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Vacation rentals with a kayak in Englewood

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Top-rated kayak rentals in Englewood

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A private backyard features a sparkling pool equipped with a slide, surrounded by lounging chairs. A shaded area is provided by a large awning over outdoor seating. Lush greenery frames the space, creating an inviting atmosphere for relaxation and enjoyment.

Home in Englewood

4.79 out of 5 average rating, 63 reviews

New Listing! Resort-like Oasis on Canal

You may not want to go to the beach once you step into this paradise! This completely private backyard has everything you could want including pool with slide, hot tub with surrounding bar to relax, horseshoe pit and cornhole, firepit and more. The homes been completely updated with a unique beach feel to it. Separate workstation area for you to get your work done (if needed) quickly so you can get back to enjoying life. Large floating dock for you to park a boat etc.. and be out in Lemon Bay.

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

5 out of 5 average rating, 13 reviews

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 for the ultimate coastal escape.

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, 148 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.

The exterior of a two-story home is depicted, featuring a light blue facade with a large archway entrance. Tall palm trees are positioned beside a neatly landscaped yard, while a driveway leads to the entrance. A pair of bicycles is visible, resting against the side of the house.

Home in Englewood

4.95 out of 5 average rating, 37 reviews

Spacious 4 BR Across From Beach w/ Heated Pool

Enjoy the ocean view from our renovated 4 bedroom haven on the coveted Manasota Key. With a new pool and deeded private beach. Relish in the breathtaking views, idyllic beaches and stunning sunsets. This home is perfect for families, providing versatile sleeping arrangements. The screened in lanai boasts ping-pong, cornhole and paddle boards. Nestled just a short bike ride or drive from the vibrant restaurants and shops on Manasota Key, where nightly live music adds a touch of local charm.

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, 59 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, 100 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

4.85 out of 5 average rating, 144 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!

Top guest favorite

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.

Home in Englewood

5 out of 5 average rating, 32 reviews

Lux Home on Gulf w/Private POOL & 100ft 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 100 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!

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, 146 reviews

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

Welcome to our Mid Century Modern waterfront getaway on the highly sought after Curry Creek. Perfectly situation between Nokomis Beach (2 miles) and Venice Beach (3 miles). Enjoy spending time fishing on the private dock or getting out on the water with our 4 kayaks and slip. We're located a half mile away from The Legacy Bike Trail (we have 6 bikes for guest use). large firepit, charcoal grill, cornhole, tons of supplies for shark teeth hunting and days spent at the beach

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, 24 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!

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

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

4.91 out of 5 average rating, 23 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.

Vacation rentals for every style

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Villas

Luxurious estates for the ultimate escape

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

Home in Placida

4.77 out of 5 average rating, 35 reviews

3/2 LGI Gulf Front w/Dock

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

Top guest favorite

A single-story home is set against a backdrop of lush green landscaping. The structure features a light-colored exterior with a spacious driveway visible. Tall trees and blue skies enhance the serene outdoor space, creating an inviting atmosphere for relaxation.

Home in Port Charlotte

5 out of 5 average rating, 11 reviews

2/2 Family Escape/Half Acre HOME/POOL/Bikes/Kayaks

An inviting pool area features a large heated saltwater pool surrounded by a screened enclosure. A spa is integrated into the pool design. Sun loungers and lush greenery can be seen beyond the pool, contributing to a relaxing outdoor atmosphere.

Home in Punta Gorda

5 out of 5 average rating, 13 reviews

Location! 1-Block To Fish Ville; Heated Salt Pool

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

A spacious screened-in lanai features a large saltwater pool with a built-in hot tub. Comfortable seating areas are positioned nearby for relaxation, with vibrant pool floats gently resting on the water's surface. Natural light illuminates the area, creating a serene outdoor retreat.

Home in Punta Gorda

5 out of 5 average rating, 35 reviews

Executive Level Home with Pool

Home in Nokomis

5 out of 5 average rating, 15 reviews

Spacious 3 Br Home w/ Heated pool -1 Mile to Beach

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, 142 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, 105 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

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, 24 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

4.85 out of 5 average rating, 124 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

A bright living area features a spacious white sofa facing a modern entertainment unit. Two dark blue armchairs are positioned nearby. A large window allows natural light to fill the room, while light wood flooring and a neutral area rug enhance the open space.

Home in Nokomis

5 out of 5 average rating, 8 reviews

Good Beach Bungalow

A light and airy living area features a cozy seating arrangement with leather recliners and a coffee table. Natural light floods in from large sliding doors, while a fireplace adds warmth to the space. Neutral tones and decorative accents enhance the relaxing atmosphere.

4.92 out of 5 average rating, 66 reviews

Ripple Inn Guest Home@ Fennario Resort Expect More

Top guest favorite

A two-story duplex is framed by lush palm trees and landscaping. The property features a welcoming front porch with white railings and ample outdoor seating. A gravel driveway leads to two designated parking spaces in front, enhancing accessibility to the entrance.

Home in Englewood

4.87 out of 5 average rating, 63 reviews

Turtle Nest Retreat - Manasota Key (upper unit)

A spacious waterfront home is surrounded by green landscaping, palm trees, and open blue skies. A large heated pool is visible in the backyard, adjacent to a well-maintained deck. Comfortable seating is positioned on the sandy area by the water, providing a relaxing atmosphere.

Villa in Osprey

5 out of 5 average rating, 11 reviews

Paradise with a pool, pier and private beach area

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, 51 reviews

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

A stylish living area is highlighted by two comfortable sofas, a large flat-screen TV, and a soft area rug. Natural light floods the space through sliding glass doors, leading to scenic water views. Decorative accents include blue pillows and a coastal-themed wall art piece.

Home in Englewood

4.93 out of 5 average rating, 89 reviews

20 Steps to Water! Sunsets, and Hot tub!

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

A modern duplex with a symmetrical façade and a paved driveway leading to two black garage doors. Large windows are framed in white, allowing ample natural light to brighten the entrance. A well-maintained lawn surrounds the structure, enhancing the inviting presence.

Home in Rotonda West

5 out of 5 average rating, 4 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
G$10,446 GYD 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

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