Vacation rentals with a kayak in Manasota Key

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Top-rated kayak rentals in Manasota Key

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Guest favorite

A cozy sleeping area features a spacious bed dressed in blue and white linens, flanked by two bedside tables with softly glowing lamps. Above the bed, a serene painting depicts a coastal scene. Natural light filters in through the nearby window.

Cottage in Englewood

5 out of 5 average rating, 27 reviews

1 Bed-Walk beach-bikes-kayaks-grill-out hot shower

Welcome to your perfect beach escape on Manasota Key! This charming 1-bedroom cottage is just a 3-minute stroll from sandy shores and stunning Gulf sunsets. Enjoy all the comforts of home, including a grill, shared laundry and cozy back patio. Located in a peaceful neighborhood with easy access to parks, kayaking, and waterfront dining. Kayaks, bikes, beach chairs, umbrella, towels and a cooler are provided for your use. Relax, explore, and make unforgettable memories in this beautiful paradise!

Guest favorite

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, 171 reviews

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

Unit # 2 Beautiful 2 bed 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. This cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

Guest favorite

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.

Home in Venice

4.95 out of 5 average rating, 149 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.

Guest favorite

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, 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

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, 34 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 cozy living area features a white sectional sofa and a wooden coffee table. Natural light enters through sheer curtains, highlighting the wood-paneled walls. A television is situated on a light-colored media console, while decorative accents add a welcoming touch to the space.

Cottage in Placida

4.98 out of 5 average rating, 53 reviews

West Coast Island Retreat, Simply Adrift Cottage

Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off FL's West Coast in the Gulf of Mexico. Access is for residents and renters only, you will arrive by your private boat or jump aboard the water taxi for a 10 minute ride to our dock. No cars, shops, or restaurants on the island. The 7 mile beach is private and uncrowded. Get around LGI by renting a golf cart or explore by foot-you decide.

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, 23 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.

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

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.

Superhost

A modern single-story house is depicted with a well-maintained lawn and tropical landscaping. Decorative planters line the front, enhancing the curb appeal. The exterior features a combination of neutral tones and natural wood accents, under a clear blue sky.

Vacation home in Venice

4.89 out of 5 average rating, 105 reviews

Sunny Florida Retreat, 8 Min to Beach, Attractions

Enjoy a bright Florida getaway just 8 minutes from the beach! Perfect for families or couples, our cozy home features fast Wi-Fi, a fully equipped kitchen, free parking, and all the essentials for a relaxing stay. Close to restaurants, local shops, and water activities, this is the ideal base for your Florida vacation. Book now for convenience, comfort, and easy access to Gulf Coast fun!

Guest favorite

A charming beachfront home is presented, featuring a raised deck with seating and palm trees surrounding the area. A pathway leads from the sandy beach to the entrance, highlighting the welcoming outdoor space. The structure displays a peaked roof and large windows, inviting natural light.

Home in Placida

4.78 out of 5 average rating, 37 reviews

3/2 LGI Gulf Front w/Dock

Gulf of America Beachfront Island Home is a perfect getaway! Enjoy the beach in your front yard and dock your boat on the bay! This three-bed, 2 bath gulf front home has an open floor plan with multiple dining areas both indoor and outdoor. Pocket sliders can be opened to extend the living space and hear the sound of the waves while you sip your morning coffee.