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Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly

Photo gallery for Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a glass table and blue patterned chairs. - Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly (Cudjoe Key)
A waterfront property with multiple houses, each featuring balconies and a pool area. - Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly (Cudjoe Key)
An aerial view of a sports complex with multiple tennis courts, a swimming pool, and adjacent parking areas. - Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly (Cudjoe Key)
A resort with multiple swimming pools, a beach area, and a view of the ocean. - Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly (Cudjoe Key)
A kitchen with a stainless steel stove, a microwave, and a built-in oven. - Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly (Cudjoe Key)
Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly provides amenities like golfing on site and a hot tub. Active travelers can enjoy boating, bicycling, and kayaking at this vacation home. Stay connected with free in-room WiFi.

Entire home

842 sq ft

Popular amenities

  • Ocean view
  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer

Add dates for prices

About this property

Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly

  • Welcome to your Florida Keys escape, a beautifully situated 2-bedroom, 2-bath waterfront home in the gated Venture Out community on Cudjoe Key. With a 35-foot concrete dock, accommodations for boats up to 32 feet, two kayaks, two bicycles, high-speed internet, generous outdoor living space, and a pet-friendly setting, this home is perfectly suited for families, couples, boaters, anglers, and anyone looking to enjoy the relaxed lifestyle of the Lower Florida Keys.
    Spend your mornings on the water, your afternoons exploring Cudjoe Key, and your evenings relaxing outdoors with a beautiful view. Whether you are here to fish, kayak, cruise the surrounding waters, or simply slow down and enjoy island life, this home provides a comfortable and convenient place to make the most of your Florida Keys vacation.
    The Space
    Inside, the home offers a welcoming and comfortable layout with plenty of room for everyone to spread out and relax. The living area is an inviting place to unwind after a day on the water and also provides additional sleeping accommodations with a queen-size sofa bed for up to two guests.
    The well-stocked kitchen (including a combo K cup/12 cup drip coffee maker) makes preparing meals at home easy, whether you are putting together a quick breakfast before heading out on the boat, packing lunch for a day of exploring, or cooking up the day's fresh catch for dinner. The home also includes high-speed internet, so guests can easily stay connected, stream their favorite shows, or catch up on work when needed.
    One of the highlights of the property is the abundance of outdoor living space. The porch features outdoor dining for four with a lovely view, creating a wonderful setting for morning coffee, casual lunches, or relaxed evening meals. Beneath the home, you will find even more space to gather, dine, and unwind in the shade. This large covered area gives guests plenty of room to enjoy the outdoors while staying comfortable throughout the day.
    Bedrooms & Sleeping Arrangements
    The primary bedroom suite features a king-size bed, providing a spacious and comfortable retreat at the end of the day. The guest bedroom offers a queen-size bed, making it ideal for another couple, family member, or friend. Each bedroom is equipped with its own TV, making it easy for guests to relax and enjoy their favorite shows in the comfort and privacy of their room.
    The living area also includes a queen-size sofa bed that can accommodate up to two additional guests, allowing the home to comfortably sleep up to six guests.
    Bathrooms
    The home features two full bathrooms, giving families and groups the added convenience of having plenty of space to get ready for the day. Whether everyone is preparing for an early morning fishing trip or cleaning up after an afternoon on the water, having two complete bathrooms makes vacation living that much easier.
    Waterfront Living, Boating & Fishing
    For guests who come to the Florida Keys to enjoy the water, this home offers an excellent setup. The property features a 35-foot concrete dock that can accommodate a boat up to approximately 32 feet, making it easy to keep your boat right at the property throughout your stay.
    The dock also includes a fish cleaning station with both water and lighting, so anglers can conveniently clean and prepare their catch when they return from a day of fishing.
    Venture Out's location on Cudjoe Key places you within easy reach of some of the Lower Keys' best boating and fishing waters. Guests can explore both the Atlantic Ocean and the Gulf backcountry, with opportunities for offshore fishing, reef fishing, flats fishing, snorkeling, diving, and leisurely days spent cruising the surrounding islands.
    Nearby Looe Key is well known for its spectacular reef system and clear waters, making it a favorite destination for snorkeling and diving. Picnic Island is another popular local spot and a wonderful place to spend an afternoon relaxing on the water.
    For days when you would rather leave the boat at the dock, the home provides two kayaks and two bicycles for guest use. Paddle through the surrounding waterways, take a leisurely ride through the community, or simply enjoy a quiet afternoon close to home.
    Community Amenities at Venture Out
    Venture Out is one of the most popular vacation communities in the Lower Florida Keys and offers a wide variety of amenities for guests to enjoy throughout their stay.
    The community features a marina with fuel, bait, and convenience items, along with a boat ramp and wash-down station for added convenience. Guests can also enjoy the beautiful oceanfront area, where thatched-roof umbrellas and lounge areas provide a relaxing place to take in the sea breeze and Florida Keys sunshine.
    The community's impressive recreational amenities include a large heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoon. Guests can also enjoy tennis, basketball, bocce, and pickleball during their stay.
    Golf carts are a popular way to get around the community, and Venture Out's relaxed, friendly atmosphere makes it easy to enjoy everything from morning bike rides to peaceful evenings by the water.
    Location
    Located on Cudjoe Key in the heart of the Lower Florida Keys, this home gives you the perfect balance between peaceful island living and convenient access to restaurants, attractions, boating, and nightlife.
    Popular local favorites such as Square Grouper, Morning Joint, The Bent Prop, Broil, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House are all just a short drive away. Boondocks also offers miniature golf, making it a fun stop for families and groups.
    When you are ready for a change of pace, head south to Key West for world-famous sunsets, historic attractions, shopping, dining, watersports, and nightlife. At the end of the day, return to the quieter surroundings of Cudjoe Key and relax at your waterfront home.
    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. Driveway size: 10.6'W x 25''L x 7H. 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.
    Good to Know
    This home is pet friendly, so your four-legged family member can join you for your Florida Keys getaway. A nonrefundable pet fee of $250 per pet is required.
    A starter supply of toilet paper and paper towels is provided for your arrival and is generally intended to last approximately one to two days.
    Venture Out charges a community registration fee of $125, which is subject to change and is paid directly to the community upon arrival. Payment methods and processing fees are determined by Venture Out.
    Guests are required to follow all Venture Out community rules and regulations during their stay, including parking requirements and designated quiet hours.
    The primary guest making the reservation must be at least 25 years of age.
    A 4-seater electric golf cart is available for an additional fee: $50 per day, $250 per week, or $750 per month. Perfect for cruising around Venture Out and exploring the community with ease. Please contact the rental manager to add this to your reservation.
    Payment & Booking Requirements
    A signed rental agreement and government-issued photo ID are required after booking. Once your Rental Agreement has been completed, please reply to the email you receive from us with a photo of your government-issued ID.
    Guests may also pay by e-check at no additional charge.
    If an e-check is returned, a $25 returned payment fee will apply, and the remaining balance must be paid by credit card.

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
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table

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
  • Kayak
  • Table tennis
  • Tennis
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming 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)
  • Fire extinguisher
  • First aid kit

General

  • Bicycles
  • Unit size: 842 square feet

Similar properties

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 allowed
Service animals are welcome, and 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 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

About the area

Located in Summerland Key, this vacation home is on the waterfront. Florida Keys Beaches and Upper Sugarloaf Key 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. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby. Visit our Summerland Key travel guide
View more Vacation homes in Summerland Key
Map
Cudjoe Key, FL

What's nearby

  • A wooden signpost with city names and distances, a beach with umbrellas, and lounge chairs.
    Florida Keys Beaches
    8 min drive - 7.7 km
  • A thatched-roof outdoor seating area with tables and chairs overlooking a body of water.
    Lower Sugarloaf Sound
    12 min drive - 12.5 km
  • Upper Sugarloaf Key
    7 min drive - 7.6 km
  • Upper Sugarloaf Sound
    9 min drive - 8.9 km
  • Boondocks Grille & Draft House
    11 min drive - 12.1 km

Getting around

  • Key West Intl. Airport (EYW)
    38 min drive

Restaurants

  • Boondock's Grille & Drafthouse
    9 min drive
  • Morning Joint
    20 min walk
  • Kiki's Sandbar
    12 min drive
  • Looe Key Tiki Bar & Restaurant
    9 min drive
  • Tonio's Seafood Shack & Tiki Bar
    6 min drive

Frequently asked questions

Does Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly have a pool?

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

How much does it cost to stay at Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly?

As of Oct 10, 2026, prices found for a 1-night stay for 2 adults at Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly on Oct 11, 2026 start from CA $336, excluding 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 Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly?

Check-out is at 10:00 AM.

Where is Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly located?

Situated on the waterfront, this vacation home is within 6 mi (10 km) of Upper Sugarloaf Key, Florida Keys Beaches, and Boondocks Grille & Draft House. Lower Sugarloaf Sound and Big Pine Key Flea Market are also within 9 mi (15 km).

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