
Vacation rentals with a pool in Englewood
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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.

Coastal Retreat Villa with pool • near beaches
🌴 Escape to your getaway in sunny Englewood, Florida! Whether you're a couple seeking romance, a solo adventurer, a business traveler, or a family with kids, our home is designed for comfort & relaxation. Nestled in a prime location, it's the ideal home base to anyone looking to unwind and explore. Indulge yourself in this executive cozy, built from the ground in 2018 & featuring 3 bedrooms, 2,5-bath house with a Large (seasonally) heated swimming Pool (heating $ included during colder months)

Escape to Casa Blu- private pool, minutes to beach
Your next retreat to Florida paradise should be Casa Blu with it's private pool and serene backyard. It's just minutes to area beaches, restaurants and parks. Let the stresses of daily life melt away as you float in the salt water pool, sipping margaritas, listening to Jimmy Buffett singing "It's Five O' Clock Somewhere" The single-floor layout, comfy bedrooms with private baths await. Fast WiFi, Smart TVs, and fully equipped kitchen. Everything's covered, from beach gear to a pack 'n play.

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.

Pool·Game Room·Beach Gear·Gulf Coast Escape
<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! 🌅

Englewood Cottage with Pool, Hot Tub, and Fire Pit
This 3-bedroom 2-bathroom cottage with a pastel beach theme is located at a serene spot in Englewood. There's a private backyard with a heated swimming pool, hot tub, and fire pit. We think it’s the perfect retreat and want you to make yourselves at home. We are just 6 miles from Englewood Beach, nearby fishing at Lemon Bay Park (7 miles) and entertainment at Lemon Bay Playhouse (5 miles). Check out Englewood Farmers Market, and try parasailing at either of the Englewood Beach locations.

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!

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 🌟

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.

*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!

Gulfstream Villa—Englewood Pool—Dog Friendly
"The pool area is heavenly!" Gulfstream Villa earns it. This single-story Englewood home wraps a heated pool inside a screened lanai, with a doggy door onto a fully fenced backyard. After a beach day on Manasota Key, rinse at the outdoor shower, settle into the lanai's wicker loveseats while the dogs zoom the lawn, then fire up the grill on the dining deck. King master with sliders to the pool, queen and twin-over-full bunk for the family. Bikes in the garage. Dog-friendly.

Studio, pool, private beach, boat dock shark teeth
Enjoy it all -Pool, private dock & private beach access-located near restaurants. Covered parking or hop on a shuttle to explore Manasota Key! Light, bright condo is complete with everything you will need to relax. Kitchenette has all the must haves-air fryer, portable stove, coffee maker, kettle & community grill. Enjoy a queen bed, full sofa bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach. Close to everything!!
Popular amenities for Englewood rentals with a pool
House rentals with a pool

Stillwater Suite | Pool • Lakefront • 6min to Gulf

Manasota Tree House • Private Beach & Bay Access

Our Happy Place. No cleaning fees! Heated pool

The Manor House on Lemon Bay. Summer availability!

Gulfstream Haven

Waterfront Key West Style Home, Heated Pool

The Windsor @ Englewood Beach

Water view Villa private Heated Pool golf beach
Condo rentals with a pool

Bay Breeze @ManasotaKeyCondos

6 Siesta Breakers - Condo, Ocean View, Heated Pool

Ocean Oasis on Manasota Key - Ocean View

Crystal House on Siesta Key Beach

Vintage Villa 35 | Steps to Beach | Pool

A little slice of paradise

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Cottage on Siesta Key Beachside & Stunning sunsets
Other vacation rentals with a pool

Family Pool Home

Mango Beach Cottage with a swim spa

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Modern Villa Heated Saltwater Pool 10 Min to Beach

3 Bedroom Home | Heated Pool | Close to Beaches

Manasota Beach Vacation Rental

The perfect retreat with canal view

1mi to Beach. 1+ acre of jungle Pool & Pickleball
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ735 | ﺩ.ﺇ892 | ﺩ.ﺇ889 | ﺩ.ﺇ731 | ﺩ.ﺇ639 | ﺩ.ﺇ628 | ﺩ.ﺇ643 | ﺩ.ﺇ591 | ﺩ.ﺇ569 | ﺩ.ﺇ569 | ﺩ.ﺇ617 | ﺩ.ﺇ668 |
| 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 |
Quick stats about vacation rentals with a pool in Englewood

Total vacation rentals
Explore 560 vacation rentals in Englewood

Nightly prices starting at
Englewood vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 11,860 verified reviews to help you choose

Family-friendly vacation rentals
470 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
280 properties have a dedicated workspace

Wi-Fi availability
560 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!
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