Holiday rentals with a kayak in Englewood

5.0 out of 5 average rating, 107 reviews

A canalfront area features a serene gazebo surrounded by lush green grass and white pebbles. The vibrant sunset sky adds warmth to the scene, and the private boat dock is visible in the background, enhancing the tranquil outdoor setting.

Home in Port Charlotte

Xanadu|Fishing/ Pool/Dock|Kayaks|Bar/Gazebo/ Kids

Welcome to XANADU Luxury Villa 🌊 your canalfront paradise with a private BOAT DOCK ☀TOP LOCATION📍, close to: beautiful beaches 🏖️ Gasparilla Island, Siesta Key, Englewood! ☀Dock Ideal to FISH 🎣| Deck🎴 ☀BAR🍷 ROOM Dancing Light 🪩 ☀DEDICATED WORKSPACE 💻 ☀GAME🎮 Room /Roblox/Arcades🕹️ ☀Smart TVs in every room📺 ☀HEATED Pool 🏊‍♀️ ☀Fast WIFI📶 ☀Ping Pong Area in Sand 🏓 ☀Fully equipped kitchen🍽️ ☀Pool Table and Games🎱♟️ ☀ Outside dining table😋/Fireplace ☀BBQ🍖Ice Maker🧊 ☀Self check in 🔐 Smart Lock

Outdoor spacesLocationCheck-in

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.

4.9 out of 5 average rating, 211 reviews

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

Unit # 2 Beautiful 2 bedrooms 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. 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!

LocationValuePets

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.

4.99 out of 5 average rating, 87 reviews

The Turtle Flat at ManasotaKeyHouse 2bed/2bath

Escape to beautiful Manasota Key and enjoy the perfect blend of beachside relaxation and coastal charm in this peaceful community. Our property is a short walk to both the Gulf beach & Lemon Bay, offering stunning sunsets and tranquil water views. Wake up to the sights of Lemon Bay, spend your days shelling, looking for sharks teeth, kayaking or biking. Unwind in our updated bright & comfortable space. Ideal for guests seeking a calm/relaxing retreat on Florida’s hidden gem of a barrier island.

LocationValueDecor

4.83 out of 5 average rating, 123 reviews

An aerial view of Manasota Key showcases the expansive beach lined with soft sand and crushed shell. The vacation home is highlighted, surrounded by lush greenery and close proximity to the warm Gulf waters, with clear blue skies enhancing the tranquil environment.

Bungalow in Englewood

LG Beach Bungalow on Gulf w/Bay Access & deck too!

Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!

LocationOutdoor spacesAccuracy

5.0 out of 5 average rating, 38 reviews

Private Beach & Bay Access. Kayak & SUP

Discover your private slice of paradise! This home offers the best of both worlds, 2 minute walk from private beach access where you can soak up the sun & enjoy the ocean waves. Plus, you have private bay & dock access 2 houses down, with a kayak & stand-up paddleboard for your water adventures. Cast a line or dock for the day while Moe & Millie (our neighborhood manatees splash around)! Sip your morning coffee in the sunroom and end the day under the tiki torches in the large private yard.

ValueOutdoor spacesBeach

5.0 out of 5 average rating, 38 reviews

Waterfront| Pool & Spa | Near Beach| No Extra Fees

Welcome to Casa-A-Mar, your private slice of coastal paradise at our newly updated waterfront retreat. Step outside and launch straight into the water with direct Gulf access or into Lemon Bay—perfect for exploring the canals on one of our kayaks. Prefer to stay in? Spend your time in the heated pool, then ease into the hot tub as the sun sets. As evening falls, transform the backyard into your own open-air theater with our outdoor projector, perfect for movie nights under the stars 🌟

Outdoor spacesLocationCleanliness

5.0 out of 5 average rating, 39 reviews

A serene canal view is showcased from a private dock, featuring two teal chairs positioned beside a small table. Lush greenery and calm waters reflect the clear blue sky, enhancing the peaceful atmosphere of the outdoor space.

Bungalow in Englewood

Waterfront/ Private Dock / 4 Mins to the Beach

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 and Manasota Key's breathtaking beaches. Myakka Pines Golf Club just 4 miles 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

LocationOutdoor spacesKitchen

Superhost

4.93 out of 5 average rating, 14 reviews

Gulf Front Escape + Beach Access, Pet Friendly

🦩 Exclusive Amenities Include: • Walk Out to the Beach – Just Down the Stairs • Historic Old Florida Charm • Coastal and Surf Decks with Outdoor Seating • Community Pool with Picnic Tables and Chaise Lounges • Community Grills and Post-Beach Outdoor Showers • Free WiFi and TV • Full Kitchen, Wares • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs and Umbrellas Provided • Tub/Shower Combo in Bathroom • Desk and Chair in Unit, Community Laundry

LocationShared spacesHospitality

Superhost

4.65 out of 5 average rating, 20 reviews

Castadiva-Your Gorgeous Gulf Coast Beach Home!

Looking for Paradise with your own Private Gulf Front Beach only for you and your Family? It Still exists at Castadiva! A Cathedral Ceiling renovated three bedroom, two bathroom Beautiful Home where you will never want to leave…ever…. Come Stay and let us Pamper You! Manatees, Dolphins Jumping, Shark Tooth Hunts, Sea Turtle Hunts, Today’s Grilled Fresh Catch caught, Frozen Island Drinks and your private Gulf Front beach only for Castadiva guests a minute walk from front door!!

LocationOutdoor spacesCleanliness

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.

5.0 out of 5 average rating, 66 reviews

Lux Home on Gulf w/Private POOL & 50ft 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 50 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!

ValueLocationQuiet

4.99 out of 5 average rating, 144 reviews

An enclosed lanai features multiple large windows with views of Lemon Bay, allowing natural light to fill the space. A palm tree is visible outside, framed by the window panes. A decorative area rug is positioned on the wooden floor, enhancing the coastal ambiance.

Villa in Englewood

Stunning Bay Waterfront! Jaw dropping Water Views!

Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchenette & family room. Enjoy “Lemon Bay-front beach” in backyard. Low-key quiet vacationers. 1 car parking spot. No visitor parking. Free 2 kayaks. Login to your favorite streaming services with Smart TVs. Beautiful Blind Pass Beach, Englewood Beach, 5 restaurants & Tiki Bars are just 1.5 mile away or hop on Stumpy's Free Shuttle (tip based)

LocationValueParking

5.0 out of 5 average rating, 38 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.

Outdoor spacesLocationAmenities

Popular amenities for kayak rentals in Englewood

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5.0 out of 5 average rating, 9 reviews

Englewood FL Waterfront | Dock+ Kayaks+Fishing

Outdoor spacesLocationGetting around

5.0 out of 5 average rating, 22 reviews

Steps to the Sand! Manasota Key Beachside Retreat!

ValueLocationWalkability

A well-lit pool area is enclosed by a screened patio, showcasing a sparkling pool and hot tub. The vibrant hues of a sunset are reflected in the water, surrounded by lush tropical landscaping and silhouettes of palm trees.

4.96 out of 5 average rating, 26 reviews

Waterfront, 3 Bed, 3 Bath, Pool/Hot Tub, Kayak

LocationOutdoor spacesBathroom

4.95 out of 5 average rating, 20 reviews

Neptune Tropical Retreat

Outdoor spacesLocationAccess

4.97 out of 5 average rating, 29 reviews

Modern beach retreat with hot tub and kayaks

Outdoor spacesLocationCleanliness

The exterior of a mid-century modern home is showcased, featuring a clean white facade and a welcoming porch. A manicured lawn with shrubs and palm trees surrounds the property. An American flag is displayed, adding a touch of character to the serene landscape.

5.0 out of 5 average rating, 33 reviews

The Mangrove House

Outdoor spacesLocationAccuracy

A sunlit outdoor space features a blue pool with a large golden inflatable swan float. Two lounge chairs are positioned nearby, while a wooden bar is seen in the background, equipped with stools and a television. Lush greenery surrounds the area, adding a tropical feel.

4.88 out of 5 average rating, 33 reviews

Private pool with outdoor bar and fenced yard

Outdoor spacesLocationHospitality

4.97 out of 5 average rating, 58 reviews

Perfect Beachy Couple Space On Manasota Key FL

Outdoor spacesValueAccess

Cottage rentals with a kayak

4.99 out of 5 average rating, 134 reviews

A screened-in porch offers a serene view of lush greenery and a calm waterway. Two wooden chairs are positioned at a white table, with a small decorative item placed on its surface. Bright sunlight filters through the trees, enhancing the natural surroundings.

Cottage in Arcadia

Quaint Cottage w/access to Peace River canoe/kayak

LocationOutdoor spacesHospitality

A living area is presented with a black sofa and a patterned armchair, complemented by light-colored wood flooring. Art featuring sailboats decorates the wall, while natural light fills the space through multiple windows. A dining area with a table and chairs is visible in the background.

5.0 out of 5 average rating, 45 reviews

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

Outdoor spacesValueHospitality

Cottage in Don Pedro Island

Island Getaway, Beach House, Dock, Pet Friendly

Outdoor spacesLocationWifi

4.99 out of 5 average rating, 80 reviews

5.0 out of 5 average rating, 14 reviews

Manasota Key Beach Bungalow

Outdoor spacesLocationSolo travel

A comfortable living space features a light grey sofa with two blue cushions and a yellow accent pillow. A round mirror hangs on the wall, reflecting natural light. The white coffee table displays a decorative bowl, with a woven rug beneath providing texture to the floor.

4.95 out of 5 average rating, 41 reviews

Oystercatcher 3min walk to sunset, bikes, kayaks

LocationOutdoor spacesView

5.0 out of 5 average rating, 7 reviews

Coastal Key Cottage on Manasota Key

Outdoor spacesLocationComfort

Cottage in Don Pedro Island

A charming island cabin is depicted, showcasing a mint green exterior and raised deck. A welcoming patio area features seating arrangements, while a boat dock extends along the waterway. Palm trees frame the scene, adding to the relaxed coastal atmosphere.

LunaSea, WATERFRONT cabin. Gilligan's Island !!

LocationOutdoor spacesParking

4.97 out of 5 average rating, 36 reviews

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.

4.89 out of 5 average rating, 193 reviews

Unit #1 Free kayak/bikes/walk to beach/fullcottage

ValueOutdoor spacesGetting around

Other holiday rentals with a kayak

4.86 out of 5 average rating, 14 reviews

A modern duplex with a symmetrical façade and a paved driveway leading to two black garage doors. Large windows are framed in white, allowing ample natural light to brighten the entrance. A well-maintained lawn surrounds the structure, enhancing the inviting presence.

Home in Rotonda

Group Waterfront Getaway | 9 Beds | Sleeps 14

LocationHospitalityComfort

4.96 out of 5 average rating, 23 reviews

A scenic rooftop deck is highlighted, featuring several bright orange high chairs positioned along a railing. The expansive view showcases the turquoise waters of the Gulf, with a clear blue sky above and a glimpse of the sandy beach below.

Flat in Englewood

#6) 30 Seconds To Beach Path/Tiki Bar/Bikes/Kayaks

Outdoor spacesLocationComfort

5.0 out of 5 average rating, 28 reviews

The image captures a serene waterfront view, showcasing a vibrant sunset with colorful streaks across the sky. Gentle ripples are observed on the water's surface, reflecting the warm hues of the evening light, creating a tranquil ambiance.

Townhouse in Englewood

Architect's waterfront home is a fisherman's dream

LocationOutdoor spacesNearby

The kitchen features pale blue walls, complemented by white cabinetry and a light wood countertop. Stainless steel appliances are arranged along the walls, while a dining area with black chairs stands to the left. A nautical-themed decor item enhances the inviting atmosphere.

4.95 out of 5 average rating, 22 reviews

Old Englewood Village Home with Fenced Yard

LocationHospitalityGetting around

5.0 out of 5 average rating, 46 reviews

Florida Vacation on the bay

Outdoor spacesLocationSleep quality

5.0 out of 5 average rating, 33 reviews

Home in Rotonda

Newer 4bd/2ba Canal Pool House, Hot Tub & Game Rm!

LocationOutdoor spacesDecor

4.9 out of 5 average rating, 21 reviews

Home in Rotonda

Villa „Maritime“ - Pool & SPA, Beach & Kajak

LocationSleep qualityAmenities