Holiday rentals with a kayak in Naples

4.95 out of 5 average rating, 193 reviews

Naples Cottage for two- your own private home

Welcome to your own, private home close to restaurants, coffee shops, parks and Naples beaches! This perfect tropical cottage for two comes with a stunning view of a natural lagoon. Fish, kayak & explore right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting. Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens, Trails, Pickle Ball courts or shops near by! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do near you

A spacious deck extends over the canal, surrounded by lush palm trees. Comfortable seating is arranged around a fire pit, with a paddleboard propped nearby. A BBQ grill is visible, inviting outdoor dining in a serene waterfront setting.

4.94 out of 5 average rating, 156 reviews

Boaters Bayshore Bungalow w/HOT TUB view of water.

BRING YOUR BOAT! This ranch home is located on a canal with direct access to the Gulf/Naples Bay(no bridges). Amazing water sports access. In the cool/hip Bayshore Arts district! Great restaurants, Naples Botanical Gardens, boating, 3 miles to DT Naples and 4 to the best beaches. This is a perfect family/friends vacation spot. We have all the gear to enjoy this location. Quiet neighborhood/newly renovated/great views. Coffee on the deck with sunrise in front of you or drinks at sunset. Serenity

4.99 out of 5 average rating, 254 reviews

The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.

Home in Pelican

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

4.88 out of 5 average rating, 32 reviews

Coffee & Wine | Hot Tub | Near Beach & Downtown

Welcome to Coffee & Wine! ☕️🍷 Why should you book with us?👇 -Best location in Naples -Private & peaceful setting -Hot tub for relaxing nights -Fully equipped kitchen -Walk to brewery, wine & dining -6 min to Downtown Naples & 5th Ave -10 min to Naples Pier & beaches -5 min Naples Bay Marina -5 min USOP National Pickleball Center -6 min Naples Airport -Gulf access canal -Boat friendly parking -Fast WiFi & Smart TVs -Washer & dryer -Sleeps up to 6 guests -Self check-in & hosts available 24/7

4.96 out of 5 average rating, 113 reviews

A sandy backyard features a fire pit surrounded by several black chairs, with a canal lining the edge. Lush greenery and palm trees provide a tropical setting, while a spacious home stands in the background, framed by clear blue skies.

Home in Bonita Springs

Canal Home- Gulf Access- PET friendly-Fenced yard

Waterfront home with Gulf access. Recently renovated 3 BR, 3 BA home on a canal off the Imperial river. Two en-suite bedrooms. The home can comfortably sleep 8 guests. Kayaks, bikes, fishing poles, yard games, backyard beach, and fire pit available for your use. Fenced in yard. Centrally located about 20 minutes from the airport, Naples, Fort Myers and only 3 miles from the beach! Close to several breweries, wine loft, local coffee shop, cocktail lounge, parks, churches, and many restaurants.

5 out of 5 average rating, 17 reviews

A spacious outdoor area is highlighted by a uniquely shaped pool surrounded by lounge chairs. Umbrellas provide shade over seating areas, and a dining table is visible in the background. Lush palm trees frame the scene under a clear blue sky.

Home in Naples Park

Resort Style Tropical Oasis

Location, location, location! This beautiful 3 bed 3 bath waterfront modern home, which offers the perfect blend of comfort, convenience and entertainment. Ideal for families and friends. Just a short walk to the beach and minutes away you can enjoy easy access to fine dinning, shops and lively nightlife. Relax in luxury at this waterfront retreat featuring a pool, hot tub, fire pit, 6 smart TVs, full outdoor kitchen, bar, and private dock. Perfect for entertaining or unwinding in style.

5 out of 5 average rating, 15 reviews

A single-story home is set amidst lush greenery and landscaped gardens. A circular driveway leads to a covered entrance, with palm trees framing the front yard. The exterior features a neutral-colored facade, complemented by a gray garage door and a welcoming front porch.

Home in North Naples

"Holiday Heaven" 4 b 3b Pool BBQ

In the Heart of Napes " Holiday Heaven" enjoy in 4 bedrooms 3 bath Heated pool house. Waterfront property in Palm River community. 10 min from the Beach. 10 people sleeping.Kitchen offers stainless appliances, granite counter tops, walk-in pantry. Breakfast bar is ideal for morning coffee while planning your perfect day in Napes! Master bathroom has stunning soaking tub, large walk-in shower with walk-in closets. The home has open layout with direct entrance to the backyard patio and pool .

4.98 out of 5 average rating, 205 reviews

A spacious outdoor seating area is featured, showcasing a glass-top table surrounded by six chairs. The patio is complemented by a gas grill on one side. Large sliding doors provide a view of the interior dining area and kitchen, blending indoor and outdoor settings.

Home in North Naples

Gulf Access Canal, Kayaks, Bikes, Dock, Wildlife

A renovated mid century modern house with natural peaceful views out of every window and slider. No detail spared, as it was going to be our forever home. Located on an ocean access canal, extremely safe, quaint and friendly neighborhood, just off 41. The backyard has a large shaded sitting area with a gas grill and fire pit. The dock hangs over the water with seating and swim ladder. 2 tandem kayaks, fishing rods & tackle, adult & children’s bicycles, beach chairs, and so much more.

4.97 out of 5 average rating, 118 reviews

"The Boho Bliss" - Reset & Recharge Wellness House

Discover Bohemian Bliss in this uniquely styled home, 2mins walk to Sudgen Lake in Naples that includes beach, lake activities, walking trails or biking. Vibrant energy with the comfort of your creatively adorned space that tells you a story. All brand new, high-quality furniture, Tempur-Pedic mattress, Very Fast WiFi, King-size bed, TVs in all bedrooms, fully equipped kitchen, Fire pit, BBQ. Reserve now so we can welcome you home, to a boho-inspired sanctuary in the heart of Naples.

4.91 out of 5 average rating, 75 reviews

Colorful pool floats are visible in the sparkling water of the large private pool. A vibrant unicorn and sparkling dragon float, along with several rings in various shades, rest atop the clear blue surface, providing relaxation options for guests.

Home in Naples Park

Private Pool + 5 mins to Beach

A rental agreement and security deposit hold is required to rent this property (allowed by Airbnb). “One of the most outstanding properties I’ve stayed at… If I could give it 5000 stars, I would.” ✨ Your Private Coastal Oasis Relax in this clean, beautifully maintained 3-bedroom home with a private, fully fenced backyard—perfect for families and dogs. Experience tranquility in our cozy cottage with a sparkling pool, ideal for refreshing dips and relaxation. Consistently rated 5⭐️