Holiday rentals with a kayak in Englewood

5 out of 5 average rating, 64 reviews

Xanadu Luxury|Fishing Dock|Kayaks|Bar

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

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.

4.93 out of 5 average rating, 14 reviews

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

Relax with the whole family at this peaceful place to stay right on the intercoastal. Enjoy the newly renovated amenities this home has to offer. Enjoy a meal in the brand new kitchen, relax in the pool/hot tub, grill poolside, take kayak's out or paddle board to float with the dolphins and soak in the beautiful sunsets. Your stay will reinvent what true relaxation feels like! Enjoy our neighborhood restaurant just walking distance from the front door. This home has the "Coastal Charm" you need!

Superhost

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

4.79 out of 5 average rating, 100 reviews

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!

The exterior of a modern family house is displayed, featuring a manicured lawn and a two-car garage. A welcoming entrance is visible, accentuated by a porch and green vines. The contemporary design is complemented by large windows and a neutral color palette.

5 out of 5 average rating, 9 reviews

The perfect retreat with canal view

Discover the perfect family house with 3 bedrooms, an office, pool, and all the necessary amenities. It is located in Port Charlotte, just minutes away from Manasota key beach! And very close to a wide variety of different beaches, restaurants and shops! This family friendly property promises a delightful retreat, even if you decide to stay at mostly inside. You can dive into the refreshing pool, go fishing, enjoy outdoor games, or just unwind in the spacious bedrooms. It'll be a great fit! .

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.

4.9 out of 5 average rating, 161 reviews

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

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.

4.98 out of 5 average rating, 108 reviews

A well-lit bedroom features a spacious wooden bed with plush white bedding. Natural light enters through the window, which is adorned with horizontal blinds. Simple wall art complements the soothing color scheme, and a ceiling fan provides ventilation.

Farm stay in Punta Gorda

Peaceful Waterfront Orchard 1

bring the whole family including your pets to this peaceful orchard and garden oasis. the action packed backyard of this duplex proudly boasts over 40 fruit trees of various varieties including banana, orange, lemon, fig, mango, papaya... and many more! choose to fish from the dock in the backyard canal, go exploring with the kayaks or paddleboards, play in the sandbox, try out the slackline, or even say hi to the chickens in the coop (maybe even grab a few fresh eggs for breakfast).

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, 37 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!

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.

4.99 out of 5 average rating, 70 reviews

The Manatee Flat at ManasotaKeyHouse 2bed/2bath

Escape to beautiful Manasota Key and enjoy the perfect blend of beachside relaxation and coastal charm. Our property sits just a short walk to both the Gulf beach and Lemon Bay, giving you easy access to stunning sunsets and peaceful water views. Wake up to the sights of Lemon Bay, spend your days shelling, looking for sharks teeth, or kayaking. Unwind in our newly updated bright and comfortable space. This is the ideal getaway on Florida’s hidden gem of a barrier island.

A stylish pool area is illuminated by soft lighting at night, featuring two large red umbrellas over submerged seating. Calm waters reflect the surroundings, while palm trees frame the view, creating a serene atmosphere by the water's edge.

4.95 out of 5 average rating, 58 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.

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 out of 5 average rating, 29 reviews

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

3min. walk to beach. 3min. drive to restaurants! -3 kayaks and launch nextdoor -Bikes, beach gear, cooler, grill -Private back patio, outdoor shower, laundry -Roku TVs, full kitchen Welcome to your perfect beach escape on Manasota Key! This charming 1-bedroom cottage located in a peaceful neighborhood with easy access to parks, kayaking, and waterfront dining. Enjoy all the comforts of home, relax, explore, and make unforgettable memories in this beautiful paradise!

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.

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.

4.94 out of 5 average rating, 16 reviews

Old Englewood Village Home!

Cute Old Englewood Village home just a few minutes walk to West Dearborn Street restaurants and shops, 1 mile to Indian Mound public boat/kayak launch, and just 3 miles to Englewood Beach! You will have two private bedrooms and a game room with two twin trundle beds. There is a great fenced backyard so feel free to bring the dog! Kayaks and other beach gear available for guest use upon request.

Popular amenities for Englewood kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.89 out of 5 average rating, 27 reviews

The beachfront cottage is surrounded by lush foliage, showcasing a two-story structure with a metal roof and large windows. Soft light spills from the interior, highlighting a welcoming atmosphere. A wooden walkway leads to the entrance, inviting guests to explore the natural surroundings.

Home in Don Pedro Island

Island Beachfront Cottage. Secluded! Lux! Extras!

5 out of 5 average rating, 12 reviews

The exterior of the home features a warm peach façade and a well-maintained lawn. An inviting front entrance is marked by arched doorways and decorative pendant lighting. A spacious garage with a wooden door complements the architecture, framed by lush landscaping and a clear blue sky.

Home in North Port

Private Oasis on Canal with Dock

4.93 out of 5 average rating, 71 reviews

Ripple Inn - lagoon pool, lanai +beach ferry ½ mi

4.93 out of 5 average rating, 55 reviews

A spacious outdoor area showcases a heated saltwater pool surrounded by a screened enclosure, allowing for relaxation in a sunlit environment. The patio features comfortable seating arrangements, with a dining area visible nearby, providing ample space for gatherings and leisure activities.

Home in Punta Gorda

Hibiscus |Waterfront|Heated Pool-Dock-Bikes-Kayaks

5 out of 5 average rating, 21 reviews

Coastal Retreat ~ Near Beaches, Parks & Shopping

5 out of 5 average rating, 16 reviews

A two-story, light blue house is shown against a backdrop of blue skies and scattered clouds. A white picket fence encloses the yard, which features a well-manicured green lawn. A gravel driveway leads to the house, and a deck is visible on the upper level.

Home in Nokomis

On the water in Venice FL.

An inviting saltwater pool is illuminated by soft lights at dusk, surrounded by lush greenery. The screened enclosure provides a sense of serenity while casting gentle reflections on the water's surface. Outdoor seating is visible nearby, creating a space for relaxation.

5 out of 5 average rating, 22 reviews

SunCoast Garden Family Retreat

4.94 out of 5 average rating, 18 reviews

House With A Boat - Boat, Heated Pool, SUP Boards

Cottages with a kayak

Two kayaks are visible on calm water, one orange and one yellow. An adult is paddling the yellow kayak while a child sits behind, wearing a red life jacket. Surrounding greenery adds a natural backdrop.

4.75 out of 5 average rating, 155 reviews

Good after Milton -Free Kayaks! Steps to Beach-bb

5 out of 5 average rating, 115 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

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.

4.96 out of 5 average rating, 26 reviews

Oystercatcher 3min walk to sunset, bikes, kayaks

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.

4.89 out of 5 average rating, 185 reviews

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

The exterior of a charming beach house features a light blue façade with a coral-colored door. A small table with a palm tree design is positioned on a stone pathway leading to the entrance. Lush greenery and a decorative fountain enhance the welcoming outdoor space.

5 out of 5 average rating, 23 reviews

The Coastal Oasis. Only 8 minutes from the Beach!

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.

4.86 out of 5 average rating, 136 reviews

Unit #3 Free Kayaks/bikes/beach/pet friendly

An open concept living area features a cozy seating arrangement and a dining table set for four. The kitchen includes modern appliances against a backdrop of white cabinetry, while a decorative area rug adds warmth to the wood flooring.

4.89 out of 5 average rating, 175 reviews

Good after Milton - Waterfall Pool! Beach! am

Cottage in Don Pedro Island

4.98 out of 5 average rating, 58 reviews

Island Getaway•Beach House•Dock•Pet Friendly

Other holiday rentals with a kayak

A light-colored, one-level ranch home with a well-manicured lawn is showcased in this image. The house is framed by lush greenery and colorful plantings, while a paved driveway leads to a two-car garage on the side. A peaceful neighborhood ambiance is apparent.

5 out of 5 average rating, 13 reviews

Venice Adventure Retreat Near Beaches & Bike Path

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.

4.87 out of 5 average rating, 23 reviews

Heated Pool, Sleeps 10. Walkable to Restaurants

5 out of 5 average rating, 8 reviews

Home in Rotonda West

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

5 out of 5 average rating, 7 reviews

A bright bedroom features a spacious bed with a yellow accent pillow and a knitted blanket draped over it. Two windows with blinds provide natural light, while wood beam ceilings add architectural interest. Nightstands flank the bed, and a small lamp offers additional lighting.

Condo in Englewood

Spot manatees from your balcony

4.95 out of 5 average rating, 20 reviews

A lighthouse is observed standing tall against a backdrop of serene blue waters and a sandy shore. The lightkeeper's balcony offers panoramic views of the ocean, reflecting shimmering sunlight, while the surrounding beach features gentle dunes and patches of vegetation.

Villa in South Gulf Cove

"Everglade Kiss" 3b 2b BBQ, hot tub

A two-story duplex is framed by lush palm trees and landscaping. The property features a welcoming front porch with white railings and ample outdoor seating. A gravel driveway leads to two designated parking spaces in front, enhancing accessibility to the entrance.

4.87 out of 5 average rating, 63 reviews

Turtle Nest Retreat - Manasota Key (upper unit)

5 out of 5 average rating, 29 reviews

A serene view showcases a manicured lawn leading to a calm lake, bordered by palms and grasses. The bright blue sky reflects softly on the water's surface, creating a peaceful outdoor ambiance.

Home in Nokomis

Lake View, 6 Miles From Beach