Vacation rentals with a kayak in Port Charlotte

A canalfront area features a serene gazebo surrounded by lush green grass and white pebbles. The vibrant sunset sky adds warmth to the scene, and the private boat dock is visible in the background, enhancing the tranquil outdoor setting.

5.0 out of 5 average rating, 106 reviews

Xanadu|Fishing/ Pool/Dock|Kayaks|Bar/Gazebo/ Kids

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

LocationOutdoor spacesCheck-in

A covered outdoor space features a view of a tranquil pool and nearby water. A table with a fire feature is positioned at the center, with a light-colored couch and a glass table nearby. Lush greenery is visible along the perimeter.

5.0 out of 5 average rating, 16 reviews

Tip Top tip lot

Relax with entire family at this peaceful home. Enjoy the privacy and the outdoors with kayaks, bikes, hot tub, boat dock and heated pool ; great views of the water, watch the fish do back flips! Play Billiards! Nice cul-de-sac with lots to see and do nearby! Short walk to great pizza. Town voted best in US, center is short drive with great restaurants & features great golf, parks with walking/bike paths, tennis, pickleball, playgrounds etc. Easy bike ride to Ponce de Leon Park for sunsets!!!

ValueOutdoor spacesAmenities

4.92 out of 5 average rating, 25 reviews

Tropical Retreat! Hot tub, pool, Kayak, pool table

Tranquil and quiet tropical getaway with beautiful water views ! Minutes away from Port Charlotte Beach Park, downtown Punta Gorda and many nearby bars and restaurants. Home has a heated pool, hot tub, kayaking, fishing, pool table, corn hole set and multi game arcade. There are 2 rooms and 5 beds including a sofa bed in the living room. Open concept makes it ideal for entertaining! Also enjoy the barbeque area with a large grill and lounge chairs. Note: At least 25 years old to book. No Pets.

LocationOutdoor spacesBeach

4.83 out of 5 average rating, 122 reviews

An aerial view of Manasota Key showcases the expansive beach lined with soft sand and crushed shell. The vacation home is highlighted, surrounded by lush greenery and close proximity to the warm Gulf waters, with clear blue skies enhancing the tranquil environment.

Bungalow in Englewood

LG Beach Bungalow on Gulf w/Bay Access & deck too!

Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!

ValueLocationAccess

5.0 out of 5 average rating, 21 reviews

Happy Tarpon |10 PPL| Deck & Pool |Games |Fire Pit

Welcome to Happy Tarpon Villa, a family-friendly home in Port Charlotte! - Pool - EV Charger - 15 mins to Sunseeker Resort - 30 mins to Gasparilla Island - 30 mins to Manasota Island - Private Deck & Boat Lift - Playground for kids - Pool Table, Air Hockey & Game Console - BBQ, Fire Pit & Outside furniture - 10 PPL (1 KING, 1 QUEEN, 1 Bunk Bed & 1 Sofa Bed) - Washer & Dryer - Kids friendly - Private Patio & Terrace - Fully equipped kitchen - Free parking - Safe neighborhood - Self-check in

LocationOutdoor spacesCheckout

5.0 out of 5 average rating, 34 reviews

A modern luxury home is presented with a tiled roof and arched entryways. The manicured lawn features lush green grass, providing a welcoming appearance. A directional map is positioned in the corner, highlighting the property's location in relation to nearby attractions.

Home in South Gulf Cove

Luxury Waterfront Home With Heated Pool & Hot Tub

New modern luxury home featuring 3 bedrooms and 3 bathrooms. 50" Flat screen TVs in all bedrooms and a 65" TV in the family room. Master suite with dual sinks large soaking tub and a walk in roman shower! Screened in heated pool with hot tub and special LED lighting. Large lanai with gas grill a table with 6 chairs and 4 loungers. Dock has sitting area to sip morning coffee or grab a cocktail and watch the fish jump. Beach chairs, pool toys and fishing rods/ tackle everything is included!!!

ValueOutdoor spacesWifi

A screened-in lanai features a spacious swimming pool, with panoramic views of intersecting canals and the surrounding neighborhood. Lush green lawns and palm trees are visible in the foreground, while serene water reflections enhance the tranquil atmosphere.

4.92 out of 5 average rating, 105 reviews

Peaceful PGI Getaway

This gorgeous 3 bedroom, 2 bathroom house is located on intersecting canals in Punta Gorda Isles, providing beautiful water views from several rooms throughout the house. With two living rooms, there is plenty of space for the whole family! You will enjoy indoor and outdoor dining tables. This quiet neighborhood is great for families, couples, or seniors. With the house at the end of the street you have plenty of privacy. The spacious pool overlooks your 145 ft water view and boat dock.

ValueOutdoor spacesWifi

Farm stay in Charlotte Harbor

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.

4.95 out of 5 average rating, 128 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).

Outdoor spacesLocationLayout

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.

4.91 out of 5 average rating, 93 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!

ValueOutdoor spacesDecor

A spacious home is set on a well-maintained lawn, featuring a white exterior complemented by lush tropical landscaping. Palm trees and shrubs enhance the entrance, while a smooth driveway leads to a two-car garage. The sky is clear and blue, adding to the inviting appearance.

5.0 out of 5 average rating, 105 reviews

Elegant heated pool canal home in very quiet area.

Great location! Bring your dog, bring your boat and enjoy the Florida sun in your heated saltwater swimming pool. Fish off your private dock while watching for dolphins or manatee. You can meet the rest of the opacarophiles who walk to the beach to view the sunset. Relax in the jacuzzi with your favorite beverage. NOTE: Beach is sandy but the water is BRACKISH, not clear. This is mostly a retirement neighborhood. This is NOT a party house and not suitable for unattended children.

ValueLocationLong stay

An aerial view captures a light blue house with a spacious driveway and manicured lawn, surrounded by lush greenery and a serene canal. The home features a charming front porch and is set within a quiet neighborhood, showcasing the tranquil natural landscape.

4.96 out of 5 average rating, 45 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 our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

LocationValueBackyard

4.89 out of 5 average rating, 18 reviews

Solar Powered Pet & Family Friendly Home + Kayaks

☀️ Welcome to our solar-powered, no fuss home in Port Charlotte, FL—perfect for families & pets! 🔌 Features Hurricane windows & a Level 2 Tesla EV charger 🍳 Fully stocked: kitchen (pots&pans, spices, grill), towels, Pack ’n Play, high chair, toys, board games, puzzles, Netflix & Disney+ Included 🌳 Backyard: 6-ft privacy fence 🏖️ Close to beaches, parks & yummy local mom-and-pop restaurants. Clean, comfy, and ready to welcome you! 2 Kayaks included

LocationFamilyCheck-in

Popular amenities for Port Charlotte kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5.0 out of 5 average rating, 27 reviews

Port Charlotte Lake front home Heated Pool, Dock

Outdoor spacesValueKitchen

A serene waterfront view showcases calm waters bordered by lush greenery and palm trees. The area features manicured lawns and docks extending toward the water, surrounded by a spacious patio with a lounge area and umbrella, ideal for relaxation and enjoying the scenery.

5.0 out of 5 average rating, 88 reviews

Luxury modern waterfront 4BR/3.5BA pool beach

ValueOutdoor spacesCheck-in

4.96 out of 5 average rating, 26 reviews

Home in South Gulf Cove

Canal Home w/ Escape Room, Pool & Dock, Pets OK

Outdoor spacesValueCleanliness

4.94 out of 5 average rating, 63 reviews

Dog Friendly | Walk to Fishermen’s Village • Pool

ValueOutdoor spacesCleanliness

5.0 out of 5 average rating, 65 reviews

An aerial view captures a two-story home nestled along a quiet waterway with lush greenery surrounding it. Nearby, other residences and a private dock are visible. The scenic backdrop showcases calm waters merging with a blue sky, highlighting the tranquil atmosphere of the location.

Home in Englewood

Lux Home on Gulf w/Private POOL & 50ft Dock

ValueOutdoor spacesQuiet

An open-concept living area reveals a modern kitchen featuring stainless steel appliances and a marble-topped island with bar seating. A comfortable couch faces a wall-mounted television, while large sliding glass doors offer views of the outdoor patio and pool area.

4.91 out of 5 average rating, 47 reviews

Renovated Modern house with pool -Port Charlotte

Outdoor spacesValueAmenities

5.0 out of 5 average rating, 12 reviews

Home in South Gulf Cove

Best Rated House w Heated Pool/Spa & Boat Dock

LocationOutdoor spacesHospitality

5.0 out of 5 average rating, 10 reviews

Home in Arcadia

Peace River Waterfront Home with Boat Lift/Dock

LocationValueAccuracy

Cottage rentals with a kayak

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.

4.85 out of 5 average rating, 163 reviews

Unit #3 Free Kayaks/bikes/beach/pet friendly

Outdoor spacesValueParking

4.99 out of 5 average rating, 134 reviews

A screened-in porch offers a serene view of lush greenery and a calm waterway. Two wooden chairs are positioned at a white table, with a small decorative item placed on its surface. Bright sunlight filters through the trees, enhancing the natural surroundings.

Cottage in Arcadia

Quaint Cottage w/access to Peace River canoe/kayak

Outdoor spacesLocationSleep quality

4.95 out of 5 average rating, 110 reviews

A screened-in pool area is presented, featuring a clear blue pool surrounded by stone pavers. Lush greenery and water views are visible through the screen, enhancing the sense of tranquility and connection with nature.

Cottage in Nokomis

New Pool Tropical Waterfront Dock & Optional Boat

ValueOutdoor spacesNearby

A living area is presented with a black sofa and a patterned armchair, complemented by light-colored wood flooring. Art featuring sailboats decorates the wall, while natural light fills the space through multiple windows. A dining area with a table and chairs is visible in the background.

5.0 out of 5 average rating, 45 reviews

1 Bed-Walk beach-bikes-kayaks-grill-out hot shower

LocationOutdoor spacesGrill

Cottage in Don Pedro Island

4.99 out of 5 average rating, 78 reviews

Island Getaway, Beach House, Dock, Pet Friendly

ValueLocationNearby

5.0 out of 5 average rating, 38 reviews

Private Beach-Luxury 4BR+SUPs&Kayaks-Pets-BBQ

LocationOutdoor spacesCleanliness

4.9 out of 5 average rating, 20 reviews

2BR Beach Cottage-Steps to Beach, Heated Pool

ValueLocationCleanliness

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.

4.95 out of 5 average rating, 40 reviews

Oystercatcher 3min walk to sunset, bikes, kayaks

LocationOutdoor spacesQuiet

Other vacation rentals with a kayak

Superhost

4.94 out of 5 average rating, 83 reviews

House With A Boat–Your Private Waterfront Resort

Outdoor spacesValueBackyard

5.0 out of 5 average rating, 11 reviews

Modern waterfront house fully equipped f/ vacation

Outdoor spacesValueNearby

5.0 out of 5 average rating, 5 reviews

Villa in Port Charlotte

Waterfront Unique Euro Villa heated salt pool dock

Outdoor spacesValueAmenities

Superhost

5.0 out of 5 average rating, 10 reviews

5 Min to Downtown • Kayaks, Bikes + Private Dock

LocationOutdoor spacesSleep quality

The modern kitchen features a large central island with four black stools. High-end appliances, including a stainless-steel refrigerator and a sleek range hood, complement the marble countertop. Natural light brightens the space, enhanced by decorative pendant lights and beach-themed artwork on the walls.

5.0 out of 5 average rating, 81 reviews

Lux Canal Front | Pool, Kayaks, Bikes, & Boat Dock

LocationOutdoor spacesAccess

4.92 out of 5 average rating, 25 reviews

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

Pro Fishing Dock Private Beach & Heated Pool!

LocationValueLayout

5.0 out of 5 average rating, 10 reviews

Serene canal front pool home

LocationViewQuiet