Vacation rentals with a kayak in Englewood

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Top-rated kayak rentals in Englewood

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Superhost

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

4.84 out of 5 average rating, 111 reviews

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, queen 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

Aerial view of a two-story condo unit located along a waterway, surrounded by lush greenery and other residences. A manicured lawn leads to a floating dock, where boats are moored. The clear blue sky reflects on the calm water, enhancing the serene setting.

Condo in Nokomis

5 out of 5 average rating, 49 reviews

Family Friendly Beach Condo

Property located on Lyon’s Bay, in Nokomis, Florida. This three-bedroom upper Condo unit is situated within a ten minute walk to Nokomis Beach on the Gulf of Mexico. Open kitchen fully equipped, Office area. Wi-Fi Large master suite, second bedroom has a queen bed. Third bedroom features four twin beds, walk-in closet and its own full bath. Your stay comes with access to paddle boards kayaks, which can be launched from a floating dock. Also available for your use are beach chairs and coolers.

Guest favorite

Two individuals are seen kayaking on a calm body of water, surrounded by lush greenery. Bright, warm sunlight reflects off the surface, while orange paddles create ripples as they navigate their kayaks. The scene emphasizes an inviting outdoor adventure atmosphere.

Tiny home in Port Charlotte

5 out of 5 average rating, 6 reviews

Minutes to Sand, Dog Friendly, Hot Tub Luxury

Watch the stars from your hot tub! Not camping, not glamping... This is luxury living for less! Private dog friendly property. Hooked up to city water, cold air in all rooms, immediate demand hot water and septic. This slice of paradise is minutes from the sand and has an elegantly appointed private master, two private loft bedrooms, sleeper sofa & 9' vaulted ceilings. Your private retreat includes the use of two kayaks, gazebo, beach chairs, 5G Wi-fi & Netflix, Prime, Paramount. Paradise!

Superhost

The living area features a spacious sectional sofa paired with a round coffee table. A small dining table accommodates four, and a flat-screen television is positioned for easy viewing. Natural light enters through multiple windows adorned with light-colored curtains, enhancing the room's brightness.

Bungalow in Siesta Key

4.89 out of 5 average rating, 9 reviews

Lagoon, pool, the Catamaran at Siesta Key Bungalow

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed and a private bathroom you'll feel at home. The Catamaran Bungalow is stocked with linens, care essentials, plus eating & cooking utensils. An additional single-roll-away-bed allows accommodations for three guests.

Guest favorite

An aerial view captures the serene surroundings of Vitamin Sea, nestled along the coastline. The image showcases the tranquil waters leading to the canal, with Turtle Beach nearby. Lush greenery and a small, quiet complex contrast against the vibrant blue ocean, reflecting a peaceful coastal retreat.

Condo in Sarasota

4.98 out of 5 average rating, 48 reviews

Gulf Views! 2 BR- Quiet-Canal-Htd Pool-Kayak/SUP

Feb 2026 2 week min Feb 1-14 or Feb 14-28 Mar 2026 2 week min Mar 1-16 or Mar 16-31 Gulf View, Top-Floor Beach Condo! Escape to Paradise Seeking a peaceful summer escape? Discover our charming coastal retreat—a perfect blend of relaxation and adventure! Nestled along a quiet canal, this cozy two-bedroom haven has everything you need for a rejuvenating getaway. Tandem Kayak & paddleboard included! Heated pool! Small, quiet complex! Less than 1/2 mile to Turtle Beach and the free trolley!

Superhost

The sun sets behind silhouetted palm trees, casting a warm glow over an open landscape. The horizon is painted with soft hues of orange and yellow, creating a serene backdrop against the evening sky.

Home in Venice

5 out of 5 average rating, 3 reviews

Tarpon Bayou

Take a break and unwind at this peaceful oasis. Right off the Myakka river. On Tarpon Bayou! Bring your small boat, kayaks and bikes. Near Myakka State Park South. Fisherman’s paradise producing Tarpon, Snook, Redfish, Snapper, Catfish, Dolphin, Manatee, Bull shark & Alligators. Close amenities include the Wellen Park baseball stadium that houses Atlanta Braves spring training. 10 minute drive to downtown Venice, Englewood, Northport and Port Charlotte nearby shopping and dining. Best Beaches.

Guest favorite

A serene outdoor space featuring a hot tub and several colorful lounge chairs facing a beautiful sunset over the water. The area is surrounded by lush greenery and includes a stone pathway leading towards the hot tub, with a wooden dock visible in the background.

Home in Englewood

4.93 out of 5 average rating, 88 reviews

20 Steps to Water! Sunsets, and Hot tub!

• The dock is being replaced and is not usable at this time. Gorgeous Sunsets: Enjoy stunning views • Spacious & Updated: Modern, comfortable stay • Relaxing Atmosphere: Your worries melt away • Wildlife: Watch dolphins & manatees play • Main Level Living: No steps, easy access • Private Entry: Lower duplex unit (others live upstairs) • Gourmet Kitchen: Granite counters • Outdoor Fun: Hot tub, enclosed porch, dock • Water Activities: 2 kayaks, 2 paddleboards • Beach: 2 miles away

Superhost

A beachfront condominium building is visible on the south end of Siesta Key, surrounded by sandy areas. The structure features multiple large windows, with a mixture of beige and colorful facades reflecting sunlight. The beach and distant coastline are seen in the foreground.

Condo in Sarasota

4.9 out of 5 average rating, 10 reviews

Beachfront - Siesta Key 2 BR walk out to beach

Sept 30, 2024. Condo was severely damaged in hurricane Helene see photos Located on the secluded south end of Siesta Key. This beachfront 2 BR condo is ground floor - literally walkout the back door and you are on the beach. includes use of owners kayaks. Boat docks are available for your use. Several restaurants within walking distance of condo or take the free trolley to the middle of the key or the village in the north end. Equipped with beach chairs, umbrellas, boogie boards

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, 53 reviews

The Manatee Flat at ManasotaKeyHouse 2bed/2bath

* Due to recent hurricanes, Manasota Key sustained heavy damage. Our property had minor damages (being on stilts), but repairs have been completed. We are excited to be renting again! Businesses and home owners are working hard to recover and rebuild. Things are constantly changing on the island, with various closures. What is mentioned or pictured in our listening is not accurate due to the constant changes. We will do our best to keep our guests up to date. Manasota Beach is open!

Guest favorite

A cozy deck area features outdoor seating with two bar stools and a small table adorned with flowers. Palm trees provide shade while a serene waterfront view is visible, with a private dock and a pool in the background.

Condo in Sarasota

4.97 out of 5 average rating, 32 reviews

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

This unique 2 bedroom/ 2 bath condo is right on the waterfront in Siesta Key! It is the upper condo of a two story complex that has a perfect view and feels like your own personal getaway! It comes with a full kitchen, living room, and two decks. Part of what makes it amazing is the private dock on the Pass. Perfect for kayaking and exploring! Or maybe you'd like to just relax and take a dip in the heated pool? Located in the quiet end, you can enjoy the calm, or head to Siesta Village!

Guest favorite

A sandy beach area is shown, featuring colorful lounge chairs and a large umbrella providing shade. Nearby picnic tables are visible, and a lush tree adds greenery to the space. The serene waterfront view reflects the surrounding nature.

Hotel room in Punta Gorda

4.85 out of 5 average rating, 20 reviews

Punta Paradise Waterfront Condo 3

Welcome to My Punta Paradise! Waterfront view Newly remodeled 1 bedroom with Queen bed Queen Sleeper sofa in the living room New tile floors New bathroom remodel with full tiled shower, easy to walk into All new kitchen cabinets, appliances, coffee & tea pots, crockpot, pots, pans, plates, silverware and more. All new furniture and accessories throughout! Nice beach area, with sand, chairs, picnic tables, barbques, corn hole, bocce ball We also have canoes and kayaks for your free use

Top guest favorite

A quaint tiny home is situated on a grassy area, with a set of wooden steps leading to the entrance. Large windows are visible, providing natural light and views of the surrounding greenery. The exterior features a light-colored facade with a red awning above the front window.

Tiny home in Arcadia

5 out of 5 average rating, 27 reviews

Riverfront Tiny house W/Kayaks

Get away from it all when you stay under the stars in this riverfront tiny home with queen bed.This 10x14 Tiny house is located directly on Horse Creek/Peace River. The perfect place to escape to nature. The 10 + acre property has kayaks and Canoes as well as a boat ramp if you want to bring your own. Enjoy the peaceful wildlife, have a bonfire and fish out your backdoor. No indoor smoking and no animals. We are a farm, so we cannot allow outside animals to the property.