunrise.Beds comfortable and the towels were large and plush.Well equipped kitchen for our cooking needs.A well maintained community with a pool, convenience store home to RVs as well as permanent places to stay.
Stayed 5 nights in Apr 2025

10/10 Excellent

Lisa F.

Liked: Cleanliness

Cozy in Cudjoe

Views from this property are amazing, accommodations were clean, well kept and private. Fully equipped kitchen. My only complaint was the pet rules in Venture Out. Inability to walk your pet within the park was odd, you are required to leave the resort to walk, even if leashed.
Stayed 3 nights in Apr 2025

10/10 Excellent

Michael W., Saint Petersburg, Florida

Liked: Cleanliness

Venture Out

The place was great and exactly what was shown. Having our boat out back was great. Great facilities including boat ramp, pool area and store. All the amenities you need at the house and Cudjoe Key is beautiful and has some great restaurants. I would recommend this home and resort to everyone.
Stayed 9 nights in Apr 2025

10/10 Excellent

Walter J.

Liked: Cleanliness

Superb!

Property exceeded expectations, and the view was spectacular! Absolutely would recommend staying here. It has everything you need for a comfy stay.
Stayed 7 nights in Mar 2025

10/10 Excellent

John N.

Liked: Cleanliness

Great location!

The property was in a great spot. Relatively shot drives to Key West, Big Pine, and Bahia Honda. Getting in and out of the gated community was no problem and the house was exactly as we expected based on the pictures and description.
Stayed 5 nights in Feb 2025

10/10 Excellent

Doug V.

Liked: Cleanliness

Coconut typhoon

Excellent views, very quiet, pool was outstanding
Stayed 7 nights in Dec 2024

8/10 Good

Meredith M.

Liked: Cleanliness

Beautiful place, good location

If you’re familiar with Venture Out, this is one of the nicest and newer units in the park. Also great location within, end of a wide canal and close to pool. My only complaint would be that the place is priced very high with none of the charm of some more loved places in the park; no bikes, few helpful kitchen items. It’s clear that it’s an investment property. My family rented other places in the park for far less ($100 a night less) and had bikes and paddle boards. I found myself borrowing their things, like martini shakers and Tupperware, in addition to the fun toys. If you want a fancy, modern place and don’t care about the other stuff, you’ll love this one.
Stayed 5 nights in Nov 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness

Comfort In paradise

Super nice place Comfortable Couch Comfortable Bed
Stayed 2 nights in Oct 2024

8/10 Good

Verified traveller

Liked: Cleanliness

Nice property, Great Location.

The property is nicely decorated just as the pictures posted in the listing. Fully equipped with everything you need in the kitchen. All very cleaned. Location is great! It is also within a reasonable driving distance to Key West.
Stayed 2 nights in Oct 2024

10/10 Excellent

Karen K.

Liked: Cleanliness

Coconut telegraph – wonderful place to stay

The coconut telegraph was a beautiful stilted home. It was very clean and decorated very nicely with light beachy colors. The best were very comfortable. Everything in the kitchen was functional. It was a great location. We kept our small boat at the dock The property management was very friendly. We were very happy with it and will stay there again..
Stayed 4 nights in Sep 2024

10/10 Excellent

Fernando L.

Liked: Cleanliness

Great spot!

The House, is beautiful, comfortable, clean and quiet!!
Stayed 9 nights in Aug 2024