Vacation rentals in Englewood

4.91 out of 5 average rating, 271 reviews

A tranquil pool reflects a colorful sunset with hues of orange and pink in the sky, surrounded by lush greenery. The paved area features decorative stonework, enhancing the serene outdoor setting by the Gulf of Mexico.

Guesthouse 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.

4.89 out of 5 average rating, 148 reviews

An aerial view captures the coastline of Manasota Key, showcasing the blue-green waters and sandy beach. The surrounding area features a mix of residential buildings and green spaces, with multiple boats visible in the water and a bridge connecting to nearby islands.

Cottage in Englewood

Free kayak/bikes/walk to beach/full cottage #1

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.

4.96 out of 5 average rating, 127 reviews

An aerial view showcases a raised townhome surrounded by palm trees, with the beach and ocean visible in the background. The home's light blue exterior complements the coastal setting, while a spacious deck on the lower level offers an inviting space for relaxation.

Townhouse in Englewood

Summer Sunsets just 50 steps to uncrowded beach

Escape to your dream coastal retreat! This exquisite 2- king bedroom, 2-bathroom home is a paradise, located just steps from the beach. Nestled among swaying palm trees, this haven offers a serene oasis where the calming sounds of the water create a tranquil atmosphere for you and your loved ones. Live among palm trees, with the ocean as your neighbor and the sand as your playground. Natural light floods the modern interior through the large windows creating a warm and inviting atmosphere.

A vibrant blue exterior of the home is showcased, framed by tall palm trees under a partly cloudy sky. A spacious driveway is visible, providing ample parking space in front of the house, which features a welcoming façade with multiple windows.

4.98 out of 5 average rating, 130 reviews

PRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!

Luxury Prime Island Location-Enjoy the best location on the island with our family & pet-friendly home (pets require approval & $125/pet fee). Just steps from our private beach & 1 mile from bars and restaurants, with a free shuttle service to beaches, dining, & nightlife. Relax in comfort w/ soft beds, a spacious couch, and flat-screen smart TVs in every room & fast WiFi. We offer bikes and beach equipment. 1 mile from Manasota Key public beach. Book now for the ultimate island retreat!

A view from the porch captures a vibrant sunset over the Gulf of Mexico, with silhouettes of palm trees and nearby buildings. The warm colors of the sky blend into the horizon, creating a serene backdrop that enhances the coastal atmosphere.

4.93 out of 5 average rating, 147 reviews

Gulf Side Condo Englewood Florida

A cozy 2 bed 2 bath condo with a full kitchen, dining area, living room, a king size master bedroom and a small 2nd bedroom. The coastal decor and furnishings create the ambiance of an island home. The condo opens onto a wide porch which has beautiful views of the Gulf of Mexico. Wander down the sandy path to a private beach and the turquoise waters of the Gulf. Enjoy sunsets from the porch or the beach. Unwind and let all of your cares float away on the Gulf breezes.

A circular gas fire pit is surrounded by four teal outdoor chairs on a gravel surface. Lush greenery and a privacy fence provide a serene backdrop, while a pool enclosure can be glimpsed in the distance under a clear blue sky.

5 out of 5 average rating, 109 reviews

*New Listing* ☀️TheAquaOasis🌴Pool-6 miles to beach

Welcome to the Aqua Oasis! This home was built in 2020 and located just 6 miles to multiple beaches in sunny Englewood, FL! The home consists of 3 bedrooms & 2 full baths, an option to heat the outdoor pool, relaxing outdoor chairs around a gas fire pit, fenced in back yard to let your pets roam, and a gas grill to whip up your favorite meals! If your family desires your own, private space and private pool, but you want close proximity to local beaches- THIS IS FOR YOU!

4.92 out of 5 average rating, 132 reviews

A private saltwater pool is surrounded by a screened lanai, featuring clear water reflecting sunlight. Poolside, a handrail is visible for safety, and tropical landscaping can be seen in the background, enhancing the outdoor recreational space.

Villa in Englewood

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.

An aerial view captures a spacious outdoor area featuring a heated saltwater pool bordered by lounge chairs and wooden furniture. Lush palm trees and plants surround the patio, while a vibrant yellow house provides a cheerful backdrop.

4.91 out of 5 average rating, 140 reviews

Island Home & Casita, Pool, Golf Cart, Beach

Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

The exterior of a modern home features a welcoming entrance with a circular window and landscaped plants. A dining area is showcased, set with vibrant dishes on a rustic table under a stylish light fixture. A tranquil view of the ocean waves and a sparkling private pool are also depicted.

4.92 out of 5 average rating, 154 reviews

Coastal Home Away From Home with Pool

Come and relax at the perfect vacation getaway for your family in peaceful Englewood Florida. Only 12 minutes from Gulf beaches. Go out and explore the many amazing beaches, bays, lakes and rivers or lay back, relax and enjoy the beautiful private pool and dining on the lanai from your back door. Fully equipped kitchen for all your cooking needs: coffee maker, blender, and more. Clean, new home that will make you feel cozy and comfortable while on vacation.

A beachfront property is depicted, featuring a two-story structure with a spacious porch. Surrounding landscape includes sand and lush greenery, leading to the waves of the Gulf of Mexico. Sunbathers are seen in the distance, enjoying the beach atmosphere.

4.88 out of 5 average rating, 197 reviews

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.

4.96 out of 5 average rating, 195 reviews

A bright and airy kitchen area is visible, featuring white cabinetry and a refrigerator. A large island with bar seating is positioned in the foreground. Light-colored tile flooring complements the soft yellow walls, and natural light streams through a window, illuminating the space.

Bungalow in Englewood

TROPICAL OASIS, MINUTES FROM THE BEACH!!

This charming 2 bedroom/2 bathroom, dog friendly home in Englewood is located 2 miles away from our beautiful Manasota Beach. Call this your home away from home, as you will find a flat screen TV, free wireless internet and a gas grill, washer/dryer, and a fully equipped kitchen. Bring your boat (boat ramp is located in the neighborhood), bathing suits, beach towels and sunscreen. We have the rest ready for you.

4.94 out of 5 average rating, 124 reviews

A private aquatic area features a heated saltwater pool surrounded by a screened patio, offering views of the Rotonda River. Two blue chairs and a sun lounger are positioned nearby, creating a relaxing outdoor space. The pool steps are visible, inviting leisurely swims.

Home in Rotonda West

Waterfront Villa Shellflower with private pool

Villa Shellflower is located in Rotonda West on a large and quiet property. Right next to the property is the Rontonda River, a wide freshwater canal. The 1564-square-foot house has been furnished with great attention to detail. The large saltwater pool, the southwest-facing sun deck, as well as the cozy dining area provide the perfect holiday feeling. The next dream beach is only 20 minutes away by car.

Vacation rentals for every style

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A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Englewood vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Englewood beach vacation rentals

Aerial view of Manasota Key showcases the serene waterways and coastal landscape. Beaches are visible in the distance, surrounded by lush greenery. Residential homes line the shore, and a prominent pavilion can be seen near the water's edge, indicating recreational areas for visitors.

4.99 out of 5 average rating, 72 reviews

On Manasota Key w direct access to our Beach! (A)

Large windows invite natural light into the space, offering a view of palm trees and the exterior of nearby buildings. A small white table is positioned near the window, enhancing the open and airy feel of the room.

4.92 out of 5 average rating, 71 reviews

Key Condo located on Manasota Key

An aerial view captures the beachfront property surrounded by palm trees and lush greenery. The ocean is visible in the distance, framed by clear blue skies. A sandy path leads from the building to the beach, emphasizing the proximity to the water.

4.79 out of 5 average rating, 128 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

4.87 out of 5 average rating, 46 reviews

A bright living space features a comfortable gray sofa complemented by a round coffee table. Light streams through large windows, enhancing the airy atmosphere. A ceiling fan circulates air while a wall-mounted television and decorative elements add charm to the area.

Apartment in Englewood

Turtle Bay 1B Manasota Key Condo

4.96 out of 5 average rating, 101 reviews

An aerial view reveals a mid-century vacation villa surrounded by lush greenery and open spaces, with the coastline and sandy beach visible in the distance. The calm ocean water stretches towards the horizon beneath a partly cloudy sky.

Condo in Venice

Vintage Villa, Thirty-Five

4.93 out of 5 average rating, 54 reviews

A paved pathway lined with palm trees leads to the front of a single-story building. The structure features large windows, allowing natural light to illuminate the interior. Parking spaces are visible along the side, and the beachfront is seen in the distance.

Condo in Venice

Beachfront Venice Villas 1-bed Condo

An aerial view captures the expansive coastline of Manasota Key, showcasing a stretch of sandy beach adjacent to turquoise waters. Green vegetation and residential areas are visible, with boats navigating the nearby waterways, illustrating the serene landscape of this coastal destination.

4.77 out of 5 average rating, 74 reviews

Gulf side condo be on the beach in minutes!

5 out of 5 average rating, 55 reviews

A sandy path lined with vibrant greenery and blooming plants leads towards the beach. Tall palm trees sway gently in the breeze under a clear blue sky, creating a serene atmosphere that invites a leisurely stroll.

Villa in Englewood

Ocean View Villa Manasota Key

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Englewood home rentals

An outdoor living space features a large screen displaying an underwater scene. Colorful lounge chairs are arranged around the area, complemented by a patterned rug and soft lighting from string lights overhead. A wooden bar and mirror add functional and aesthetic elements.

4.95 out of 5 average rating, 83 reviews

Welcome to one of Florida’s best hidden gems! A beautiful beach home with private beach access, a butterfly garden and a game room. Enjoy a dream stay by the sea in one of most beautiful Keys in Florida.

A private pool rests within a screened enclosure, surrounded by a paved patio. Colorful lounge chairs are positioned beside the clear blue water, with palm trees and an umbrella visible in the background, creating a serene outdoor space for relaxation.

5 out of 5 average rating, 21 reviews

A Perfect Escape Near the Beach (Pet friendly)

4.94 out of 5 average rating, 115 reviews

An outdoor lanai features a swimming pool surrounded by a screened enclosure, providing a secure and open space. Comfortable seating arrangements are visible, with a decorative rug underfoot. Lush greenery can be seen beyond the pool area, enhancing the tranquil setting.

Home in Venice

Spacious 2 Bedroom Home | Near Beach | Heated Pool

A screened-in patio features a serene saltwater pool, bordered by tan pavers. Lounge chairs and a dining table are positioned nearby, with teal and white area rugs adding a splash of color. The pool is framed by large windows, enhancing the open feel of the space.

4.98 out of 5 average rating, 63 reviews

5 O'Clock Somewhere - 2/2 - screened heated pool

5 out of 5 average rating, 27 reviews

The front of the home is framed by several palm trees and succulent plants, providing a tropical ambiance. A well-maintained lawn is visible, leading up to the entrance, which features a modern design with large windows and a covered porch.

Home in Rotonda West

Beautiful Floridian Oasis

An aerial view captures the coastal landscape, featuring turquoise waters intertwining with sandy shores and lush greenery. Distinct islands and winding waterways create a serene scene, with the nearby town visible in the background, showcasing the beauty of Englewood Beach.

5 out of 5 average rating, 62 reviews

Perfect location

A wooden dock extends over calm waters, leading towards lush greenery on one side and a house partially visible through trees on the other. The clear sky reflects the serene atmosphere of this waterfront space.

5 out of 5 average rating, 39 reviews

Manasota key house with private boat dock

5 out of 5 average rating, 24 reviews

A well-maintained exterior of a villa features a neatly landscaped front yard with green grass and a planted palm tree. The building showcases a combination of white walls and reddish roof tiles, with a front door framed by bright lighting.

Home in Port Charlotte

Lake Marlin Villa 2

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Beach home rentals in Englewood

A bright yellow kayak is positioned on a sandy pathway, leading towards a charming cottage surrounded by lush palm trees. The cottage is nestled within a natural setting, hinting at accessibility to outdoor activities and a tranquil atmosphere.

4.88 out of 5 average rating, 26 reviews

Island Beachfront Cottage. Secluded! Lux! Extras!

The beachfront home is elevated, showcasing a spacious deck with seating areas. Lush greenery surrounds the property, while a sandy path leads to the beach. Large windows offer views of the outdoor space and invite natural light into the interior.

4.77 out of 5 average rating, 35 reviews

3/2 LGI Gulf Front w/Dock

5 out of 5 average rating, 42 reviews

An aerial view showcases a charming beach town along the coastline, with the ocean's turquoise waters visible in the background. Several buildings with distinct architectural styles blend harmoniously, while palm trees punctuate the landscape, enhancing the coastal ambiance.

Home in Manasota Key

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

A vibrant yellow sign displays the name 'Sunflower' prominently, accompanied by the address '2530' and the website 'EnglewoodCottage.com.' The sign is framed by lush green foliage, providing a welcoming entrance to the property.

5 out of 5 average rating, 48 reviews

Sunflower House - PRIVATE - Directly on the Gulf!

A panoramic view of the beachfront displays soft white sand and gentle waves lapping at the shore. Lush palm trees frame the scene, with the vibrant blue sky and scattered clouds enhancing the tranquil coastal atmosphere.

5 out of 5 average rating, 67 reviews

Lu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI

The open-concept living area features comfortable seating arranged around a glass coffee table. A television is positioned on a media console, with natural light filtering through large glass doors that open to an outdoor space. Light-colored walls complement the airy atmosphere.

5 out of 5 average rating, 4 reviews

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

A spacious dining area is set with a colorful tablecloth and comfortably accommodates multiple guests. The large windows offer unobstructed views of the ocean, allowing natural light to fill the room and creating a bright, inviting space.

4.95 out of 5 average rating, 42 reviews

CocoHut

Four beach chairs with vibrant tropical patterns are positioned on sandy shore, facing the sparkling Gulf waters. The bright sunlight reflects off the water's surface, creating a serene coastal scene perfect for relaxation.