We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Some info has been automatically translated. Show original language

Vacation rentals with a kayak in Englewood

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Englewood

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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, 148 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.

Top guest favorite

An aerial view showcases a spacious waterfront property surrounded by lush landscaping and palm trees. A winding canal runs adjacent to the home, while neighboring houses are visible in the distance. The vibrant blue water and clear sky enhance the tranquility of the setting.

Home in Punta Gorda

5 out of 5 average rating, 27 reviews

Sensational! Sunny, Heated Pool-Endless waterviews

**NEW LISTING/HUGE DISCOUNTED PRICE*** LUXURY PGI home; 1.5 mile/5 minute distance to Fisherman’s Village and attention to detail with remodel and brand new furnishings. Take advantage of tremendously discounted Prime dates available in 2024 AND 2025 Winter Season. Check PREMIER HOST reviews averaging 5.0 on other site.

Top guest favorite

A vibrant coral wall features a large mural showcasing 'Sunset Beach Retreat' with a colorful beach umbrella. Hanging swings with plush cushions provide a cozy spot for relaxation, surrounded by tropical plants and pavers adding to the outdoor ambiance.

Home in Englewood

5 out of 5 average rating, 22 reviews

Beach Retreat, Families, Bachelorette, Pool, Kayak

Your dream beach getaway awaits at Sunset Beach Retreat, on Manasota Key— 2 blocks from the beach! Whether you’re planning a family vacation or a girls’ weekend, this retreat has everything you need for relaxation, adventure, and unforgettable memories. Unwind and recharge with our heated pool, 5-person infrared sauna, and cold plunge. For those who love to stay active, enjoy our kayaks, kids play set, bicycles, putting green, or rent our 6-person golf cart to explore the island in style.

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

4.89 out of 5 average rating, 150 reviews

Free kayak/bikes/walk to beach/full cottage #1

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.

Top guest favorite

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.

Home in Englewood

4.98 out of 5 average rating, 61 reviews

The Manatee Flat at ManasotaKeyHouse 2bed/2bath

* Due to hurricanes in Sept. 2024, Manasota Key sustained heavy damage. We have completed repairs and are excited to be renting again, but other businesses and home owners are working hard to recover/rebuild. Things are constantly changing on the island, with some closures. What is mentioned/pictured in our listing may not be exact due to the constant changes. We will do our best to keep our guests up to date. The beaches are open and as beautiful as ever! Most restaurants have reopened.

Top guest favorite

A well-lit bedroom features a spacious wooden bed with plush white bedding. Natural light enters through the window, which is adorned with horizontal blinds. Simple wall art complements the soothing color scheme, and a ceiling fan provides ventilation.

Farm stay in Punta Gorda

4.98 out of 5 average rating, 101 reviews

Peaceful Waterfront Orchard 1

bring the whole family including your pets to this peaceful orchard and garden oasis. the action packed backyard of this duplex proudly boasts over 40 fruit trees of various varieties including banana, orange, lemon, fig, mango, papaya... and many more! choose to fish from the dock in the backyard canal, go exploring with the kayaks or paddleboards, play in the sandbox, try out the slackline, or even say hi to the chickens in the coop (maybe even grab a few fresh eggs for breakfast).

A large screened-in patio surrounds a sparkling Gunite pool, with a pink float in the water. Comfortable seating is provided at the bar area and poolside loungers, while palm trees and greenery are visible in the background.

Vacation home in Venice

4.86 out of 5 average rating, 145 reviews

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬

Escape to our charming Venice pool home, where relaxation meets adventure! Perfectly located near the water, this tranquil three-bedroom retreat is nestled on a quiet, palm-lined street. Enjoy easy access to bikes and kayaks for exploring, plus all the beach essentials: cooler, umbrella, and chairs. The pool awaits for sunny days and peaceful evenings (note: a brand-new pool cage is on its way, expected in December). Book now to experience Venice’s beauty from your private oasis!

A screened-in lanai features a private pool, surrounded by paved tiles and comfortable sun loungers. Lush greenery is visible in the background, providing a serene view. A dining area with wooden chairs is positioned nearby, enhancing the outdoor space for relaxation and entertainment.

Home in Rotonda West

4.88 out of 5 average rating, 25 reviews

Paradise Pool Oasis Vacation Home in Rotonda

Paradise Pool Oasis in Rotonda Heights, FL! This new 1,753 sq. ft. 3BR/2BA home sleeps 6 and features a heated private pool, screened lanai, spacious kitchen, dining area, primary suite with private bath, laundry, and 2-car garage. Just 7 miles to Englewood Beach and 10 to Boca Grande. A golfer’s dream with 5+ courses nearby. Short drive to restaurants and tiki bars. Pets welcome with fee. No commercial vehicles allowed in driveway. Your perfect Florida escape awaits!

Top guest favorite

A bright entryway features a modern door with glass panels, inviting natural light. Foldable beach chairs are neatly arranged on a wall-mounted rack, and a round mirror hangs above the chairs. A woven basket is positioned on the floor, providing additional storage space.

Condo in Englewood

5 out of 5 average rating, 22 reviews

Bayfront Condo Walkable to Everything. Unit 3

Welcome to Chadwick Cove Marina! This brand new condo features an open layout with balcony overlooking Lemon Bay. Sleeps up to 4 guest when using queen Murphy bed off living room. Washer/dryer. Boat slips bookable through DockWa. Beaches located across the street allowing you to enjoy both beach and bay in one location. Just steps away from restaurants and shops. Outdoor kitchen with a grill, tiki bar and fire pit. We also have a 3 bedroom unit on the 1st floor.

A front porch is framed by pink hibiscus flowers and lush greenery. Rocking chairs are positioned along the porch, with a view of a well-kept garden and trees in the background. The overall atmosphere reflects a serene outdoor space.

Guest suite in Englewood

4.98 out of 5 average rating, 209 reviews

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The Front porch pictured is part of the main house and is NOT included for use while renting the Blue Cottage Suite. IF the main home is vacant during your stay, I will let you know and it can be used during that time.

Top guest favorite

Home in Port Charlotte

4.92 out of 5 average rating, 24 reviews

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 the pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

A sandy beach stretches along the calm waters, showcasing gentle waves under a partly cloudy sky. Lush greenery lines the shoreline, and a wooden staircase leads to the beach, providing access to the serene outdoor environment.

Cottage in Englewood

5 out of 5 average rating, 29 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.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Englewood kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Top guest favorite

A spacious area designed for recreational equipment is visible, featuring two vibrant green kayaks resting on a tiled surface. Bicycles and additional gear are neatly arranged against the wall, with light streaming through slatted partitions, creating a pattern on the floor.

Home in Placida

5 out of 5 average rating, 13 reviews

Sea La Vie

The image reveals an inviting pool area within a screened lanai, featuring sun loungers adorned with black and white stripes. A glass-topped dining table accommodates four, accompanied by a potted plant. The pool glimmers with clear water, surrounded by lush greenery.

Home in Rotonda West

4.92 out of 5 average rating, 38 reviews

Tropical Retreat-HeatedPool Tennis PickleBall Golf

The image captures a sandy beach shoreline, where gentle waves caress the shore. A vibrant blue sky complements the turquoise waters. The smooth sand glistens under sunlight, creating a serene coastal atmosphere. Beach chairs are seen in the distance, offering a glimpse of relaxation.

Home in Port Charlotte

5 out of 5 average rating, 10 reviews

Private, Dog Friendly Hot Tub Retreat with Kayaks

Top guest favorite

A panoramic view of the beachfront displays soft white sand and gentle waves lapping at the shore. Lush palm trees frame the scene, with the vibrant blue sky and scattered clouds enhancing the tranquil coastal atmosphere.

Home in Placida

5 out of 5 average rating, 69 reviews

Lu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI

Top guest favorite

A tranquil pool area is highlighted by a heated lap pool with a dolphin fountain, surrounded by lush coconut palms. The water view captures a serene canal lined with boats and docks, framed by a screened enclosure that invites natural sunlight.

Home in Punta Gorda

5 out of 5 average rating, 37 reviews

Luxury long waterview w/pool-kayaks-clubs-bikes!

Top guest favorite

The modern kitchen features a large central island with four black stools. High-end appliances, including a stainless-steel refrigerator and a sleek range hood, complement the marble countertop. Natural light brightens the space, enhanced by decorative pendant lights and beach-themed artwork on the walls.

Home in Punta Gorda

5 out of 5 average rating, 52 reviews

Lux Canal Front | Pool, Kayaks, Bikes, & Boat Dock

Top guest favorite

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

4.93 out of 5 average rating, 29 reviews

AMAZING Cape Haze Location -community kayak launch

Home in Englewood

4.93 out of 5 average rating, 89 reviews

20 Steps to Water! Sunsets, and Hot tub!

Cottage rentals with a kayak

Two kayaks are visible on calm water, one orange and one yellow. An adult is paddling the yellow kayak while a child sits behind, wearing a red life jacket. Surrounding greenery adds a natural backdrop.

Cottage in Englewood

4.75 out of 5 average rating, 143 reviews

Good after Milton -Free Kayaks! Steps to Beach-bb

Top guest favorite

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

5 out of 5 average rating, 107 reviews

Quaint Cottage w/access to Peace River canoe/kayak

Two kayaks are positioned on calm water, with a yellow kayak in the foreground and a red kayak behind it. A person is paddling in the yellow kayak, while a child is seated in the red kayak, both wearing life jackets. Surrounding foliage reflects off the water's surface.

Cottage in Englewood

4.89 out of 5 average rating, 129 reviews

Good after Milton - Kayaks & Steps to Beach-pc

Top guest favorite

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

4.96 out of 5 average rating, 25 reviews

Oystercatcher 3min walk to sunset, bikes, kayaks

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.

Cottage in Englewood

4.9 out of 5 average rating, 168 reviews

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

Top guest favorite

The exterior of a charming beach house features a light blue façade with a coral-colored door. A small table with a palm tree design is positioned on a stone pathway leading to the entrance. Lush greenery and a decorative fountain enhance the welcoming outdoor space.

Cottage in Englewood

5 out of 5 average rating, 23 reviews

The Coastal Oasis. Only 8 minutes from the Beach!

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.

Cottage in Englewood

4.86 out of 5 average rating, 125 reviews

Free Kayaks/bikes/walk to beach/pet friendly #3

An open concept living area features a cozy seating arrangement and a dining table set for four. The kitchen includes modern appliances against a backdrop of white cabinetry, while a decorative area rug adds warmth to the wood flooring.

Cottage in Englewood

4.89 out of 5 average rating, 170 reviews

Good after Milton - Waterfall Pool! Beach! am

Other vacation rentals with a kayak

Top guest favorite

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 Port Charlotte

4.97 out of 5 average rating, 38 reviews

Unique loft experience for motorcycle enthusiasts

Home in Nokomis

5 out of 5 average rating, 3 reviews

Waterfront Home, Walk to the Beach & Dining

Top guest favorite

Hut in Port Charlotte

4.98 out of 5 average rating, 48 reviews

Coco Plum

4.93 out of 5 average rating, 68 reviews

Ripple Inn @Fennario: Lagoon pool + SVB ferry ½ mi

Top guest favorite

Home in Port Charlotte

5 out of 5 average rating, 11 reviews

2/2 Half Acre HOME @Pt Charlotte/POOL/Bikes/Kayaks

Top guest favorite

The entrance of the cottage is framed by palm trees and features a vintage Texaco gas station design. A custom made Hotrod sculpture emerges from the side of the house, enhancing the unique character of this welcoming space.

Home in Englewood

4.98 out of 5 average rating, 41 reviews

Unique Cotton Cottage

An open-concept living area reveals a modern kitchen featuring stainless steel appliances and a marble-topped island with bar seating. A comfortable couch faces a wall-mounted television, while large sliding glass doors offer views of the outdoor patio and pool area.

Home in Port Charlotte

4.96 out of 5 average rating, 23 reviews

Renovated Modern house with pool -Port Charlotte

Home in Rotonda West

5 out of 5 average rating, 5 reviews

Waterfront Family Getaway, Sleeps 14 , 9 Beds

Quick stats about vacation rentals with a kayak in Englewood

Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
40 properties have a pool

Destinations to explore