
Holiday 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.

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.

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.

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!

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.

Gulfstream Haven
Welcome to Gulfstream Haven, a 1700 sf 3 bedroom 2 bath pool home conveniently located 8 minutes from Englewood beach with many shops and restaurants nearby. The home features a king size bed in the master bedroom, 2 singles in 1 bedroom and a king size in another. There is a double sleeper sofa in the family room for 2 extra guests. All bedrooms feature walk in closets. The large screened-in lanai has plenty of seating for all occupants, with direct access to the guest bathroom.

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.

The Oz Tree House 2.9 m beach
The Tree house apartment has its own entrance and off street parking. Two blocks from Dearborn St. and 2.9 miles to the beach. Light and airy in a private setting with gardens, hammock, fire pit a quiet and peaceful, walking distance to everything the historic district of Old Englewood has to offer. Public tennis courts, great restaurants with live music and once a week a fantastic Farmers Market comes to town! Lemon Bay and Indian Mound are a nice walk to enjoy the sunsets

*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!

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, full sofa bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach. Close to everything!!

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!
Popular amenities for Englewood rentals with a pool
House rentals with a pool

Peaceful Villa Retreat – Pool/Spa, Manasota Key

Luxury Port Charlotte Waterfront Home – Pool & Spa

Seas The Day! No cleaning fee's! Heated pool.

3 Bedroom Home | Heated Pool | Close to Beaches

Water view Villa private Heated Pool golf beach

Villa Sanddollar Awaits ! 1071HS

3 Bed/2bath beautiful New Home with Pool

Heated Pool• Pool Table•2 King Beds•BBQ•Fast WiFi
Apartment rentals with a pool

Sunset Beach

Bay Breeze @ManasotaKeyCondos

Vintage Villa, Thirty-Five

Spacious 2BR 2BA Beach Condo for Perfect Vacation

A little slice of paradise

Tiki Time with prime beach access

Beach Bliss Retreat on Manasota Key - Ocean View

Steps to Water! Beach to Bay, Penthouse!
Other holiday rentals with a pool

Manasota Tree House • Private Beach & Bay Access

Florida Serene Luxury Retreat | Pool & Spa Oasis

Modern Villa Heated Saltwater Pool 10 Min to Beach

Heated Pool | Pet Friendly | Beach Gear | Big Yard

The Windsor @ Englewood Beach

The Mangrove House

Paradise Palms | Private Pool | 10 min to Beach

Huge Pool, Gulf Coast Luxury, Peace & Quiet, Bikes
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $257 SGD | $302 SGD | $315 SGD | $256 SGD | $224 SGD | $220 SGD | $225 SGD | $207 SGD | $199 SGD | $199 SGD | $216 SGD | $234 SGD |
| 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 holiday rentals with a pool in Englewood

Total holiday rentals
Explore 580 holiday rentals in Englewood

Nightly prices starting at
Englewood holiday rentals start at $51 SGD per night before taxes and fees

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

Family-friendly holiday rentals
480 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
270 properties have a dedicated workspace

Wifi availability
580 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!
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