Holiday rentals with a pool in Englewood

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Englewood

  • Total holiday rentals

    Explore 560 holiday rentals in Englewood

  • Nightly prices starting at

    Englewood holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 11,860 verified reviews to help you choose

  • Family-friendly holiday rentals

    470 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 130 rentals that welcome pets

  • Rentals with dedicated workspaces

    280 properties have a dedicated workspace

  • Wifi availability

    560 of Englewood holiday rentals include wifi 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 favourite
Bungalow in Englewood
4.96 out of 5 average rating, 23 reviews

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

Over 1.2 acres of scenic Florida landscape to explore. Home to 50+ different plants, birds, animals and walking trails you are sure to feel like you are in a jungle. Just 1 mile to Manasota Beach the shark tooth capital! Explore all the beach has to offer with a 3-4min car/bike ride. huge lanai with pool, tv and seating areas. Two bedrooms and 1 bathroom with a tub. Just ten 5 min away 20+ restaurants and grocery stores. We have a guest house in the back my wife & I live in depending on the year

Top guest favourite
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 favourite
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

Top guest favourite
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, 18 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 favourite
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 favourite
Home in Englewood East
4.98 out of 5 average rating, 58 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 favourite
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, 56 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!

Guest favourite
A spacious exterior view of the home showcases a large tree with sprawling branches and a well-maintained yard featuring gravel and greenery. The structure is painted in a light color, with large windows reflecting natural light.
Home in Englewood
4.95 out of 5 average rating, 44 reviews

Manasota Tree House • Private Beach & Bay Access

Welcome to Manasota Tree House, our piece of paradise on Manasota Key. The location is the best on the island & we are family friendly. Just steps to the bay & a short walk to private beach access, 1 mile to bars & restaurants w/ free shuttle! Amazing beds, comfy couches, flat screen smart TV's & free fast Wifi. Private over sized lot, outdoor quiet oasis under the beautiful trees w/ chairs & gas grill, 2 SUP's, beach chairs, & towels. 1 mile to public Englewood Beach.

Guest favourite
An open-concept kitchen features a large granite island with seating, surrounded by white cabinetry and modern appliances. Natural light floods the space, highlighting the stylish chandelier above. The dining area is visible in the background, along with inviting seating arrangements in the family room.
Villa in Englewood
4.98 out of 5 average rating, 132 reviews

Stunning Bay Waterfront! Jaw dropping Views!

Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchen & 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)

Top guest favourite
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.
Apartment 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
A spacious single-story home is presented, featuring a light-colored exterior and a gabled roof. The landscaped front yard includes decorative stones and palm trees, with large windows reflecting the evening sky. A paved driveway leads to the attached garage.
Home in Englewood
4.93 out of 5 average rating, 59 reviews

Luxury Beach Retreat w/ Heated Pool

Welcome to our luxurious home, just 5 minutes from Manasota Key! Enjoy two master suites, a bunk room, and a gourmet kitchen with granite countertops. Relax in the screened lanai with a heated pool, outdoor dining, and lounge chairs. Additional features include high-speed internet, smart TVs, and an attached garage with entertainment options. Perfect for families or groups, this home is your ideal coastal retreat for relaxation and fun!

Top guest favourite
Home in Rotonda West
4.9 out of 5 average rating, 10 reviews

Luxury House Florida, Golf View, Privacy Pool.

Enjoy a Stylish Experience at this Centrally-Located Place. Rotonda West A Deed Restricted Community. Located on the SouthWest Coast of Florida. Gulf of America Best Beach 12 min. Boating is popular in Lemon Bay and around Boca Grande. Around the Rotonda a Lot of Gulf Places, Water Canal, Lakes. GOLFING, BOATING, FISHING, TENNIS,HIKING, CLUBS & GROUPS. Is a lovely, established community in the picturesque area known as Cape Haze.

Popular amenities for Englewood rentals with a pool

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