Vacation rentals with a kayak in Manasota Key

5 out of 5 average rating, 26 reviews

Cottage in Englewood

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!

4.85 out of 5 average rating, 124 reviews

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

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

"Perfect for family / friends/pets, who want to escape the stress into paradise on Manasota Key. One block from beach. 1 bed 1 bath beach cottage 1st floor has great spaces, king size bed and aqueen sofa bed, full kitchen, private lanai, electric grill/ garage/laundry area/free bikes/kayaks/ that you can enjoy at the beach or the bay. Great restaurants/bars/trails and much more just walking distance from the house. Beach toy, chairs/umbrellas/snorkeling gear included. Just come relax and enjoy.

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

Escape to 3 acres of tropical bliss on exclusive Palm Island, where luxury meets seclusion. This beautifully updated 5-bedroom, 4-bathroom retreat offers breathtaking views of a serene pond and the Gulf of America. Heated pool & jacuzzi, 50-ft private boat dock, Home theater & game room, Kayaks, bikes, pool table, ping pong, and more, Fire pit, basketball court, volleyball, Steps from a private beach. Accessible only by private ferry, this is more than a getaway; it’s your slice of paradise.

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.

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.

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.

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

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.

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!

4.98 out of 5 average rating, 209 reviews

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

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.

5 out of 5 average rating, 28 reviews

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

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.

4.95 out of 5 average rating, 20 reviews

An aerial view captures the beachfront condo, featuring a light-colored exterior with a dark roof. Surrounding greenery and palm trees create a natural border, while the ocean waves gently lap against the shore in the foreground, providing a serene coastal environment.

Condo in Englewood

Beachfront Condo on Manasota Key

This 2 bedroom 2 bathroom condo sits right on the beach and is just a 10-15 minute walk to all Manasota Key has to offer! Completely remodeled in 2024. This condo can accommodate 6-8 guest. The master has a king bed, there are 2 queens in the guest room, and 2 large couches that can accommodate 2 guest. Kitchen is equipped with everything you will need for your stay! All windows are brand new and hurricane impact.

4.77 out of 5 average rating, 35 reviews

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

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.

A two-story coastal home is presented, featuring a light grey exterior with multiple gabled roofs and large windows. The front entrance is accented by wide stairs leading to a double door entrance, surrounded by landscaped shrubs and palm trees, with a driveway visible below.

5 out of 5 average rating, 5 reviews

4BR Bayfront Home – Dock, Pool & Beach Access

This spacious tri-level waterfront home on Lemon Bay offers the ultimate coastal lifestyle, with deeded beach access, private dock, and incredible water views from nearly every level. Whether you're launching kayaks, soaking in the heated pool, or relaxing on the balcony with a drink in hand, this Manasota Key retreat is made for Gulf Coast living.