
Holiday rentals with a kayak in Englewood
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Top-rated Accommodation with a Kayak in Englewood
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Dockside Delight:Waterfront/Gulf Access/4minsbeach
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. 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 Manasota Key's breathtaking beaches 2 miles away. Myakka Pines Golf Club just 4 miles

#6) 30 Seconds To Beach Path/Tiki Bar/Bikes/Kayaks
Welcome to Stump Pass Place! A perfect mix of comfort, nature and unmatched amenities. Just a 30 second walk to our beautiful neighborhood beach or a just 4 minute walk to Stump Pass State Park at the end of our street. Here you can go to the beach, launch the water toys, and make some lifelong memories. Stump Pass State Park has one of the most beautiful pristine beaches in all of Florida! FREE Kayaks, Sups, beach cruiser bikes, beach chairs, umbrellas, boogie boards, coolers and so much more!

The Manatee 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.

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!

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.

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.

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 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!

Island Getaway•Beach House•Dock•Pet Friendly
Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off Florida’s West Coast in the Gulf of Mexico. Access is for residents and renters only, you will arrive by your private boat or jump aboard the water taxi for a 10 minute ride to our dock. No cars, shops, or restaurants on the island. The 7 mile beach is private and uncrowded. Get around LGI by renting a golf cart or explore by foot-you decide.

Steps to the Sand! Manasota Key Beachside Retreat!
BEACH LOVERS' DREAM! Only Steps from the Sand! Experience Old Florida charm in this renovated Gulf-view condo with an updated kitchen, open living area, and flexible sleeping options including a queen suite, twin to king beds, and a cozy flex space. Enjoy direct access to your own sandy beach, relax by the pool, or watch stunning sunsets from the shoreline. Explore scenic trails with complimentary bikes and kayaks. Your perfect Englewood beach getaway awaits, book today!

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.

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!
Popular amenities for Englewood kayak rentals
Holiday House Rentals with a Kayak

Bayfront House, Private Dock, Steps to the Beach!

Nokomis Waterfront Unit Walk to the Beach & Dining

Sea La Vie

3/2 LGI Gulf Front w/Dock

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

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

North Port - Canal Home- Fish & Canoe

Daze Inn Between: lagoon pool ½ mi to beach ferry!
Cottages with a kayak

Quaint Cottage w/access to Peace River canoe/kayak

Oystercatcher 3min walk to sunset, bikes, kayaks

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

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

Good after Milton - Waterfall Pool! Beach! am

Great after Milton -Pool & Waterfall! Beach! im

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

New Pool Tropical Waterfront Dock & Optional Boat
Other holiday rentals with a kayak

Hot Tub Tropical Escape, Kayak, Minutes to Sand

Luxe 5 BR/4 bath. Dock/Lift. View. Pool. Hot Tub.

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

The perfect retreat with canal view

Peaceful Guesthouse Getaway! On a 7 Acre Estate!

Fantastic! Luxury-Remodel-Sunny Heated Pool

Turtle Nest Retreat - Manasota Key (upper unit)

Island Getaway Pool-Ferry-Grocery Delivery Incl.
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $336 NZD | $384 NZD | $430 NZD | $326 NZD | $298 NZD | $255 NZD | $265 NZD | $265 NZD | $248 NZD | $248 NZD | $265 NZD | $296 NZD |
| 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 |
Quick stats about holiday rentals with a kayak in Englewood

Total holiday rentals
Explore 110 holiday rentals in Englewood

Nightly prices starting at
Englewood holiday rentals start at $99 NZD per night before taxes and fees

Verified guest reviews
Over 3,850 verified reviews to help you choose

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

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Englewood rentals

4.9 Average rating
Englewood stays are highly rated by guests—averaging 4.9 out of 5!
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