Holiday rentals with a kayak in South Venice

5 out of 5 average rating, 101 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

ValueLocationIndoor spaces

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.

4.89 out of 5 average rating, 206 reviews

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

Unit # 2 Beautiful 2 bedrooms 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

LocationValueBathroom

5 out of 5 average rating, 12 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

LocationComfortView

4.82 out of 5 average rating, 119 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!

LocationValueBackyard

4.96 out of 5 average rating, 53 reviews

Perfect Beachy Couple Space On Manasota Key FL

"Green Gecko" is a roomy and comfortable one bedroom unit, steps from the pool, and a short walk to either our dock or the beach. Enjoy amazing sunrises at the dock and spectacular sunsets at the Gulf! Access to the beach is deeded and insures you can relax minus the crowds. The saltwater pool is a guest favorite and will de-stress you in no time. Inside enjoy a NECTAR queen bed, roomy bathroom and a full kitchen. Come rest and relax, swim in the ocean, collect shells or just lay by the pool.

Outdoor spacesValueFamily

5 out of 5 average rating, 34 reviews

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

Welcome to Casa-A-Mar, your private slice of coastal paradise at our newly updated waterfront retreat. Step outside and launch straight into the water with direct Gulf access or into Lemon Bay—perfect for exploring the canals on one of our kayaks. Prefer to stay in? Spend your time in the heated pool, then ease into the hot tub as the sun sets. As evening falls, transform the backyard into your own open-air theater with our outdoor projector, perfect for movie nights under the stars 🌟

Outdoor spacesLocationBackyard

4.95 out of 5 average rating, 418 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)

ValueOutdoor spacesQuiet

5 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.

Outdoor spacesLocationDecor

5 out of 5 average rating, 19 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 spacesLocationAccess

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 out of 5 average rating, 31 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.

Outdoor spacesLocationPool

4.99 out of 5 average rating, 125 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.

Outdoor spacesLocationCleanliness

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

4.7 out of 5 average rating, 281 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 spacesValueKitchen

Popular amenities for South Venice kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

5 out of 5 average rating, 9 reviews

Cape Haze Cottage

LocationOutdoor spacesNearby

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, Outdoor Bar, BBQ, Fully Fenced Yard

LocationOutdoor spacesPool

5 out of 5 average rating, 35 reviews

Private Beach & Bay Access. Kayak & SUP

LocationOutdoor spacesCleanliness

4.88 out of 5 average rating, 25 reviews

An inviting outdoor space features a spacious pool and attached spa, surrounded by a laid stone patio. A covered area is accessible, providing seating options. The two-story house has multiple balconies, with the blue sky and serene clouds creating a relaxed atmosphere.

Home in Grove City

Englewood 3 Bedroom Private Pool+Spa on Lemon Bay

ValueOutdoor spacesKitchen

4.95 out of 5 average rating, 43 reviews

A private pool area features a heated pool and spa, surrounded by a screened enclosure. The serene outdoor space includes textured stone decking and seating, while lush greenery frames the view. Panoramic sliding doors lead into an inviting interior living space.

Home in Placida

AMAZING Cape Haze Location -community kayak launch

LocationValueLayout

5 out of 5 average rating, 39 reviews

An inviting saltwater pool is illuminated by soft lights at dusk, surrounded by lush greenery. The screened enclosure provides a sense of serenity while casting gentle reflections on the water's surface. Outdoor seating is visible nearby, creating a space for relaxation.

Home in South Venice

SunCoast Garden Family Retreat

Outdoor spacesValueIndoor spaces

5 out of 5 average rating, 28 reviews

Newly renovated home on canal with salt water pool

Outdoor spacesLocationCheck-in

4.94 out of 5 average rating, 16 reviews

Neptune Tropical Retreat

Outdoor spacesLocationIndoor spaces

Cottages with a kayak

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

LocationOutdoor spacesPets

4.97 out of 5 average rating, 37 reviews

Cottage in Lido Key

Lido Key Beach Bungalow with Private Heated Pool!

Outdoor spacesLocationBathroom

5 out of 5 average rating, 10 reviews

Manasota Key Beach Bungalow

ValueLocationAmenities

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.

4.89 out of 5 average rating, 184 reviews

Unit #1 Free kayak/bikes/walk to beach/fullcottage

Outdoor spacesValueAccess

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

LocationOutdoor spacesIndoor spaces

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, 158 reviews

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

Outdoor spacesLocationParks

Cottage in Don Pedro Island

4.99 out of 5 average rating, 74 reviews

Island Getaway•Beach House•Dock•Pet Friendly

ValueLocationFamily

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 out of 5 average rating, 39 reviews

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

Outdoor spacesLocationBathroom

Cabin rentals with a kayak

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

LocationNearbyKitchen

Superhost

Private room in Manatee County

Glamping on the Myakka River in the Prairie Cabin

BathroomCheck-inAccuracy

5 out of 5 average rating, 69 reviews

The serene waterfront area features a wooden dock extending into calm waters, surrounded by lush trees and cypress knees. A large building is visible in the background, and a small splash of color indicates a kayak or canoe nearby.

Cabin in Arcadia

Waterfront Retreat- w/Kayaks & Peace River access

Outdoor spacesLocationCheckout