Holiday rentals with a kayak in South Venice

5 out of 5 average rating, 24 reviews

A serene canal view is showcased from a private dock, featuring two teal chairs positioned beside a small table. Lush greenery and calm waters reflect the clear blue sky, enhancing the peaceful atmosphere of the outdoor space.

Bungalow in Englewood

Dockside Delight:Waterfront/Gulf Access/4minsbeach

Canal-Front, Direct Gulf Access & Private Dock Stylish home w/ hotel-grade amenities Prime Location: Just 2-5 minutes from Englewood's vibrant dining, shopping, and entertainment on Dearborn Street. Outdoor Fun & Watersports: Guests can enjoy scenic paddles with our complimentary kayaks or unwind in style with lounge chairs, a hammock, firepit, BBQ, games and cozy ambiance, perfect for day or night relaxation Manasota Key's breathtaking beaches 2 miles away. Myakka Pines Golf Club just 4 miles

4.98 out of 5 average rating, 53 reviews

A spacious living area features a light-colored sectional sofa and a round coffee table in the center. Natural light pours in through large windows, illuminating the room's wood accents and open layout. A dining area with a wooden table and chairs is visible in the background.

Home in Osprey

Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

4.8 out of 5 average rating, 105 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!

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.

4.95 out of 5 average rating, 164 reviews

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 6 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, olive oil, spices, and a welcome bottle of wine — so you can arrive, unpack, and relax.

A light-colored, one-level ranch home with a well-manicured lawn is showcased in this image. The house is framed by lush greenery and colorful plantings, while a paved driveway leads to a two-car garage on the side. A peaceful neighborhood ambiance is apparent.

5 out of 5 average rating, 13 reviews

Venice Adventure Retreat Near Beaches & Bike Path

Bring all your beach & boating toys to this fully renovated home situated in a quiet neighborhood, just off the Venetian Trail/Bike path & intracoastal waterway. Short bike ride to downtown Venice, Caspersen and Venice Beaches & easy access to golfing, parks, and waterways. Gourmet kitchen and spa-grade bathrooms w/ ample storage throughout; ideal layout for privacy between guests. Lots of living space inside and out w/ fenced private yard, fire pit & outdoor shower. Room for Boat/RV parking!

4.98 out of 5 average rating, 103 reviews

Home in North Port

North Port Home on Canal

Relax in this well appointed guest house as you enjoy the warmth of the Florida sunshine. Read a book on the garden swing next to the canal while you watch the birds, fish off the dock or canoe. Immaculate 2 bed/2 bath home with sun porch and patio complete with BBQ grill located in lovely neighborhood next to lighted bike paths. Close to Routes 41 and 75 for beaches, shopping, restaurants, sports events etc. Our favorite thing to do is beach combing the fabulous beaches -equipment provided.

Superhost

Home in Englewood

4.83 out of 5 average rating, 6 reviews

Gulf Front Escape + Beach Access, Pet Friendly

🦩 Exclusive Amenities Include: • Walk Out to the Beach – Just Steps from Your Door • Historic Old Florida Charm • Coastal and Surf Decks with Outdoor Seating • Community Pool with Picnic Tables and Chaise Lounges • Community Grills and Post-Beach Outdoor Showers • Free WiFi and TV • Full Kitchen, Wares • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs and Umbrellas Provided • Tub/Shower Combo in Bathroom • Desk and Chair in Unit, Community Laundry

4.9 out of 5 average rating, 168 reviews

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.

Cottage in Englewood

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

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

5 out of 5 average rating, 21 reviews

Coastal Retreat ~ Near Beaches, Parks & Shopping

Welcome to this sunny coastal retreat in beautiful Venice, renowned as the Shark Tooth Capital of the World! This bright and breezy home offers comfort, convenience, and adventure-all just a short drive from beaches buzzing with fossil-hunting fun! Shamrock Park & Nature Center is a short walk away-perfect for a quick game of tennis or basketball and has a beautiful kids park. Historic downtown Venice 8 mins away offers a variety of shopping, restaurants and weekly farmers market.

5 out of 5 average rating, 28 reviews

Place to stay in Venice

Halo cottage pool, hot tub ,Myakka River

Reconnect with nature at this unforgettable escape. In the beautiful RV resort park that offers a resort style swimming pool and hot tub, fully equipped exercise gym, pickle ball, tennis courts, billiards room and so much more. Halo cottage is fully remodeled mobile home. The kitchen in stocked with basic needs, dishwasher, fridge and a washer/dryer. Enjoy the Myakka River view and head out and enjoy coffee in the morning at the dock, or launch a kayak. Absolutely no smoking.

4.94 out of 5 average rating, 32 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

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

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.

5 out of 5 average rating, 24 reviews

SunCoast Garden Family Retreat

Welcome to this charming luxury home in Venice, designed for a memorable vacation. This open-concept retreat features 4 bedrooms 1 king, 2 queens, 2 twins 2 bathrooms, perfect for families or groups. Extended lanai with lounge chairs and outdoor TV, private, saltwater, heated pool. The home also offers space for a boat and RTV,located just 6 minutes from second home SunCoast Luxury Estates. Comfort, style, and relaxation everything you need for the perfect getaway

Popular amenities for South Venice kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.97 out of 5 average rating, 156 reviews

A serene waterfront view is captured from a dock, showcasing calm waters reflecting palm trees and houses along the shore. The dock is anchored with sturdy posts topped by black finials and surrounded by a gentle rope, emphasizing the peaceful ambiance.

Home in Cape Coral

Flirty Flamingo Gulf Access Cape Coral Home

5 out of 5 average rating, 13 reviews

The exterior of the home features a warm peach façade and a well-maintained lawn. An inviting front entrance is marked by arched doorways and decorative pendant lighting. A spacious garage with a wooden door complements the architecture, framed by lush landscaping and a clear blue sky.

Home in North Port

Private Oasis on Canal with Dock

4.98 out of 5 average rating, 117 reviews

The backyard features a hot tub in the foreground, with a clear view of a pool in the background. Colorful adirondack chairs are arranged around the pool area, and a spacious house is visible with a screened porch. String lights are seen overhead, enhancing the outdoor ambiance.

Home in Cape Coral

Private Oasis with Pool, Hot Tub, & Fence

4.88 out of 5 average rating, 24 reviews

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.

Home in Englewood

Heated Pool, Sleeps 10. Walkable to Restaurants

4.8 out of 5 average rating, 5 reviews

Home in Englewood

Waterfront 3BR – Pool, Dock, Kayaks & Beach

5 out of 5 average rating, 8 reviews

Home in Nokomis

Waterfront retreat with kayaks, walk to the beach

4.98 out of 5 average rating, 124 reviews

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

Home in Cape Coral

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

4.95 out of 5 average rating, 143 reviews

A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.

Home in Captiva

Steps to Beach Captiva Includes CLUB & Golfcart

Cottages with a kayak

4.91 out of 5 average rating, 23 reviews

A cozy deck is featured with two chairs and a hammock, overlooking the peaceful landscape. Strings of lights enhance the space, while the sky transitions from blue to dusk. Nearby, views of open fields can be seen, creating a tranquil outdoor retreat.

Cottage in Myakka City

New Country Cottage on Lake Manatee Lakewood Ranch

5 out of 5 average rating, 10 reviews

The cottage exterior features a light blue facade with a centered front door, flanked by two large windows. A small porch with a bench is present, along with potted plants. A single-car garage is visible, and a manicured lawn surrounds the home.

Cottage in Sarasota

Cottage & Tree ~ by the Sea

4.96 out of 5 average rating, 27 reviews

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.

Cottage in Englewood

Oystercatcher 3min walk to sunset, bikes, kayaks

4.96 out of 5 average rating, 53 reviews

An aerial view highlights the river house set amid lush greenery, featuring a large wooden deck and fenced yard. The property is bordered by the Braden River, with its tranquil waters reflecting the surrounding trees and homes.

Cottage in Bradenton

2/2 Charming Riverfront Cottage w Deck & Kayaks

Cottage in Don Pedro Island

4.98 out of 5 average rating, 61 reviews

Island Getaway•Beach House•Dock•Pet Friendly

4.97 out of 5 average rating, 67 reviews

An aerial view captures a serene coastal neighborhood surrounded by lush greenery, with the beach visible in the distance. The beach house is nestled among palm trees, indicating its close proximity to the shoreline and other scenic homes in the area.

Cottage in Captiva

The FlipFlopper Beach House - North Captiva Island

4.91 out of 5 average rating, 184 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!

5 out of 5 average rating, 26 reviews

A spacious living area features light-colored furniture arranged for comfort. Large windows allow for abundant natural light while offering views of the lake. Decorative elements include a flat-screen television and beach-themed art, creating a relaxed ambiance within the home.

Cottage in Cape Coral

Sunset Cottage: Lake Front

Cabin rentals with a kayak

4.98 out of 5 average rating, 42 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 Gulf Cove

Unique loft experience for motorcycle enthusiasts

Superhost

Private room in Manatee County

Glamping on the Myakka River in the Prairie Cabin

5 out of 5 average rating, 63 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