Vacation rentals with a kayak in South Venice

5.0 out of 5 average rating, 103 reviews

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

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

Outdoor spacesValueCondition

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.

4.84 out of 5 average rating, 160 reviews

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

"Perfect for family / friends/pets, who want to escape the stress into paradise on Manasota Key. One block from beach. 1 bed 1 bath beach cottage 1st floor has great spaces, king size bed and aqueen sofa bed, full kitchen, private lanai, electric grill/ garage/laundry area/free bikes/kayaks/ that you can enjoy at the beach or the bay. Great restaurants/bars/trails and much more just walking distance from the house. Beach toy, chairs/umbrellas/snorkeling gear included. Just come relax and enjoy.

ValueOutdoor spacesLong stay

4.94 out of 5 average rating, 16 reviews

Gulf Front Escape + Beach Access, Pet Friendly

🦩 Exclusive Amenities Include: • Walk Out to the Beach – Steps from Your Door • Coastal & Surf Decks - Outdoor Seating • Historic Old Florida Charm • Beach Towels, Chairs & Umbrellas Provided • Community Pool with Picnic Tables & Chaise Lounges • Community Grills & Post-Beach Outdoor Showers • Free WiFi & TV • Coffee Maker & Kitchenette Smallwares Provided • Starter Packs of Essentials for Kitchen & Bath • Enhanced Cleaning Protocols • Combo Tub/Shower Bathroom • Desk/Chair in Unit

LocationValueComfort

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!

LocationValueLaundry

4.95 out of 5 average rating, 420 reviews

Tiny home in Sarasota

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

LocationOutdoor spacesDecor

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.

5.0 out of 5 average rating, 65 reviews

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

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

ValueOutdoor spacesBackyard

5.0 out of 5 average rating, 38 reviews

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

Charming 4 Bed Cottage (sleeps 9), Private Beach to Gulf Across Street, with Large Screened Porch, Super Shark Tooth Hunting, Free use of 2 Kayaks and SUPs, Restaurants, Live Music, Golf, and Tennis . Uber Eats & Grocery delivery, 50 Minutes from Sarasota Airport (75 minutes from Fort Myers airport). Lush tropical rainforest in the "Old Florida" region on the Gulf surrounds this cute cottage. *Please note small extra $50 pp nightly fee for guests 7-9.

LocationOutdoor spacesAccuracy

4.99 out of 5 average rating, 126 reviews

Paradise on the Bay

Waterfront pool home just a short drive to Boca Grande with all the amenities that you would expect. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fantastic fishing from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 3 Kayaks and a canoe are available for your enjoyment.

LocationOutdoor spacesCondition

The exterior of a mid-century modern home is showcased, featuring a clean white facade and a welcoming porch. A manicured lawn with shrubs and palm trees surrounds the property. An American flag is displayed, adding a touch of character to the serene landscape.

5.0 out of 5 average rating, 32 reviews

The Mangrove House

Enjoy this mid-century modern gem "The Mangrove House". Walk out to the dock, and enjoy the fish jumping, egret's wading in the water, and the occasional Manatee. Bask in the sun by the pool, after kayaking, and enjoy what nature has to offer at this unique property. Manasota Beach is a 5 minute drive, for a day at the beach finding sharks teeth, or taking in the sunset. Venice and Old Englewood are just minutes away while exploring the area.

LocationOutdoor spacesLayout

Superhost

An inviting pool area is enclosed by a screened lanai, featuring a turquoise pool surrounded by white decking. Two lounge chairs are positioned nearby, offering a place to relax under the clear blue sky. Lush greenery can be seen beyond the enclosure.

Apartment in South Venice

4.71 out of 5 average rating, 282 reviews

Gulf Getaway, pool, hot tub & kayak to the beach

Paradise Getaway with heated Pool, and Kayaking to the Beach. This ground floor apartment is part of my Key West-style home located on the shores of the Intracoastal Waterway in South Venice, FL. This is a two-bedroom open floor with full kitchen, and direct access to pool, and Tiki bar and includes free use of 4 kayaks. There is a kayak launch in the backyard it´s only a 5-10 minute paddle to beautiful Caspersen Beach on the Gulf of Mexico.

Outdoor spacesValueAccuracy

5.0 out of 5 average rating, 8 reviews

Canal-Front 3BR – Pool, Hot Tub & Boat Access

Experience Old Florida charm reimagined for modern coastal living at this fully renovated 1960 canal-front retreat in Englewood. With direct boating access to Lemon Bay and Stump Pass, private dock for up to a 30ft boat, heated pool, hot tub, outdoor bar lounge, and premium indoor-outdoor sound system, this 3BR waterfront escape blends heritage, luxury, and laid-back Gulf Coast living just minutes from beaches and waterfront dining.

LocationOutdoor spacesFamily

A sunlit outdoor space features a blue pool with a large golden inflatable swan float. Two lounge chairs are positioned nearby, while a wooden bar is seen in the background, equipped with stools and a television. Lush greenery surrounds the area, adding a tropical feel.

4.87 out of 5 average rating, 31 reviews

Private pool with outdoor bar and fenced yard

❤️This listing to save for later! Welcome to Pineapple in Paradise 🍍 a tropical getaway where old Florida charm meets modern luxury. This newly remodeled home features two private living spaces, a sparkling pool, and a fenced backyard with a bar. Perfect for families, couples, or friends to relax, unwind, and make unforgettable memories under the palms. 📩Send us a message to book your vacation.

Outdoor spacesLocationNearby

Popular amenities for South Venice kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.96 out of 5 average rating, 178 reviews

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.

Home in Venice

MCM Waterfront Retreat • Dock, Kayaks & Beaches

Outdoor spacesValueBathroom

4.94 out of 5 average rating, 17 reviews

Neptune Tropical Retreat

LocationOutdoor spacesDecor

5.0 out of 5 average rating, 35 reviews

Waterfront| Pool & Spa | Near Beach| No Extra Fees

LocationOutdoor spacesTV

5.0 out of 5 average rating, 7 reviews

Home in Venice

Aqua Vista Too

LocationOutdoor spacesKitchen

5.0 out of 5 average rating, 37 reviews

Private Beach & Bay Access. Kayak & SUP

LocationOutdoor spacesKitchen

An aerial view showcases a vibrant blue stilt home among tropical surroundings. The turquoise waters of the Gulf are visible in the background, complemented by sandy beach access. Surrounding properties exhibit a mix of colors and styles, highlighting the coastal essence of the area.

4.99 out of 5 average rating, 86 reviews

The Manatee Flat at ManasotaKeyHouse 2bed/2bath

Outdoor spacesLocationFamily

5.0 out of 5 average rating, 9 reviews

Cape Haze Cottage

LocationOutdoor spacesSleep quality

4.95 out of 5 average rating, 44 reviews

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.

Home in Port Charlotte

Peaceful waterfront home

ValueOutdoor spacesCondition

Cottage rentals with a kayak

4.95 out of 5 average rating, 109 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

Outdoor spacesLocationCondition

4.91 out of 5 average rating, 206 reviews

A sunken living room is seen, featuring a gray sectional sofa and a blue sofa. A coffee table sits between them, complemented by a unique side table. A television is positioned on a stand opposite the sofas, with light streaming through the window-covered double doors.

Cottage in Siesta Key

Siesta Key Cozy Cottage across from the beach!

Outdoor spacesValueLong stay

A comfortable living area features a black leather sofa and two blue armchairs surrounding a round coffee table. A starfish wall decoration is displayed above the sofa, while a wall-mounted TV is visible. A doorway leads to another room in the background.

5.0 out of 5 average rating, 40 reviews

2 bedroom, walk to beach-bikes-kayaks-grill-picnic

Outdoor spacesLocationAccuracy

4.97 out of 5 average rating, 38 reviews

Cottage in Lido Key

Lido Key Beach Bungalow with Private Heated Pool!

Outdoor spacesLocationCondition

Cottage in Don Pedro Island

4.99 out of 5 average rating, 77 reviews

Island Getaway•Beach House•Dock•Pet Friendly

Outdoor spacesLocationAccess

5.0 out of 5 average rating, 12 reviews

Manasota Key Beach Bungalow

LocationOutdoor spacesAmenities

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, 39 reviews

Oystercatcher 3min walk to sunset, bikes, kayaks

Outdoor spacesLocationSleep quality

5.0 out of 5 average rating, 7 reviews

Coastal Key Cottage on Manasota Key

Outdoor spacesLocationCleanliness

Cabin rentals with a kayak

4.97 out of 5 average rating, 62 reviews

The bedroom features a spacious bed with a blue coverlet complemented by a seating area with light blue cushions. A ceiling fan provides air circulation, and natural light enters through a window with blinds. Two framed pictures adorn the wall near the bed.

Cabin in Arcadia

Riverfront Cabin W/ Kayaks

ValueLocationSleep quality

4.98 out of 5 average rating, 45 reviews

The interior features a collection of motorcycle memorabilia displayed on the walls, alongside vintage drag racing images. Two motorcycles are showcased on a smooth floor, with a colorful carpet beneath. A staircase lined with motorcycle wheels leads to a loft space, enhancing the room's unique style.

Cabin in Englewood East

Unique loft experience for motorcycle enthusiasts

LocationAccuracyAir conditioning

Superhost

Private room in Manatee County

Glamping on the Myakka River in the Prairie Cabin

Check-inBathroomAccuracy