Holiday rentals with a kayak in South Venice

5.0 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 spacesValueBackyard

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!

LocationOutdoor spacesWalkability

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!

Outdoor spacesLocationCleanliness

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 spacesLocationTV

5.0 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 🌟

Outdoor spacesLocationCheck-in

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 spacesLayout

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, 63 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!

LocationValueKitchen

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.

ValueOutdoor spacesGetting around

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, 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.

LocationOutdoor spacesPool

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 spacesLocationLong stay

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

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

Located on a highly desirable street, the house is perched high above Curry Creek offering spectacular water views from every room. The property includes a boat ramp to avoid the public launch. Three kayaks (two tandems and one single). Two miles from Nokomis Beach and only half a mile from The Legacy Bike Trail. You can do so many fun things, or just have a drink on the dock and watch the manatees. Pet Friendly

Outdoor spacesValueBackyard

Popular amenities for South Venice kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

5.0 out of 5 average rating, 7 reviews

Home in Venice

Aqua Vista Too

LocationOutdoor spacesHospitality

5.0 out of 5 average rating, 37 reviews

Private Beach & Bay Access. Kayak & SUP

ValueOutdoor spacesAmenities

5.0 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

ValueLocationAccuracy

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

Outdoor spacesValueAmenities

5.0 out of 5 average rating, 9 reviews

Cape Haze Cottage

LocationOutdoor spacesAmenities

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 spacesLocationAmenities

4.96 out of 5 average rating, 54 reviews

Perfect Beachy Couple Space On Manasota Key FL

LocationOutdoor spacesIndoor spaces

5.0 out of 5 average rating, 7 reviews

Englewood FL Waterfront | Dock+ Kayaks+Fishing

LocationOutdoor spacesBeach

Cottages with a kayak

4.91 out of 5 average rating, 205 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!

ValueOutdoor spacesCleanliness

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 spacesLocationCleanliness

4.97 out of 5 average rating, 38 reviews

Cottage in Lido Key

Lido Key Beach Bungalow with Private Heated Pool!

Outdoor spacesLocationComfort

5.0 out of 5 average rating, 12 reviews

Manasota Key Beach Bungalow

Outdoor spacesValueGetting around

Cottage in Don Pedro Island

4.99 out of 5 average rating, 77 reviews

Island Getaway•Beach House•Dock•Pet Friendly

Outdoor spacesLocationAmenities

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 spacesLaundry

5.0 out of 5 average rating, 7 reviews

Coastal Key Cottage on Manasota Key

LocationOutdoor spacesView

Cottage in Don Pedro Island

A charming island cabin is depicted, showcasing a mint green exterior and raised deck. A welcoming patio area features seating arrangements, while a boat dock extends along the waterway. Palm trees frame the scene, adding to the relaxed coastal atmosphere.

4.97 out of 5 average rating, 36 reviews

LunaSea, WATERFRONT cabin. Gilligan's Island !!

Outdoor spacesLocationBeach

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

LocationValueGetting around

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

LocationHospitalityBiking

Superhost

Private room in Manatee County

Glamping on the Myakka River in the Prairie Cabin

AccuracyCheck-inBathroom