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 560 vacation rentals in Englewood

  • Nightly prices starting at

    Englewood vacation rentals start at G$8,359 GYD 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!

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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Top guest favorite
A private saltwater pool is surrounded by a screened lanai, featuring clear water reflecting sunlight. Poolside, a handrail is visible for safety, and tropical landscaping can be seen in the background, enhancing the outdoor recreational space.
Villa in Englewood East
4.92 out of 5 average rating, 146 reviews

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.

Guest favorite
Home in Englewood
5 out of 5 average rating, 7 reviews

Gulf Front Escape + Beach Access

🦩 Exclusive Amenities Include: • Walk Out to the Beach – Steps from Your Door • Coastal & Surf Decks - Outdoor Seating • Historic Old Florida Charm • Beach Towels, Chairs & Umbrellas Provided • Community Pool with Picnic Tables & Chaise Lounges • Community Grills & Post-Beach Outdoor Showers • Free WiFi & TV • Coffee Maker & Kitchenette Smallwares Provided • Starter Packs of Essentials for Kitchen & Bath • Enhanced Cleaning Protocols • Combo Tub/Shower Bathroom • Desk/Chair in Unit

Guest favorite
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, 301 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 favorite
An aerial view captures the estate surrounded by lush greenery and palm trees. The circular driveway leads to the custom home, positioned gracefully with a backdrop of serene water and distant land. Sunlight enhances the inviting outdoor scenery.
Home in Englewood
5 out of 5 average rating, 19 reviews

Englewood Private Paradise near beach

This wonderful estate is ready to be your temporary home. With 2600 ft of luxury and exterior cameras for your peace of mind, you are more than inclined to relax at this gorgeous location. Close to restaurants and parks such as Manasota Beach, Stump Pass Beach Park and others, this is an ideal location. This custom-built home features 3 bedrooms, 2.5 baths, saltwater, heated pool with a waterfall, outdoor shower and an oversized 2.5 car garage. Perfect vacation home. Beach just 5 minutes away.

Top guest favorite
Home in Manasota Key
4.98 out of 5 average rating, 62 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 favorite
Home in Englewood
5 out of 5 average rating, 27 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 🌟

Top guest favorite
An aerial view of the Aqua Oasis highlights a screened patio area with a gas grill and outdoor seating around a fire pit. A private pool, illuminated in soft green, adds a tranquil touch. Surrounding greenery enhances the outdoor space.
Home in Englewood East
4.99 out of 5 average rating, 128 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!

Top guest favorite
Home in Englewood East
4.98 out of 5 average rating, 59 reviews

Heated Pool—Manasota Key—Dog Friendly

“Leisurely breakfasts out on the lanai while our dogs basked in the sunshine.” That's what guests keep saying about our Englewood home, 10 minutes from Manasota Key. Mornings start with breakfast on the lanai while your dogs claim the fenced yard. Afternoons are for the pool - kids on floats, the grill going for dinner. Sleeps nine, queen master with pool sliders, second queen, full-over-full bunk with trundle. Bikes and beach chairs in the garage, Publix 7 minutes away.

Top guest favorite
An aerial view captures a two-story home nestled along a quiet waterway with lush greenery surrounding it. Nearby, other residences and a private dock are visible. The scenic backdrop showcases calm waters merging with a blue sky, highlighting the tranquil atmosphere of the location.
Home in Englewood
5 out of 5 average rating, 57 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!

Top guest favorite
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, 227 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.

Superhost
Home in Englewood
5 out of 5 average rating, 4 reviews

Canal-Front 3BR – Pool, Hot Tub & Boat Access

Experience Old Florida charm reimagined for modern coastal living at this fully renovated 1960 canal-front retreat in Englewood. With direct boating access to Lemon Bay and Stump Pass, private dock for up to a 30ft boat, heated pool, hot tub, outdoor bar lounge, and premium indoor-outdoor sound system, this 3BR waterfront escape blends heritage, luxury, and laid-back Gulf Coast living just minutes from beaches and waterfront dining.

Top guest favorite
Home in Englewood East
5 out of 5 average rating, 31 reviews

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

Unwind in this thoughtfully designed 3-bedroom Florida retreat just 5 miles from Englewood Beach. Enjoy a private, heated pool with swim-up bar, screened lanai, and lush tropical privacy. Inside, you’ll find an open-concept living space, fully equipped kitchen, spa-style primary suite, and comfortable guest rooms. Ideal for families, couples, or friends seeking comfort, privacy, and easy access to beaches, golf, and dining.

Popular amenities for Englewood rentals with a pool

When is the best time to visit Englewood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$41,797 GYDG$50,784 GYDG$50,575 GYDG$41,588 GYDG$36,364 GYDG$35,737 GYDG$36,573 GYDG$33,647 GYDG$32,393 GYDG$32,393 GYDG$35,110 GYDG$38,035 GYD
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