Vacation rentals with a pool in Manasota Key

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Top-rated rentals with a pool in Manasota Key

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious screened lanai features a heated swimming pool with clear blue water. Lounge chairs are positioned around the pool area, providing ample space for relaxation. The surrounding pavers and greenery contribute to a serene outdoor atmosphere.

Villa in Englewood

4.98 out of 5 average rating, 102 reviews

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)

Top guest favorite

A thatched-roof gazebo is positioned on a grassy area, surrounded by tranquil water. A circular stone patio features a table and chairs beneath the gazebo, with a stunning sunset illuminating the sky in warm hues over the horizon.

Cottage in Englewood

4.98 out of 5 average rating, 58 reviews

Waterfront! Sunset Views Nightly!

Welcome to Tiki In Paradise! Enjoy the tropical setting in this restored fishing cottage with direct Lemon Bay front cottage views! Sit back & relax and enjoy Lemon Bay water views from every window in our cottage! All the comforts you want and deserve. You will never find another property with the character, views & cleanliness like this special place. Completely remodeled. We are moments from Gulf front beaches, Historic Dearborn Street & fantastic restaurants! Private, Unique & Special!

Superhost

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, 274 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

An aerial view showcases a charming beach town along the coastline, with the ocean's turquoise waters visible in the background. Several buildings with distinct architectural styles blend harmoniously, while palm trees punctuate the landscape, enhancing the coastal ambiance.

Home in Manasota Key

5 out of 5 average rating, 43 reviews

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Luxury beach house with pool in a charming old-FL beach town, one of FL’s best kept secrets! New kitchen, 2 covered balconies & a walled backyard oasis. Spend sunny days by turquoise waters of the Gulf & host a cookout on the covered patio & pool. Enjoy the sea breeze while sipping your favorite beverage on the covered balcony off the living area. Lounge in style in the patio or go for a swim in the 6’ deep heated pool. You're walking distance to restaurants/bars and 57 seconds to the beach!

Top guest favorite

The outdoor pool area features a clear blue pool with a shallow entry. Surrounding the pool are various seating options, including lounge chairs and a table with chairs, all under a screened enclosure allowing natural light to filter through.

Home in Englewood

4.84 out of 5 average rating, 208 reviews

Manasota Beach Home w/heated pool walk to 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!

Top guest favorite

A pool area is enclosed by a screened patio, featuring a curvilinear pool with clear water. Lounge chairs and a vibrant red umbrella are positioned beside the water. The home’s large windows offer views of the surrounding outdoor space.

Home in North Port

4.97 out of 5 average rating, 144 reviews

Cozy & Beautiful Pool Villa in Sarasota County, FL

Welcome to our home! It’s our pleasure to host you! Your family & friends will be close to everything when you stay at this centrally-located place: shopping, dining, beaches, entertainment, Warm Mineral Springs, Aquatic Center, etc. This charming house located in a beautiful & quiet neighborhood, tastefully furnished & decorated, fenced for your privacy & perfect for making memories with family & friends. Plenty of amenities to make your stay as comfortable as possible. Great location.

Superhost

An aerial view captures the beachfront property surrounded by palm trees and lush greenery. The ocean is visible in the distance, framed by clear blue skies. A sandy path leads from the building to the beach, emphasizing the proximity to the water.

Condo in Englewood

4.77 out of 5 average rating, 132 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

STEPS TO WORLD FAMOUS Manasota Key BEACH, FREE PARKING. Private beach access. WALKING DISTANCE TO MANY LOCAL RESTAURANTS. 2 Bedroom, 1 Bathroom, beach themed condo with pool access. Complimentary grill for your dinner paired with an amazing Gulf sunset. Your morning coffee is on us! Beach chairs & towels supplied. Kitchen is updated and all utensils supplied. Master Bedroom has a queen sized bed. Boat dock slip available upon request. HEATED POOL located directly across the street.

Top guest favorite

An outdoor pool area is enclosed with a screened lanai, featuring a shaped pool surrounded by neutral-toned flooring. Relaxing lounge chairs are positioned nearby, and colorful pool floats rest on the water's surface, providing a vibrant touch to the tranquil setting.

Home in Englewood

4.99 out of 5 average rating, 103 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.

Top guest favorite

A cozy sleeping area features a spacious bed with light-colored bedding and decorative pillows. An ornate mirror and a television are positioned on a fireplace mantel. Warm light filters through sheer curtains, illuminating the inviting space decorated with tasteful artwork.

Apartment in Englewood

4.97 out of 5 average rating, 289 reviews

The Oz Tree House over looking Hot tub, Pool

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

Guest favorite

Home in Englewood

4.92 out of 5 average rating, 144 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!

Guest favorite

A sparkling swimming pool features clean, blue water surrounded by a spacious pool deck. The area is enclosed by a white fence, providing a safe environment. Sun loungers are positioned nearby, offering a place to relax under the clear sky.

Condo in Englewood

4.89 out of 5 average rating, 200 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.

Guest favorite

A covered outdoor patio features a rectangular table surrounded by six black chairs. Palm trees and the tranquil waters of Lemon Bay are visible in the background, providing a scenic view. The spacious area is ideal for relaxation and dining.

Condo in Englewood

4.95 out of 5 average rating, 21 reviews

Bay Breeze @ManasotaKeyCondos

We are welcoming guests post Hurricane Milton! Please note that the El Galeon East dock is in process of being rebuilt. Timing is July 2025. COMPLETELY RENOVATED IN 2024! 1st floor, open floor plan, end unit. This unit overlooks beautiful Lemon Bay and the end unit position lends to a unique panoramic view. Less than two minute walk to the Gulf Beach and just steps away from our heated swimming pool and the island's best restaurants.