Holiday rentals with a kayak in Englewood

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

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 🌟

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!

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.

Stay on Fray

🌴Welcome to Stay on Fray, a home perfectly located just steps from Englewood’s beloved Dearborn Street, lined with local restaurants, coffee shops, wine bars, and boutiques. Englewood Beach is just a 7-minute drive over the bridge. The local boat ramp is just down the street & there is ample boat parking at the house! Whether you’re here for a weekend festival, a beach getaway, or a longer stay, Stay on Fray puts you right where you want to be!