
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, 173 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, 306 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, 70 reviews
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.
4.99 out of 5 average rating, 68 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, 240 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
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 🌟
5.0 out of 5 average rating, 36 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, 135 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!
5.0 out of 5 average rating, 65 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, 170 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

Villa Sanddollar Awaits 1071HS
4.97 out of 5 average rating, 38 reviews
Family Fun-Relaxing Home w/heated Pool & Game Room
5.0 out of 5 average rating, 60 reviews
10 mins to Beach, Heated Pool, Beach Gear & Games
4.87 out of 5 average rating, 86 reviews
Coastal Sanctuary - Pool & Privacy
4.97 out of 5 average rating, 36 reviews
Stillwater Suite | Pool • Lakefront • 6min to Gulf
4.92 out of 5 average rating, 86 reviews
Heated Pool—Manasota Key—Dog Friendly
4.99 out of 5 average rating, 67 reviews
Luxury Beach Retreat w/ Heated Pool
4.94 out of 5 average rating, 67 reviews
Peaceful waterfront home
4.96 out of 5 average rating, 45 reviewsCondo rentals with a pool

Sunset Beach
4.96 out of 5 average rating, 137 reviews
Studio, pool, private beach, boat dock shark teeth
4.97 out of 5 average rating, 135 reviews
Steps to Water! Beach to Bay, Penthouse!
4.94 out of 5 average rating, 101 reviews
A Beautiful Sunset Awaits - Steps to Beach
4.9 out of 5 average rating, 152 reviews
Vintage Villa 35 | Steps to Beach | Pool
4.96 out of 5 average rating, 111 reviews
Private Beachside Kitchenette
4.87 out of 5 average rating, 191 reviews
Boardwalk Beachfront Getaway
4.96 out of 5 average rating, 24 reviews
Beach Bliss Retreat on Manasota Key - Ocean View
5.0 out of 5 average rating, 31 reviewsOther vacation rentals with a pool

Saltwater Pool & Spa Villa on a Gulf-Access Canal
5.0 out of 5 average rating, 8 reviews
Private Heated Pool + Swim-Up Bar • Mins to Beach
5.0 out of 5 average rating, 39 reviews
Pebble House w/ Screened Pool, Horseshoes, & more
4.94 out of 5 average rating, 18 reviews
luxury Brand new villa with pool
5.0 out of 5 average rating, 40 reviews
1mi to Beach. 1+ acre of jungle Pool & Pickleball
4.96 out of 5 average rating, 26 reviews
Saltwater Villa/Pool/Jacuzzi/MovieTheater/FishDock
4.95 out of 5 average rating, 95 reviews
Private pool with outdoor bar and fenced yard
4.88 out of 5 average rating, 32 reviews
Manasota Tree House • Private Beach & Bay Access
4.96 out of 5 average rating, 48 reviewsWhen is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €173 | €210 | €209 | €174 | €155 | €160 | €151 | €139 | €134 | €134 | €145 | €157 |
| 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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