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Englewood Vacation Rentals with Private Pool

(31 rentals)
Englewood House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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...

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$133
avg per night
Englewood Villa
Sleeps 14, 5 bedrooms, 3 bathrooms
41 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

**Experience paradise in a Luxurious Villa at Manasota Beach, where stunning sunsets and soft sands await your arrival Spacious 3600 sqft, 2 storied, 5 Bed/3Ba Villa with deeded beach access 2 mins walk. Relax in a salt water pool or unwind in the Jacuzzi. Beautifully curated & accommodates multiple...

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$945
avg per night
New
Englewood House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your tranquil getaway at this 2BR 2Bath oasis just 5 mins away from downtown and the picturesque Manasota Key. Whether you're looking to explore exciting attractions, spend the day at the beach, or sample local cuisine, this prime location provides the perfect starting point for your...

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$181
avg per night
Englewood Villa
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

"Pelican Nest" Beautiful Manasota Key Beach Villa with all the amenities; heated pool, electric fireplace, skylights, granite counters, stainless appliances. Very inviting for fun with family and friends by the beach, or in the bay. Has 4bedroom , 3 bath sleeps 10 people, with 2pull up sofas,...

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$599
avg per night
Englewood House
Sleeps 7, 3 bedrooms, 2.5 bathrooms

Distance to beach: 3 miles to Englewood Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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...

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$312
avg per night

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Englewood House
Sleeps 7, 3 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 4 miles to Englewood Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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...

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Featured review

"Perfect home with the best hosts"

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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$228
avg per night
Englewood Estate
Sleeps 8, 3 bedrooms, 2.5 bathrooms
24 reviews

Distance to beach: 1 miles to Manasota Key Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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...

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Featured review

"Great Experience!"

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...

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$350
avg per night
Englewood House
Sleeps 5, 2 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 7 miles to Manasota Key Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Come stay at our newly renovated 2 bed/2 bath traditional Florida home! We recently completed work on our brand new heated 14'x25' salt water swimming pool. Take a dip in the morning or after a long day of exploring. We are blocks from the recently renovated Dearborn Street. Come enjoy the action...

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Featured review

"The Best!!"

We had the pleasure of renting this lovely home with a pool for a month in Englewood, our favourite Florida destination. The home was outfitted with everything you would need. It was most comfortable &...

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$199
avg per night
Englewood Villa
Sleeps 8, 2 bedrooms, 2 bathrooms
95 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Star Fish Villa - 5★ Beach villa - most sought-after home in Englewood! 1.6 Miles to Englewood Beach/Manasota Key Private in ground Pool Centrally located to shopping Game room with Darts, Pool, Air hockey & Table tennis Screened Lanai facing Pool & landscaped garden Blackstone...

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$248
avg per night
Englewood House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Private pool

About this property

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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$220
avg per night
New
Englewood House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 7 miles to Englewood Beach

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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...

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$274
avg per night
Englewood Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautifully decorated 2 bedroom, 2 bathroom condo has updated, comfy furnishings, brand new bathrooms and kitchen, new tile floors throughout, its own washer/dryer, and most importantly, great views of the Gulf of Mexico from the screened lanai, living, and dining rooms.The complex is right on...

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$210
avg per night
Englewood House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 2 miles to Englewood

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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....

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Featured review

"Beautiful and Spacious"

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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$146
avg per night
Englewood House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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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$406
avg per night
Englewood Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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....

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$242
avg per night
Englewood House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Private pool

About this property

Beach to Bay - - Tamarind CondominiumsThis nicely furnished 2 bedroom, 2-bathroom first floor end-unit condo with a screened lanai offers a courtyard view with a 30 second walk to the Gulf of Mexico and newly restored beach. To use the heated pool, clubhouse, or boat docks, take a short 3-minute walk...

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$278
avg per night
Englewood House
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 8 miles to Englewood Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

An immaculate house in a quiet, friendly neighborhood. Locates at: 7474 Quarry Street. Englewood, FL 34224. This house has a total of 1633 sq. and offers 3 bedrooms, 2 bathrooms. The living room has a Sofa bed and a 65" inch smart TV. The double sliding doors leads directly out onto the patio and...

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Featured review

"Quiet & Peaceful neighborhood!"

Let me start with a splendid home with very gracious & accommodating hosts A very delightful home with a refreshing pool. We will come back again when available to meet our needs and schedule, and close...

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$147
avg per night
Englewood Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Tamarind Gulf & Bay Condominiums – Direct Gulf-Front Beauty!2 Bed + Loft | 2.5 Bath | Gulf Views | Beach to Bay Living Welcome to your slice of paradise at Tamarind Gulf & Bay, Manasota Key's premier beach-to-bay condominium complex. This direct Gulf-front 2-bedroom + loft, 2.5-bathroom...

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$310
avg per night
Englewood Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Private pool
  • WiFi

About this property

Fall in Love with Beachfront Luxury at The PalmsWelcome to The Palms, where your dream beach vacation begins! This stunning 3-bedroom, 2.5-bath condo offers approximately 2,000 sq ft of luxurious living space, perched on the 2nd floor (just one floor above the garage) for the perfect blend of convenience...

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$357
avg per night
New
Englewood House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 3 miles to Englewood Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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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$200
avg per night
Englewood Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Bright and beautiful 2-bedroom, 2-bathroom condo with views of the Gulf of Mexico and Lemon Bay from the upper deck. This is a nicely furnished, updated, cheerful condo; the living room has a vaulted ceiling, huge windows with lots of sunlight, and a ceiling fan. During the winter months, the lower deck's...

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$295
avg per night
Englewood House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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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$167
avg per night
Englewood Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

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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$211
avg per night
Englewood House
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 4 miles to Manasota Key Beach, 8570 Manasota KeyRd, Englewood

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

THURSDAY, Dec 4, 2025 ~"Three things cannot be long hidden: the sun, the moon, and the truth." —Buddha (FULL MOON Dec 4, 2025)Wide water View over Crystal Clear Pool! This relaxing retreat is positioned on deep water 'Forked Creek' which leads to the Intracoastal Waterway...

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Featured review

"Our Summer Beach Home"

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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$183
avg per night
Englewood House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Private pool
  • WiFi

About this property

Pelican Landing A-202 Welcome to your stunning beach view vacation home located on the Gulf of Mexico at the Pelican Landing Condominiums in Manasota Key home of Englewood Beach recognized as one of the most beautiful beaches in Florida. The Pelican Landing complex has lots to offer. This is a beach-to-bay...

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$280
avg per night
Englewood Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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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$357
avg per night
New
Englewood House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Stunning Canal-Front Retreat. Welcome to your dream Florida getaway. This completely renovated waterfront retreat sits on a beautifully landscaped tip lot with nearly 280 feet of Gulf-access frontage, offering sweeping intersecting canal views from almost every room. Designed with both relaxation and...

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$456
avg per night
Englewood House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

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...

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$689
avg per night
Englewood House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Private pool

About this property

Very nice 3 bedroom, 2 1/2 bathroom condo at Barefoot Beach, one of the more prestigious condo complexes on Manasota Key. This spacious unit has a screened balcony overlooking the heated pool with a partial view of the Gulf of Mexico. Nice tropical decor throughout the condo. King bed in the master bedroom...

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$385
avg per night
Englewood Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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...

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$229
avg per night
Englewood Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

10% OFF ANY RENTAL OF 30 DAYS OR MORE January and February must be booked togetherWaterfront Island 2/2 Condo-Perfect for Boaters and Beach LoversATTENTION BOATERS BEACH LOVERS! You will love this Updated Ground Floor 2/2 Condo that sits right on Lemon Bay with access to the beautiful beaches...

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