
Holiday rentals with a kayak in Englewood
Find and book unique kayak rentals on Airbnb
Quick stats about holiday rentals with a kayak in Englewood

Total holiday rentals
Explore 130 holiday rentals in Englewood

Nightly prices starting at
Englewood holiday rentals start at $70 AUD per night before taxes and fees

Verified guest reviews
Over 3,570 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Holiday rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
130 of Englewood holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Englewood rentals

4.9 Average rating
Englewood stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated Accommodation with a Kayak in Englewood
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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

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!

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!

Perfect Beachy Couple Space On Manasota Key FL
"Green Gecko" is a roomy and comfortable one bedroom unit, steps from the pool, and a short walk to either our dock or the beach. Enjoy amazing sunrises at the dock and spectacular sunsets at the Gulf! Access to the beach is deeded and insures you can relax minus the crowds. The saltwater pool is a guest favorite and will de-stress you in no time. Inside enjoy a NECTAR queen bed, roomy bathroom and a full kitchen. Come rest and relax, swim in the ocean, collect shells or just lay by the pool.

Gulf Front Escape + Beach Access, Pet Friendly
🦩 Exclusive Amenities Include: • Walk Out to the Beach – Just Steps from Your Door • 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

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.

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 🌟

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!

Peaceful waterfront home
Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

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)

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.

Paradise on the Bay
Waterfront pool home just a short drive to Boca Grande with all the amenities that you would expect. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fantastic fishing from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 3 Kayaks and a canoe are available for your enjoyment.
Popular amenities for Englewood kayak rentals
Holiday House Rentals with a Kayak

Bayview: Waterfront sunsets, pool, hot tub, dock

Cape Haze Cottage

Luxury Waterfront Home With Heated Pool & Hot Tub

The Turtle Flat at ManasotaKeyHouse 2bed/2bath

Private Dock & Beach Access + Hot Tub, Bay Views

Castadiva-Your Gorgeous Gulf Coast Beach Home!

The Mangrove House

Neptune Tropical Retreat
Cottages with a kayak

New Pool Tropical Waterfront Dock & Optional Boat

Quaint Cottage w/access to Peace River canoe/kayak

2 bedroom, walk to beach-bikes-kayaks-grill-picnic

Island Getaway•Beach House•Dock•Pet Friendly

Oystercatcher 3min walk to sunset, bikes, kayaks

2BR Beach Cottage-Steps to Beach, Heated Pool

Coastal Key Cottage on Manasota Key

LunaSea, WATERFRONT cabin. Gilligan's Island !!
Other holiday rentals with a kayak

Dockside Delight:Waterfront/Gulf Access/4minsbeach

Spot manatees from your balcony

Key Condo located on Manasota Key

Lu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI

Florida Vacation on the bay

20 Steps to Water! Dock, Sunsets, and Hot tub!

little Gasparilla Island Beach house-Dog friendly

Steps to the Sand! Manasota Key Beachside Retreat!
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $311 AUD | $361 AUD | $390 AUD | $331 AUD | $323 AUD | $294 AUD | $223 AUD | $223 AUD | $209 AUD | $209 AUD | $223 AUD | $249 AUD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
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