Holiday rentals with a kayak in Naples

Guest house in Fort Myers

The modern kitchen is equipped with white cabinetry and stainless-steel appliances. A circular table with seating for four is positioned near a large glass sliding door that allows natural light and offers views of the outdoor space. A ceiling fan adds comfort to the room.

4.98 out of 5 average rating, 202 reviews

Waterfront Hideaway

This picturesque Airbnb is a hidden gem nestled along a canal, one minute boat ride to the Caloosahatchee River. The living room, bathed in natural light is perfect for taking in the scenic views. The spacious bedroom has a king-size bed, ensuring a night of blissful rest. The full kitchen is equipped with all modern appliances. Close to Sanibel & Fort Myers Beach. Bring your boat & dock it on the seawall, ready to set sail whenever your heart desires. Book now - your coastal paradise awaits!

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.

4.95 out of 5 average rating, 126 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

The backyard features a hot tub in the foreground, with a clear view of a pool in the background. Colorful adirondack chairs are arranged around the pool area, and a spacious house is visible with a screened porch. String lights are seen overhead, enhancing the outdoor ambiance.

4.98 out of 5 average rating, 116 reviews

April Deals! Hot Tub+Ping Pong+Just 5 min to Town

-5 min to Downtown Cape/10 min to Yacht Club Beach, 20 min to Causeway Beach, 25 min to Ft Myers & Sanibel Beach -Tropical fenced backyard w/ pool, hot tub, gas firepit, swing chair, hammock & Blackstone grill -Beach essentials, boogie boards, umbrellas, beach wagon, cooler & chairs -Board games, ping-pong, corn-hole, darts, 2 kayaks+life jackets -2 Beach Cruiser bikes + helmets -Relaxing enclosed covered patio + string lights, neon sign & grass wall -Canal access for kayak launch 5 min away!

A spacious covered porch offers a view of a tranquil lagoon surrounded by tropical foliage. Comfortable outdoor seating is complemented by a small table, while vibrant flowers are arranged in a vase. Sunlight reflects off the water, enhancing the outdoor ambiance.

4.96 out of 5 average rating, 175 reviews

Tropical Cottage by the Sea- your own private home

Welcome to your own private waterfront home on private lot close to Naples beaches! This small cottage comes with a big view of a tropical, peaceful lagoon. Fish and kayak right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting and lots of wild life to see too! Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens or one of the many restaurants close by! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do close by!

4.89 out of 5 average rating, 74 reviews

Home in Bonita Springs

Bonita Beach Beauty

Relax with the whole family at this peaceful pool home in Bonita Shores. Enjoy the newly added pool surrounded by beautifully landscaped tropical grounds that bring true Key West vibes. Just 1.1 miles from Bonita Beach, this charming home is located near N. Naples, Gulf beaches, shopping, restaurants, and mini-golf. Guests can enjoy complimentary use of kayaks, bicycles, beach chairs, and a beach umbrella. Book this 2-bed, 1-bath home for your next SWFL getaway! (Small pets may be considered)

An inviting outdoor area showcases a pool and spa, surrounded by lush greenery. The sky is tinted with vibrant pink and purple hues at sunset. A pink flamingo float rests in the water, adding a playful element to the serene setting.

4.99 out of 5 average rating, 108 reviews

5 Star Paradise Plus/Canal/Pool/Spa/KayaksSp.offer

This renovated luxurious, charming 4 bedroom home has stunning updates. It is a former model home. It has 2 master bedroom suites/private bathrooms & sliding glass doors leading out to the pool & spa area & 2 bedrooms share a bathroom. We love hosting baseball players, pickle ball enthusiasts & families who enjoy the Waterpark or Mini Golf all minutes away. Just a short walk to The Courts which is new with 32 Pickleball courts & 12 tennis courts. Play either from 1-3 PM for FREE.cahis

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.

4.98 out of 5 average rating, 192 reviews

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.

4.99 out of 5 average rating, 154 reviews

An open living area features a cozy seating arrangement with a brown armchair and a textured ottoman. Wall art depicting botanical themes complements the neutral walls. A modern kitchen bar with three stools is visible, lending to the inviting and functional design of the space.

Home in Naples Park

Pool Bikes & Beach | Paddle Board Included

We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

4.98 out of 5 average rating, 121 reviews

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

Guest suite in Bonita Springs

A spacious sleeping area features a king-size bed with a white, textured comforter and two dark blue pillows. A wall-mounted HD TV is positioned for viewing. A white dresser and wardrobe complement the decor, with light streaming in from a window adorned with soft curtains.

4.98 out of 5 average rating, 321 reviews

1Rm Studio-Pool, HotTub, Bikes, Kayaks, Near Beach

This is a separate, private studio with private entrance attached to the main house, but on the second floor above the garage. Your studio is completely separate upstairs floor behind a locked door. Laundry room is a connecting, shared space. I live in the main house. We will not cross paths unless you want to meet. Reminder: Airbnb is now charging hosts a 15% fee, so the price you see is not the price we gets. If you want to spend less, check out my Additional Photos.

5 out of 5 average rating, 19 reviews

A gold-colored mermaid statue is positioned on a pedestal against a backdrop of vertical blinds. The walls are painted in soft blue, and warm wooden trim outlines the space, contributing to a nautical-inspired ambiance.

Apartment in Naples

Up in the Aerie

Live like an artist in Naples’ Arts District! A second-story walk-up to an airy loft in the trees on the water. Walking distance to some of the area’s hippest new eating establishments, galleries, parks, botanical gardens, and activities. Direct boat access to Naples bay through mysterious mangrove lagoons and waterways. Five minutes to downtown Naples by car or fifteen minutes by bike. Our community is vibrant, innovative and culturally diverse.

5 out of 5 average rating, 14 reviews

An aerial view of a large outdoor pool surrounded by palm trees and lounge chairs. Umbrellas provide shade over several seating areas, and vibrant landscaping enhances the tropical setting, complementing the pool's unique shape and inviting blue water.

Flat in Naples

GreenLinks Retreat - Pool, Hot Tub, Tennis, Golf

Welcome to your paradise at Lely Resort! This spacious 2-bedroom, 2-bath condo offers a perfect blend of comfort and luxury. Enjoy access to a huge pool, two golf courses, and well-maintained tennis and pickleball courts. Indulge in delicious meals at nearby restaurants or explore the area with convenient bike rentals. Our second floor location offers you the perfect spot to take in the beautiful views on a private balcony.

Popular amenities for kayak rentals in Naples

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A serene waterfront view is captured from a dock, showcasing calm waters reflecting palm trees and houses along the shore. The dock is anchored with sturdy posts topped by black finials and surrounded by a gentle rope, emphasizing the peaceful ambiance.

4.97 out of 5 average rating, 155 reviews

Flirty Flamingo Gulf Access Cape Coral Home

4.97 out of 5 average rating, 161 reviews

A serene outdoor space features elegant seating with plush cushions and wooden tables, set against the backdrop of a softly illuminated pool. The area is accented by vibrant blue drapes and warm lighting, creating a calm atmosphere for relaxation.

Home in Bonita Springs

Imperial Garden Riverside Retreat

4.84 out of 5 average rating, 120 reviews

Home in Old Naples

Waterfront Delights

A screened lanai features a rectangular pool surrounded by tropical greenery. Outdoor dining furniture is visible near a glass table, offering a place to enjoy meals. Colorful pool floats and lounge chairs add to the inviting space, with the waterfront just beyond the pool area.

4.84 out of 5 average rating, 112 reviews

Peaceful Oasis

A spacious living area features a light brown sectional sofa and a wooden coffee table. A textured rug lies beneath, while a large decorative vase with pink floral arrangements stands beside the sofa. Natural light filters in through two windows with light blinds.

4.96 out of 5 average rating, 57 reviews

'The Morning Star' w/ spa & Private Mini Beach

An expansive outdoor area features a massive infinity pool reflecting the colors of the sunset. Lounge chairs are positioned around the pool, while the villa’s modern architecture and wide glass doors provide a seamless connection to the inviting interior space.

5 out of 5 average rating, 10 reviews

Intervillas Florida - Xanadu Villa

A welcoming entrance to the home is framed by palm trees and landscaped gardens. The curved driveway leads to a well-maintained façade featuring stone accents and large windows that allow natural light to illuminate the interior.

5 out of 5 average rating, 24 reviews

Weekly Stay Discount+Heated Pool/Hot Tub+PuttPutt

A heated pool is visible, surrounded by a spacious deck that accommodates lounge chairs and includes views of the river and palm trees. The water's surface reflects the clear blue sky, creating a serene outdoor atmosphere.

5 out of 5 average rating, 20 reviews

Riverview@EndPoint -Sunrises+Sunsets - Heat Pool

Cottage rentals with a kayak

Cottage in Bonita Springs

A serene view of the Enchanted Cottage is showcased amidst lush tropical landscaping. Pathways with stone pavers lead towards the quaint entrance, bordered by various palms and flowering plants that enhance the peaceful garden setting.

4.99 out of 5 average rating, 70 reviews

The Enchanted Cottage on the Imperial River

The exterior of the villa features a light-colored façade with a sloped roof and a well-maintained lawn adorned with tropical plants. A driveway leads up to a garage on one side, while a double entrance door provides access to the home.

Cottage in Cape Coral

4.65 out of 5 average rating, 51 reviews

Villa The Island Hideaway 2

4.91 out of 5 average rating, 264 reviews

A private heated saltwater pool is surrounded by vibrant palm trees, creating a lush outdoor oasis. White lounge chairs are positioned along the poolside, inviting relaxation under a clear blue sky. A well-maintained grassy area adds to the serene atmosphere.

Cottage in Naples Park

Cottage Close to Vanderbilt Beach Heated Pool

A tranquil waterway is visible, reflecting the surrounding structures and sky. A private boat dock extends into the canal, offering access to boats moored nearby. The scene features well-maintained properties lining the banks, framed by palm trees and grassy areas.

Cottage in Saint James City

5 out of 5 average rating, 7 reviews

Flamingo Bay Cottage

Cottage in Bonita Springs

4.54 out of 5 average rating, 26 reviews

Snowbird-friendly 3BR historical cottage with W/D

A bright and inviting living area features pastel yellow walls complemented by an array of furnishings in varied hues. The space includes a dining table with chairs, a cozy seating area with a striped sofa, and decorative artwork adorning the walls.

Cottage in Hamlet

4.88 out of 5 average rating, 42 reviews

The Coqui Palace

Cottage in Bonita Springs

An outdoor seating area features a round black table surrounded by six metal chairs, set against a backdrop of white siding. A potted plant sits in the center of the table. Sunlight filters through the nearby window, enhancing the inviting atmosphere.

5 out of 5 average rating, 17 reviews

Quiet Riverside Cottage in Downtown Bonita Springs

Superhost

A serene outdoor space features a clear, heated saltwater pool surrounded by lush palm trees. Colorful kayaks are visible along the lakefront, while blue lounge chairs provide comfort for relaxing under the sun. The tranquil water reflects the blue sky and nearby greenery.

Cottage in Cape Coral

4.29 out of 5 average rating, 7 reviews

Cape Lake House Lake Front

Other holiday rentals with a kayak

An aerial view of a spacious home features a heated infinitive pool and hot tub, surrounded by lounge chairs on a patio. A private dock accommodates a boat, with manicured lawns and tropical landscaping completing the outdoor setting.

5 out of 5 average rating, 37 reviews

Waterfront Cape Coral Oasis+ Heated Pool | Kayaks

4.97 out of 5 average rating, 33 reviews

Home

Last Minute-Villa Seven Oceans-stylish, new, pool

5 out of 5 average rating, 55 reviews

An aerial view of the villa showcases a spacious property with a large custom heated saltwater pool, surrounded by a screened lanai. Two kayaks rest on the lush green lawn, and the private dock extends into the calm canal waters.

Villa in Cape Coral

Luxury new construction Villa Ocean Kiss on canal

5 out of 5 average rating, 59 reviews

A heated pool and spa are set within a sun-drenched patio area, complemented by lounge chairs and an umbrella for shade. The surrounding deck features a waterfront view of the canal, enhancing the relaxing outdoor atmosphere.

Villa in Cape Coral

Pool & Spa Villa with Waterfront Views and Kayaks!

4.92 out of 5 average rating, 24 reviews

Townhouse in Cape Coral

Waterfront Condo with Pool & Boat Slip

4.97 out of 5 average rating, 37 reviews

An aerial view showcases a waterfront property surrounded by palm trees and a canal. The home features a terracotta tiled roof and a large backyard with a hot tub and lounge chairs. Two kayaks are visible near the dock, enhancing the outdoor space.

Home in North Fort Myers

Winter Deal: Hot Tub+Kayaks+Fishing & Pets Welcome