
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 $40 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.
FamilyLocationParks

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.
ValueLocationBackyard

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.
ValueFamilyShared spaces

2 - bedroom home with pool and private boat ramp
This home features 2 bedrooms and 2 full bathrooms. Master has a king bed and walk-in closet. 2nd bedroom has two queen beds and walk-in closet. One pullout queen couch for extra sleeping space located in living room. The home is located close to Englewood beach and Boca Grande. There is a private neighborhood boat ramp on Oyster Creek just two blocks from the home. Enjoy a 10 min boat ride to intercoastal which leads to many beaches and the Gulf. Backyard/pool area are fenced in for privacy.
FamilyLocationSleep quality

Pvt Pool·Game Room·Beach Gear·Shark Teeth Paradise
<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! 🌅
ValueLocationAir conditioning

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!
ValueLocationParking

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 🌟
FamilyLocationLaundry

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.
LocationValueAir conditioning

*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!
FamilyValueLaundry

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!
FamilyValueBackyard

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!!
FamilyValuePool

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!
LocationFamilyAccess
Popular amenities for Englewood rentals with a pool
House rentals with a pool

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN
LocationFamilyBiking

Cape Haze Cottage
LocationFamilySleep quality

10 mins to Beach, Heated Pool, Beach Gear & Games
ValueFamilyCleanliness

luxury Brand new villa with pool
LocationFamilyQuiet

Sun-Soaked & Tranquil Getaway Relaxing Pool Area
LocationFamilyBeach

Water view Villa private Heated Pool golf beach
FamilyLocationAmenities

Villa Sanddollar Awaits 1071HS
FamilyLocationNearby

3 Bed/2bath beautiful New Home with Pool
LocationValueKitchen
Condo rentals with a pool

Sunset Beach
ValueLocationAmenities

Beach Studio 55
ValueFamilyAmenities

Ocean Oasis on Manasota Key - Ocean View
FamilyLocationOutdoor spaces

Vintage Villa 35 | Steps to Beach | Pool
ValueFamilyBathroom

Bay Life @ ManasotaKeyCondos
LocationFamilyQuiet

Spacious Beachfront 3br Manasota Key Condo
LocationFamilyWalkability

A little slice of paradise
LocationFamilyQuiet

Boardwalk Beachfront Getaway
FamilyLocationPool
Other vacation rentals with a pool

1mi to Beach. 1+ acre of jungle Pool & Pickleball
ValueFamilySleep quality

Turtle Bay - minutes to Boca Grande!
FamilyLocationBeach

The Windsor @ Englewood Beach
FamilyLocationHot tub

Lazy Days at Lemon Bay *Bay view from the couch*
FamilyLocationPool

Private Heated Pool + Swim-Up Bar • Mins to Beach
LocationFamilyNearby

6min to Beach. Saltwater Pool, Jacuzzi. Fits 8ppl.
FamilyValueHeating

Pebble House w/ Screened Pool, Horseshoes, & more
ValueFamilyGetting around

Heated Pool Oasis w/ Game Room & BBQ Grill
ValueLocationCheck-in
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $200 | $243 | $242 | $202 | $180 | $185 | $175 | $161 | $155 | $155 | $168 | $182 |
| Avg. temp | 61°F | 64°F | 67°F | 72°F | 77°F | 81°F | 82°F | 82°F | 81°F | 76°F | 69°F | 64°F |
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