
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 €35 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wi-Fi availability
590 of Englewood vacation rentals include wi-fi 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.

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.
4.8 out of 5 average rating, 174 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!
4.91 out of 5 average rating, 100 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.
4.91 out of 5 average rating, 308 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!
4.99 out of 5 average rating, 73 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! 🌅
4.98 out of 5 average rating, 121 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.
4.89 out of 5 average rating, 203 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!
4.84 out of 5 average rating, 241 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.
4.99 out of 5 average rating, 145 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, 138 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)
4.99 out of 5 average rating, 144 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!
4.93 out of 5 average rating, 172 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.
4.91 out of 5 average rating, 235 reviewsPopular amenities for Englewood rentals with a pool
House rentals with a pool

Our Happy Place. Heated Saltwater pool
4.99 out of 5 average rating, 113 reviews
Lux Home on Gulf w/Private POOL & 50ft Dock
5.0 out of 5 average rating, 66 reviews
Waterfront| Pool & Spa | Near Beach| No Extra Fees
5.0 out of 5 average rating, 38 reviews
10 mins to Beach, Heated Pool, Beach Gear & Games
4.88 out of 5 average rating, 90 reviews
Villa Sanddollar Awaits 1071HS
4.97 out of 5 average rating, 38 reviews
3 Bedroom Home | Heated Pool | Close to Beaches
4.95 out of 5 average rating, 99 reviews
Saltwater Villa/Pool/Jacuzzi/MovieTheater/FishDock
4.95 out of 5 average rating, 96 reviews
Luxury Beach Retreat w/ Heated Pool
4.94 out of 5 average rating, 69 reviewsCondo rentals with a pool

Sunset Beach
4.96 out of 5 average rating, 138 reviews
Studio, pool, private beach, boat dock shark teeth
4.97 out of 5 average rating, 136 reviews
Steps to Water! Beach to Bay, Penthouse!
4.94 out of 5 average rating, 102 reviews
A Beautiful Sunset Awaits - Steps to Beach
4.9 out of 5 average rating, 153 reviews
Private Beachside Kitchenette
4.87 out of 5 average rating, 193 reviews
Vintage Villa 35 | Steps to Beach | Pool
4.96 out of 5 average rating, 111 reviews
Beach studio 56
4.87 out of 5 average rating, 159 reviews
Boardwalk Beachfront Getaway
4.96 out of 5 average rating, 25 reviewsOther vacation rentals with a pool

Saltwater Pool & Spa Villa on a Gulf-Access Canal
5.0 out of 5 average rating, 10 reviews
Manasota Tree House • Private Beach & Bay Access
4.96 out of 5 average rating, 48 reviews
Luxury 3-bedroom Villa with Heated pool and spa
4.87 out of 5 average rating, 30 reviews
Hidden Gem in Punta Gorda
4.98 out of 5 average rating, 57 reviews
The Windsor @ Englewood Beach
5.0 out of 5 average rating, 27 reviews
Luxury Waterfront Oasis w/ Pool, Hot Tub & Dock
4.92 out of 5 average rating, 13 reviews
Englewood Beach Villa - 3 min Walk to the Beach!
5.0 out of 5 average rating, 18 reviews
Steps to the Sand! Manasota Key Beachside Retreat!
5.0 out of 5 average rating, 22 reviewsWhen is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €174 | €212 | €211 | €176 | €157 | €161 | €153 | €140 | €135 | €135 | €147 | €159 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
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- Anna Maria Island
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- Anna Maria Island Beach
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- Blind Pass Beach





