Family-friendly vacation rentals in Englewood

4.97 out of 5 average rating, 166 reviews

Townhouse in Englewood

Beautiful sunsets-50 steps to uncrowded beach

Imagine waking up to the gentle lull of waves right outside your bedroom window. This exquisite 2-king bedroom, 2-bathroom raised townhome is nestled among palm trees in close proximity to the beach where your children can build sandcastles and explore the wonders of the shoreline while listening to the symphony of waves and coastal breezes. The rhythmic melody of the ocean serves as a soothing backdrop, creating a peaceful ambiance that instantly melts away stress. Escape to a coastal paradise!

4.83 out of 5 average rating, 123 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, 73 reviews

Home in Manasota Key

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Luxury beach house with pool in a charming old-FL beach town, one of FL’s best kept secrets! New kitchen, 2 covered balconies & a walled backyard oasis. Spend sunny days by turquoise waters of the Gulf & host a cookout on the covered patio & pool. Enjoy the sea breeze while sipping your favorite beverage on the covered balcony off the living area. Lounge in style in the patio or go for a swim in the 6’ deep heated pool. You're walking distance to restaurants/bars and 57 seconds to the beach!

4.98 out of 5 average rating, 121 reviews

Villa in Englewood

Heated Pool·Game Rm·Spotless.5 min to Beach. Grill

<b>🏖️ Come & Enjoy FL as it should be! 🏖️ Your beach paradise awaits minutes from Englewood's Gulf Coast! 🌊 Heated Pool (FREE Nov-Apr!) 🎮 Game Room - Pool, Darts, Air Hockey 🌴 Screened Lanai & Tiki Bar 🔥 Cozy Fireplace & Reading Nook 🏄 Beach Gear Included 🍹 Blackstone Grill 📺 2 Smart TVs & High-Speed WiFi 🍳 Fully Stocked Kitchen - Spices, Pots, Pans and cutlery 🗺️ Minutes to Englewood, Manasota & Gasparilla Beaches ⭐ 4.97 Rating - Book Now !Don't miss your Gulf Coast escape! 🌅

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

Relax in your own private coastal retreat just minutes from Manasota Key. Spend your days at the beach and come home to unwind in a heated pool designed for year-round enjoyment. Start your mornings with coffee by the pool, head to the beach with provided chairs and gear, and end the day with a sunset swim in a quiet, private neighborhood. This new home is perfect for families, couples, or groups looking for a clean, modern space close to everything—but tucked away enough to truly relax.

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!

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, 146 reviews

Green Bamboo - saltwater pool, great backyard.

Welcome to Green Bamboo, the charming and cozy vacation rental located in the beautiful Englewood, Florida! With its prime location, Green Bamboo is the perfect place to explore all that the area has to offer, from the most amazing beaches in the US to world-class golf courses and spectacular sunsets. Home is situated in a peaceful and gorgeous neighborhood. Just a short drive away (5 miles) you will find beautiful beaches, boat rentals and vibrant shopping and dining options.

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, 137 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!

4.99 out of 5 average rating, 144 reviews

An enclosed lanai features multiple large windows with views of Lemon Bay, allowing natural light to fill the space. A palm tree is visible outside, framed by the window panes. A decorative area rug is positioned on the wooden floor, enhancing the coastal ambiance.

Villa in Englewood

Stunning Bay Waterfront! Jaw dropping Water Views!

Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchenette & family room. Enjoy “Lemon Bay-front beach” in backyard. Low-key quiet vacationers. 1 car parking spot. No visitor parking. Free 2 kayaks. Login to your favorite streaming services with Smart TVs. Beautiful Blind Pass Beach, Englewood Beach, 5 restaurants & Tiki Bars are just 1.5 mile away or hop on Stumpy's Free Shuttle (tip based)

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!

5.0 out of 5 average rating, 38 reviews

Cottage in Englewood

Private Beach-Luxury 4BR+SUPs&Kayaks-Pets-BBQ

Charming 4 Bed Cottage (sleeps 9), Private Beach to Gulf Across Street, with Large Screened Porch, Super Shark Tooth Hunting, Free use of 2 Kayaks and SUPs, Restaurants, Live Music, Golf, and Tennis . Uber Eats & Grocery delivery, 50 Minutes from Sarasota Airport (75 minutes from Fort Myers airport). Lush tropical rainforest in the "Old Florida" region on the Gulf surrounds this cute cottage. *Please note small extra $50 pp nightly fee for guests 7-9.

4.91 out of 5 average rating, 235 reviews

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.

Condo in Englewood

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.

Popular amenities for Englewood family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 123 reviews

3 miles to beach, hottub & fenced yard

4.88 out of 5 average rating, 218 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

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, 111 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

5.0 out of 5 average rating, 38 reviews

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

4.94 out of 5 average rating, 18 reviews

Manasota Key Beachfront Oasis w/ Private Jacuzzi

5.0 out of 5 average rating, 10 reviews

Canal-Front 3BR – Pool, Hot Tub & Boat Access

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, 66 reviews

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

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 172 reviews

Island Home & Casita, Pool, Golf Cart, Beach

4.9 out of 5 average rating, 211 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

4.94 out of 5 average rating, 221 reviews

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

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, 158 reviews

"Lighthouse" 7 mins from Beach, direct gulf access

Vacation 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, 123 reviews

The welcoming entrance features a covered porch with three pink rocking chairs and nautical decor. A decorative compass hangs above a door painted in calming turquoise, while a garage door blends seamlessly into the clean, white exterior under a bright sky.

5.0 out of 5 average rating, 51 reviews

5 mins to Beach~ Beach Gear, Bikes, Firepit, Grill

Superhost

4.65 out of 5 average rating, 20 reviews

Castadiva-Your Gorgeous Gulf Coast Beach Home!

5.0 out of 5 average rating, 54 reviews

"The Lost Loon" Oceanfront Cottage by Roxy Rentals

Family-friendly home rentals with a pool

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, 241 reviews

Manasota Beach Home w/Pool. Steps To The Beach

4.99 out of 5 average rating, 127 reviews

Paradise on the Bay

Vacation home in Port Charlotte

Aerial view of a waterfront property featuring a modern single-story house with a red-tiled roof. Surrounding palm trees are visible, and the serene waterway reflects the sunset colors. Lush greenery is present nearby, enhancing the peaceful ambiance of the landscape.

Jaw-Dropping Waterfront Sunset Views and Gameroom!

4.9 out of 5 average rating, 101 reviews

4.8 out of 5 average rating, 175 reviews

Condo in Englewood

Entire Beachside Condo! Don’t worry Beach Happy!

4.94 out of 5 average rating, 124 reviews

Apartment in Englewood

Super cute fun studio steps from everything beachy

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, 61 reviews

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

A screened pool area features a clear blue pool surrounded by a spacious patio. Comfortable seating options are visible, and the backdrop includes a sprawling sky filled with wispy clouds. Lush grass and landscaping frame the outdoor space.

4.97 out of 5 average rating, 62 reviews

Pool Home