
Holiday rentals with a kayak in Englewood
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Englewood
Guests agree: these rentals with 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

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.

#2) Bikes, Kayaks Sups, unmatched amenities & More
Welcome to Stump Pass Place! A perfect mix of comfort, nature and unmatched amenities. Just a 3 minute 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!

Gulf Front Escape + Beach Access, Pet Friendly
🦩 Exclusive Amenities Include: • Walk Out to the Beach – Steps from Your Door • Coastal & Surf Decks - Outdoor Seating • Historic Old Florida Charm • Beach Towels, Chairs & Umbrellas Provided • Community Pool with Picnic Tables & Chaise Lounges • Community Grills & Post-Beach Outdoor Showers • Free WiFi & TV • Coffee Maker & Kitchenette Smallwares Provided • Starter Packs of Essentials for Kitchen & Bath • Enhanced Cleaning Protocols • Combo Tub/Shower Bathroom • Desk/Chair in Unit

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!

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!

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!

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.

Bayview: Waterfront sunsets, pool, hot tub, dock
Escape to “Bayview”, a newly remodeled three bedroom 2 1/2 bath luxury home on the Intracoastal. Enjoy stunning sunsets, a private heated pool, attached relaxing hot tub, dock with boat lift, great fishing with underwater green light, with regular visits from the dolphins and manatees. Two Kayaks and two paddle boards included, as well as brand-new modern amenities. Perfect for families, couples, or boating enthusiasts seeking the ultimate waterfront getaway!
Popular amenities for kayak rentals in Englewood
House rentals with a kayak

Sea La Vie

3/2 LGI Gulf Front w/Dock

Tropical Retreat-HeatedPool Tennis PickleBall Golf

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

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

House With A Boat–Your Private Waterfront Resort

Florida Vacation on the bay

Waterfront Paradise w/ Private Pool & Nearby Beach
Cottage rentals with a kayak

Quaint Cottage w/access to Peace River canoe/kayak

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

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

Island Getaway•Beach House•Dock•Pet Friendly

New Pool Tropical Waterfront Dock & Optional Boat

Private Beach-Luxury 4BR+SUPs&Kayaks-Pets-BBQ
Other holiday rentals with a kayak

Unique loft experience for motorcycle enthusiasts

Key Condo located on Manasota Key

Coco Plum

Harbor Side Retreat

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

Private Beach, Fishing Dock & Heated Pool Paradise

Daze Inn Between: lagoon pool ½ mi to beach ferry!

Stunning! Luxury waterfront home-Heated Salt Pool
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $259 SGD | $296 SGD | $332 SGD | $252 SGD | $230 SGD | $197 SGD | $204 SGD | $204 SGD | $192 SGD | $192 SGD | $204 SGD | $229 SGD |
| 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 $77 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
110 of Englewood holiday rentals include wifi 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!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Family-friendly rentals Englewood
- Beach house rentals Englewood
- Rentals with outdoor seating Englewood
- Villa rentals Englewood
- Rentals with pools Englewood
- Apartment rentals Englewood
- Fitness-friendly rentals Englewood
- Rentals with a firepit Englewood
- Flat rentals Englewood
- House rentals Englewood
- Rentals with beach access Englewood
- Rentals with a hot tub Englewood
- Rentals with a fireplace Englewood
- Rentals with a washing machine and dryer Englewood
- Rentals with lake access Englewood
- Rentals with a patio Englewood
- Beachfront rentals Englewood
- Beach apartment rentals Englewood
- Waterfront rentals Englewood
- Pet-friendly rentals Englewood
- Rentals with a kayak Sarasota County
- Rentals with a kayak Florida
- Rentals with a kayak United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- Turtle Beach
- Coquina Beach
- Caspersen Beach
- Lido Key Beach
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Manasota Key Beach
- Lovers Key Beach
- River Strand Golf and Country Club
- Englewood Beach
- Myakka River State Park
- Lakewood National Golf Club
- Stump Pass Beach State Park
- Img Academy
- Marie Selby Botanical Gardens
- Blind Pass Beach
- Tara Golf & Country Club
- North Jetty Beach
- South Jetty Beach




