Vacation rentals with a kayak in North Port

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.

5.0 out of 5 average rating, 102 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

ValueOutdoor spacesCondition

4.96 out of 5 average rating, 23 reviews

A modern kitchen space features a bright white countertop with high-backed stools arranged along one side. Pendant lights hang above, illuminating the area. The backdrop includes a light-colored stone accent wall and stainless-steel appliances, while a hint of another room is visible in the background.

Home in North Port

Home •POOL•15 min to BEACH•Kayaks•Pet Friendly!

☀️Escape to Paradise in PORT CHARLOTTE ☀️ 🌺2 🛏️bed | 2 🛁bath en-suites that sleeps 12 💦 Heated POOL 🎣 BOATERS: Dock for fishing and accessibility to FREE boat ramp (across street) 🏖 Short drive to the Gulf COAST Famous beach/beach towels, chairs, umbrella, coolers and beach toys provided 🌸 Close to SHOPPING, DINING 🎱 Pool table ⛳️ Close to the Golf activities 🌅 Private patio - perfect spot for your morning coffee ☕️ 🏀 Game Room 🛶 Kayaks 🚴 Bikes 🐾🐾We are PET Friendly!!🐾🐾

LocationOutdoor spacesCondition

4.83 out of 5 average rating, 120 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!

LocationValueHospitality

5.0 out of 5 average rating, 10 reviews

Home in Arcadia

Peace River Waterfront Home with Boat Lift/Dock

Welcome to your waterfront escape on the Peace River! Whether you're bringing your own boat or renting one locally, this property is the perfect home base for adventure and relaxation. Enjoy direct access to some of Southwest Florida's best boating, fishing, jet skiing, and sandbar destinations, with the river leading all the way to the Gulf. Located just one minute from the popular Nav-A-Gator Bar & Grill and public boat ramp, quick access to waterfront dining, live music, and local events.

LocationValueBackyard

5.0 out of 5 average rating, 18 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

Outdoor spacesLocationWalkability

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!!!

Outdoor spacesLocationHospitality

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, 126 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 spacesLocationCondition

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, 104 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.

LocationValueBeach

4.88 out of 5 average rating, 17 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

LocationPetsBeach

5.0 out of 5 average rating, 20 reviews

Home in North Port

Waterfront Oasis w/ Pool on Myakka – Near Beaches

Waterfront oasis on the Myakka River. Watch manatees, ospreys & native Florida wildlife from your backyard. Spacious 2BR/2BA updated home with screened pool & patio with a kitchen pass-through window for indoor-outdoor living. Full home water filtration system. Just 5 minutes to Wellen Park, 20 mins to Manasota Beach & Historic Downtown Venice, 35 mins to Siesta Key & Punta Gorda. Perfect blend of relaxation, adventure & coastal Florida charm.

Outdoor spacesLocationRiver