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Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

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A resort with a large pool, sun loungers, and palm trees.
A coastal property with a dock, white buildings, and a clear view of the ocean.
A coastal resort area with a marina, beachfront properties, and a prominent flag.
A resort with a pool area, palm trees, and a pier extending into the water.
Outdoor dining

Reviews

9.6 out of 10
Exceptional

Entire home

2 bedrooms2 bathrooms864 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

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

Room options

About the neighborhood

Summerland Key

This vacation home places you within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key. The vacation home includes a kitchen, a balcony, and a dining area.

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 4.5 miles
  • Florida Keys Beaches - 8 min drive - 4.6 miles
  • Upper Sugarloaf Sound - 8 min drive - 5.3 miles
  • Lower Sugarloaf Sound - 11 min drive - 7.6 miles
  • Key West Visitors Center - 17 min drive - 12.8 miles

Getting around

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

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬17 min walk
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪The Bent Prop - ‬7 min drive
  • ‪Square Grouper Bar and Grill - ‬3 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Discover elevated coastal living at Coconut Telegraph #221, a beautifully updated 2-bedroom, 2-bath waterfront retreat nestled within the exclusive gated community of Venture Out on Cudjoe Key. Thoughtfully designed with refined finishes, curated coastal décor, and breathtaking open ocean views, this exceptional home offers the perfect blend of luxury, comfort, and effortless island living.
Ideal for couples, boaters, and anglers, this inviting retreat places you just steps from direct water access and Venture Out's resort-style amenities.
The Space
Perfectly positioned along the open ocean, this elevated home showcases panoramic water views and endless horizons right from your back porch. Start your mornings with spectacular sunrises over the Atlantic and unwind each evening to the soothing sounds of the sea from your private outdoor living space.
Inside, the bright and airy open-concept layout has been meticulously updated and beautifully appointed with high-end furnishings, custom finishes, and sophisticated coastal touches throughout. The gourmet kitchen features custom countertops, quality cabinetry, modern appliances, and everything needed to prepare meals with ease. Gather around the dining table with seating for five, plus additional breakfast bar seating for two.
Whether you're brewing your morning coffee with the Keurig or Black + Decker drip coffee maker, or relaxing after a day on the water, every detail has been thoughtfully considered for your comfort.
The living area offers plush seating, a 75-inch Samsung Smart TV, and unobstructed ocean views, creating a warm and inviting space to unwind.
Additional conveniences include high-speed Wi-Fi, central air conditioning, an in-home washer and dryer, and a spotless, professionally maintained environment designed to make extended stays feel effortless.
Bedrooms & Sleeping Arrangements
Designed for exceptional comfort and restful nights, both bedrooms feature premium bedding, luxurious linens, and Smart TVs.
Primary Suite: A serene waterfront retreat featuring a king-size bed, a 32-inch Vizio Smart TV, and a beautifully updated ensuite bathroom with a spacious walk-in shower.
Guest Suite: Thoughtfully designed with a king-size bed that can easily convert into two twin beds, a 32-inch Vizio Smart TV, and convenient access to a fully renovated bathroom with a walk-in shower.
Maximum Occupancy: 4 guests
To ensure your vacation home is perfectly prepared for your arrival, please contact our Bluescape office to specify whether you would prefer the guest room configured with two twin beds or a single king bed.
Bathrooms
Both custom bathrooms have been beautifully updated with modern finishes and walk-in showers, creating spa-inspired spaces to refresh and recharge after a day in the Florida Keys.
Waterfront Living, Boating & Fishing
Coconut Telegraph #221 is a dream destination for boaters and anglers alike. Set directly on the open ocean, the property features a private 35-foot concrete dock that comfortably accommodates boats up to approximately 32 feet, offering effortless access to some of the Florida Keys' most sought-after waters.
Just a short boat ride away is Looe Key, one of the world's premier reef systems, known for its exceptional snorkeling, diving, and vibrant marine life. Nearby Picnic Island is a local favorite for relaxing, socializing, and enjoying the beauty of the Lower Keys after a day on the water.
Whether you're setting out for a day of fishing, exploring the reefs, or simply soaking in the extraordinary ocean views, Coconut Telegraph #221 offers an unforgettable waterfront escape.
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.
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony. There's space to spread out with 2 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and a kitchen island.

Similar properties

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundromat nearby
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Bicycles
  • Billiards/pool table
  • Boat
  • Golf
  • Heated pool
  • Table tennis
  • Tennis
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Bicycles
  • Unit size: 864 square feet

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

  • This property welcomes pets
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 0-17

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 and a first aid kit
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit.

Property is also known as

1081562

Frequently asked questions

What's there to see around this vacation home?

This vacation home is located in Summerland Key, close to Florida Keys Beaches, Upper Sugarloaf Key, and Sugarloaf Beach. Boondocks Grille & Draft House is also within a driving distance of 4.9 mi.

How much does it cost to stay at Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise?

As of Jul 5, 2026, prices found for a 1-night stay for 2 adults at Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise on Jul 6, 2026 start from $815, 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.

Will I be able to park at Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise?

No, there isn't parking available at the vacation home.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there is a hot tub.

Is Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise a good place to stay for couples?

Amenities that appeal to couples at this waterfront vacation home include a smart TV and a kitchen along with a hot tub.

Does Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise have a hot tub?

No, but guests can enjoy a heated pool at this vacation home.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

Although pets can't stay for free, they are welcome at this vacation home.

Does Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise have connecting rooms available?

No, there aren't connecting guestrooms at this vacation home.

How far is the airport from this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 21.4 mi away (32 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 29.3 mi away (39-minute drive).

Can I book a room with a balcony at Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise?

Yes, every house at Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise comes with a balcony and some offer water views.

Oceanfront 2BR Retreat - 35' Dock, Sunrise 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

Verified

10/10 Excellent

Kathy A.

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

10/10 Excellent

Piotr P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place!
Stayed 6 nights in Nov 2025
Verified

10/10 Excellent

Nathan M.

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

10/10 Excellent

Dana C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was amazing! Right on the water and very comfortable!
Stayed 6 nights in Nov 2025
Verified

10/10 Excellent

mary b.

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

10/10 Excellent

Ben D.

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

10/10 Excellent

Jeff M.

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

Great place

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

10/10 Excellent

Mandy P.

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

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
Verified

10/10 Excellent

Karen K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house, great boating and lobster area
Stayed 5 nights in Sep 2025
Verified

4/10 Poor

Michael G.

Disliked: Cleanliness, communication, location, listing accuracy
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
Verified

8/10 Good

Alice c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was nicely decorated. Appreciated the coffee maker, nightlights etc
Stayed 5 nights in Oct 2025
Verified

8/10 Good

tammy f.

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

Enjoyed our stay

Very clean and comfortable property
Stayed 3 nights in Nov 2023
From a partner site

10/10 Excellent

Howard t.

Beautiful view

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: House was very clean!! Great location not far from key west and good food and drinks only slept on the master bed was very comfy and I’m pretty picky about my bed our property management rep. Alli was also great!!! Quick response if I had any questions just an overall great experience!
Verified

10/10 Excellent

Walter J.

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

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
Verified

10/10 Excellent

Jennifer B.

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

10/10 Excellent

Coreen J.

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

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
Verified

10/10 Excellent

Amy K.

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

Enjoyed very much!

Perfect place to stay in the keys! Close to attractractions and very accommodating!
Stayed 3 nights in Oct 2022
Verified

10/10 Excellent

Fernando L.

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

Great spot!

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

10/10 Excellent

Jeff R.

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

Venture out

Very nice place to stay!
Stayed 3 nights in Jun 2023
Verified

8/10 Good

Brad P.

Liked: Cleanliness, location, listing accuracy
Disliked: Check-in

stay

great location and amenities
Stayed 6 nights in May 2024
Verified

10/10 Excellent

Verified traveler

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

Comfort In paradise

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

10/10 Excellent

Doug V.

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

Coconut typhoon

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

10/10 Excellent

Rachael C.

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

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
Verified

10/10 Excellent

Michael W.

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

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
Verified

10/10 Excellent

Reuben M.

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

Perfect vacation spot

We really enjoyed everything at this house , newer home , very clean , the patio is right by the water , good neighborhood to stay , great food close by ! Definitely going back 😊
Stayed 4 nights in Feb 2023