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Vacation rentals with a kayak in North Port

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Top-rated kayak rentals in North Port

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Top guest favorite

A private heated pool area features clear water surrounded by comfortable seating and vibrant blue umbrellas. A large pink flamingo float is visible in the water, alongside other colorful poolside furnishings. Lush greenery is present in the background, enhancing the outdoor atmosphere.

Home in Port Charlotte

5 out of 5 average rating, 54 reviews

Xanadu Luxury|Fishing Dock|Kayaks|Bar

Welcome to XANADU Luxury Villa 🌊 your canalfront paradise with a private BOAT DOCK ☀TOP LOCATION📍, close to: beautiful beaches 🏖️ Gasparilla Island, Siesta Key, Englewood! ☀Dock Ideal to FISH 🎣| Deck🎴 ☀BAR🍷 ROOM Dancing Light 🪩 ☀DEDICATED WORKSPACE 💻 ☀GAME🎮 Room /Roblox/Arcades🕹️ ☀Smart TVs in every room📺 ☀HEATED Pool 🏊‍♀️ ☀Fast WIFI📶 ☀Ping Pong Area in Sand 🏓 ☀Fully equipped kitchen🍽️ ☀Pool Table and Games🎱♟️ ☀ Outside dining table😋/Fireplace ☀BBQ🍖Ice Maker🧊 ☀Self check in 🔐 Smart Lock

An outdoor seating area is presented with dark wicker furniture, blue cushions, and an orange throw draped over the arm. A table sits in the center, with manicured grass and a view of the waterfront in the background, framed by a decorative gazebo.

4.95 out of 5 average rating, 149 reviews

MCM Waterfront Retreat • Dock, Kayaks & Beaches

Welcome to our Mid-Century Modern waterfront escape on Curry Creek, minutes from Nokomis Beach (2 miles) and Venice Beach (3 miles). Spend your days fishing from the private dock, paddling one of 4 kayaks, or biking the Legacy Trail with 6 bikes. Evenings are for the firepit, grilling on the charcoal BBQ, or cornhole under the stars. We’ve stocked shark tooth gear, beach essentials, toiletries, coffee, tea, olive oil, spices, and a welcome bottle of wine — so you can arrive, unpack, and relax.

Top guest favorite

A living room is displayed with two comfortable seating areas featuring neutral-toned sofas. A geometric patterned area rug lies beneath, while large windows dressed with light curtains allow natural light to fill the space. A small lamp and a potted plant add warmth and greenery.

Home in North Port

4.98 out of 5 average rating, 98 reviews

North Port - Canal Home- Fish & Canoe

Relax in this well appointed guest house as you enjoy the warmth of the Florida sunshine. Read a book on the garden swing next to the canal while you watch the birds, fish off the dock or canoe. Immaculate 2 bed/2 bath home with sun porch and patio complete with BBQ grill located in lovely neighborhood next to lighted bike paths. Close to Routes 41 and 75 for beaches, shopping, restaurants, sports events etc. Our favorite thing to do is beach combing the fabulous beaches -equipment provided.

An aerial view captures the coastline of Manasota Key, showcasing the blue-green waters and sandy beach. The surrounding area features a mix of residential buildings and green spaces, with multiple boats visible in the water and a bridge connecting to nearby islands.

Cottage in Englewood

4.9 out of 5 average rating, 153 reviews

Free kayak/bikes/walk to beach/full cottage #1

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

Top guest favorite

A well-lit bedroom features a spacious wooden bed with plush white bedding. Natural light enters through the window, which is adorned with horizontal blinds. Simple wall art complements the soothing color scheme, and a ceiling fan provides ventilation.

Farm stay in Punta Gorda

4.98 out of 5 average rating, 102 reviews

Peaceful Waterfront Orchard 1

bring the whole family including your pets to this peaceful orchard and garden oasis. the action packed backyard of this duplex proudly boasts over 40 fruit trees of various varieties including banana, orange, lemon, fig, mango, papaya... and many more! choose to fish from the dock in the backyard canal, go exploring with the kayaks or paddleboards, play in the sandbox, try out the slackline, or even say hi to the chickens in the coop (maybe even grab a few fresh eggs for breakfast).

A spacious saltwater pool is enclosed by a screened lanai, featuring comfortable lounge floats and pool toys. Sunlight reflects off the clear water, surrounded by serene greenery and a well-maintained patio area. The inviting ambiance creates a perfect setting for relaxation and outdoor enjoyment.

Home in Port Charlotte

4.91 out of 5 average rating, 81 reviews

"Waterfront Oasis with Heated Saltwater pool"

Location! Lovely 3 bedroom 2 bath saltwater pool home. Set alongside a picturesque canal, this enchanting getaway has all the amenities,close to fantastic beaches, shopping and restaraunts! Access to the canal from the backyard grants you endless kayaking (kayak included) adventures right from the comfort of your backyard dock. Generously-sized, Saltwater Heated Pool, perfect for soothing relaxation. Nestled within a tranquil neighborhood, indulge in the ultimate vacation experience!

A large screened-in patio surrounds a sparkling Gunite pool, with a pink float in the water. Comfortable seating is provided at the bar area and poolside loungers, while palm trees and greenery are visible in the background.

Vacation home in Venice

4.86 out of 5 average rating, 145 reviews

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬

Escape to our charming Venice pool home, where relaxation meets adventure! Perfectly located near the water, this tranquil three-bedroom retreat is nestled on a quiet, palm-lined street. Enjoy easy access to bikes and kayaks for exploring, plus all the beach essentials: cooler, umbrella, and chairs. The pool awaits for sunny days and peaceful evenings (note: a brand-new pool cage is on its way, expected in December). Book now to experience Venice’s beauty from your private oasis!

An open-concept living area features a dining table with four chairs and a well-equipped kitchen with modern appliances. A large stainless steel refrigerator stands next to a kitchen island with seating for three. Bright natural light is provided by multiple windows.

Home in Port Charlotte

4.98 out of 5 average rating, 40 reviews

Home on the waters Edge

Fully renovated home in the heart of Port Charlotte. The home is 2 bedroom and 1 bath. 1 queen bed and 1 bunk bed, the bunk bed is full size and twin size. Home is also located on a canal. We have all the essentials you may need for a great stay, including bikes and kayaks. Please feel free to reach out if you have any questions. 7 Minutes to Sunseeker Resort and Charlotte Harbor 3 Minutes to William R Gaines Jr Veterans Memorial Park 3 Minutes to Port Charlotte Beach park

Top guest favorite

A well-appointed bedroom features a spacious bed with a decorative quilt in soft ocean-themed colors. Pillows are artfully arranged, and light filters through sheer curtains, revealing a view of the private pool and patio area beyond sliding glass doors.

Home in Port Charlotte

5 out of 5 average rating, 21 reviews

The Harbor House - Waterfront - Private Pool

Escape the cold to this bright and sunny two- bedroom, two-bath, waterfront, gulf access, pool home with private dock. This home is located within minutes of Charlotte Harbor and the Gulf of Mexico. The pool is enclosed with a large covered lanai which is perfect for barbecuing and enjoying evenings by the gas fire pit. Be amazed by the beautiful sunsets and tranquil waterfront views along the serene saltwater canal where snook, tarpon, manatees and dolphins frolic nearby.

A front porch is framed by pink hibiscus flowers and lush greenery. Rocking chairs are positioned along the porch, with a view of a well-kept garden and trees in the background. The overall atmosphere reflects a serene outdoor space.

Guest suite in Englewood

4.98 out of 5 average rating, 209 reviews

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The Front porch pictured is part of the main house and is NOT included for use while renting the Blue Cottage Suite. IF the main home is vacant during your stay, I will let you know and it can be used during that time.

Top guest favorite

Home in Port Charlotte

4.92 out of 5 average rating, 25 reviews

Peaceful waterfront home

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in the pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

Top guest favorite

Home in Port Charlotte

5 out of 5 average rating, 11 reviews

2/2 Family Escape HOME/POOL/Bikes /Kayaks and MORE

★Welcome to HALF acre PARADISE HOME ★ ★Perfect for your next FAMILY VACATION or a romantic COUPLES trip 🧑‍🧑‍🧒‍🧒 ★Spacious backyard, and plenty of natural light, you’ll never want to leave. ★We accommodate up to 12 GUEST . 🏡The home are MODERN & fresh . ⚓️ FREE boat RAMP just across street from our lovely home . ⚓️ 🛍️Close to SHOPPING, DINING , and a short ride to must GULF coast FAMOUS BEACHES. ⚠️MUST be 24 years old or older to stay with us⚠️

Vacation rentals for every style

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Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for North Port kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Nokomis

5 out of 5 average rating, 4 reviews

Nokomis Waterfront Unit Walk to the Beach & Dining

4.93 out of 5 average rating, 69 reviews

Ripple Inn @Fennario: Lagoon pool + SVB ferry ½ mi

A two-story coastal home is presented, featuring a light grey exterior with multiple gabled roofs and large windows. The front entrance is accented by wide stairs leading to a double door entrance, surrounded by landscaped shrubs and palm trees, with a driveway visible below.

Home in Englewood

5 out of 5 average rating, 6 reviews

4BR Bayfront Home – Dock, Pool & Beach Access

An open living area features a stone fireplace as its focal point, flanked by a large window overlooking the private pool area. Comfortable seating is arranged around a glass coffee table, with a wall clock and decorative accents enhancing the space.

Home in Nokomis

5 out of 5 average rating, 15 reviews

Spacious 3 Br Home w/ Heated pool -1 Mile to Beach

Home in Rotonda West

5 out of 5 average rating, 5 reviews

Large Waterfront Getaway | Sleeps 14 w/ 9 Beds

Top guest favorite

A waterfront patio is furnished with two lounge chairs positioned beneath a vibrant red umbrella. A small table holds a bottle of wine, and the serene view of the water, lined with palm trees and boats, creates a relaxing atmosphere.

Home in Port Charlotte

5 out of 5 average rating, 74 reviews

NEW 4BR/2BA MODERN WATERFRONT HOME POOL AND DOCK

Top guest favorite

A serene sunset is captured over the ocean, with warm hues of orange and yellow reflecting on the water. Gentle waves lap at the sandy shore, while soft clouds are illuminated by the fading sunlight, creating a peaceful coastal scene.

Home in Rotonda West

4.97 out of 5 average rating, 59 reviews

Waterfront 3bdr 2ba Beaches Golfing Fishing

Top guest favorite

An enclosed outdoor area features a heated swimming pool surrounded by a spacious patio. Colorful lounge chairs are positioned around the pool, alongside floating pool toys. Lush palm trees add to the tropical ambiance, with views of the private dock visible in the background.

Home in Port Charlotte

4.91 out of 5 average rating, 35 reviews

Waterfront*3BED/2BATH *NO FEE Heated Pool*Kayaks

Cottage rentals with a kayak

Two kayaks are visible on calm water, one orange and one yellow. An adult is paddling the yellow kayak while a child sits behind, wearing a red life jacket. Surrounding greenery adds a natural backdrop.

Cottage in Englewood

4.75 out of 5 average rating, 145 reviews

Good after Milton -Free Kayaks! Steps to Beach-bb

Two kayaks are positioned on calm water, with a yellow kayak in the foreground and a red kayak behind it. A person is paddling in the yellow kayak, while a child is seated in the red kayak, both wearing life jackets. Surrounding foliage reflects off the water's surface.

Cottage in Englewood

4.89 out of 5 average rating, 129 reviews

Good after Milton - Kayaks & Steps to Beach-pc

Top guest favorite

A comfortable living space features a light grey sofa with two blue cushions and a yellow accent pillow. A round mirror hangs on the wall, reflecting natural light. The white coffee table displays a decorative bowl, with a woven rug beneath providing texture to the floor.

Cottage in Englewood

4.96 out of 5 average rating, 25 reviews

Oystercatcher 3min walk to sunset, bikes, kayaks

Two individuals ride bicycles along a sandy beach at sunset, with vibrant hues of orange and purple in the sky. Gentle waves lap at the shore, and distant figures can be seen walking along the coastline, creating a serene beach atmosphere.

Cottage in Englewood

4.9 out of 5 average rating, 171 reviews

Free bikes/kayaks/walk to beach/2bed/2bath #2

Top guest favorite

The exterior of a charming beach house features a light blue façade with a coral-colored door. A small table with a palm tree design is positioned on a stone pathway leading to the entrance. Lush greenery and a decorative fountain enhance the welcoming outdoor space.

Cottage in Englewood

5 out of 5 average rating, 23 reviews

The Coastal Oasis. Only 8 minutes from the Beach!

Two dolphins are positioned beside each other as they leap from the ocean waves, creating splashes against the turquoise water. The scene captures the dynamic movement and playful nature of the dolphins, set against a vibrant sea backdrop.

Cottage in Englewood

4.86 out of 5 average rating, 126 reviews

Free Kayaks/bikes/walk to beach/pet friendly #3

An open concept living area features a cozy seating arrangement and a dining table set for four. The kitchen includes modern appliances against a backdrop of white cabinetry, while a decorative area rug adds warmth to the wood flooring.

Cottage in Englewood

4.89 out of 5 average rating, 171 reviews

Good after Milton - Waterfall Pool! Beach! am

Top guest favorite

A cozy living area features a white sectional sofa and a wooden coffee table. Natural light enters through sheer curtains, highlighting the wood-paneled walls. A television is situated on a light-colored media console, while decorative accents add a welcoming touch to the space.

Cottage in Don Pedro Island

4.98 out of 5 average rating, 53 reviews

West Coast Island Retreat, Simply Adrift Cottage

Other vacation rentals with a kayak

Top guest favorite

A single-story home is set against a clear blue sky, featuring light-colored exterior walls and a peaked roof. Lush green grass surrounds the yard, which includes decorative palm trees and circular flower beds with white stones. A white fence is visible in the background.

Home in Englewood

5 out of 5 average rating, 91 reviews

Englewood, Fl 2 bedroom home with heated pool.

Top guest favorite

A spacious area designed for recreational equipment is visible, featuring two vibrant green kayaks resting on a tiled surface. Bicycles and additional gear are neatly arranged against the wall, with light streaming through slatted partitions, creating a pattern on the floor.

Home in Don Pedro Island

5 out of 5 average rating, 14 reviews

Sea La Vie

The image reveals an inviting pool area within a screened lanai, featuring sun loungers adorned with black and white stripes. A glass-topped dining table accommodates four, accompanied by a potted plant. The pool glimmers with clear water, surrounded by lush greenery.

Home in Rotonda West

4.92 out of 5 average rating, 39 reviews

Tropical Retreat-HeatedPool Tennis PickleBall Golf

A light-colored, one-level ranch home with a well-manicured lawn is showcased in this image. The house is framed by lush greenery and colorful plantings, while a paved driveway leads to a two-car garage on the side. A peaceful neighborhood ambiance is apparent.

5 out of 5 average rating, 13 reviews

Venice Adventure Retreat Near Beaches & Bike Path

A year-round heated pool is surrounded by sun loungers, offering a spacious area for relaxation. Palm trees line the background, and the view extends toward the water under a clear blue sky with scattered clouds.

Condo in Port Charlotte

5 out of 5 average rating, 14 reviews

Private Beach, Fishing Dock & Heated Pool Paradise

A spacious waterfront home is surrounded by green landscaping, palm trees, and open blue skies. A large heated pool is visible in the backyard, adjacent to a well-maintained deck. Comfortable seating is positioned on the sandy area by the water, providing a relaxing atmosphere.

Villa in Osprey

5 out of 5 average rating, 12 reviews

Paradise with a pool, pier and private beach area

Two individuals are seen kayaking on a calm body of water, surrounded by lush greenery. Bright, warm sunlight reflects off the surface, while orange paddles create ripples as they navigate their kayaks. The scene emphasizes an inviting outdoor adventure atmosphere.

Tiny home in Port Charlotte

5 out of 5 average rating, 8 reviews

Minutes to Sand, Dog Friendly, Hot Tub Luxury

Two kayaks in blue are positioned near a wooden dock, alongside a stand-up paddleboard. The peaceful canal water reflects surrounding greenery, while the sun creates a warm glow over the area. The grassy shoreline provides additional space for relaxation.

Home in Port Charlotte

4.94 out of 5 average rating, 33 reviews

Waterfront Gem, waterfront. fish, kayak, relax!

Quick stats about vacation rentals with a kayak in North Port

Total rentals
100 properties
Nightly prices starting at
R874 ZAR before taxes and fees
Total number of reviews
2.6K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
70 properties have a pool

Destinations to explore