Holiday rentals with a pool in Manasota Key

Find and book unique homes with a pool on Airbnb

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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Guest favourite
Condo in Englewood
4.79 out of 5 average rating, 141 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 favourite
A vibrant sunset is depicted, with warm hues of orange and pink reflecting on the calm water. Silhouetted against the sky, a palm tree stands tall beside a figure, creating a serene coastal atmosphere.
Apartment in Englewood
5 out of 5 average rating, 28 reviews

#2) Bikes, Kayaks Sups, unmatched amenities & More

Welcome to Stump Pass Place! A perfect mix of comfort, nature and unmatched amenities. Just a 3 minute walk to our beautiful neighborhood beach or a just 4 minute walk to Stump Pass State Park at the end of our street. Here you can go to the beach, launch the water toys, and make some lifelong memories. Stump Pass State Park has one of the most beautiful pristine beaches in all of Florida! FREE Kayaks, Sups, beach cruiser bikes, beach chairs, umbrellas, boogie boards, coolers and so much more!

Guest favourite
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 favourite
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, 34 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 favourite
A private pool is surrounded by a screened enclosure, offering a clear view of the tranquil water. The area includes a seating set consisting of a table and chairs, with lush greenery visible beyond the enclosure.
Home in Englewood
5 out of 5 average rating, 12 reviews

Cozy beach house with pool

Charming Beach House with Private Pool on Manasota Key Escape to paradise at this beautiful beach house located on the serene shores of Manasota Key, Florida. Perfect for families or groups looking for a relaxing getaway, this home offers the best of both worlds—steps from the beach and your own private pool to unwind after a day of sun and sand. Key Features:     •    Direct beach access just a short stroll away     •    Private pool, perfect for relaxing or swimming laps     

Top Guest favourite
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.

Top Guest favourite
A serene beach view is captured under a clear sky, with sunlight reflecting on the calm water. The sandy path leads to the shoreline, where lounge chairs and umbrellas are positioned for comfort. Lush greenery outlines the beach area, enhancing the natural landscape.
Condo in Englewood
4.98 out of 5 average rating, 50 reviews

A little slice of paradise

This 2 bedroom 1 bath fully renovated, immaculate beach condo is located a mere 80 steps from front door to the amazing Englewood Beach on Manasota Key with your private beach access. The gulf breeze is indescribable. This could be your home away from home. We have added many personal touches for your convenience and comfort. Multiple restaurants, bars, gift/souvenir shops, and convenience store (Circle K) have re-opened since the hurricanes and are within walking distance.

Guest favourite
Home in Englewood
5 out of 5 average rating, 11 reviews

Steps to the Sand! Manasota Key Beachside Retreat!

BEACH LOVERS' DREAM! Only Steps from the Sand! Experience Old Florida charm in this renovated Gulf-view condo with an updated kitchen, open living area, and flexible sleeping options including a queen suite, twin to king beds, and a cozy flex space. Enjoy direct access to your own sandy beach, relax by the pool, or watch stunning sunsets from the shoreline. Explore scenic trails with complimentary bikes and kayaks. Your perfect Englewood beach getaway awaits, book today!

Guest favourite
Home in Englewood
4.92 out of 5 average rating, 157 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!

Top Guest favourite
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 favourite
Condo in Englewood
4.97 out of 5 average rating, 105 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.

Guest favourite
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, 22 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.

Popular amenities for Manasota Key rentals with a pool

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Quick stats about holiday rentals with a pool in Manasota Key

  • Total holiday rentals

    Explore 280 holiday rentals in Manasota Key

  • Nightly prices starting at

    Manasota Key holiday rentals start at $15 AUD per night before taxes and fees

  • Verified guest reviews

    Over 6,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    220 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    280 of Manasota Key holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Manasota Key rentals

  • 4.9 Average rating

    Manasota Key stays are highly rated by guests—averaging 4.9 out of 5!

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