Vacation rentals with a kayak in Englewood

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Top-rated kayak rentals in Englewood

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Guest favorite

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.

Top guest favorite

An aerial view captures the property nestled among coastal homes, with the vibrant turquoise waters of the Gulf and the sandy beach in the background. Palm trees sway gently, framing the scene, while the stilt home showcases its unique colors and neighboring greenery.

Home in Englewood

5 out of 5 average rating, 69 reviews

The Turtle Flat at ManasotaKeyHouse 2bed/2bath

* Due to hurricanes in Sept. 2024, Manasota Key sustained damage. We are thrilled and fortunate that our property had minimal damage and we were able to complete repairs quickly. However, there are still some businesses and home owners who are working hard to rebuild. What is mentioned/pictured in our listing may not be exact due to potential changes on the island. 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

The exterior of a modern family house is displayed, featuring a manicured lawn and a two-car garage. A welcoming entrance is visible, accentuated by a porch and green vines. The contemporary design is complemented by large windows and a neutral color palette.

Home in Port Charlotte

5 out of 5 average rating, 9 reviews

The perfect retreat with canal view

Discover the perfect family house with 3 bedrooms, an office, pool, and all the necessary amenities. It is located in Port Charlotte, just minutes away from Manasota key beach! And very close to a wide variety of different beaches, restaurants and shops! This family friendly property promises a delightful retreat, even if you decide to stay at mostly inside. You can dive into the refreshing pool, go fishing, enjoy outdoor games, or just unwind in the spacious bedrooms. It'll be a great fit! .

Guest favorite

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

4.9 out of 5 average rating, 154 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

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, 102 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).

Guest favorite

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, 39 reviews

Tropical Retreat-HeatedPool Tennis PickleBall Golf

Do you want to relax in the sun near the Gulf Coast? Welcome to your Tropical Retreat! Beautiful heated pool house and large lanai with high and luxury living upgrades. Located in a quiet community 10 miles to the beach near stunning Boca Grande, Manasota Key and Englewood area. Golf enthusiasts will appreciate the five championship courses (99 holes) found within the community. Spend your days enjoying pool, golfing, fishing or exploring everything that makes Rotonda West unique.

Guest favorite

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!

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, 35 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!

Top guest favorite

A riverside cabana is visible alongside palm trees, with comfortable seating under its roof. Bright orange lounge chairs are positioned near the water's edge. The scene is complemented by a serene sky transitioning from blue to soft orange during sunset.

Home in Port Charlotte

4.95 out of 5 average rating, 58 reviews

Amazing Peace River Views

House is a 2 bed, 2 bath layout. The Master bed is a king bed and the guest bedroom is a queen. Both bedrooms have walks in closets with easy and convenient shelving and built in hampers. The laundry is stocked with liquid soap and fragrance free powder with fast efficient machines. There are speakers in the house, lanai and pergola. You will be able to control them via your phone. There is a desk work area with extra monitor for laptops and a printer for your use.

Guest favorite

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.

Guest favorite

Home in Port Charlotte

4.92 out of 5 average rating, 26 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.

Guest favorite

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.