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Looking for a serene coastal retreat? Our monthly rentals in Englewood, Florida, offer the perfect long-term getaway in a charming beach town along the Gulf Coast. Whether you’re planning a winter escape or an extended vacation, Englewood’s relaxed atmosphere, beautiful beaches, and outdoor activities make it a fantastic destination.
Distance to beach: 1 miles to Manasota Beach
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**Escape to Paradise in Southwest Florida!**Why use a hotel when you can cook at home and enjoy this beautiful property located just a few short miles from Manasota Key and Venice/Nokomis beaches!Discover the ultimate getaway in this beautifully refurbished 1-bedroom, 1-bath condo, perfectly nestled...
Featured review
Great condo! Everything I needed was provided and the king size bed was very comfortable. Very clean; furniture and appliances appear to be new. I liked the location, not far from three different beaches,...
Distance to beach: 5 miles to Englewood Beach
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NOW AVAILABLE Pending Cancellation “COTTAGE ON COCOANUT" Classic Beach Cottage in Downtown "Old Englewood Village."WATER VIEW OF LEMON BAY1/2 block to downtown shops, restaurants,events,and all Old Englewood has to offer!! 5 Minutes to the Beach or 1 mile to boat launch....
Featured review
Excellent location to enjoy the local attractions on Dearborn Street. Walking distance to Farmers Market, restaurants, shops and parks. Landlord quick to respond to any concern. Screen lanai a bonus to...
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Beautiful 3 bedroom pool home 1.25 miles from manasota beach quick walk or drive through the neighborhood to beach home is well stocked with all amenities outdoor lanai and pool area with large dining area interior comfort has two living rooms cable and internet provided 30 day rental minimum no...
Distance to beach: 1 miles to Englewood Public Beach
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Enjoy having breakfast along with serenity & beauty of Gulf, viewed from Alcove downstairs else the den upstairs. Great comfort and luxury of home at beach side condo at Tamarind Gulf & Bay condominiums. Very quiet & relaxed area of the Manasota Key , about walking distance for plenty of restaurants...
Featured review
Great location, layout, and furnishings. We felt most welcome by Julie's very generous communications. We would recommend this great unit to anyone who likes a quiet & serene beach vacation!We hope...
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GORGEOUS, GULF FRONT VILLA CONDO AT “ EL GALEON BY THE SEA”This lovely 2 bedroom/2 bath unit is part of a 20 unit villa condo complex, situated directly on the beach on beautiful Manasota Key. Because this is a relatively small complex, it offers guests a more lay back, relaxing atmosphere....
Featured review
Love staying here even though there's a lot of clean-up working happening around the area from the hurricanes! This place had a beautiful view of the sunsets from the living room picture window! The balcony...
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Distance to beach: 5 miles to Englewood Beach
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Clean ,comfortable and centrally located.. Two bedroom, 2 bath, sleeps six with large screened in Florida room. Pet friendly with a fenced in yard, washer and dryer, wifi, beach toys and chairs, 2 bicycles and a bbq grill. Two blocks from Ricaltinis bar and restaurant and 6 blocks to Stump Pass Lighthouse...
Featured review
We have been coming to Englewood for 7 years . We stayed at this awesome home December 2024-february 2025. We have had a great stay and are signed up for next year. The owners are attentive and responsive....
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Charming Old Florida Condo…Minutes to World Famous Beaches. 2 Bedroom, 2 Bathroom Condo in Active Adult Community with Pool. Spacious Condo with plenty of room for 4 with screened in porch and all the necessities for a short vacation or a seasonal stay!
Distance to beach: 3 miles to Englewood Beach
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A beautifully remodeled home with a spacious lanai, a swimming pool, and 25 feet of seawall for a boat—plus the convenience of being just a short walk from Dearborn Street and Indian Mound Park & Boat Ramp. It strikes the perfect balance between accessibility and privacy, making it feel like...
Distance to beach: 4 miles to Englewood Beach
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Enjoy the beach life or choose to stay in your spacious home and relax around a beautiful pool area which overlooks a spring-fed lake. Our 3 bedroom, 2 bathroom pool home with modern furnishings is located in a quiet, safe location just a few short miles from area beaches and is conveniently located...
Featured review
Cindy and Rich are the best hosts! They made sure everything was perfect before our arrival. We absolutely love their place.Their home is clean and inviting, the pool is always warm and the yard is large,...
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Luxury Penthouse Condo with Breathtaking Water Views – 8581 Amberjack Circle #301, Placida (Near Boca Grande) Indulge in coastal luxury at its finest in this turnkey furnished 4-bedroom, 3-bath penthouse condo at the Hammocks of Cape Haze, located in Placida, just minutes from the world-renowned...
Distance to beach: 1 miles to Manasota Key Beach
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This stunning recently remodeled 2,400 square foot home is located in beautiful North Englewood, (2 blocks from Venice) Florida. With multiple beaches so close, it's only a quick drive to get to some world class beaches including Manasota Key Beach, Casey Key, Venice Beach and 30 minutes to Siesta...
Featured review
This home fit our needs perfectly. It was extremely clean and well organized. We loved the layout and functionality of the home. We enjoyed the pool area and spent quite a bit of time out back. Access to...
Distance to beach: 3 miles to Boca Grande, Palm Island South , Manasota Key
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Four-bedroom condo. Quiet & secluded. Newly renovated pickle ball court!! Minimum stay: 14 days No Pets or SmokingGorgeous newly renovated condo. Professionally decorated & carefully designed to provide the perfect blend of space & functionality. With an open & airy plan, the...
Featured review
Location was what initially attracted us to The Sanctuary. Out your back door is Florida nature at its best between Lemon Bay Conservancy and Amberjack Environmental Park. However, our experience has...
Distance to beach: 4 miles to Englewood Beach
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Welcome to this lovely spacious house in Englewood in the Grove City District. Fantastic for families, golfers, fishermen and, girls or boys weekend. This adorable property features 4 cozy bedrooms that sleep 2 in each- 3 rooms with king beds and 1 with a queen bed. Enjoy the convenience of 2 bathrooms,...
Distance to beach: 4 miles to Manasota Key Beach, 8570 Manasota KeyRd, Englewood
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FRIDAY, Dec 5, 2025 ~"Don't worry if you're making waves just by being yourself. The moon does it all the time." —Scott StabileWide water View over Crystal Clear Pool! This relaxing retreat is positioned on deep water 'Forked Creek' which leads to the Intracoastal...
Featured review
Our stay is from May through June. It's been 8 years that we have enjoyed your beach home and always look forward to our next summer again 2026. Linda & Bobby are the best hosts anyone could have. They...
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2 bedroom 2 bath condo with full kitchen, living and dining area, and lanai. Condo is a first floor corner unit located next to the pool and clubhouse. All bedding and bath towels are supplied. Complete kitchen with all utensils, dishes (etc.), dishwasher, washer and dryer. The Living Room has a 55”...
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Beachy furnished 2/1 home in historic Englewood. Great location, just 2 miles to Englewood Beach, 1 mile to Dearborn Street. Easy 5 minute walk to Lemon Bay Park with boat launch. Carefree Boat Club is also a short walk away.Newly remodeled kitchen and bath. All new appliances, cabinets, quartz...
Featured review
I had to relocate because of Ian and I saw this on Zillow and I called the owner and she was more than willing to rent to me for the 3 months that I needed as I was awaiting my home to be replaced. She's...
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DECEMBER AND JANUARY SPECIAL!!! HURRY!!! Everything You Could Ask For and More in this beautiful and relaxing 2 bedroom condo with a Gulf view. This condo complex is one of only two on the island that is gated for your security. As you enter the condo, you are greeted by a wet-bar and cabinets for extra...
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Welcome to Your Home Away From Home – A Spacious 3-Bedroom, 2-Bath Condo at The Surf ClubRelax and unwind in this beautifully updated, spacious 3-bedroom / 2-bath condo, fully equipped with everything you need to feel right at home. This condo has all the comforts and conveniences to make your...
Distance to beach: 2 miles to Englewood
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San Casa is a beautiful and luxurious three bedroom home, situated in Grove City, Englewood on Florida's Gulf Coast. it is the ideal place for a truly relaxing vacation.Our beautiful Gulf Coast home has three large bedrooms , two bathrooms and an extended private, heated pool for your enjoyment....
Featured review
The location of this house was perfect for us, close to the stores we need, the beach and the wonderful Englewood Farmer's Market. The house is beautifully decorated, the beds comfortable and the pool...
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Beautiful 3 bedroom, 2 bath, 2 car garage pool home situated on a private greenbelt garden setting available for Seasonal Rental. Very spacious and roomy home with vaulted ceilings with 1762 square feet of air-conditioned living area. This beauty is a split plan offering maximum privacy for you and your...
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Large 3 bedroom/2.5 bathroom condo, fully tiled, high ceilings with a screened balcony facing the pool. It's less than a 2-minute walk to the Gulf of Mexico - so close that you can hear the waves on the wide beach when the sliding glass doors are open. Just outside the screened balcony, there is...
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WELCOME TO SERENITY! Your Exquisite Getaway on Lemon Bay Welcome to Serenity, a stunning retreat perfectly nestled on Lemon Bay, and just a 5 minute drive to the beautiful Manasota Key Beach. This beautifully designed home offers seamless indoor-outdoor living, with floor-to-ceiling windows providing...
Distance to beach: 6 miles to Englewood Beach
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New House build 2024. 3 Beds with TV, 3 Baths, 6 Guests, nice view to the lake from the living room, communitiy pool with gym 24/7 and 4 pickelball places,
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Welcome to Sun, Sand & Serenity! Walk in, kick off your shoes, and relax. This sun filled 2 bedroom/2bath plus loft with extra bed and with a lanai condo is ready to be your home away from home with a coastal feel and an open floorplan.Pelican Landing #E-204 is located in a wonderful gulf to bay...
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BRAND NEW! Dream Vacation. Crystal blue waters and uncrowded beaches.Welcome to "Bayfront Retreat", your premier destination for an unforgettable waterfront vacation experience! Manasota Key is one of Florida's best kept secrets with its unspoiled beaches and clear blue waters...
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Condominium, second floor, corner unit, one king bed, 2 single bed, all equipped, washer dryer, stove, refrigerator, dish washer, A/C , Lanai, pool, BBQ area, tennis court, shuffle board, club house with pool table, library. WIFI, 2 TV, Cable. 5 minutes from beaches, restaurants, all you can ask for...
Featured review
After showed available, was told it was not really available for month of February, so we were unable to stay. Very disappointed.
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Beautiful two bedroom two bath recently redecorated condominium in Fiddlers Green In Englewood Florida. Great location with one Italian restaurant right at the entrance within walking distance. Many restaurants nearby and is only a few miles from the bridge going over to BocaGrand. This condominium has...
Distance to beach: 4 miles to Englewood Beach
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IDEAL LOCATION!! Walk to Lemon Bay and Dearborn Sts. shops, restaurants, Farmer’s Market!!!!!Mermaid Cove is an oasis in the heart of Old Englewood VillageThis vintage-style 1940's renovated bungalow is just one block from the Dearborn artistic district where you will enjoy Art Festivals,...
Featured review
The bungalow was exactly what we wanted- close to beaches, restaurants, hiking, fishing and other activities! The bungalow was clean and well equipped with everything we needed to comfortably spend two...
Distance to beach: 3 miles to Manasota
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Experience the perfect peace of comfort, and coastal life in this meticulously enhanced 1 bd/ bth, 55+ condo. Nestled in the Englewood Isles community, this residence overlooks (2nd floor) the tranquil Intracoastal Waterway and sits just one scenic bridge from the bay.Relax in style at the heated...
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Welcome to your charming slice of paradise in Englewood, FL. This 2 bedroom, 1 1/2 bathroom home has undergone a recent renovation, offering the perfect blend of coastal and modern comfort.Upon entering the home, you will feel the open and airy living space and seamless flow from the living room...
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Welcome to Tamarind – Your Perfect Beach-to-Bay EscapeDiscover coastal living at its best in this comfortable ground-floor 2-bedroom, 2-bathroom condo with stunning Gulf views. Step right outside your patio and enjoy peaceful mornings listening to the waves with your favorite beverage in hand....
Distance to beach: 3 miles to Englewood Beach
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Attention Snowbirds. Three bedroom Two bath private home available with open floor plan. Perfect for family gatherings. Large master bedroom and bath are separated from the two guest bedrooms. Outside is a large swimming pool with large deck and covered porch when you need to escape the sun. Located...
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Breathtaking views of the Gulf of Mexico! Just steps from the beautiful beach of Manasota Key Spacious, 3 bedroom, 2 1/2 bathroom 2nd floor Condo in the gated community of Boulder Pointe. Large, open kitchen has plenty of counter space and two breakfast bars to enjoy coffee or a cocktail at sunset. Master...
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This two bedroom, two bathroom is in a beautiful location and minutes from 4 beaches, water sports and golf courses, restaurants, hiking and shopping. Enjoy two pools on the premises, one is directly across this unit. Shuffle board, pickleball and tennis courts are also available. The unit backs...
Featured review
We stayed in December of last year, and the place was immaculate. It is a great location to get to other areas in this area of Florida. And the pool and vicinity was well maintained. We would definitely...
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THIS PROPERTY IS A SATURDAY CHECK IN DAY ONLY!!Experience magnificent Gulf views from almost every room of this top-floor duplex. Built in 2018, this property has many high-end finishes and is modern coastal living at its finest. The property has yards of PRIVATE beachfront on the Gulf, and lots of...
Distance to beach: 7 miles to Englewood Beach
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Discover our Paradise 3-bedroom, 2-bathroom Palms Retreat. Embrace the beach vibes, perfect your golf swing, reel in the excitement of prime snook and tarpon fishing spots or relax by the inclusive private pool. A short drive away is the Tampa Bay Rays Stadium. Stay seamlessly connected with our high-speed...
Distance to beach: 5 miles to Englewood Beach
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Available to pet free and non-smoking households. 30-day min off-season, 75-90 day minimum high season. --------- Relax in this cozy 2 bedroom / 2 bathroom private bungalow home with coastal decor throughout. Furnished with two queen sized bedroom sets and leather seating in living areas. The dining...
Browse through a variety of monthly rentals in Englewood, from waterfront condos to spacious homes. Whether you want to be close to Manasota Key or enjoy a quiet spot near Lemon Bay, you’ll find the perfect rental to suit your needs. Experience the comfort and convenience of a long-term stay in this peaceful town.
Secure your long-term rental in Englewood today by browsing our listings. Whether you’re visiting for the season or planning an extended trip, Englewood provides the perfect backdrop for a relaxing and enjoyable stay.
Booking in advance ensures you get the best rental for your desired dates. Englewood’s popularity as a winter retreat means rentals fill up fast, so plan ahead to lock in your preferred property
Group-Friendly Rentals
Planning a family reunion or getaway with friends? Englewood offers spacious rentals with multiple bedrooms, large living spaces, and often direct access to the beach or water, making them ideal for group vacations.
Family-Friendly Monthly Rentals
Englewood is perfect for families looking for outdoor activities and beach days. Attractions like Stump Pass Beach State Park and Lemon Bay Park offer nature trails, kayaking, and wildlife viewing. Our family-friendly rentals come with spacious living areas, outdoor spaces, and proximity to family-friendly attractions.
Romantic Getaways for Couples
Englewood’s quiet beaches and stunning sunsets make it the perfect spot for couples. Cozy monthly rentals offer private outdoor spaces, ocean views, and peaceful surroundings for a romantic retreat.
Winter Retreats for Snowbirds
Englewood is a top destination for snowbirds seeking warm weather and a laid-back lifestyle during the winter months. Our monthly rentals provide the perfect home base for exploring Englewood’s beaches, parks, and dining options, all while escaping the cold northern winters.
Plan your winter escape to Englewood by booking your long-term rental today. Enjoy the warm weather, friendly community, and relaxed coastal lifestyle that make Englewood a favorite among snowbirds and long-term visitors.
Englewood is known for its outdoor adventures and beautiful beaches. When you stay in one of our monthly rentals, you’ll have access to:
💰 Highest rates
February and March
🎉 Busiest month
March
🏠 Popular home types
Beachfront condos and single-family homes
🔥 Hottest months
July and August
❄️ Coldest months
January and December
☔ Rainiest month
June through September
🌺 Best months for flowers
April and May
🌴 Peak tourist season
December through March
🍂 Quietest months
September and October
🌊 Best beach months
March through May
🏌️ Best golfing months
November through April
🎨 Top cultural events
Englewood Seafood & Music Festival (February), Pioneer Days Parade (July)
🍽️ Best dining months
January through March
🦋 Best months for nature activities
March through May
🛶 Best water sports season
June through September
🏖️ Best months for shelling
May and June
📅 Local festivals peak
January through March
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