Family-friendly holiday rentals in Englewood

4.89 out of 5 average rating, 209 reviews

Two individuals ride bicycles along a sandy beach at sunset, with vibrant hues of orange and purple in the sky. Gentle waves lap at the shore, and distant figures can be seen walking along the coastline, creating a serene beach atmosphere.

Cottage in Englewood

Unit #2 Free bikes/kayaks/walk to beach/2bed/2bath

Unit # 2 Beautiful 2 bedrooms 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

4.83 out of 5 average rating, 122 reviews

An aerial view of Manasota Key showcases the expansive beach lined with soft sand and crushed shell. The vacation home is highlighted, surrounded by lush greenery and close proximity to the warm Gulf waters, with clear blue skies enhancing the tranquil environment.

Bungalow in Englewood

LG Beach Bungalow on Gulf w/Bay Access & deck too!

Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!

4.99 out of 5 average rating, 68 reviews

A serene beach view is captured under a clear sky, with sunlight reflecting on the calm water. The sandy path leads to the shoreline, where lounge chairs and umbrellas are positioned for comfort. Lush greenery outlines the beach area, enhancing the natural landscape.

Condo in Englewood

A little slice of paradise

This 2 bedroom 1 bath immaculate beach condo is located a mere 80 steps from front door to the amazing Englewood Beach on Manasota Key with your private beach access. The gulf breeze is indescribable. This could be your home away from home. We have added many personal touches for your convenience and comfort. Multiple restaurants, bars, gift/souvenir shops, and convenience store (Circle K) are within walking distance. Magnolias, an upscale restaurant, is located directly across the street.

The exterior of a spacious home features a light-colored facade framed by lush, mature palm trees. A manicured lawn extends in front, and large windows offer a glimpse of the inviting interior. The roof exhibits a gentle slope, contributing to the overall elegance of the residence.

4.84 out of 5 average rating, 240 reviews

Manasota Beach Home w/Pool. Steps To The Beach

Custom built large home only 2 blocks to Manasota Beach. Most guests walk and a beach wagon is provided. Located in a quiet neighborhood with easy access to downtown Venice and Englewood. Very large and private lot with beautiful mature palms! The home has tray and soaring vaulted ceilings. The whole home opens up onto the pool area with sliders in every room. The bedrooms are configured in a split style with the very large master suite being totally private. Rare beach home for rent left!

4.96 out of 5 average rating, 161 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

Amazing 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.

5.0 out of 5 average rating, 36 reviews

Waterfront| Pool & Spa | Near Beach| No Extra Fees

Welcome to Casa-A-Mar, your private slice of coastal paradise at our newly updated waterfront retreat. Step outside and launch straight into the water with direct Gulf access or into Lemon Bay—perfect for exploring the canals on one of our kayaks. Prefer to stay in? Spend your time in the heated pool, then ease into the hot tub as the sun sets. As evening falls, transform the backyard into your own open-air theater with our outdoor projector, perfect for movie nights under the stars 🌟

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, 146 reviews

Steps to Private beach, Prime Location! Dogs ok!

Luxury Prime Island Location-Enjoy the best location on the island with our family & pet-friendly home (pets require approval & $200/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!

4.94 out of 5 average rating, 18 reviews

Manasota Key Beachfront Oasis w/ Private Jacuzzi

Welcome to “Sea Garden” a delightful, tranquil, beachfront home on Manasota Key. Enjoyment will be plentiful in this 4 bedroom, 3 bath open concept home. This stilt home is multilevel for privacy if needed or all gather around the kitchen or game table for some fun. Two primary en suite bedrooms with updated bathrooms. 3rd and 4th bedrooms are located on the lower level with shared updated bathroom. Climb up to the crow’s nest with a good book with twin bed, and enjoy the view!

An aerial view of the Aqua Oasis highlights a screened patio area with a gas grill and outdoor seating around a fire pit. A private pool, illuminated in soft green, adds a tranquil touch. Surrounding greenery enhances the outdoor space.

4.99 out of 5 average rating, 135 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!

An aerial view captures a two-story home nestled along a quiet waterway with lush greenery surrounding it. Nearby, other residences and a private dock are visible. The scenic backdrop showcases calm waters merging with a blue sky, highlighting the tranquil atmosphere of the location.

5.0 out of 5 average rating, 65 reviews

Lux Home on Gulf w/Private POOL & 50ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

A serene beach scene showcases gentle waves lapping at a sandy shore. Lush greenery is visible along the coastline, with a residential property nestled among the trees. The clear blue sky complements the tranquil waters, creating a peaceful environment.

4.96 out of 5 average rating, 101 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.

Relax with the whole family at this peaceful place to stay.Our home offers you at-home comfort for up to 8 people. Large spacious bedrooms, a fully equipped kitchen with breakfast bar, and multiple patios and balconies to enjoy. For winding down after a long day, spend some quality family time in our game room. Your little ones can pretend to grill up some burgers while mom and dad play a round of ping pong or get the whole family together for some board games!

4.93 out of 5 average rating, 170 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!

Popular amenities for Englewood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The exterior of the home is framed by lush greenery and a mature tree, creating a welcoming entrance. A paver driveway leads to the garage, and flower beds with vibrant sunflowers add a touch of color to the neatly landscaped yard.

4.91 out of 5 average rating, 109 reviews

Quiet Englewood Home Near Manasota Key

4.98 out of 5 average rating, 116 reviews

A spacious living area is highlighted by a large sectional sofa arranged around a low coffee table. A wall-mounted TV and decorative plant enhance the bright atmosphere. Sliding glass doors offer views of the outdoor space, while warm yellow walls create a welcoming setting.

Home in Rotonda

Tropical Paradise

4.98 out of 5 average rating, 367 reviews

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

SEPT SALE! Sarasota #1 Luxury Villa! PRIV BEACH!

4.93 out of 5 average rating, 117 reviews

3 miles to beach, hottub & fenced yard

4.88 out of 5 average rating, 216 reviews

A spacious living area features two large sofas and a patterned accent chair arranged around a central coffee table. Tall windows allow natural light to fill the room, highlighting the neutral color palette. A staircase leads to the upper level, enhancing the open layout.

Home in Nokomis

4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres

A tranquil pool area is enclosed by a black screen, offering privacy and protection. The crystal-clear water of the pool reflects the surroundings, with lush greenery visible through the screens. The shallow ledge provides an inviting space for relaxation.

4.97 out of 5 average rating, 38 reviews

Villa Sanddollar Awaits 1071HS

4.99 out of 5 average rating, 70 reviews

Home in Manasota Key

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Holiday home in Englewood

A tranquil shoreline is observed, with gentle waves lapping at the sandy beach. The sky displays soft hues of pink and blue as the sun sets over the Gulf of Mexico, creating a serene coastal scene.

Ocean view, Totally remodeled, Beach Home!

4.94 out of 5 average rating, 69 reviews

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 218 reviews

2BR Oasis • Dog Friendly • 5 min to Manasota Beach

A dining area features a wooden table surrounded by six chairs, complemented by a patterned tablecloth. A large TV mounted on the wall showcases a scene of The Beatles. A bench and a small outdoor-style table are positioned nearby on tile flooring.

4.92 out of 5 average rating, 142 reviews

Tranquil, pet-friendly-yard and 6 mins from beach

A modern single-story home is presented with a light-colored exterior and a dark roof. The entrance features a covered porch with large windows and a blue front door. Lush green grass frames the driveway, leading to a spacious garage.

4.89 out of 5 average rating, 203 reviews

Home w/ Pool, 10 mins to Manasota Key beaches

A spacious patio area is showcased, featuring a comfortable sectional sofa adorned with colorful pillows. A coffee table is positioned in front, while the heated pool and a wooden pergola are visible through large screened windows, enhancing the outdoor experience.

4.99 out of 5 average rating, 145 reviews

Green Bamboo - saltwater pool, great backyard.

Holiday home in Englewood

The exterior of the house is showcased, featuring a two-story structure with a blue façade. A staircase leads to the upper level, which is adorned with a porch that includes white railings and welcoming outdoor seating. Palms and other greenery surround the property, complementing the coastal ambiance.

Beachy 2BR Upper House · Gulf Views · Pets OK

4.97 out of 5 average rating, 120 reviews

A spacious screened-in pool area is showcased, featuring a large heated pool with clear blue water. Comfortable lounge chairs and an umbrella are positioned nearby, and a well-maintained outdoor area surrounded by greenery is visible beyond the pool.

4.98 out of 5 average rating, 113 reviews

Iguana Alley, Beach HEATed Saltwater Pool on Canal

Lush palm trees frame a vibrant yellow birdhouse, situated near a serene canal. The calm water reflects the green landscape, with a glimpse of wooden docks visible in the background. A variety of native plants and textured bushes add to the natural setting.

4.91 out of 5 average rating, 156 reviews

"Lighthouse" 7 mins from Beach, direct gulf access

5.0 out of 5 average rating, 106 reviews

A canalfront area features a serene gazebo surrounded by lush green grass and white pebbles. The vibrant sunset sky adds warmth to the scene, and the private boat dock is visible in the background, enhancing the tranquil outdoor setting.

Home in Port Charlotte

Xanadu|Fishing/ Pool/Dock|Kayaks|Bar/Gazebo/ Kids

Family-friendly home rentals with a pool

4.8 out of 5 average rating, 173 reviews

Condo in Englewood

Entire Beachside Condo! Don’t worry Beach Happy!

4.99 out of 5 average rating, 126 reviews

Paradise on the Bay

4.96 out of 5 average rating, 137 reviews

A two-story building is shown, featuring a wraparound porch adorned with railings and chairs. Lush green foliage leads to a sandy path, inviting access to the beach. The sky is partly cloudy, enhancing the coastal ambiance of the location.

Condo in Englewood

Sunset Beach

4.97 out of 5 average rating, 118 reviews

Villa in Englewood

Pool·Game Room·Beach Gear·Spotless.5 min to Beach

An inviting outdoor space features a screened lanai with a private pool. A colorful sunset casts reflections on the water. Comfortable seating areas are positioned nearby, along with a dining space and a small basketball hoop at the poolside.

5.0 out of 5 average rating, 60 reviews

Family Fun-Relaxing Home w/heated Pool & Game Room

5.0 out of 5 average rating, 5 reviews

Ibis Cottage | Beachfront Retreat on Manasota Key

4.89 out of 5 average rating, 28 reviews

Coastal escape across from the beach