Holiday rentals with a kayak in South Venice

5 out of 5 average rating, 102 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 spacesValueBiking

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, 207 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!

Outdoor spacesValueCondition

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!

LocationValueCondition

4.94 out of 5 average rating, 17 reviews

Neptune Tropical Retreat

Enjoy a Family Friendly Waterfront Retreat in a safe and quiet neighborhood offering everything needed for a relaxing fun filled vacation. Launch our kayaks from the floating kayak dock, exploring Forked Creek or take a short boat ride to the beautiful blue Intercoastal Waterways. Enjoy our large, heated pool & catch fish off the dock. Manasota Beach and the boat ramp are in the neighborhood less than 10 minutes to either. Hang out in our game room for friendly competitions when indoors.

Outdoor spacesLocationComfort

5 out of 5 average rating, 35 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 🌟

LocationOutdoor spacesBackyard

4.95 out of 5 average rating, 419 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)

Outdoor spacesValueAccuracy

4.99 out of 5 average rating, 139 reviews

An enclosed lanai features multiple large windows with views of Lemon Bay, allowing natural light to fill the space. A palm tree is visible outside, framed by the window panes. A decorative area rug is positioned on the wooden floor, enhancing the coastal ambiance.

Villa in Englewood

Stunning Bay Waterfront! Jaw dropping Water Views!

Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchenette & family room. Enjoy “Lemon Bay-front beach” in backyard. Low-key quiet vacationers. 1 car parking spot. No visitor parking. Free 2 kayaks. Login to your favorite streaming services with Smart TVs. Beautiful Blind Pass Beach, Englewood Beach, 5 restaurants & Tiki Bars are just 1.5 mile away or hop on Stumpy's Free Shuttle (tip based)

LocationValueParking

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 spacesLocationAmenities

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 spacesLocationSleep quality

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 spacesCleanliness

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.

LocationOutdoor spacesHospitality

5 out of 5 average rating, 7 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.

Outdoor spacesLocationFamily

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, 29 reviews

The exterior of the home is showcased against a colorful sunset sky. Lush landscaping includes well-kept grass and vibrant plantings. The entrance features a spacious porch, framed by tropical palm trees, creating a welcoming atmosphere.

Home in Punta Gorda

Incredible Water View! Heated/Salt/Sun filled pool

LocationOutdoor spacesWalkability

5 out of 5 average rating, 9 reviews

Cape Haze Cottage

LocationOutdoor spacesPool

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

Outdoor spacesLocationComfort

5 out of 5 average rating, 37 reviews

Private Beach & Bay Access. Kayak & SUP

Outdoor spacesValueWi-Fi

4.96 out of 5 average rating, 54 reviews

Perfect Beachy Couple Space On Manasota Key FL

Outdoor spacesValueCondition

5 out of 5 average rating, 20 reviews

Home in North Port

Waterfront Oasis w/ Pool on Myakka – Near Beaches

LocationOutdoor spacesAccuracy

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

LocationValueAmenities

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

ValueOutdoor spacesLayout

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 spacesBiking

4.97 out of 5 average rating, 38 reviews

Cottage in Lido Key

Lido Key Beach Bungalow with Private Heated Pool!

Outdoor spacesLocationAccuracy

5 out of 5 average rating, 12 reviews

Manasota Key Beach Bungalow

Outdoor spacesValueParks

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, 187 reviews

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

ValueLocationCheckout

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 spacesView

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, 159 reviews

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

ValueOutdoor spacesComfort

Cottage in Don Pedro Island

4.99 out of 5 average rating, 76 reviews

Island Getaway•Beach House•Dock•Pet Friendly

ValueOutdoor spacesQuiet

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, 40 reviews

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

LocationOutdoor spacesNearby

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

LocationDecorAccuracy

Superhost

Private room in Manatee County

Glamping on the Myakka River in the Prairie Cabin

BathroomAccuracyCheck-in

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

LocationOutdoor spacesFamily