Home Vacation Rentals By Owner In Englewood, FL

Showing 540 Of 1188 Vacation Rentals
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$1519.73

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Private Vacation Home

Seahorse Place I - Waterfront Tropical Paradise! Accessible Friendly w/ Elevator

Englewood, Florida, United States

Escape to Seahorse Place I—a private single-family retreat thoughtfully designed for relaxation, adventure, and comfort. Perfectly situated on the Peninsula, this coastal escape offers breathtaking views of both Lemon Bay and the Gulf of America, creating a rare balance of luxury and tranquility.brbrProperty HighlightsbrbrPrivate Pool & SpabrUnwind in your own private oasis. The sparkling pool and rejuvenating spa invite you to relax after a day in the sun or exploring the nearby shoreline. Whether it’s an afternoon swim or a peaceful evening soak, this space is all about indulgence and serenity.brbrWaterfront ViewsbrWith Lemon Bay and the Gulf of America surrounding the property, every sunset feels like a postcard. Guests can enjoy stunning panoramas from multiple vantage points, turning each day into a unique coastal experience.brbrAccessibility & ComfortbrSeahorse Place I is fully handicap accessible with elevator, ensuring that all guests can enjoy its amenities. An in-home elevator provides convenient access throughout the property, making comfort and ease a top priority.brbrScuba AdventuresbrTake your adventure underwater with Seahorse Scuba, offering PADI-certified scuba lessons directly from your stay. Whether you’re a first-time diver or an experienced explorer, the vibrant marine life and crystal waters promise unforgettable experiences.
Bed 4

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Bath 3

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Sleep 8

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Exceptional(14)

$127.65

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Mobile Home

The Beach Bus - Skoolie Camping!

Englewood, Florida, United States

Welcome to the Beach Bus!brEmbark on a one-of-a-kind adventure where the nostalgia of schoolyard memories meets the tranquility of Florida’s coastal charm. Our lovingly converted 2007 Thomas school bus, once a beacon of learning, now offers a serene escape nestled among the whispering palms and lush greenery of Florida’s beautiful gulf coastline! But don't stop there...your only minutes to the best beaches the Gulf has to offer!brbrMake it memorable, make itbrBeach BusbrbrThe spacebrSecluded Serenity with a Touch of Home Step aboard and discover a cozy haven crafted with care from local materials. The private deck, adorned with outdoor seating and handcrafted tables from the surrounding trees, invites you to unwind under the stars or greet the morning sun with your favorite brew.brbrModern Amenities in a Rustic Setting Inside, the Beach Bus boasts all the comforts of home. A full shower, a bathroom with a flushing toilet, and a kitchenette equipped with a full-size fridge, oven, and gas range await to fulfill your domestic needs. Ample seating and storage space ensure a clutter-free stay, while the rear bedroom promises restful nights on a king-size memory foam mattress, complete with a closet to tuck away your clothing and shoes.brbrCool Comforts for Warm Florida Days Dimmable lights set the mood for relaxation, and when the Florida heat beckons, two air conditioning units stand ready to envelop you in cool comfort.brbrFrom Classroom to Cozy Retreat This unique abode has journeyed from the bustling hallways of a Pennsylvania elementary school to provide you with an unforgettable stay. The Beach Bus is not just a place to sleep—it’s a destination that tells a story, inviting you to write the next chapter!brbrGuest accessbrYou have access to the area where the bus is parked, your parking area and trail coming in!
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Bath 1

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Sleep 2

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Exceptional(1)

$268.83

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Apartment

Gulf Sands – 3BR Steps to Pool & Private Beach

Englewood, Florida, United States

Discover coastal living at Gulf Sands Condominiums on beautiful Manasota Key. This 3-bedroom, 2-bath retreat offers partial Gulf views, a heated pool, and private beach access just steps from your door. Enjoy island dining, live music, and sunsets all within walking distance — the perfect blend of comfort and convenience for your Gulf Coast getaway.brbrWhy You’ll Love Itbr• Prime beachfront complex with private beach accessbr• Heated pool, grilling area, and covered under-building parkingbr• Walk to local restaurants, bars, and shops on the south end of Manasota Keybr• Free shuttle service available through Stumpy’s Free RidebrbrSleeping Arrangementsbr• Primary Bedroom – King bed, ensuite bathroom, access to screened patiobr• Guest Bedroom 1 – Queen bedbr• Guest Bedroom 2 – Two twin bedsbr• Second Bathroom – Shower/tub combobrbrOutdoor Highlightsbr• Large screened-in patio with partial Gulf viewbr• Heated community pool and sundeckbr• Gas grilling area and shaded picnic tablesbrbrInterior Comfortsbr• Spacious open layout with coastal décor and natural lightbr• Stainless steel appliances and fully equipped kitchenbr• Dedicated dining area and comfortable living spacebr• Washer and dryer in unitbrbrKitchen & Diningbr• Modern stainless steel appliancesbr• Breakfast bar and dining tablebr• Well-stocked with cookware, dinnerware, and small appliancesbrbrIncluded Home Essentialsbr• Wi-Fi and smart TVsbr• Washer and dryerbr• Beach chairs and umbrellabr• Central A/C and ceiling fans throughoutbrbrNeighborhood Perksbr• Steps from the Gulf of Mexico and minutes from Lemon Baybr• Walkable to Lock ‘N Key, SandBar Tiki & Grille, White Elephant, and morebr• Peaceful, laid-back setting on the quiet south end of Manasota KeybrbrAccess & Parkingbr• Stairs required for entry to the condobr• Private covered parking under the buildingbr• Free island shuttle via Stumpy’s Free RidebrbrFrom beach days to sunset strolls, Gulf Sands is where Vacay Your Way comes alive. Book now with Gulf Coast Vacations!
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Bath 2

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Sleep 6

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$262.62

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Condo

Lemon Bay Waterfront Condo w Patio

Englewood, Florida, United States

Summary:brEnglewood Cozy Vacation Condo - 5 Miles To Gulf Beaches PLEASE NOTE ENGLEWOOD BEACH IS STILL CLOSED BUT WE ARE HAPPY TO REPORT THAT VENICE BEACH NOKOMIS BEACH CASEY KEY BEACH AND SIESTA KEY BEACH ARE OPEN Our 2-bedroom 1-bathroom cozy condo offers a charming and full of character Old Florida style waterfront property for your relaxing South Florida Gulf Coast Vacation Englewood 1st Floor Condo with Dockspace on Canal 2 Bedrooms 1 Bathroom Deck Space with water views and access to canal 5 miles to Englewood Beach Fully Equipped Kitchen Dining for up to 4 at the dining table BBQ Just south of Stump Pass Close to the Bill Coy Preserve BEDROOMS First-Floor Unit - Bedroom 1 One Queen Bedroom - Bedroom 2 One Queen Bedroom- Driveway is limited to one vehicle and shared with the upstairs and side condo neighbors The condo is not shared and the deck off the condo is not shared but the upstairs condo has the lower deck space BBQ - There is a BBQ at this property for complimentary guest use - While there is a propane tank included with the BBQ we do not provide refills - Guests are welcome to swap the tank at any local store - BBQ must be cleaned upon guest departure or an additional 56 fee will be charged Distances to Shopping Attractions The home is located on Lake Drive - Chadwick Park at Englewood Beach 5 7 miles- Boca Grande 13 miles- Englewood Farmers Market 6 miles- Publix at Merchants Crossing 3 miles- Ken Barb s Grove City Kitchen 2 miles- Ann Chuck Dever Regional Park 2 miles- Punta Gorda Airport 30 miles- Sarasota Bradenton Intl Airport SRQ 46 milesWhy Choose this Rental - Professionally managed to serve all your needs- Management company has over 26 years of experience hosting well over 200 000 families- Go straight to your rental with online email check-in- 24 7 on-call maintenance- Smoke-free and pet-free for your comfort- Towels and linens are provided- Complimentary WiFiStarter welcome packet supplies - 2 rolls of toilet paper per bathroom- 1 round hotel-size bar soap per bathroom- 1 hotel-size shampoo conditioner per full bathroom- 1 roll of paper towels- 2 packets of dishwasher detergent- 2 trash bags size-13-gallon- 2 pods of laundry detergent - Garbage can liners in each bedroom bathroom small garbage cansAny supplies beyond this are up to the guest to replenish we do not restock these items No salt pepper or cleaning supplies are stocked due to safety issues This is an industry-standard practice FOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS this does not apply if you are staying less than 30 nights We will collect a 1 500 deposit Balance is due 60 days prior to arrivalIf canceled 90 days or more before arrival we keep with us 250 00 1 250 00 will be refunded If canceled between 61 and 89 days prior to arrival we keep with us the 1 500 00 deposit No cancellation or modification 60 days or less prior to arrival
Bed 2

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Bath 1

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Sleep 4

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$253.44

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Private Vacation Home

Lemon Bay Townhome Su

Englewood, Florida, United States

Summary:brEnglewood Cozy Vacation Condo - 3 Miles To Gulf Beaches PLEASE NOTE ENGLEWOOD BEACH IS STILL CLOSED BUT WE ARE HAPPY TO REPORT THAT VENICE BEACH NOKOMIS BEACH CASEY KEY BEACH AND SIESTA KEY BEACH ARE OPEN Our 2-bedroom 2-bathroom cozy condo offers a charming and full of character Old Florida style waterfront property for your relaxing South Florida Gulf Coast Vacation Englewood three floor Condo 2 Bedrooms 2 BathroomsBalconies overlooking Oyster Creek3 miles to Englewood BeachFully Equipped KitchenDining for up to 4 at the dining tableRight across from Oyster Creek Environmental Park and Kayak Launch BEDROOMS Three-Floor Unit - Bedroom 1 One King Bedroom top floor ensuite Balcony- Bedroom 2 One Queen Bedroom main floor - One-car garage- Elevator from garage to main floor- does not go to third-floor bedroom- 30-night minimum stay per HOA rulesGuests who stay here must complete a background check per the HOA requirements This is an additional non-refundable 100 additional fee paid directly to the HOA once the reservation is made Distances to Shopping Attractions The home is located on Oregon Trail- Chadwick Park at Englewood Beach 3 miles- Boca Grande 13 miles- Englewood Farmers Market 6 miles- Publix at Merchants Crossing 3 miles- Ken Barb s Grove City Kitchen 2 miles- Ann Chuck Dever Regional Park 2 miles- Punta Gorda Airport 30 miles- Sarasota Bradenton Intl Airport SRQ 46 milesWhy Choose this Rental - Professionally managed to serve all your needs- Management company has over 26 years of experience hosting well over 200 000 families- Go straight to your rental with online email check-in- 24 7 on-call maintenance- Smoke-free and pet-free for your comfort- Towels and linens are provided- Complimentary WiFiStarter welcome packet supplies - 2 rolls of toilet paper per bathroom- 1 round hotel-size bar soap per bathroom- 1 hotel-size shampoo conditioner per full bathroom- 1 roll of paper towels- 2 packets of dishwasher detergent- 2 trash bags size-13-gallon- 2 pods of laundry detergent - Garbage can liners in each bedroom bathroom small garbage cansAny supplies beyond this are up to the guest to replenish we do not restock these items No salt pepper or cleaning supplies are stocked due to safety issues This is an industry-standard practice FOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS this does not apply if you are staying less than 30 nights We will collect a 1 500 deposit Balance is due 60 days prior to arrivalIf canceled 90 days or more before arrival we keep with us 250 00 1 250 00 will be refunded If canceled between 61 and 89 days prior to arrival we keep with us the 1 500 00 deposit No cancellation or modification 60 days or less prior to arrival
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Bath 2

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Sleep 4

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Exceptional(17)

$749.41

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Private Vacation Home

New Construction Modern POOL Home...LESS than 57 seconds walk to the BEACH!

Englewood, Florida, United States

This high-end house is located on a corner lot in a charming old-Florida neighborhood with a beach town atmosphere. From your front door walk to the beach in less than 60 seconds! brHighlights include a brand-new kitchen, two covered balconies, and a walled backyard oasis with pool and jacuzzi where you host a cookout under the covered patio. This luxurious getaway is within walking distance of dining options, a state park, and less than 300 feet from the beach. Spend sunny days by the turquoise waters of the Gulf. Explore the trail at Stump Pass Beach State Park, a 12-minute walk away. Venture to North Beach Road for a selection of dining options within a 15-minute walk. Walk trails, rent a jetski, take a dolphin/manatee tour or try your luck with some in-shore fishing! Additional options, along with shops, farmer's markets the minor league team for the Tampa Bay Rays are a short drive across Tom Adams Bridge.brbrUnwind in the bright and welcoming living room, complete with beach chic decor and a smart TV. Create delectable dishes in the gleaming kitchen, fitted with a full suite of appliances including a French-door fridge. Your guests can keep the chef company at the breakfast bar. Serve tasty meals at the table and converse as you indulge.brbrEnjoy the sea breeze while sipping your favorite beverage on the covered balcony off the living area. Lounge in style on the covered patio, walled for ultimate privacy. Go for a swim in the six-foot-deep unheated pool. Fire up the gas grill, then dine alfresco at the table. Complimentary WiFi and a washer & dryer are provided.brbrTHINGS TO KNOWbrThe unheated pool is 6’ deep and available year-round. Access is via the garage, or via the spiral staircase at the end of the 2nd-floor hallway.brThe pool is normally cleaned on Thursday. The cleaning day can vary.brStreaming services are available, but guests must log in using their accounts.brThis three-story house is accessed via one step at the entryway.brbrParking notes: There is free parking available for 2 vehicles.brbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brbrMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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Bath 3

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Sleep 8

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$124.86

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Apartment

Fiddler’s Green 2BR Getaway

Englewood, Florida, United States

Located in Placida just off Cape Haze, this Fiddler’s Green condo blends natural beauty with resort-style amenities. Relax on your private screened lanai overlooking lush Florida scrubland, or spend your days at the heated pool, tennis courts, and shuffleboard. With Boca Grande and Manasota Key beaches just minutes away, this is the perfect Gulf Coast retreat.brbrWhy You’ll Love Itbr• Peaceful condo community surrounded by Florida naturebr• Heated pool, clubhouse, tennis, shuffleboard & grillsbr• Prime Placida location near Boca Grande & Manasota KeybrbrSleeping Arrangementsbr• Master Suite – Queen bed, ensuite with tub/shower combo, lanai walkoutbr• Guest Suite – Two twin beds, ensuite bathroom with showerbrbrOutdoor Highlightsbr• Heated pool with sundeck and loungersbr• Clubhouse with community events and gathering spacesbr• Tennis and shuffleboard courtsbr• Gas grills available for guest usebr• Screened lanai with views of tropical greenery for added privacybrbrInterior Comfortsbr• Spacious open floor plan with natural lightbr• Dedicated workspace with window viewsbr• Large flat-screen TV in the living areabr• Washer & dryer located just off the kitchenbrbrKitchen & Diningbr• Fully equipped kitchen with modern appliancesbr• Plenty of counter space for meal prepbr• Dining table with seating for 4br• Coffee maker, toaster, blender, and cookware includedbrbrIncluded Home Essentialsbr• Wi-Fi and cable TVbr• Central A/C and ceiling fansbr• Fresh linens and towels providedbr• Washer & dryer in unitbr• Designated parking spacebrbrNeighborhood Perksbr• Boca Grande – charming village, beaches & world-class fishingbr• Manasota Key – laid-back beach bars, pristine Gulf coastlinebr• Lighthouse Grill & Tiki Bar – waterfront dining nearbybr• Dearborn Street – local shops, dining & weekly farmers marketbr• Outdoor adventures: kayaking, paddleboarding, and golf courses in RotondabrbrAccess & Parkingbr• Single-level living once insidebr• Dedicated parking space for guestsbrbrFrom tennis matches in the morning to sunsets on Boca Grande, Fiddler’s Green offers a peaceful coastal lifestyle. brbrBook your stay with Gulf Coast Vacations and Vacay Your Way on Florida’s Gulf Coast.
Bed 2

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Bath 2

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Sleep 4

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Exceptional(12)

$198.61

/ Nightly
Private Vacation Home

* Where beach days, pool nights, and unforgettable memories begin! *

Englewood, Florida, United States

Welcome to Villa Sanddollar – Your Slice of Paradise Awaits! brbrbrbrGet ready to kick back, relax, and soak up the Florida sunshine at Villa Sanddollar, a vibrant and stylish 3-bedroom, 2-bath custom-built escape nestled in the community of Englewood. Just minutes from the sparkling shores of Manasota Key, fabulous dining, and fun local shops, this cheerful getaway has everything you need for an unforgettable vacation—for up to 6 guests!brbrbrbrStep inside and feel the stress melt away as the bright, open great room greets you with comfy seating, a large flat-screen TV, and views of the crystal-clear saltwater pool and spa. With a relaxed, coastal vibe and neutral tones, it’s the perfect place to unwind with your favorite people and a bowl of popcorn after a sun-filled day. Need a cozy reading nook Head into the inviting study with an electric fireplace—a quiet hideaway to catch up on that novel or enjoy your morning coffee in peace.brbrbrbrAn open concept kitchen is a chef’s delight, creating a great flow for festive vacation meals. Offering granite countertops, wine cooler, dishwasher, microwave, large island with bar stools, and a convenient pantry ensures ample storage. A dedicated breakfast bar features a toaster, Keurig K-Duo single-serve and carafe coffee maker, electric kettle, and everything you need to start your mornings right! Thoughtfully stocked with extra gadgets and cooking tools, this kitchen makes preparing your favorite vacation meals feel effortless and fun.brbrbrReady to recharge The spacious primary suite is your private sanctuary, complete with a king bed, flat-screen TV, walk-in closet, and sliders to the pool deck. The spa-like en-suite bathroom features dual vanities, a walk-in shower, and a luxurious soaking tub for when you're in full vacation mode! Across the home, two more inviting bedrooms offer plenty of privacy for your guests. The second bedroom has a queen bed, flat-screen Smart TV, and walk-in closet. The third bedroom features a queen sleeper sofa, its own TV, and direct access to the lanai—perfect for extra guests or teens looking for a bit of privacy and their own retreat. The shared guest bathroom includes a single vanity, walk-in shower and direct pool access for easy rinse-offs after a swim.brbrbrbrStay connected with high-speed Wi-Fi and cable TV, and pack light—there’s a washer/dryer, plus all towels, linens, and pool towels are provided. The 2 car garage is stocked with 3 adult bikes and beach chairs, perfect for your coastal adventures! This home also facilitates a convenient self-check-in lockbox process, so you can start your vacation from the moment you arrive! brbrbrbrBut the real showstopper The outdoor space. Your private screened-in lanai features a sparkling saltwater pool and spa with optional heat, sun loungers for those golden tan days, a shaded dining area for alfresco meals, and a standalone BBQ grill for sizzling up your favorite vacation eats. Whether you're lounging with a cocktail, playing games poolside, or sharing s’mores under the stars, it’s made for memory-making!brbrbrbrWhen it’s time to explore beyond the pool, adventure is just minutes away! You're only 5 minutes from the pristine beaches of Manasota Key—where soft sands, turquoise waters, and breathtaking sunsets set the scene for shelling, kayaking, boating, or simply strolling along the shore. Craving more coastal charm Take a 20-minute scenic drive to Boca Grande, known for its world-class fishing, laid-back island vibes, and stunning Gulf views.brbrbrbrBack on land, discover a variety of local restaurants to satisfy every craving—from fresh seafood to international flavors. Dive into the local culture with year-round events like farmers markets, art shows, live music, and more. Whether you're sipping coffee at a seaside café, browsing local boutiques, or paddling through peaceful waterways, this slice of Florida paradise is packed with unforgettable experiences!brbrbrbrVilla Sanddollar is more than a vacation home—it’s where beach days, pool nights, and unforgettable memories begin. Come live your best Florida life!brbr
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Exceptional(7)

$318.11

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Private Vacation Home

Private Luxury renovated pool house 1.5 miles to Manasota Beach.

Englewood, Florida, United States

Newly renovated “Old Florida Modern “ pool house located on Bayshore Dr. across the street from the inttracoastal waterway and just 3 minutes to Manasota Beach Park . See VRBO listing # 2939628 3/3 for 5 star reviews .brSituated on over an acre with a private, sprawling backyard. The property is surrounded by a forested nature sanctuary .This unique vacation property is within 1.5 miles of Manasota Beach Park with boat ramp, picnic areas and full facilities .The main house front entrance features a succulent rock garden courtyard and bench . A perfect spot to enjoy a glass of wine and watch the evening sunsets.brThe house interior has a MidCentury Modern aesthetic, with an open layout , disappearing glass doors and direct views out to the pool , backyard and forest preserve. Two bright, cozy, coastal bedrooms both with gorgeous bathrooms that feature floor to ceiling, Mother-of-Pearl and sea glass tiles with floating vanities. The main bedroom has a king size bed and opens up to the patio with sliding glass doors and a walk-in closet. The second bedroom has a queen size bed and is located at the front of the home with minimal water, forest and evening sunset views .The open concept, living / dining room has a full wall of disappearing, sliding glass doors that open to the patio and pool area for an indoor outdoor experience. The gourmet kitchen has new stainless appliances with wine fridge and stacked washer /dryer unit hidden in the utility closet. Upscale features like floor to ceiling, mother of pearl tile, quartz counters tops and a sliding glass door that opens to the patio dining area.brbrThe large patio and pool deck features a covered dining area with ceiling fan, bistro lights and cabana curtains. The pool deck has a barbecue grill as well as comfortable lounge chairs to relax and enjoy the best of Florida living .brThe newly renovated, crushed marble , 35 ft. heated kidney pool with glass tile, resting ledge and controllable multi colored light show is the center of relaxation and fun . Pool floats and toys are available for use as well as beach chairs , umbrellas …brThe upscale Bayshore Dr. neighborhood is a safe, quiet and picturesque area for bike riding, running or peaceful walks .brA butterfly meditation garden with bench and surrounding nature preserve allow you to view nature at its best with frequent sightings of hawks, eagles, resident gopher turtles, rabbits, and an occasional Florida bobcat or panther.brbrConveniently located within 15 minutes of downtown Venice, with its many wonderful beaches, restaurants, shops, farmers market, entertainment, and various cultural activities.brOld Englewood town is also within a 15 minute drive to the south with its great restaurants, shops, farmers market and nightlife and beaches. Walmart , Publix , CVS and Target are all within a few miles.brbrThis Bayshore Drive vacation rental is an ideal peaceful sanctuary to relax and enjoy your next family vacation in the beauty and nature of coastal Florida.brbr* An Additional 450 sq ft Luxury Studio Apartment with separate entrance is also available for larger parties. Please see listing and reviews at VRBO # 2939628. “Bayshore Vacation Property.”Additional fees apply . *They are not rented separately to different parties .
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Bath 3

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Sleep 5

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