Vacation rentals with a kayak in 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 spacesLocationBathroom

5 out of 5 average rating, 88 reviews

Aerial view of a two-story condo unit located along a waterway, surrounded by lush greenery and other residences. A manicured lawn leads to a floating dock, where boats are moored. The clear blue sky reflects on the calm water, enhancing the serene setting.

Condo in Nokomis

Family Friendly Beach Condo

Property located on Lyon’s Bay, in Nokomis, Florida. This three-bedroom upper Condo unit is situated within a ten minute walk to Nokomis Beach on the Gulf of Mexico. Open kitchen fully equipped, Office area. Wi-Fi Large master suite, second bedroom has a queen bed. Third bedroom features four twin beds, walk-in closet and its own full bath. Your stay comes with access to paddle boards kayaks, which can be launched from a floating dock. Also available for your use are beach chairs and coolers.

LocationOutdoor spacesFamily

4.93 out of 5 average rating, 15 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

LocationTVPool

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!

LocationValueTV

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 spacesQuiet

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)

LocationOutdoor spacesHeating

4.97 out of 5 average rating, 34 reviews

A modern kitchen is highlighted by navy blue cabinetry and white quartz countertops. Stainless steel appliances, including a refrigerator and microwave, are visible. Pendant lights hang above an island with seating for several. The space is brightened by recessed lighting and a window offering natural light.

Home in Nokomis

La Niña 5 minutes to Nokomis Beach Fenced In Yard

Welcome to our charming and completely remodeled 3 bedroom, 2 bathroom house in beautiful Nokomis, Florida! With its large and fully fenced backyard, this pet-friendly home is perfect for families and groups of up to 8 guests. As you step inside, you'll be impressed by the modern and stylish decor throughout the spacious living areas. The fully equipped kitchen features stainless steel appliances and quarts countertops, making it easy to cook your favorite meals during your stay…

Outdoor spacesLocationBackyard

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

Welcome to our Mid-Century Modern waterfront escape on Curry Creek, minutes from Nokomis Beach (2 miles) and Venice Beach (3 miles). Spend your days fishing from the private dock, paddling one of 4 kayaks, or biking the Legacy Trail with 3 bikes. Evenings are for the firepit, grilling on the charcoal BBQ, or cornhole under the stars. We’ve stocked shark tooth gear, beach essentials, toiletries, coffee, tea and candles— so you can arrive, unpack, and relax.

Outdoor spacesLocationAmenities

5 out of 5 average rating, 19 reviews

Home in Nokomis

Nokomis Beach | Canal Front Unit | Boat Friendly

Escape to this newly renovated waterfront retreat in Nokomis, just a 10-minute walk to Nokomis Beach. Spend your mornings kayaking from the backyard, your afternoons relaxing on the Gulf Coast, and your evenings enjoying waterfront restaurants just minutes away. Whether you’re planning a couples getaway, family beach vacation, or snowbird stay, this peaceful canal-front home makes it easy to enjoy everything Nokomis, Venice, and Casey Key have to offer.

Outdoor spacesValueBathroom

5 out of 5 average rating, 38 reviews

Cottage in Englewood

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 spacesWalkability

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 spacesBathroom