Vacation rentals with a pool in Englewood

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Englewood

  • Total vacation rentals

    Explore 600 vacation rentals in Englewood

  • Nightly prices starting at

    Englewood vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 12,590 verified reviews to help you choose

  • Family-friendly vacation rentals

    490 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wifi availability

    590 of Englewood vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Englewood rentals

  • 4.9 Average rating

    Englewood stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Englewood

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite
Condo in Englewood
4.8 out of 5 average rating, 173 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

BOOK HERE!!! STEPS TO WORLD FAMOUS Manasota Key BEACH, FREE PARKING. Private beach access. WALKING DISTANCE TO MANY RESTAURANTS. 2 Bedroom, 1 Bathroom, beach themed condo with HEATED POOL access across street. Complimentary grill and Gulf sunsets. Your morning coffee is on us! Beach chairs, towels, and sand toys supplied. Kitchen is updated with filtered water, ice, and utensils supplied. Master Bedroom has a queen sized bed, pull out drawers and fireplace. Boat dock slip available upon request.

Guest favourite
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
4.91 out of 5 average rating, 307 reviews

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.

Top guest favourite
The private heated saltwater pool is framed by a screened enclosure, allowing for natural light and views of the surrounding greenery. Sunlight reflects off the clear water, and a patio area is visible, creating a serene outdoor space.
Home in Englewood East
4.99 out of 5 average rating, 113 reviews

Our Happy Place. Heated Saltwater pool

Our Happy Place is a newly remodeled smoke free, pet free home located in a quiet residential neighborhood! It has a private heated saltwater pool, 3 bedroom, 2 bath, located 2 miles to the intercoastal and 6 miles to Englewood beach! Very close to some of Southwest Florida's best shopping, golf courses, and restaurants! Our home is fully furnished, and includes everything you need for a long weekend getaway or for staying longer term! We know Our Happy Place will also become Your Happy Place!

Guest favourite
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.
Vacation home in Port Charlotte
4.91 out of 5 average rating, 100 reviews

Jaw-Dropping Waterfront Sunset Views and Gameroom!

Welcome to SUNSET MANOR! This waterfront property sits on a beautiful and spacious corner lot with all the amenities including a heated pool with a tranquil waterfall feature. The preserve across the way provides the ultimate private oasis. This is one of THE BEST views in all of Charlotte County! The house is located in a beautiful and quiet waterfront community - just a few miles from the beach, Boca Grande, Punta Gorda, Fort Myers, and more. World-class Florida living at your fingertips!

Top guest favourite
Home in Manasota Key
4.99 out of 5 average rating, 72 reviews

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!

Top guest favourite
Villa in Englewood
4.97 out of 5 average rating, 119 reviews

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! 🌅

Top guest favourite
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.
Home in Englewood East
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.

Guest favourite
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.
Home in Englewood
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!

Top guest favourite
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.
Home in Englewood East
4.99 out of 5 average rating, 145 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.

Guest favourite
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
4.99 out of 5 average rating, 142 reviews

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)

Guest favourite
Home in Englewood
4.93 out of 5 average rating, 172 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!

Top guest favourite
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
4.91 out of 5 average rating, 235 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.

Popular amenities for Englewood rentals with a pool

When is the best time to visit Englewood?

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