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 $58 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    Find 130 rentals that welcome pets

  • Rentals with dedicated workspaces

    280 properties have a dedicated workspace

  • Wi-Fi availability

    560 of Englewood holiday 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 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, 26 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
The private heated saltwater pool is framed by a screened enclosure, allowing for natural light and views of the surrounding greenery. Sunlight reflects off the clear water, and a patio area is visible, creating a serene outdoor space.
Home in Englewood East
4.99 out of 5 average rating, 108 reviews

Our Happy Place. No cleaning fees! Heated pool

Our Happy Place is a newly remodeled pool home located in a quiet residential neighborhood! It has a private heated saltwater pool, 3 bedroom, 2 bath, located 2 miles to the intercoastal and 6 miles to Englewood beach! Very close to some of Southwest Florida's best shopping, golf courses, and restaurants! Our home is fully furnished, and includes everything you need for a long weekend getaway or for staying longer term! We know Our Happy Place will also become Your Happy Place!

Top Guest favourite
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!

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)

Guest favourite
A private pool features clear turquoise water, with colorful inflatable floaties in shades of pink, yellow, and green. The pool area is surrounded by a light-colored deck, providing a relaxing outdoor space for leisure and enjoyment.
Home in Englewood East
4.85 out of 5 average rating, 33 reviews

Paradise Palms | Private Pool | 10 min to Beach

Discover our Paradise 3-bedroom, 2-bathroom Palms Retreat. Embrace the beach vibes, perfect your golf swing, reel in the excitement of prime snook and tarpon fishing spots or relax by the inclusive private pool. A short drive away is the Tampa Bay Rays Stadium. Stay seamlessly connected with our high-speed 1 Gbps fiber internet, ideal for streaming or remote work. Your perfect blend of comfort and convenience awaits in this relaxing Florida getaway!

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.
Condo in Englewood
4.91 out of 5 average rating, 226 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, 58 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!

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 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

When is the best time to visit Englewood?

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