What are the opening hours?

Monday 9am - 5pm Tuesday 9am - 5pm Wednesday 9am - 5pm Thursday 9am - 5pm Friday 9am - 5pm

Keezy Vacation Rentals

Home
United States
Cudjoe Key, FL
Keezy Vacation Rentals

Contact information, map and directions, contact form, opening hours, services, ratings, photos, videos and announcements from Keezy Vacation Rentals, Vacation Home Rental, 701 Spanish Main Drive, Cudjoe Key, FL.

Keezy Vacation Rentals offers luxurious properties in the Florida Keys with stunning views and easy access to local attractions, focusing on excellent service and memorable experiences for guests.

09/07/2026

Dreaming of a tropical escape!

Now is the perfect time to park your RV in paradise and save!

25% OFF select RV lots at Venture Out in the Florida Keys! 🌴🚐

From September through the end of November, enjoy 25% OFF stays at 5 select empty RV lots located inside the gated Venture Out community in Cudjoe Key.

Choose the spot that fits your Keys getaway:
🌊 Waterfront RV lots with beautiful views
🚤 Canalfront options perfect for enjoying life by the water
🌴 Spacious interior lots for an easy island home base

Plus, every stay includes access to Venture Out’s resort-style amenities:
• Oceanfront heated saltwater pool & jacuzzi
• Marina, fuel dock, ship store & boat launch
• Pickleball, tennis, bocce & basketball courts
• Recreation center & community activities
• Just 19 miles from Key West

Bring your RV and spend your days boating, fishing, exploring the Lower Keys, or simply relaxing under the palms.

Save 25% from now through November on these 5 select RV lots!

📲 Explore all available lots and book your stay:
🌐 KeezyVacationRentals.com
📞 Contact Kim at (305) 315-6197

Realtor with Expert Realty

09/04/2026

Wake up to breathtaking Ocean Views from Sunrise to Sunset at Vacation Rental #469 🌊☀️🌴

🛏 2 Bedrooms | 🛁 2 Bathrooms | 👥 Sleeps 4

Welcome to Ocean Vue, an upscale waterfront retreat designed for the ultimate Florida Keys escape. With panoramic ocean views, quick access to both the Atlantic Ocean and Gulf of Mexico, and a private 35-foot seawall, this home is a boater’s dream and a vacationer’s paradise.

Spend your mornings watching the sunrise over the water, your afternoons exploring the Keys by boat, and your evenings unwinding in total comfort as the sun sets over paradise.

Inside you’ll find:
• 2 spacious bedrooms & 2 full bathrooms
• High-end fully equipped kitchen
• 3 Smart TVs for entertainment
• WiFi & air conditioning
• Washer & dryer
• Bright, modern coastal design

🚤 Bringing your boat? Enjoy a 35-foot seawall with direct water access for easy days on the water—fish, snorkel, cruise, or island hop with ease.

Located in a gated community, guests also enjoy resort-style amenities including:
• Oceanfront heated saltwater pool
• Marina with convenience store, fuel dock & boat launch
• Pickleball, tennis, basketball & bocce courts
• Beautifully maintained grounds & community spaces

Whether you’re here for adventure on the water or pure relaxation by the pool, Ocean Vue #469 delivers the perfect balance of luxury and laid-back Keys living.

📲 Contact Kim for pricing & availability:
📞 (305) 315-6197
🌐 https://keezyvacationrentals.com/en/ocean-vue-in-cudjoe-key-469

Realtor with Expert Realty

08/31/2026

Discover the best of Venture Out at Cudjoe Key 🌴🚤

This highly sought-after gated waterfront community is one of the Florida Keys’ true hidden gems—offering the perfect blend of vacation lifestyle, boating convenience, and island living.

Residents and guests enjoy incredible resort-style amenities, including:
• Oceanfront heated saltwater pool & jacuzzi
• Full-service marina with boat ramp & fuel dock
• On-site convenience store
• Pickleball, tennis, bocce & basketball courts
• Community recreation areas & year-round activities
• 24/7 gated security for peace of mind

Whether you’re here for a weekend escape or a seasonal stay, Venture Out offers something for everyone—and the boating access is unmatched with direct access to both the Atlantic Ocean and Gulf of Mexico.

🏡 We currently manage multiple vacation rentals within Venture Out, giving guests a variety of waterfront stays to choose from.

📍 And for those dreaming of owning a piece of paradise, there are also several lots currently available for sale inside the community—perfect for building your own Keys getaway or investment property.

From vacation rentals to future ownership opportunities, Venture Out is more than a destination—it’s a lifestyle. 🌊

📲 Contact Kim for rentals or real estate opportunities:
📞 (305) 315-6197
🌐 KeezyVacationRentals.com

Video by Key West Virtual Tours

Realtor with Expert Realty

08/28/2026

Bring the boat and make the Florida Keys your playground at Vacation Rental #573. 🚤🌴

🛏 2 Bedrooms | 🛁 2 Bathrooms | 👥 Sleeps 5

Located directly on a wide canal, this coastal retreat was made for days spent on the water. With your own 35’ private dock and quick access to both the Gulf and Atlantic, your next fishing trip, snorkeling adventure, or sunset cruise can start right outside your door.

After a day on the water, head inside to a comfortable 2-bedroom, 2-bath home featuring a beautifully updated kitchen — perfect for cooking up the day’s fresh catch and enjoying dinner with family or friends.

Guests also have access to Venture Out’s resort-style amenities:
• Oceanfront heated saltwater pool & jacuzzi
• Marina with boat launch & fuel dock
• Convenient on-site store
• Pickleball, tennis, bocce & basketball courts
• Recreation areas & community activities
• Gated community in beautiful Cudjoe Key

Whether your idea of paradise is fishing all morning, lounging poolside all afternoon, or simply enjoying the waterfront Keys lifestyle, #573 is ready for your next getaway. 🌊

📲 Contact Kim for pricing & availability:
📞 (305) 315-6197
🌐 https://keezyvacationrentals.com/en/waterfront-with-boat-dock-heated-pool-amenities

Realtor with Expert Realty

08/26/2026

Your Florida Keys home away from home awaits at Casa Van Ness #512. 🌴🌊

🛏 2 Bedrooms | 🛁 2 Bathrooms | 👥 Sleeps 4

Escape to Cudjoe Key and settle into the laid-back island lifestyle at Casa Van Ness, a cozy waterfront retreat perfect for couples, families, or a getaway with friends.

One of the highlights? A 43’ private seawall, giving boaters the perfect place to dock and making it easy to spend your vacation doing what the Keys are famous for — getting out on the water. 🚤

Inside, you’ll have all the comforts of home:
• 2 bedrooms & 2 full bathrooms
• Fully equipped kitchen
• Air conditioning & WiFi
• Washer & dryer
• Comfortable living spaces for relaxing after a day of adventure

Located inside the gated Venture Out community, your stay also gives you access to incredible resort-style amenities:
• Oceanfront heated saltwater pool & jacuzzi
• Marina with fuel dock, ship store & boat launch
• Pickleball, tennis, basketball & bocce courts
• Recreation center & community activities
• Beautiful streets for walking and biking
• Just 19 miles from Key West

Spend your mornings on the water, your afternoons exploring the Lower Keys, and your evenings relaxing back at Casa Van Ness.

Your tropical escape is waiting. ☀️

📲 Contact Kim for pricing & availability:
📞 (305) 315-6197
🌐 https://keezyvacationrentals.com/en/casa-van-ness

Realtor with Expert Realty

08/24/2026

Wake up to breathtaking Atlantic Ocean views from sunrise to sunset at Tropical Tides 🌊☀️🌴

🛏 2 Bedrooms | 🛁 2 Bathrooms | 👥 Sleeps 4

Welcome to Tropical Tides, a fabulous open-water vacation home designed for the ultimate Florida Keys escape. With sweeping Atlantic Ocean views, incredible boating access, and a private 35’ seawall, this home is a true boater’s paradise and island getaway all in one.

Spend your mornings sipping coffee on the covered waterfront porch, your afternoons cruising the crystal-clear waters of the Keys, and your evenings relaxing by the heated pool as the sun sets over paradise.

Inside you’ll find:
• 2 spacious bedrooms & 2 full bathrooms
• Updated fully equipped kitchen with modern appliances
• Comfortable coastal living spaces
• WiFi & air conditioning
• Washer & dryer
• Bright, open layout designed for relaxation

🚤 Bringing your boat? Enjoy a 35’ seawall with direct water access—perfect for fishing, snorkeling, island hopping, or exploring the Atlantic at your own pace.

Located in a gated community, guests also enjoy resort-style amenities including:
• Oceanfront heated saltwater pool
• Marina with convenience store, fuel dock & boat launch
• Pickleball, tennis, basketball & bocce courts
• Beautifully maintained grounds & community spaces

Conveniently located near restaurants, shopping, and nightly entertainment—everything you need is just minutes away.

Whether you’re here for adventure on the water or peaceful days by the pool, Tropical Tides #135 delivers the perfect balance of comfort, convenience, and Florida Keys beauty.

📲 Contact Kim for pricing & availability:
📞 (305) 315-6197
🌐 https://keezyvacationrentals.com/en/tropical-tides-135

Realtor with Expert Realty

Shot by Key West Virtual Tours

08/21/2026

Wake up with the Atlantic Ocean right outside your door at Vacation Rental #214. 🌊🌴

🛏 2 Bedrooms | 🛁 2 Bathrooms | 👥 Sleeps 4

This upscale oceanfront retreat combines incredible water views, boating access, and all the comforts of home for the perfect Florida Keys escape.

Start your morning taking in the waterfront views, spend the afternoon out on the boat, and come back to relax by the heated pool before another beautiful evening in paradise.

Inside, you’ll enjoy:
• 2 comfortable bedrooms & 2 full bathrooms
• Fully equipped kitchen
• WiFi & air conditioning
• Washer & dryer
• Bright, relaxing coastal living spaces

🚤 Bringing the boat? Take advantage of the private boat dock and spend your vacation fishing, cruising, snorkeling, or exploring the surrounding waters.

Located inside the gated Venture Out community, guests also have access to resort-style amenities including:
• Oceanfront heated saltwater pool & jacuzzi
• Marina with fuel dock, boat launch & ship store
• Pickleball, tennis, bocce & basketball courts
• Recreation center & community activities
• Just 19 miles from Key West

Whether your perfect Keys vacation means days on the water or doing absolutely nothing by the pool, #214 gives you the best of both.

📲 Contact Kim for pricing & availability:
📞 (305) 315-6197
🌐 https://keezyvacationrentals.com/en/oceanfront-heated-pool-boat-dock-upscale-214

Realtor with Expert Realty

08/19/2026

Welcome to 701 Spanish Main Drive #265, a truly spectacular oceanfront opportunity in the Florida Keys. 🌴

🛏 2 Bedrooms | 🛁 2 Bathrooms | 📐 816 SF | 💰 $879,000

This one-of-a-kind waterfront property offers the ultimate coastal lifestyle with an impressive 98’ of total seawall frontage. Perfectly designed for boaters and ocean lovers alike, it features 72’ of protected canal frontage plus 26’ of direct Atlantic Ocean frontage, giving you the best of both calm harbor access and open-water beauty.

A true boater’s dream, the canal side is fully equipped with six heavy-duty dock posts and cleats, making docking, fishing, and water access effortless.

Inside, you’ll find a beautifully maintained coastal home featuring:
• Tile flooring throughout for easy maintenance
• Metal roof for durability and peace of mind
• Central air conditioning for year-round comfort
• Abundant storage space
• Bright, open living area surrounded by windows that frame stunning water views and fill the home with natural light
• Two spacious bedrooms and two full bathrooms

Located in the highly desirable Venture Out on Cudjoe Key, a private gated community offering 24-hour security and patrol, plus short-term rental flexibility and two-pet allowance.

Community amenities include:
• Oceanfront heated saltwater pool & hot tub
• Marina with ship store, fuel dock & two boat ramps
• Pickleball, tennis, basketball & bocce courts
• Playground and community gathering areas
• Easy access to both Atlantic Ocean and Gulf waters

This is a rare opportunity to own a true slice of paradise in one of the Florida Keys’ most sought-after waterfront communities.

🌊 Seller says bring offers!

📲 Contact Kim for pricing and private showings:
📞 (305) 315-6197
🌐 https://my.flexmls.com/KimBabenzien/search/office_listing_categories/Active/listings/20260119002644716124000000

Realtor with Expert Realty

08/17/2026

Welcome to Tiki Time in Cudjoe Key #136, your upscale oceanfront escape in the Florida Keys. 🌴

TIKI TIME #136 | VACATION RENTAL | CUDJOE KEY

🛏 2 Bedrooms | 🛁 2 Bathrooms | 👥 Sleeps 4

This waterfront gem offers breathtaking views of the Atlantic Ocean and the perfect setting for your next getaway in paradise. With quick access to both the Atlantic Ocean and the Gulf of Mexico, it’s an ideal location for boaters and adventure seekers alike.

Inside, you’ll find a beautifully designed coastal retreat featuring:
• High-end, fully equipped kitchen with stainless steel appliances
• Bright and comfortable living spaces with coastal charm
• Three smart TVs for entertainment and relaxation
• Two spacious bedrooms designed for comfort and rest
• Two full bathrooms for convenience
• Everything you need for a relaxing Keys vacation

Step outside to your 54-foot private seawall, perfect for docking your boat and heading straight out to world-class fishing, snorkeling, and island hopping.

Located in a gated community, your stay includes access to incredible resort-style amenities:
• Oceanfront heated saltwater pool & hot tub
• Marina with convenience store, fuel dock & boat launch
• Pickleball, tennis, basketball & bocce courts
• Beautiful walking areas and community spaces
• Easy access to both ocean and gulf waters

Whether you’re boating, exploring, or simply relaxing by the water, Tiki Time delivers the ultimate Florida Keys lifestyle.

🌊 Your oceanfront escape is waiting.

📲 Contact Kim for pricing and availability:
📞 (305) 315-6197
🌐 https://keezyvacationrentals.com/en/tiki-time-in-cudjoe-key-136

Realtor with Expert Realty

08/14/2026

Welcome to Paradise Palms #635, where your Florida Keys getaway feels like home. 🌴

PARADISE PALMS #635 | VACATION RENTAL | CUDJOE KEY

🛏 2 Bedrooms | 🛁 2 Bathrooms | 👥 Sleeps 5

Tucked among tropical foliage inside the gated Venture Out community, Paradise Palms is made for slow mornings, sunny Keys adventures, and relaxing evenings with the people you love.

Inside, you’ll find:
• Bright, open floor plan with high ceilings
• Fully equipped kitchen with stainless steel appliances
• Large center island perfect for cooking and entertaining
• Primary suite with private en-suite bathroom
• Second full bathroom with washer & dryer
• Plenty of space for up to 5 guests

Step outside onto your private porch surrounded by tropical greenery and start your morning with coffee or wind down after a day of exploring with a cocktail in hand.

Your stay also includes access to all the amenities Venture Out has to offer:
• Oceanfront heated saltwater pool & hot tub
• Marina with fuel dock, boat launch & convenience store
• Pickleball, tennis, bocce & basketball courts
• Playground, community activities & more
• 4 miles of paved streets for walking and biking

Plus, you’re close to restaurants, shopping, parks and all the adventures waiting for you throughout the Lower Keys.

Paradise is closer than you think. ☀️

📲 Contact Kim for pricing and availability:
📞 (305) 315-6197
🌐 https://keezyvacationrentals.com/en/paradise-palms-in-cudjoe-key-635

Realtor with Expert Realty

Address

701 Spanish Main Drive
Cudjoe Key, FL
33042

Opening Hours

Monday	9am - 5pm
Tuesday	9am - 5pm
Wednesday	9am - 5pm
Thursday	9am - 5pm
Friday	9am - 5pm

Telephone

+13053156197

Website

http://keezyvacationrentals.com/

Alerts

Be the first to know and let us send you an email when Keezy Vacation Rentals posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Hotel

Send a message to Keezy Vacation Rentals:

Want your hotel to be the top-listed Hotel in Cudjoe Key?