
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.

Coastal Retreat Villa with pool • near beaches
🌴 Escape to your getaway in sunny Englewood, Florida! Whether you're a couple seeking romance, a solo adventurer, a business traveler, or a family with kids, our home is designed for comfort & relaxation. Nestled in a prime location, it's the ideal home base to anyone looking to unwind and explore. Indulge yourself in this executive cozy, built from the ground in 2018 & featuring 3 bedrooms, 2,5-bath house with a Large (seasonally) heated swimming Pool (heating $ included during colder months)

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.

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.

Lemon Bay Canal Home – Pool, Hot Tub & Boat Dock
Welcome to your private escape nestled on a secluded peninsula in Lemon Bay, just minutes from the Gulf of Mexico. This 2-bedroom, 3-bathroom pool home is a boater’s dream with direct canal access to open water—no bridges, no height restrictions. Just tie up at your private dock and you’re off to explore Lemon Bay, Stump Pass, and the Gulf in no time. Whether you’re into fishing, beachcombing, or simply relaxing poolside, this home offers the perfect blend of privacy, comfort, and location.

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 oasis. Just 1 mile to Manasota Beach the shark tooth capital of the world! Explore all the beach has to offer with a 3-4min car/bike ride. The house has a 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. Escape the noise and enjoy nature.

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.

Peaceful waterfront home
Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

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!

Refreshing! SW FL Home Pool near Boca Grande Beach
This 3 bedroom home is nestled in the quiet and really peaceful neighborhood of Rotonda West Fl. Relax at your own private pool, go to the Beach, fish, golf or visit multiple Major League Baseball locations. Beaches: ✔Englewood Beach- Only 20 minute drive to a really cozy and family friendly environment also with many bike paths ✔Boca Grande Beaches only 20 min away ✔Venice Beaches- Only a 30 minute drive to Shark tooth capital of the world

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.

New house, heated saltwater pool, 13 min to beach
Relax in this beautiful 3BR/2BA home just 13 minutes from the beach! Features all new furnishings, spacious living areas, heated saltwater pool with color lights (no extra charge for heating), screened lanai with outdoor seating, BBQ grill, and egg swing. Conveniently located near golf, shops, and restaurants — your perfect Florida getaway! New to Airbnb — check our reviews from other listings! 🌴

The Manor House on Lemon Bay. Available April 6th!
The Manor House on Lemon Bay will be your escape from reality as you relax and enjoy the laid back waterfront atmosphere at Tiki on the Bay. This small, inviting community is perfectly located. You're just moments from multiple Gulf front beaches, Historic Dearborn Street, and fantastic restaurants.
Popular amenities for Englewood rentals with a pool
House rentals with a pool

CLEAN*Great Location*Dockage Available*HEATED Pool

3 Bedroom Home | Heated Pool | Close to Beaches

Luxurious Resort Pool & Spa home

Golf Course Oasis: Cozy 2BD/Office/Pool

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

Water view Villa private Heated Pool golf beach

3 Bed/2bath beautiful New Home with Pool

Beautiful 3 bdrm home on a canal with heated pool.
Condo rentals with a pool

Sunset Beach

Entire Beachside Condo! Don’t worry Beach Happy!

Vintage Villa, Thirty-Five

Bay Life @ ManasotaKeyCondos

Studio, pool, private beach, boat dock shark teeth

A little slice of paradise

Pro Fishing Dock Private Beach & Heated Pool!

Beach Bliss Retreat on Manasota Key - Ocean View
Other vacation rentals with a pool

SunshineVilla/Pool/spa/beach /luxury/new

#7) 30 Seconds To Beach Path! Bikes, Kayaks Sups!

New house w/pool close to beach & mineral springs

Boaters Dream, full refund*, heated pool, sleeps 6

Canal front, gulf access, pool, spa, game room

The Lakeview Getaway

Sunset Retreat - Private Pool Near Gulf Beaches

Edison's Pool House
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ735 | ﺩ.ﺇ863 | ﺩ.ﺇ900 | ﺩ.ﺇ731 | ﺩ.ﺇ639 | ﺩ.ﺇ628 | ﺩ.ﺇ643 | ﺩ.ﺇ591 | ﺩ.ﺇ569 | ﺩ.ﺇ569 | ﺩ.ﺇ617 | ﺩ.ﺇ668 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about vacation rentals with a pool in Englewood

Total vacation rentals
Explore 580 vacation rentals in Englewood

Nightly prices starting at
Englewood vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 11,960 verified reviews to help you choose

Family-friendly vacation rentals
480 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
270 properties have a dedicated workspace

Wi-Fi availability
580 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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- Anna Maria Island
- Siesta Beach
- Crescent Beach
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- Turtle Beach
- Coquina Beach
- Lido Key Beach
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- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
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