Vacation rentals with a pool in Englewood

Find and book unique homes with a pool on Airbnb

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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Guest favorite
Condo in Englewood
4.79 out of 5 average rating, 140 reviews

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.

Top 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, 281 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
The exterior of a remodeled home is shown with a spacious driveway leading to an attached one-car garage. A welcoming enclosed front porch is visible, complemented by lush green trees and palm fronds lining the property. The sky reflects soft hues during sunset.
Home in Englewood
5 out of 5 average rating, 33 reviews

Beautiful pool home with golf cart by the beach

Welcome to this beautifully remodeled Home with golf cart, nestled within the idyllic community of Grove City in Englewood, Florida. This home offers two bedrooms and one bath, crafting an inviting haven suited for both small families and individuals in pursuit of comfort and ease. Notable features include a welcoming enclosed front porch and expansive back sunroom, alongside an attached one-car garage and a spacious backyard adorned with a convenient shed. With everything at your fingertips.

Top guest favorite
A private swimming pool is surrounded by several lounge chairs, providing a relaxing space under a clear blue sky. A patio area is visible in the background, featuring outdoor seating and lush greenery that enhances the peaceful atmosphere.
Home in Englewood
4.95 out of 5 average rating, 43 reviews

Your Coastal Getaway!

Your vacation home is on a peaceful street in a quiet neighborhood within an 8 minute drive of Englewood Beach and within 15 minutes of several other popular beaches. This home is convenient to shops, restaurants and famous Dearborn street. Property comfortably sleeps up to 6 guests with a fully furnished kitchen, 2 bathrooms, a lanai, Swimming pool and it is pet friendly! Relax with the whole family at this peaceful place to stay. Maximum of 2 PETS ONLY! PETS MUST BE 30 LBS or LESS.

Guest favorite
Home in Englewood
5 out of 5 average rating, 6 reviews

January & February Now Available. Act Fast

Kick back and relax in this calm, stylish space. Every inch has been updated, upgraded, and designed with your comfort, relaxation, and enjoyment in mind. Lemon Bay is a special place on its own accord. When you add to it the magic the Tiki on the Bay Community adds to the mix, we believe you’ve found paradise. Tiki on the Bay is a small, inviting community that's perfectly located. You're just moments from multiple Gulf front beaches, Historic Dearborn Street, and fantastic restaurants.

Top guest favorite
A contemporary dining area features a round table set for four, surrounded by sleek chairs. Large glass walls provide abundant natural light, revealing views of the outdoor space. A modern chandelier hangs above, adding an elegant touch to the inviting atmosphere.
Home in Rotonda West
5 out of 5 average rating, 9 reviews

Turtle Bay - minutes to Boca Grande!

Welcome to Turtle Bay Haven – Your Dream Escape on the Gulf Coast! Stay in your own private natural oasis, surrounded by lush greenery and the vibrant tropics of Florida wildlife. - Grocery Stores: just 5-10 min away - Dining Options: A variety of local restaurants are just min away. - Boca Grande: 11 mi (20 min) away, known for stunning beaches. - Manasota Key Beaches : 10 mi (20 min) - Activities: Kayaking, paddleboarding, fishing, hiking, biking, and over 20 golf courses await!

Top guest favorite
A spacious patio area is showcased, featuring a comfortable sectional sofa adorned with colorful pillows. A coffee table is positioned in front, while the heated pool and a wooden pergola are visible through large screened windows, enhancing the outdoor experience.
Home in Englewood
4.99 out of 5 average rating, 114 reviews

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.

Superhost
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
4.85 out of 5 average rating, 20 reviews

Paradise Palms Retreat

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 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, 211 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.

Top guest favorite
Condo in Englewood
4.97 out of 5 average rating, 104 reviews

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, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach.

Top guest favorite
Home in Englewood
5 out of 5 average rating, 22 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.

Guest favorite
Home in Venice
4.91 out of 5 average rating, 129 reviews

Spacious 2 Bedroom Home | Near Beach | Heated Pool

This beautiful home just minutes from the beach offers 2 spacious king bedrooms, a queen sofa bed in the large open living area, and a full kitchen ready for entertaining. Gather your family around the dining room table for food and games and then relax on the lanai or have a float in the pool. The hosts provide Margaritaville frozen concoction machine, 2 bicycles, beach chairs, beach towels, shark tooth tools, and more.

Popular amenities for Englewood rentals with a pool

When is the best time to visit Englewood?

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Avg. price€ 172€ 202€ 211€ 171€ 150€ 147€ 150€ 138€ 133€ 141€ 142€ 148
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Quick stats about vacation rentals with a pool in Englewood

  • Total vacation rentals

    Explore 520 vacation rentals in Englewood

  • Nightly prices starting at

    Englewood vacation rentals start at € 34 per night before taxes and fees

  • Verified guest reviews

    Over 11,700 verified reviews to help you choose

  • Family-friendly vacation rentals

    440 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 130 rentals that welcome pets

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wi-Fi availability

    510 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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