Holiday rentals with a kayak in Englewood

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

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

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!

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.

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!

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.