Waterfront holiday rentals in Englewood

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

The Windsor @ Englewood Beach

Absolutely no Hurricane damage. 6 minutes to Englewood Beach! Experience a one of a kind, private lush tropical vacation rental overlooking a canal {5 minutes to open water} in Englewood, FL. Enjoy a completely remodeled 3 BR, 2 BA home (with additional office with a sofa bed). Heated saltwater pool & hot tub under an enclosed pool cage. Unwind in a secluded and fenced in backyard paradise with tropical foliage, mangroves and deck overlooking a gulf-access canal. This place has it all.

Peaceful Waterfront Orchard 1

bring the whole family including your pets to this peaceful orchard and garden oasis. the action packed backyard of this duplex proudly boasts over 40 fruit trees of various varieties including banana, orange, lemon, fig, mango, papaya... and many more! choose to fish from the dock in the backyard canal, go exploring with the kayaks or paddleboards, play in the sandbox, try out the slackline, or even say hi to the chickens in the coop (maybe even grab a few fresh eggs for breakfast).

Bali Bliss Villa • Pool • 6 Min Drive to Beach

Welcome to Dolphin Villa- your dreamy retreat in the heart of Venice! This enchanting 3-bed, 2-bath home blends modern luxury with bohemian charm and features a refreshing pool. Just moments from Venice's pristine beaches, charming shops, and dining options, it offers the perfect mix of serenity and convenience. Ideal for a romantic getaway, family retreat, or friends' gathering, this modern bohemian oasis promises an unforgettable stay. We can't wait to have you stay with us!

Unwind at Casa Blu: Sun, fun, pool, close to Beach

Welcome to Casa Blu, your cozy retreat in Florida's sun-kissed paradise. Close to restaurants, parks, and beaches, and Old Englewood. Just 7 miles to Englewood Beach. The stresses of daily life melts away with its single-floor layout, comfy bedrooms with private baths await. Enjoy fast WiFi, Smart TVs, and a fully equipped kitchen. Unwind on the screened lanai or take a dip in the private saltwater pool. Everything's covered, from beach gear to a pack 'n play.

Suite Sun

Welcome to your tropical oasis in Englewood, Florida! Step outside and prepare to be amazed by the stunning outdoor space. The inground pool beckons you to take a refreshing dip on warm Florida days. Imagine sipping your favorite beverage as the sky transforms into a canvas of vibrant colors each evening. For the fishing enthusiasts, a private dock awaits your arrival. Cast your line and enjoy the serenity of the lake, all from the comfort of your backyard.

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

Studio, pool, private beach, boat dock shark teeth

Enjoy it all -Pool, private dock & private beach access-located near restaurants. Covered parking or hop on a shuttle to explore Manasota Key! Light, bright condo is complete with everything you will need to relax. Kitchenette has all the must haves-air fryer, portable stove, coffee maker, kettle & community grill. Enjoy a queen bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach.

Huge NOV SALE, EXCL Sarasota #1 Luxery beach Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Great boater's spot

Take it easy at this unique and tranquil getaway. Great location for boaters or for those who love to be near the water. On a deep water canal, close to a boat ramp. Walking distance to the historic Bean Depot Cafe. Just relax in the lanai and watch the boats come in and out of the canal. There is a bird sanctuary across the canal so it is very peaceful and private.

Waterfront Getaway, a Boating Paradise

Visualize it this way, you can drop your boat in across the street at the public boat ramp, and store your trailer behind the property and dock your boat steps from our place. Just grab your cooler and sunscreen and head out for a day of fishing or to the sandbar. Guests have use of the entire house on the canal. It’s super convenient to drop in and go!

Bunk Up by the Beach – 3BR Just Steps to Beach

Just steps from the sandy shores of Manasota Key, this ground-level 3-bedroom, 2-bath home offers classic Old Florida vibes with modern comforts. With terrazzo floors, an open layout, and a unique bunk room for the kids, it’s perfect for family vacations filled with beach days, cookouts, and coastal memories.