Vacation rentals with a kayak in Englewood

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Top-rated kayak rentals in Englewood

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Guest favorite

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

4.83 out of 5 average rating, 59 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.

Guest favorite

Bungalow in Englewood

5 out of 5 average rating, 9 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.

Guest favorite

A tranquil beach scene captures soft white sand meeting calm turquoise waves under a bright blue sky. Gentle clouds drift above, while a few distant figures enjoy the shoreline, surrounded by lush greenery along the beach's edge, enhancing the serene atmosphere.

Apartment in Englewood

4.93 out of 5 average rating, 44 reviews

Upscale Beachfront 1+BR,Kayaks,SUPs,Pets OK

Cozy/Private 1+ Bedroom Private Waterfront Suite (King and Sleep Sofa) with Kitchen and Full Bath with the Beach literally 5 Steps from your Front Door. This rental is in a quiet residential neighborhood, further away from restaurants and bars. This property is one of the last remaining "Old Florida" regions of the Gulf Coast of Florida, with subtropical rainforest flora and fauna surrounding the property, a hammock waiting for you on the beach, and a dock for fishing or boating 100 yds away.

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

4.89 out of 5 average rating, 140 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.

Guest favorite

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

4.94 out of 5 average rating, 31 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 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, 62 reviews

The Turtle Flat at ManasotaKeyHouse 2bed/2bath

* Due to recent hurricanes, Manasota Key sustained heavy damage. Repairs have been completed on our property and we are excited to be renting again! 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 accurate due to the constant changes. We will do our best to keep our guests up to date. Englewood and Manasota Beaches are open! Most restaurants are open.

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 rental includes use of bikes and kayaks. Kayaks are kept at 998 Oxford Dr. We are available to launch or to help you launch kayaks at a local spot. Front porch pictured is part of the main house and is use of this space is not included.

Superhost

A comfortable living room features a light-colored sectional sofa with a decorative pillow. A flat-screen TV is mounted above a brick fireplace, enhancing the space's functionality. Natural light filters through the nearby windows, illuminating the wood-look flooring.

Home in Englewood

4.78 out of 5 average rating, 36 reviews

Englewood beach and Dearborn St!

Welcome Home! Newly renovated, tastefully decorated 4/3 home. Come enjoy everything Englewood has to offer! Open eat-in, well stocked kitchen for the chef, a gas bbq grille for the grill masters. Smart tv’s in all the rooms and living. Centrally located less than 10 minutes from Manasota key, Englewood beach and 5 minutes from famous Dearborn Street. We are also less than 20 minutes from Venice. World class fishing, golf and dining Come relax and enjoy laid back coastal living.

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

4.85 out of 5 average rating, 139 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, 23 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!

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

4.94 out of 5 average rating, 53 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.

Top guest favorite

A scenic view of the marina features several boats docked in calm waters, surrounded by a vibrant collection of buildings and lush greenery. The backdrop includes a clear blue sky meeting the ocean, illustrating a peaceful coastal environment.

Condo in Englewood

5 out of 5 average rating, 25 reviews

Bayfront 3 Bedroom Condo Walkable to Beach. Unit 1

Walk to everything the key has to offer. This 3 bedroom 2 bath bay-front condo is 1500 sq. ft. and features an open layout with large balcony expanding the entire condo. Full size washer/dryer. The Master and guest bedroom have a king bed, the 3rd bedroom has two sets of twin over full bunk beds. Outdoor kitchen area with a grill, tiki bar and fire pit. Have a boat? Reserve your slip using the DockWa App.