
Vacation rentals with a kayak in Englewood
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Englewood

Total vacation rentals
Explore 130 vacation rentals in Englewood

Nightly prices starting at
Englewood vacation rentals start at $50 per night before taxes and fees

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

Family-friendly vacation rentals
90 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
130 of Englewood vacation 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 kayak rentals in Englewood
Guests agree: these kayak rentals 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

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!

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

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!

2 BR/2 BA Beach Front Suite-Kayaks-SUPs-Bikes-Pets
Waterfront 2 Bed/2Bath (sleeps 7-8) so close to the water that you can hear the waves all day and night with the windows open. One bedroom is extra large with separate sitting and work area, and a king bed and queen sleep sofa and work area. The second bedroom has a queen bed and full size sleep sofa. Both have televisions. The kitchen seats 6. The front door is a double french door that opens out to a small sitting area where the BBQ grill is located, adjacent to the outdoor hot water shower.

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 🌟

Cape Haze Cottage
2023 Cape Haze Cottage , 3 bedroom 2.5 bath elevated canal front pool home. Quiet waterfront neighborhood with easy access to everything this amazing area has to offer. Screened lanai provides sunset views, private pool, outside shower, steps away from canal front for Kayaking and fishing or just watching the endless variety of nature. Situated just six minutes from stump pass by boat, access to the gulf , beaches and fishing both inshore and offshore. This is a piece of heaven.

Modern beach retreat with hot tub and kayaks
Discover your perfect beach getaway in this modern, family-friendly home near Englewood Beach, designed for relaxing days and fun-filled nights. With space to sleep up to 8 across 2 bedrooms and 4 beds (including full size bunk beds), plus 2 full bathrooms, it’s a great fit for families and groups who want comfort, convenience, and plenty to do. Enjoy the private backyard, outdoor shower, BBQ, hot tub, ping pong, bikes, kayaks, and a full kitchen with quality appliances and cookware.

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!

"Seaglass" Dazzles with Exceptional Bay Views&Pool
Fantastic Manasota Key Location! Upstairs at Blue Island Inn, waterfront “Seaglass Villa” dazzles with spectacular Bay views! 2 cozy bedrooms; 1 bathroom, kitchen & 1 cozy family room. On-site resort pool overlooks stunning Lemon Bay. 5-minute walk to ocean-side beach or enjoy “Bay-front beach” out back. Quiet island street. low-key quiet respectful vacationers. 1 car parking spot. No visitor parking. No boats. No pets. No smoking. Free use of kayaks!

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
House rentals with a kayak

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

Florida Vacation on the bay

Englewood FL Waterfront | Dock+ Kayaks+Fishing

Perfect Beachy Couple Space On Manasota Key FL

Englewood 3 Bedroom Private Pool+Spa on Lemon Bay

The Mangrove House

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

Newly renovated home on canal with salt water pool
Cottage rentals with a kayak

Quaint Cottage w/access to Peace River canoe/kayak

Manasota Key Beach Bungalow

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

Oystercatcher 3min walk to sunset, bikes, kayaks

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

Island Getaway•Beach House•Dock•Pet Friendly

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

Coastal Key Cottage on Manasota Key
Other vacation rentals with a kayak

Private Dock & Beach Access + Hot Tub, Bay Views

Castadiva-A Gorgeous Gulf Coast Beach Home!

Dockside Delight:Waterfront/Gulf Access/4minsbeach

Water View 3bdr,2ba, Close to Beaches Golf/Fishing

Architect's waterfront home is a fisherman's dream

Canal Home w/ Escape Room, Pool & Dock, Pets OK

Turtle Nest Retreat - Manasota Key (upper unit)

Waterfront Oasis w/ Pool on Myakka – Near Beaches
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $223 | $259 | $280 | $238 | $232 | $211 | $160 | $160 | $150 | $150 | $160 | $179 |
| Avg. temp | 61°F | 64°F | 67°F | 72°F | 77°F | 81°F | 82°F | 82°F | 81°F | 76°F | 69°F | 64°F |
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