Remarks: REASONABLE SEASONAL RENTAL ~ Not AVAILABLE DECEMBER 2026 TO MARCH,2027 SEASON~1 MONTH MINIMUM ~787 Liberty St., Englewood, 34223~ Centrally located! Bike to downtown Englewood or Manasota Beach. Quiet area close to shopping, Thursday farmers market, car shows, art shows, golfing, fishing and beaching. 10 miles from the new Wellen Park and the Braves Stadium. 2 BR, 1 BA home with screened lanai & carport. Tile throughout. Full bath with tub & shower. Both bedrooms have queen beds. $2,900/mo. + 13% tax. $250 departure cleaning fee. $500 security deposit. Pet considered with $300 non-refundable fee (NO CATS owner allergic). Call Pineapple Gulf Property Mgmt. for details Voted Best of Englewood 2024/2025

Listing is courtesy of: CELEBRATION RENTAL GROUP (407-566-8009)

Listing Agent: Dane Bradley (407-566-8009)

Remarks: Spend the Winter months in Sunny Englewood, Florida! FULLY FURNISHED RENTAL PROPERTY AT 1153 Clark St...2 bedroom, 2 bath, 1 car garage home located in Englewood on a quiet dead end street.  Boat dock will accommodate up to 24 ft. Easy access to Gulf.  Fully furnished home awaits you for your winter getaway.  Includes all the houseware items, linens, pots and pans, beach chairs and umbrellas. 2 nice size walk in closets. Split floor plan.  Coffee bar. Very nicely decorated. Both bathrooms have walk-in showers. Full size washer and dryer.  All new furnishings. Brand new kitchen. Screened lanai with a view of the canal. Close to local beaches, Wellen Park & Cool Today & Atlanta Braves stadium, Thursday downtown Englewood farmers market, shopping, local restaurants, golfing and fishing.  Includes all utilities and internet.  Streaming service only.  Rent is $4,000 + 12% sales tax, $250 departure cleaning fee and $500 security deposit will confirm your rental.  THIS IS A NON SMOKING RENTAL PROPERTY.  SORRY, PETS ARE NOT WELCOME. Call Pineapple Gulf Property Mgmt. for details on this property. Voted Best of Englewood 2024/2025/2026

Listing is courtesy of: CELEBRATION RENTAL GROUP (407-566-8009)

Listing Agent: Dane Bradley (407-566-8009)

Remarks: Enjoy the best of historic Englewood living in this charming updated rental just blocks from Indian Mound Park and its public boat launch. This home offers a convenient location close to everything that makes Englewood special. The home features a brand-new fully renovated bathroom completed in 2026, along with major system updates including a roof replaced in 2017 and HVAC system replaced in 2020. An indoor storage area off the kitchen provides valuable extra space for pantry items, hobbies, or household storage. Outside, relax on the screened front porch, enjoy the spacious backyard and patio, or take advantage of the property's ample parking and storage possibilities. There is room to accommodate a boat, making it ideal for those who enjoy Florida's outdoor lifestyle. Located just a short walk or bike ride from downtown Dearborn Street, you'll have easy access to local restaurants, shops, community events, and the popular Englewood Farmers Market. Indian Mound Park is only blocks away and offers a beautiful setting to launch a boat, fish, or enjoy spectacular sunsets over Lemon Bay. Englewood Beach is approximately 3 miles away, putting morning beach walks, yoga, and sunset strolls within easy reach. The home can be offered partially furnished although not all photos have current furnishings. Tenant is responsible for electric, water, cable/internet, and lawn care. Don't miss this opportunity to enjoy a comfortable home in one of Englewood's most desirable and walkable locations.

Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)

Listing Agent: Lauren Hofing (773-960-1122)

Remarks: Welcome to this charming 2BR and 2BA home near historic Dearborn Street in Englewood. Walk to your favorite restaurants, live music, shopping and activities. Short 10-minute drive to Englewood Beaches and 20-minute ride to downtown Venice and beaches. The backyard paradise features a playground, fire pit area and multiple sitting areas for relaxing in the Florida sun. The fenced in yard is perfect for your dog's enjoyment. The large, air-conditioned lanai has abundant light and is filled with custom built in cabinets and a desk area. An artist or crafters dream come true. Special Summer rate at $1,995 monthly. Rented for the 2027 season. 30 Day minimum. 6 month plus lease available that would save guests paying the 13% State and Tourist Tax.

Listing is courtesy of: FLORIDA DREAMIN' REALTY GROUP INC (941-303-0855)

Listing Agent: Bill Williams (941-303-0855)

Remarks: Welcome to your dream home in the heart of Englewood, Florida! This recently renovated 3-bedroom, 2-bathroom gem is now available for rent, offering a perfect blend of modern comfort and Florida charm. With a refreshing pool and a host of upgrades, this residence promises a lifestyle of relaxation and style. Property Details: Address: 11065 Waterford Ave, Englewood, FL 34224 Bedrooms: 3 Bathrooms: 2 Square Footage: 1271 Rent: $2,400.00 Features: Modern Kitchen: The heart of this home features a brand-new kitchen with stainless steel appliances, granite countertops, and ample cabinet space. It's a chef's delight! Spacious Living Areas: Enjoy the open and airy living spaces, perfect for entertaining friends and family. The living room is bathed in natural light, creating a warm and inviting atmosphere. Master Suite: Retreat to the luxurious master suite with a private bathroom. The master bathroom boasts contemporary finishes and a walk-in shower for a spa-like experience. Two Additional Bedrooms: The two additional bedrooms are generously sized and can be utilized as guest rooms, home offices, or however best suits your lifestyle. Sparkling Pool: Beat the Florida heat in your own private pool! Whether you're taking a refreshing dip or lounging by the water, the pool area is perfect for relaxation and entertainment. Outdoor Living: Embrace the Florida lifestyle with an outdoor space that's perfect for grilling, dining, and enjoying the beautiful weather. Updated Bathrooms: The additional bathroom has also been tastefully updated with modern fixtures and finishes. Convenient Location: Located in the vibrant community of Englewood, you'll be close to shopping, dining, parks, and beautiful Gulf Coast beaches. Additional Information: Availability: Ready for immediate move-in. Pets: Pets may be considered with an additional deposit. Utilities: Tenant responsible for utilities. Lease Terms: 12-month lease preferred. Schedule a Showing: Don't miss the opportunity to make this stunning property your new home! Contact us today to schedule a showing and experience the beauty and comfort of this renovated Englewood residence.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Richard Carey (913-963-9800)

Remarks: Seasonal or Annual Rental. Fully turnkey/furnished 3 bedroom, 2 bath home. ONLY 2 miles to Manasota Key Beach. All you need to bring is your toothbrush and a suitcase. The home is extremely well equipped with everything you need including beach chairs, towels and even ice coolers. Master suite with king size bed, 2nd bedroom has a queen size bed, 3rd bedroom has 2 double beds. Kitchen was completely remodeled with all stainless steel appliances. It was designed for entertaining, with everything you need and more. The bathrooms and bedrooms are stocked with an abundance of linens & towels. The backyard is a vacation Paradise with your own bocce ball court, outdoor shower and large covered, screened in Lanai. The home is well equipped with electronics - every room has a flat screen TV, even the Lanai! Tile flooring throughout. No HOA. Small dogs or cats accepted. No smoking. Available June 2026 through January 2027. Everything is included!

Listing is courtesy of: SECURE DOOR PROPERTY MANAGEMENT (941-231-4065)

Listing Agent: Alan Myhre (941-866-6685)

Remarks: Welcome to your beautifully remodeled coastal retreat at 275 Pineapple Street in Englewood, Florida! This charming 2-bedroom, 1-bath home has been thoughtfully updated from top to bottom, offering a fresh, modern feel with all the comforts you’re looking for. Step inside to discover stylish luxury vinyl plank flooring throughout, complemented by a bright and open living space. The fully renovated kitchen is a standout feature, boasting sleek granite countertops, stainless steel appliances, and plenty of cabinet space—perfect for cooking and entertaining. Both bedrooms are well-sized with great natural light, while the updated bathroom showcases clean, contemporary finishes. A single-car garage adds convenience and includes a washer and dryer for your everyday needs. Location is everything, and this home truly delivers. Nestled in a quiet neighborhood, you’re just minutes from the stunning beaches of Manasota Key, local dining, shopping, and all that Englewood has to offer. If you’re looking for a move-in-ready rental in a prime location with modern upgrades throughout, this home is a must-see!

Listing is courtesy of: LANDMARK REALTY (941-575-4550)

Listing Agent: Lisa Blanchard (941-575-4550)

Remarks: Listing reflects peak season rate. Escape to Good Vibrations, a dog-friendly canal-front home in Englewood, designed for a serene and stylish escape. Swim in your private, heated saltwater pool or relax on the spacious screened lanai, perfect for sun-kissed afternoons and starlit gatherings. With direct access to the tranquil canal, you can launch kayaks or paddleboards right from your backyard and explore scenic waterways. Inside, discover an an open, light-filled haven boasting a bohemian flair, a fully equipped kitchen for whipping up vacation feasts, and the convenience of an in-home washer and dryer. We've got you covered with a complimentary starter kit and all the essentials, including cozy linens, fluffy towels, and beach-ready gear. Sleeping up to 4 guests, you'll find comfort in the primary bedroom with a king bed and the guest bedroom with a queen bed, both offering private spaces. Plus, enjoy complimentary Wi-Fi and a work space in the living area for those who work remote. Immerse yourself in the local scene with vibrant arts, lively festivals, delicious dining, and charming shops on Downtown Dearborn Street. Step out and explore Englewood's stunning Manasota Key Beach, a treasure trove of crystal-clear waters and shark teeth. Getting around is a breeze: we're just 10 minutes from the Tom Adams Bridge (to get you to Manasota Key), and you can even hop on Stumpy’s Free Ride for complimentary shuttle service around Manasota Key. While exploring by car lets you uncover hidden gems at your own pace, our local team is always here to ensure your stay is relaxing, enjoyable, and filled with fantastic recommendations. Book your vibrant escape today! Please note: If you are bringing a pet, there is a $250 pet fee (per pet). We encourage you to inquire about the specific pet policy applicable to your reservation for clarification, including how and when the pet fee will be collected.

Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)

Listing Agent: Beth Dilley (941-400-1322)

Remarks: Turnkey Furnished Private Pool Home in Boating Community – Englewood Isles Retreat! 2BR | 2BA | Screened Pool | 2-Car Garage | Sleeps up to 6 people. Welcome to your perfect Florida escape in the sought-after boating community of Englewood Isles. This beautifully maintained 2-bedroom, 2-bathroom pool home is designed for comfort, relaxation, and convenience—ideal for a seasonal getaway, snowbird stay, or monthly vacation rental. From the moment you arrive, a new impact-rated front door welcomes you into a sunlit open living space with elegant ceramic tile throughout (no carpet!) and fresh interior paint. The formal living and dining areas are outfitted with electric blinds, custom drapes, and a pocket slider leading to the screened lanai and pool—perfect for indoor-outdoor living. Split Floor Plan for Privacy. The primary suite features a walk-in closet, ensuite bathroom, and Plantation shutters for a calm, coastal feel. On the opposite side, the spacious guest bedroom offers a walk-in closet and nearby access to a pool bath with granite vanity and impact door to the lanai—great for guests! Whip up meals in the Chef’s Kitchen equipped with: granite countertops, Thomasville soft-close cabinets, pull-out spice rack & touchless faucet, tile backsplash and newer appliances, accent cabinet lighting. Just off the kitchen is a pantry closet and a breakfast area that opens to a light-filled family room with views of the pool. Interior laundry room with washer & Dryer. Spacious 2-car garage with a fresh epoxy floor, double utility sink, and impact garage door. Outdoor Oasis where you can relax on your freshly painted lanai, enjoy a swim in the private screened-in pool, or take a walk through this serene, well-kept neighborhood. Englewood Isles sits on Forked Creek with a nearby community marina & boat ramp. Boat slips with access to Lemon Bay and the Gulf are available for rent. It's perfect for boating enthusiasts or anyone looking to enjoy coastal living. You're just minutes from Manasota Key beaches, golf, shopping, dining, and the charm of downtown Englewood. Whether you're looking for sun, sand, or simply serenity—this home has it all. Now booking for seasonal and monthly stays! Rental rates: *Off-Season: $3,000 per month plus taxes & fees. *In-Season: $6,000 / month plus taxes & fees. Additional rental fees include: (13%) Sales & Resort Tax, ($100) booking fee, ($350) exit cleaning fee, ($400) pool heater fee (mandatory from Nov - Apr). Pet Friendly: up to 3 pets, under 60 lbs each with $250 pet fee per animal * (see breed restrictions). *Prices based on 2-person occupancy. Additional persons staying in the unit for a period of longer than 7 days may be considered additional occupants and subject to additional rental fees being charged and/or application and approval process if the community is governed by association rules and regulations. Your rental Agent must be advised of all additional occupants and dates they will be in the unit. Note that rates are subject to change without notice and reservations are not guaranteed until an initial reservation deposit is received. Also available for long-term lease (over 6 months stay) at discounted rate of $2,500.00 per month plus utilities.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Tanya Agle (484-904-5588)

Remarks: Beautifully furnished and recently renovated 2-bedroom, 1.5-bath home available for month-to-month or short-term rental terms of 3 to 6 months. Located in a quiet Englewood neighborhood, this home is less than 10 minutes from Manasota Key Beach and approximately 1 mile from Dearborn Street’s restaurants, shops, and local attractions. Offered fully furnished, the tenant only needs to bring personal belongings. The home also a fully fenced in yard, laundry area, garage, and long driveway. Tenant is responsible only for water and electricity. A great option for anyone needing temporary housing, a shorter-term rental, or a comfortable furnished home for a few months in a convenient Englewood location.

Listing is courtesy of: KW COASTAL LIVING (941-473-7399)

Listing Agent: Veronica Diquez (561-809-1769)

Remarks: This home is a "Must-See" for anyone who the tropical settings and comforts that this home offers. Landscape and foliage makes for great privacy for this fully furnished bungalow home. The home has a 2-space carport and a thatch roofed sitting area out front. The home has an open floor plan that is full of light. The kitchen has modern appliances and a center island. Both bathrooms have walk-in showers and the living room has a stained-wood plank ceiling with wood support beams. The yard has several trees that offer plenty of shade and relief from the Florida heat. The home is one block from the canals that are part of the lush, tropical environment.

Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)

Listing Agent: Michael Bouchard (407-443-1284)

Remarks: RARE BEACHFRONT PROPERTY AVAILABLE NOW! Step into a world renowned paradise on Manasota Key. Located within 1 hr of all major airports in Southwest Florida. This is private island living at its finest. This house boasts a beautiful open floorplan with each room having a view of the beach and Gulf of Mexico. The property is gated and has a secure backyard. Walk just steps onto the powdered beach sand and Gulf of Mexico. Call now for this great opportunity to live on a private beach.

Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)

Listing Agent: Andrew Martell (941-350-3190)

Remarks: This charming 2 bedroom, 2 bath, open concept Florida Bungalow is situated on the Intracoastal. The waterfront location offers breathtaking views of the Intracoastal Waterway and Endless Sunset Lemon Bay Views. Imagine waking up to the tranquil sound of the water and its truly a rare find. Enjoy your morning coffee while watching boats go by. With its prime location, your guests will have easy access to water activities, fishing, and beach relaxation. The proximity to the water adds a touch of tranquility and serenity to the overall vacation experience. One of the standout features of this property is the dockage with a convenient jet ski lift. Your guests will have the incredible opportunity to dock their watercraft right at their doorstep, making it effortless to explore the waters and enjoy various water sports. Whether it's a leisurely boat ride or thrilling jet ski adventure, this added amenity elevates the overall experience and provides endless possibilities for entertainment. This property also offers a unique feature where the garage has been transformed into a personal fitness room. This space is fully equipped with exercise equipment, providing ample room for workouts and promoting a healthy lifestyle. You will have the convenience of staying active without even leaving the house, ensuring your overall well-being is prioritized during your stay. Come see what Florida Living is all about.

Listing is courtesy of: TARPON REAL ESTATE, INC. (941-697-7575)

Listing Agent: Stephinie Futch (941-662-7451)

Remarks: Welcome to The Crab Apple. This waterfront home is the perfect escape from life's hustle and bustle. Relax and enjoy this home's beautiful landscaping and tropical pool. The home offers 2 bedrooms and 2 baths. The home is fully equipped and ready for guests. French doors leading to the lanai add a charming touch. The street is very quiet with minimal traffic. There is a 250-acre regional park a few blocks away with hiking/biking trails, and many other amenities. Located in quaint Englewood Florida. This home is close to beaches, shopping, golf, and restaurants. Come and enjoy the Florida sunshine.

Listing is courtesy of: TARPON REAL ESTATE, INC. (941-697-7575)

Listing Agent: Stephinie Futch (941-662-7451)