
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 600 vacation rentals in Englewood

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

Verified guest reviews
Over 12,590 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wi-Fi availability
590 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.

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.
4.8 out of 5 average rating, 173 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.
4.91 out of 5 average rating, 306 reviews
Pool·Game Room·Beach Gear·Spotless.5 min to Beach
<b>🏖️ Come & Enjoy FL as it should be! 🏖️ Your beach paradise awaits minutes from Englewood's Gulf Coast! 🌊 Heated Pool (FREE Nov-Apr!) 🎮 Game Room - Pool, Darts, Air Hockey 🌴 Screened Lanai & Tiki Bar 🔥 Cozy Fireplace & Reading Nook 🏄 Beach Gear Included 🍹 Blackstone Grill 📺 2 Smart TVs & High-Speed WiFi 🍳 Fully Stocked Kitchen - Spices, Pots, Pans and cutlery 🗺️ Minutes to Englewood, Manasota & Gasparilla Beaches ⭐ 4.97 Rating - Book Now !Don't miss your Gulf Coast escape! 🌅
4.97 out of 5 average rating, 118 reviews
Manasota Beach Home w/Pool. Steps To The Beach
Custom built large home only 2 blocks to Manasota Beach. Most guests walk and a beach wagon is provided. Located in a quiet neighborhood with easy access to downtown Venice and Englewood. Very large and private lot with beautiful mature palms! The home has tray and soaring vaulted ceilings. The whole home opens up onto the pool area with sliders in every room. The bedrooms are configured in a split style with the very large master suite being totally private. Rare beach home for rent left!
4.84 out of 5 average rating, 240 reviews
Iguana Alley, Beach HEATed Saltwater Pool on Canal
Englewood home, open floor plan, tastefully decorated for an original Florida beach vibe. privatly set on brakish water canal with no shortage of fish. large Heated pool is screened in with covered outdoor eat/cook area. yard is fully fenced in. all Bedrooms feature New high end Beds and sheets. 5 tvs with basic channels. bathrooms have bidet wash. 7 ceiling fans.master bedroom has a separate french door entrance into pool area, plus private en suite bathroom with large walk in shower.
4.98 out of 5 average rating, 113 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.
4.99 out of 5 average rating, 145 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!
5.0 out of 5 average rating, 65 reviews
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!
4.93 out of 5 average rating, 170 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.
4.91 out of 5 average rating, 234 reviews
Paradise on the Bay
Waterfront pool home just a short drive to Boca Grande with all the amenities that you would expect. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fantastic fishing from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 3 Kayaks and a canoe are available for your enjoyment.
4.99 out of 5 average rating, 126 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!
4.94 out of 5 average rating, 67 reviews
The Oz Parlor 2.9 mi beach
The Oz Parlor apartment was originally the main house of this whimsical property. It has loads of charm It is a great place to relax and Just Bee... Please note I don’t have cable TV my TVs are wireless. I have Netflix. I will also add additional streaming channels for longer term stays. Located in the Historic District of Englewood a lovely walk to fine restaurants, Indian Mound Park on Lemon Bay and 2.9 miles to Englewood Beach.
5.0 out of 5 average rating, 267 reviewsPopular amenities for Englewood rentals with a pool
House rentals with a pool

Home w/ Pool, 10 mins to Manasota Key beaches
4.89 out of 5 average rating, 203 reviews
Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN
4.99 out of 5 average rating, 70 reviews
Waterfront| Pool & Spa | Near Beach| No Extra Fees
5.0 out of 5 average rating, 36 reviews
Villa Sanddollar Awaits 1071HS
4.97 out of 5 average rating, 38 reviews
10 mins to Beach, Heated Pool, Beach Gear & Games
4.87 out of 5 average rating, 86 reviews
3 Bedroom Home | Heated Pool | Close to Beaches
4.95 out of 5 average rating, 94 reviews
Coastal Sanctuary - Pool & Privacy
4.97 out of 5 average rating, 36 reviews
Stillwater Suite | Pool • Lakefront • 6min to Gulf
4.92 out of 5 average rating, 86 reviewsCondo rentals with a pool

Sunset Beach
4.96 out of 5 average rating, 137 reviews
Steps to Water! Beach to Bay, Penthouse!
4.94 out of 5 average rating, 101 reviews
Studio, pool, private beach, boat dock shark teeth
4.97 out of 5 average rating, 135 reviews
Vintage Villa 35 | Steps to Beach | Pool
4.96 out of 5 average rating, 111 reviews
A Beautiful Sunset Awaits - Steps to Beach
4.9 out of 5 average rating, 152 reviews
Private Beachside Kitchenette
4.87 out of 5 average rating, 191 reviews
A little slice of paradise
4.99 out of 5 average rating, 68 reviews
Boardwalk Beachfront Getaway
4.96 out of 5 average rating, 24 reviewsOther vacation rentals with a pool

Heated Pool—Manasota Key—Dog Friendly
4.99 out of 5 average rating, 67 reviews
luxury Brand new villa with pool
5.0 out of 5 average rating, 40 reviews
Private Heated Pool + Swim-Up Bar • Mins to Beach
5.0 out of 5 average rating, 39 reviews
Coastal escape across from the beach
4.89 out of 5 average rating, 27 reviews
Saltwater Villa/Pool/Jacuzzi/MovieTheater/FishDock
4.95 out of 5 average rating, 95 reviews
1mi to Beach. 1+ acre of jungle Pool & Pickleball
4.96 out of 5 average rating, 26 reviews
Pebble House w/ Screened Pool, Horseshoes, & more
4.94 out of 5 average rating, 18 reviews
Vacation Paradise in Rotonda
4.93 out of 5 average rating, 72 reviewsWhen is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €172 | €209 | €208 | €174 | €155 | €159 | €151 | €139 | €133 | €133 | €145 | €157 |
| 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 |
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